Routes to xanthones: An update on the synthetic approaches

Current Organic Chemistry

Volumn 16, Issue 23, 2012, Pages 2818-2867

  Azevedo, Carlos Miguel Gonçalves ^a   Afonso, Carlos Manuel Magalhães ^a   Pinto, Madalena Maria Magalhães ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Benzophenones; Chromen 4 ones; Chromones; Diarylethers; O heterocycles; Xanthen 9 ones; Xanthenes; Xanthones

Indexed keywords

CATALYSIS; XANTHENES;

BENZOPHENONE; CHROMEN-4-ONE; CHROMONES; DIARYLETHER; HETEROCYCLES; O-HETEROCYCLE; PHARMACOLOGICAL ACTIVITY; SYNTHETIC APPROACH; XANTHEN-9-ONE; XANTHONE;

SCAFFOLDS;

EID: 84872562120     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212804546921     Document Type: Article

References (240)

1. Cragg, G.M.; Grothaus, P.G.; Newman, D.J., Impact of Natural Products on Developing New Anti-Cancer Agents. Chem. Rev., 2009, 109(7), 3012-3043.
2. Mishra, B.B.; Tiwari, V.K., Natural products: An evolving role in future drug discovery. Eur. J. Med. Chem, 2011, 46(10), 4769-4807.
3. Lee, K.-H., Discovery and Development of Natural Product-Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach. J. Nat. Prod., 2010, 73(3), 500-516.
4. Chin, Y.-W.; Balunas, M.J.; Chai, H.B.; Kinghorn, A.D., Drug Discovery From Natural Sources The AAPS J., 2006, 8(2), E239-E253.
5. Ganesan, A., The impact of natural products upon modern drug discovery. Curr. Opin. Chem. Biol., 2008, 12(3), 306-317.
6. Newman, D.J.; Cragg, G.M., Natural Products as Sources of New Drugs over the Last 25 Years. J. Nat. Prod., 2007, 70(3), 461-477.
7. Harvey, A.L., Natural products in drug discovery. Drug Discov. Today, 2008, 13(19/20), 894-901.
8. Butler, M.S., Natural products to drugs: natural product-derived compounds in clinical trials. Nat. Prod. Rep., 2008, 25(3), 475-516.
9. Koehn, F.E.; Carter, G.T., The Evolving Role of Natural Products in Drug Discovery. Nat. Rev. Drug Discov., 2005, 4(206-220).
10. Liu, E.H.; Qi, L.W.; Wu, Q.; Peng, Y.B.; Li, P., Anticancer Agents Derived from Natural Products. Mini-Rev. Med. Chem., 2009, 9(13), 1547-1555.
11. Pinto, M.M.M.; Sousa, M.E.; Nascimento, M.S.J., Xanthone Derivatives: New Insights in Biological Activities. Curr. Med. Chem., 2005, 12(21), 2517-2538.
12. Pouli, N.; Marakos, P., Fused Xanthone Derivatives as Antiproliferative Agents Anti-Cancer Agents Med. Chem., 2009, 9(1), 77-91.
13. Fottie, J.; Bohle, D.S., Pharmacological and Biological Activities of Xanthones. Anti-Infect. Agents Med. Chem., 2006, 5(1), 15-31.
14. Chin, Y.-W.; Kinghorn, A.D., Structural Characterization, Biological Effects, and Synthetic Studies on Xanthones from Mangosteen (Garcinia mangostana), a Popular Botanical Dietary Supplement Mini-Rev. Org. Chem., 2008, 5(4), 355-364.
15. Pinto, M.M.M.; Castanheiro, R.A.P., Synthesis of Prenylated Xanthones: An Overview. Curr. Org. Chem., 2009, 13(12), 1215-1240.
16. Na, Y., Recent cancer drug development with xanthone structures. J. Pharm. Pharmacol., 2009, 61(6), 707-712.
17. Chantarasriwong, O.; Batova, A.; Chavasiri, W.; Theodorakis, E.A., Chemistry and Biology of the Caged Garcinia Xanthones. Chem. Eur. J., 2010, 16(33), 9944-9962.
18. Anantachoke, N.; Tuchinda, P.; Kuhakarn, C.; Pohmakotr, M.; Reutrakul, V., Prenylated caged xanthones: Chemistry and biology. Pharm. Biol., 2012, 50(1), 78-91.
19. Han, Q.-B.; Xu, H.-X., Caged Garcinia Xanthones: Development Since 1937. Curr. Med. Chem., 2009, 16(28), 3775-3796.
20. Shan, T.; Ma, Q.; Guo, K.; Liu, J.; Li, W.; Wang, F.; Wu, E., Xanthones from Mangosteen Extracts as Natural Chemopreventive Agents: Potential Anticancer Drugs. Curr. Mol. Med., 2011, 11(8), 666-677.
21. Nguyen, H.T.; Lallemand, M.-C.; Boutefnouchet, S.; Michel, S.; Tillequin, F., Antitumor Psoropermum Xanthones and Sarcomelicope Acridones: Privileged Structures Implied in DNA Alkylation. J. Nat. Prod., 2009, 72(3), 527-539.
22. Pinto, M.M.M.; Castanheiro, R.A.P. In Natural Products: Chemistry, Biochemistry and Pharmacology. Brahmachari, G., Ed.; Narosa Publishing House PVT, LTD: New Delhi, 2009, pp 520-675.
23. Vieira, L.M.M.; Kijjoa, A., Naturally-Occurring Xanthones: Recent Developments. Curr. Med. Chem., 2005, 12(21), 2413-2446.
24. El-Seedi, H.R.; El-Ghorab, D.M.H.; El-Barbary, M.A.; Zayed, M.F.; Göransson, U.; Larsson, S.; Verpoorte, R., Naturally Occurring Xanthones; Latest Investigations: Isolation, Structure Elucidation and Chemosystematic Significance. Curr. Med. Chem., 2009, 16(20), 2581-2626.
25. Sousa, M.E.; Pinto, M.M.M., Synthesis of Xanthones: An Overview. Curr. Med. Chem., 2005, 12(21), 2447-2479.
26. Afzal, M.; Alhassan, J.M., Synthesis and Biosynthesis of phytoxanthones. Heterocycles, 1980, 14(8), 1173-1205.
27. Dean, F.M. In The Total Synthesis of Natural Products. Apsimon, J., Ed.; Wiley-Interscience, 1973; Vol. 1, pp 534-562.
28. Williams, A.C.; Camp, N. In Science of Synthesis. Thomas, E.J., Ed.; Thieme: Manchester, 2003; Vol. 14, pp 589-610.
29. Hepworth, J.D.; Heron, B.M. In Progress in Heterocyclic Chemistry. Gordon, W.G.; Thomas, L.G., Eds.; Elsevier, 2002; Vol. 14, pp 332-355.
30. Hepworth, J.D.; Heron, B.M. In Progress in Heterocyclic Chemistry. Gordon, W.G.; John, A.J., Eds.; Elsevier, 2003; Vol. 15, pp 360-384.
31. Hepworth, J.D.; Mark Heron, B. In Progress in Heterocyclic Chemistry. Gribble Gordon, W.; Joule John, A., Eds.; Elsevier, 2005; Vol. 16, pp 405-430.
32. Hepworth, J.D.; Heron, B.M. In Progress in Heterocyclic Chemistry. Gordon, W.G.; John, A.J., Eds.; Elsevier, 2007; Vol. 18, pp 376-401.
33. Hepwort, J.D.; Heron, B.M. In Progress in Heterocyclic Chemistry. Gordon, W.G.; John, A.J., Eds.; Elsevier, 2009; Vol. 21, pp 455-490.
34. Hepworth, J.D.; Heron, B.M. In Progress in Heterocyclic Chemistry. Gordon, G.; John, A.J., Eds.; Elsevier, 2011; Vol. 22, pp 449-490.
35. Hepworth, J.D.; Heron, B.M. In Progress in Heterocyclic Chemistry. Gordon, W.G.; John, A.J., Eds.; Elsevier, 2011; Vol. 23, pp 427-463.
36. Diderot, N.T.; Silvere, N.; Etienne, T. In Advances in Phytomedicine. Mahmud, T.H.K.; Arjumand, A., Eds.; Elsevier, 2006; Vol. 2, pp 273-298.
37. Grover, P.K.; Shah, G.D.; Shah, R.C., Xanthones. Part IV. A new synthesis of hydroxyxanthones and hydroxybenzophenones. J. Chem. Soc., 1955, 3982-3985.
38. Zhao, J.; Larock, R.C., One-pot synthesis of xanthones and thioxanthones by the tandem coupling-Cyclization of arynes and salicylates. Org. Lett., 2005, 7(19), 4273-4275.
39. Zhao, J.; Larock, R.C., Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates. J. Org. Chem., 2007, 72(2), 583-588.
40. Okuma, K.; Nojima, A.; Matsunaga, N.; Shioji, K., Reaction of Benzyne with Salicylaldehydes: General Synthesis of Xanthenes, Xanthones, and Xanthols. Org. Lett., 2009, 11(1), 169-171.
41. Dubrovskiy, A.V.; Larock, R.C., Intermolecular C-O Addition of Carboxylix Acids to Arynes. Org. Lett., 2010, 12(14), 3117-3119.
42. Wang, S.; K., X.; Tan, Z.; An, X.; Zhou, X.; Guo, C.-C.; Peng, Z., One-step preparation of xanthones via Pd-catalyzed annulation of 1,2-dibromoarenes and salicylaldehydes. Chem. Commun., 2009(42), 6469-6471.
43. Kostanecki, V., Ber. D. Chem, 1892, 25, 1649-1651.
44. Michael, A., Ann. Chem. J., 1883(5), 81.
45. Pankajamani, K.S.; Seshadri, T.R., Synthetic Experiments in the Benzopyrone Series: Part XLVI-Application of the Nencki Reaction in the Synthesis of Xanthones. J. Sci. Industr. Res., 1954, 13B, 396-400.
46. Desai, B.M.; Desai, P.R.; Desai, R.D., J. Indian Chem. Soc., 1960, 37, 53-55.
47. Pillai, R.K.M.; Naiksatam, P.; Johnson, F.; Rajagopalan, R.; Watts, P.C.; Cricchio, R.; Borras, S., Thermorubin II-1,3-dihydroxy-9H-xanthone and 1,3-dihydroxy-9H-xanthenes-new methods of synthesis. J. Org. Chem., 1986, 51(5), 717-723.
48. Patolia, R.J.; Trivedi, K.N., New one-step synthesis of xanthones. Chem. Ind., 1978, 7, 235.
49. Locksley, H.D.; Moore, I.; Scheinmann, F., Extractives from Guttiferae. Part II. The isolation and Structure of Four Polyhydroxyxanthones in Symphonia globulifera L. J. Chem. Soc. (C), 1966, 430-432.
50. Liu, Y.; Zou, L.; Ma, L.; Chen, W.H.; Wang, B.; Xu, Z.L., Synthesis and pharmacological activities of xanthone derivatives as alpha-glucosidase inhibitors. Bioorg. Med. Chem., 2006, 14(16), 5683-5690.
51. Verbanac, D.; Jain, S.C.; Jain, N.; Chand, M.; Čipčić Paljetak, H.; Matijašić, M.; Perić, M.; Stepanić, V.; Saso, L., An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization. Bioorg. Med. Chem., 2012, 20(10), 3180-3185.
52. Castanheiro, R.A.P.; Pinto, M.M.M.; Silva, A.M.S.; Cravo, S.M.M.; Gales, L.; Damas, A.M.; Nazareth, N.; Nascimento, M.S.J.; Eaton, G., Dihydroxyxanthones prenylated derivatives: Synthesis, structure elucidation, and growth inhibitory activity on human tumor cell lines with improvement of selectivity for MCF-7. Bioorg. Med. Chem., 2007, 15(18), 6080-6088.
53. Woo, S.; Jung, J.; Lee, C.; Kwon, Y.; Na, Y., Synthesis of new xanthone analogues and their biological activity test-Cytotoxicity, topoisomerase II inhibition, and DNA cross-linking study. Bioorg. Med. Chem. Lett., 2007, 17(5), 1163-1166.
54. Li, N.G.; You, Q.D.; Huang, X.F.; Wang, J.X.; Guo, Q.L.; Chen, X.G.; Li, Y.; Li, H.Y., Synthesis and antitumor activities of structure-related small molecular compounds of gambogic acid. Chinese Chem. Lett., 2007, 18(6), 659-662.
55. Shen, R.; Wang, P.; Tang, N., Cytotoxic Activity and DNA-binding Properties of Xanthone Derivatives. J. Fluoresc., 2010, 20(6), 1-11.
56. Sun, H.; Chen, F.; Wang, X.; Liu, Z.; Yang, Q.; Zhang, X.; Zhu, J.; Qiang, L.; Guo, Q.; You, Q., Studies on gambogic acid (IV): Exploring structureactivity relationship with IκB kinase-beta (IKKβ). Eur. J. Med. Chem., 2012, 51, 110-123.
57. Li, N.G.; Wang, J.X.; Liu, X.R.; Lin, C.J.; You, Q.D.; Guo, Q.L., A novel and efficient route to the construction of the 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold. Tetrahedron Lett., 2007, 48(37), 6586-6589.
58. Liu, Z.-L.; Wang, X.-J.; Li, N.-G.; Sun, H.-P.; Wang, J.-X.; You, Q.-D., Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A. Tetrahedron, 2011, 67(26), 4774-4779.
59. Sittisombut, C.; Boutefnouchet, S.; Van-Dufat, H.T.; Tian, W.; Michel, S.; Koch, M.; Tillequin, F.; Pfeiffer, B.; Pierre, A., Synthesis and cytotoxic activity of benzo[a]pyrano[3,2-h] and [2,3-i]xanthone analogues of psorospermine, acronycine, and benzo[a]acronycine. Chem. Pharm. Bull., 2006, 54(8), 1113-1118.
60. Sousa, E.; Paiva, A.; Nazareth, N.; Gales, L.; Damas, A.M.; Nascimento, M.S.J.; Pinto, M.M.M., Bromoalkoxyxanthones as promising antitumor agents: Synthesis, crystal structure and effect on human tumor cell lines. Eur. J. Med. Chem, 2009, 44(9), 3830-3835.
61. Varache-Lembège, M.; Moreau, S.; Larrouture, S.; Montaudon, D.; Robert, J.; Nuhrich, A., Synthesis and antiproliferative activity of aryl-and heteroaryl-hydrazones derived from xanthone carbaldehydes. Eur. J. Med. Chem, 2008, 43(6), 1336-1343.
62. Wu, Z.; Wei, G.; Lian, G.; Yu, B., Synthesis of Mangiferin, Isomangiferin, and Homomangiferin. J. Org. Chem., 2010, 75(16), 5725-5728.
63. Pintori, D.G.; Greaney, M.F., Insertion of Benzene Rings into the Amide Bond: One-Step Synthesis of Acridines and Acridones from Aryl Amides. Org. Lett., 2010, 12(1), 168-171.
64. Dubrovskiy, A.V.; Larock, R.C., Synthesis of o-(Dimethylamino)aryl Ketones and Acridones by the Reaction of 1,1-Dialkylhydrazones and Arynes. Org. Lett., 2011, 13(15), 4136-4139.
65. Rogness, D.C.; Larock, R.C., Synthesis of Acridines by the [4 + 2] Annulation of Arynes and 2-Aminoaryl Ketones. J. Org. Chem., 2010, 75(7), 2289-2295.
66. Okuma, K.; Nojima, A.; Nakamura, Y.; Matsunaga, N.; Negahora, N.; Shioji, K., Reaction of Benzyne with Formamides and Acetylimidazole. Bull. Chem. Soc. Jpn, 2011, 8(3), 328-332.
67. Casillas, L.K.; Townsend, C.A., Total Synthesis of OMethylsterigmatocystin Using N-Alkylnitrilium Salts and Carbonyl-Alkene Interconversion in a New Xanthone Synthesis. J. Org. Chem, 1999, 64(11), 4050-4059.
68. Finnegan, R.A.; Merkel, K.E., The Synthesis of 2,5-and 4,5-Dihydroxyxanthone. J. Org. Chem, 1972, 37(19), 2986-2989.
69. Horne, S.; Rodrigo, R., A Complex Induced Proximity Effect in the Anionic Fries Rearrangement of o-1odophenyl Benzoates: Synthesis of Dihydro-Omethylsterigmatocystin and Other Xanthones. J. Org. Chem., 1990, 55(15), 4520-4522.
70. Lampe, J.W.; Hughes, P.F.; Biggers, C.K.; Smith, S.H.; Hu, H., Total Synthesis of (-)-and (+)-Balanol. J. Org. Chem., 1996, 61(14), 4572-4581.
71. Nicolaou, K.C.; Bunnage, M.E.; Koide, K., Total Synthesis of Balanol. J. Am. Chem. Soc., 1994, 116(18), 8402-8403.
72. Couture, A.; Deniau, E.; Lebrun, S.; Grandclaudon, P., Total syntheses of (±)-cherylline and (±)-latifine. J. Chem. Soc., Perkin Trans. I, 1999(7), 780-794.
73. Sandifer, R.M.; Bhattacharya, A.K.; Harris, T.M., Acylation of Multiple Anions of Poly-B-ketones by Hydroxy-and Alkoxybenzoates. Cyclization of the Resultant Tetraketones to Benzophenones and Xanthones. J. Org. Chem., 1981, 46(11), 2260-2267.
74. Martin, R. Handbook of Hydroxybenzophenones. Kluwer Academic Publishers: Dordrecht, 2000.
75. Ruske, W. Olah, G.A., Ed.; John Willey & Sons: New York, 1964, p 383.
76. Quillinan, A.J.; Scheinmann, F., Studies in the xanthone series. Part XII. A general synthesis of polyoxygenated xanthones from benzophenone precursors. J. Chem. Soc., Perkin Trans., 1973, 1329-1337.
77. Li, N.G.; Wang, J.X.; You, Q.D.; Chu, G.; Guo, Q.L., Cascade reaction and synthesis of bicyclo[2,2,2]octenones. Chinese J. Chem., 2008, 26(2), 363-367.
78. Kuemmerle, J.; Jiang, S.; Tseng, B.; Kasibhatla, S.; Drewe, J.; Cai, S.X., Synthesis of caged 2,3,3a,7a-tetrahydro-3,6-methanobenzofuran-7(6H)-ones: Evaluating the minimum structure for apoptosis induction by gambogic acid. Bioorg. Med. Chem., 2008, 16(8), 4233-4241.
79. Barbero, N.; SanMartin, R.; Domínguez, E., A Convenient Approach To The Xanthone Scaffold By An Aqueous Aromatic Substitution Of Bromo-And Iodoarenes. Tetrahedron, 2009, 65(29-30), 5729-5732.
80. Barbero, N.; Sanmartin, R.; Domínguez, E., An efficient copper-catalytic system for performing intramolecular O-arylation reactions in aqueous media. New synthesis of xanthones. Green Chem., 2009, 11(6), 830-836.
81. Hu, H.; Liao, H.; Zhang, J.; Wu, W.; Yan, J.; Yan, Y.; Zhao, Q.; Zou, Y.; Chai, X.; Yu, S.; Wu, Q., First identification of xanthone sulfonamides as potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(10), 3094-3097.
82. Palmeira, A.; Paiva, A.; Sousa, E.; Seca, H.; Almeida, G.M.; Lima, R.T.; Fernandes, M.X.; Pinto, M.; Vasconcelos, M.H., Insights into the in vitro Antitumor Mechanism of Action of a New Pyranoxanthone. Chem. Biol. Drug. Des., 2010, 76(1), 43-58.
83. Chantarasriwong, O.; Cho, W.C.; Batova, A.; Chavasiri, W.; Moore, C.; Rheingold, A.L.; Theodorakis, E.A., Evaluation of the pharmacophoric motif of the caged Garcinia xanthones. Org. Biomol. Chem., 2009, 7(23), 4886-4894.
84. Batova, A.; Lam, T.; Wascholowski, V.; Yu, A.L.; Giannis, A.; Theodorakis, E.A., Synthesis and evaluation of caged Garcinia xanthones. Org. Biomol. Chem., 2007, 5(3), 494-500.
85. Zhang, L.; Zhang, J.Y., Microwave-assisted, boron trichloride mediated acylation of phenols-synthesis of (o-hydroxyaryl)(aryl)methanones and xanthones. J. Comb. Chem., 2006, 8(3), 361-367.
86. Dodean, R.A.; Kelly, J.X.; Peyton, D.; Gard, G.L.; Riscoe, M.K.; Winter, R.W., Synthesis and heme-binding correlation with antimalarial activity of 3,6-bis-([omega]-N, N-diethylaminoamyloxy)-4,5-difluoroxanthone. Bioorg. Med. Chem., 2008, 16(3), 1174-1183.
87. Kuhakarn, C.; Surapanich, N.; Kamtonwong, S.; Pohmakotr, M.; Reutrakul, V., Friedel-Crafts-Type Alkylation with Bromodifluoro(phenylsulfanyl) methane through α-Fluorocarbocations: Syntheses of Thioesters, Benzophenones and Xanthones. Eur. J. Org. Chem., 2011(29), 5911-5918.
88. Clayden, J. Organolithiums: Selectivity for synthesis. Pergamon, 2002.
89. Mondal, M.; Puranik, V.G.; Argade, N.P., Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: Simple and efficient access to osajaxanthone and nigrolineaxanthone F. J. Org. Chem, 2006, 71(13), 4992-4995.
90. Johnson, M.M.; Naidoo, J.M.; Fernandes, M.A.; Mmutlane, E.M.; Otterlo, W.A.L.v.; Koning, C.B.d., CAN-Mediated Oxidations for the Synthesis of Xanthones and Related Products. J. Org. Chem., 2010, 75(24), 8701-8704.
91. Locksley, H.D.; Murray, I.G., Extractives from Guttiferae. Part XVI. Biogenetic-type Synthesis of Xanthones from their Benzophenone Precursors. J. Chem. Soc. (C), 1970, 392-398.
92. Iikubo, K.; Ishikawa, Y.; Ando, N.; Umezawab, K.; Nishiyama, S., The first direct synthesis of alpha-mangostin, a potent inhibitor of the acidic sphingomyelinase. Tetrahedron Lett., 2002, 43(2), 291-293.
93. Jeso, V.; Nicolaou, K.C., Total Synthesis of Tovophyllin B. Tetrahedron Lett., 2009, 50(11), 1161-1163.
94. Hintermann, L.; Masuo, R.; Suzuki, K., Solvent-Controlled Leaving-Group Selectivity in Aromatic Nucleophilic Substitution. Org. Lett., 2008, 10(21), 4859-4862.
95. Masuo, R.; Ohmori, K.; Hintermann, L.; Yoshida, S.; Suzuki, K., First Stereoselective Total Synthesis of FD-594 Aglycon. Angew. Chem. Int. Ed., 2009, 48(19), 3462-3465.
96. Zhou, C.X.; Larock, R.C., Synthesis of aryl ketones or ketimines by palladium-catalyzed arene C-H addition to nitriles. J. Org. Chem, 2006, 71(9), 3551-3558.
97. Suzuki, Y.; Toyota, T.; Miyashita, A.; Sato, M., Synthesis of heterocyclic compounds via nucleophilic aroylation catalyzed by imidazolidenyl carbene. Chem. Pharm. Bull., 2006, 54(12), 1653-1658.
98. Suzuki, Y.; Fukuta, Y.; Ota, S.; Kamiya, M.; Sato, M., Xanthone Natural Products via N-Heterocyclic Carbene Catalysis: Total Synthesis of Atroviridin. J. Org. Chem., 2011, 76(10), 3960-3967.
99. Kraus, G.A.; Mengwasser, J., Quinones as Key Intermediates in Natural Products Synthesis. Syntheses of Bioactive Xanthones from Hypericum perforatum Molecules, 2009, 14(8), 2857-2861.
100. Barton, D.H.R.; Scott, A.I., The Constitutions of Geodin and Erdin. J. Chem. Soc., 1958, 1767-1771.
101. Lewis, J.R., Biogenetic Type Synthesis of the Xanthone Nucleus. Proc. Chem. Soc., 1963, 373.
102. Steinberg, N.G.; Arisen, B.A.; Beck, J.L., A synthesis of 2-Hydroxyxanthone. J. Heterocyclic Chem., 1972, 9(5), 1181-1184.
103. th ed. Springer, 2007.
104. th ed. John Willey & Sons: New Jersey, 2007.
105. Evangelista, E.A.; Couri, M.R.C.; Alves, R.B.; Raslan, D.S.; Gil, R.P.F., Microwave-assisted xanthone synthesis. Synth. Commun., 2006, 36(16), 2275-2280.
106. Chen, Q.; Espey, M.G.; Sun, A.Y.; Lee, J.H.; Krishna, M.C.; Shacter, E.; Choyke, P.L.; Pooput, C.; Kirk, K.L.; Buettner, G.R.; Levine, M., Ascorbate in pharmacologic concentrations selectively generates ascorbate radical and hydrogen peroxide in extracellular fluid in vivo. Proc. Natl. Acad. Sci. USA, 2007, 104(21), 8749-8754.
107. Woydziak, Z.R.; Fu, L.; Peterson, B.R., Synthesis of Fluorinated Benzophenones, Xanthones, Acridones, and Thioxanthones by Iterative Nucleophilic Aromatic Substitution. J. Org. Chem., 2012, 77(1), 473-481.
108. Omolo, J.J.; Johnson, M.M.; Vuuren, S.F.v.; Koning, C.B.d., The synthesis of xanthones, xanthenediones, and spirobenzofurans: Their antibacterial and antifungal activity. Bioorg. Med. Chem. Lett., 2011, 21(23), 7085-7088.
109. Tisdale, E.J.; Kochman, D.A.; Theodorakis, E.A., Total synthesis of atroviridin. Tetrahedron Lett., 2003, 44(16), 3281-3284.
110. Ellis, R.C.; Whalley, W.B.; K., B., Biogenetic-type syntheses of xanthones. Chem. Comm., 1967(16), 803-804.
111. Lown, J.W.; Sondhi, S.M.; Mandal, S.B.; Murphy, J., Synthesis and Redox Properties of Chromophore Modified Glycosides Related to Anthracyclines. J. Org. Chem., 1982, 47(22), 4304-4310.
112. Elix, J.A.; Gaul, K.L.; Jiang, H., The Structure and Synthesis of Some Minor Xanthones from the Lichen Rinodina thiomela. Aust. J. Chem., 1992, 46(1), 95-110.
113. Pfister, J.R., Application of the Smiles Rearrangement to the Synthesis of 5,7-disubstituted Xanthone-2-carboxilic Acids. J. Heterocyclic Chem., 1982, 19(5), 1255-1256.
114. Ullmann, F.; Sponagel, P., Ueber die Phenylirung von Phenolen. Chem. Ber., 1905, 38(2), 221-2212.
115. Moroz, A.A.; Shvartsberg, M.S., The Ullmann Ether Condensation. Russ. Chem. Rev., 1974, 43(8), 679-689.
116. Frlan, R.; Kikelj, D., Recent Progress in the diaryl ether synthesis. Synthesis, 2006, 14, 2271-2285.
117. Ley, S.V.; Thomas, A.W., Modern Synthetic Methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S Bond Formation. Angew. Chem. Int. Ed., 2003, 42(44), 5400-5449.
118. Monnier, F.; Taillefer, M., Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions. Angew. Chem. Int. Ed., 2009, 48(38), 6954-6971.
119. Evano, G.; Blanchard, N.; Toumi, M., Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis. Chem. Rev., 2008, 108(8), 3054-3131.
120. Piazzi, L.; Belluti, F.; Bisi, A.; Gobbi, S.; Rizzo, S.; Bartolini, M.; Andrisano, V.; Recanatini, M.; Rampa, A., Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[w-(benzylmethylamino)alkoxy]xanthen-9-ones. Bioorg. Med. Chem., 2007, 15(1), 575-585.
121. Palmer, B.D.; Henare, K.; Woon, S.T.; Sutherland, R.; Reddy, C.; Wang, L.C.S.; Kieda, C.; Ching, L.M., Synthesis and biological activity of azido analogues of 5,6-dimethylxanthenone-4-acetic acid for use in photoaffinity labeling. J. Med. Chem., 2007, 50(16), 3757-3764.
122. Watson, S.E., Synthesis of 4-methyl pyrrolo[2,3-b]-xanthone, a novel ring system. Synth. Commun., 2005, 35(20), 2695-2701.
123. Kostakis, I.K.; Pouli, N.; Marakos, P.; Kousidou, O.C.; Roussidis, A.; Tzanakakis, G.N.; Karamanos, N.K., Design, synthesis and cell growth inhibitory activity of a series of novel aminosubstituted xantheno[1,2-d]imidazoles in breast cancer cells. Bioorg. Med. Chem., 2008, 16(6), 3445-3455.
124. Kostakis, I.K.; Tenta, R.; Pouli, N.; Marakos, P.; Skaltsounis, A.; Pratsinis, H.; Kletsas, D., Design, synthesis, and antiproliferative activity of some novel aminosubstituted xanthenones, able to overcome multidrug resistance toward MES-SA/Dx5 cells. Bioorg. Med. Chem. Lett., 2005, 15(22), 5057-5060.
125. Kostakis, I.K.; Pouli, N.; Marakos, P.; Skaltsounis, A.-L.; Pratsinis, H.; Kletsas, D., Design and synthesis of novel amino-substituted xanthenones and benzo[b]xanthenones: Evaluation of their antiproliferative activity and their ability to overcome multidrug resistance toward MES-SA/D × 5 cells. Bioorg. Med. Chem., 2006, 14(9), 2910-2934.
126. Giannouli, V.; Kostakis, I.K.; Pouli, N.; Marakos, P.; Kousidou, O.C.; Tzanakakis, G.N.; Karamanos, N.K., Design, synthesis, and evaluation of the antiproliferative activity of a series of novel fused xanthenone aminoderivatives in human breast cancer cells. J. Med. Chem., 2007, 50(7), 1716-1719.
127. Goodell, J.R.; Madhok, A.A.; Hiasa, H.; Ferguson, D.M., Synthesis and evaluation of acridine-and acridone-based anti-herpes agents with topoisomerase activity. Bioorg. Med. Chem., 2006, 14(16), 5467-5480.
128. Giri, R.; Goodell, J.R.; Xing, C.; Benoit, A.; Kaur, H.; Hiasa, H.; Ferguson, D.M., Synthesis and cancer cell cytotoxicity of substituted xanthenes. Bioorg. Med. Chem., 2010, 18(4), 1456-1463.
129. Blake, J.A.; Gagnon, E.; Lukernan, M.; Scaiano, J.C., Photodecarboxylation of xanthone acetic acids: C-C bond heterolysis from the singlet excited state. Org. Lett., 2006, 8(6), 1057-1060.
130. Ghosh, K.K.; Ha, H.-H.; Kang, N.-Y.; Chandran, Y.; Chang, Y.-T., Solid phase combinatorial synthesis of a xanthone library using click chemistry and its application to an embryonic stem cell probe. Chem. Comm., 2011, 47(26), 7488-7490.
131. Dallacker, F.; Damó, Z., Derivate des Methylendioxybenzols, 26 Darstellung des 4-Methoxy-und des 4-Hydroxy-2.3-methylendioxy-xanthons. Chem. Ber., 1969, 102(7), 2414-2418.
132. Simon, L.; Muniz, F.M.; Saez, S.; Raposo, C.; Sanz, F.; Moran, J.R., Xanthone receptors as oxyanion-hole mimics in artificial enzymes. Helv. Chim. Acta, 2005, 88(7), 1682-1701.
133. Zhao, J.; Yue, D.W.; Campo, M.A.; Larock, R.C., An aryl to imidoyl palladium migration process involving intramolecular C-H activation. J. Am. Chem. Soc., 2007, 129(16), 5288-5295.
134. Müller, P.; Venakis, T.; Eugster, C.H., Aktivierte Chinone: O-versus CAddition von Phenolen; eine neue, regiospezifische Synthese von Xanthonen, Thioxanthonen und N-Methyl-9-acridonen. Helv. Chim. Acta, 1979, 62(7), 2350-2360.
135. Kelly, T.R.; Jagoe, C.T.; Li, Q., Synthesis of (±)-Cervinomycins A1 and A2. J. Am. Chem. Soc., 1989, 111(12), 4522-4524.
136. Simoneau, B.; Brassard, P., A New Regiospecific Synthesis of 1,4-Dihydroxyxanthones. J. Chem. Soc., Perkin Trans. I, 1984, 1507-1510.
137. Yadav, J.S., Synthesis of antitumor agents. Pure & Appl. Chem., 1993, 65(6), 1349-1356.
138. Mroß, G.; Reinke, H.; Fischer, C.; Langer, P., Synthesis of Functionalized 2-Alkoxybenzoates, 2-Aryloxybenzoates and Xanthones based on Formal [3+3] Cyclocondensations of 3-Alkoxy-and 3-Aryloxy-1-silyloxy-1,3-butadienes with 3-Silyloxy-2-en-1-ones. Tetrahedron, 2009, 65(19), 3910-3917.
139. Portela, C.; Afonso, C.M.M.; Pinto, M.M.M.; Lopes, D.; Nogueira, F.; do Rosario, V., Synthesis and antimalarial properties of new chloro-9Hxanthones with an aminoalkyl side chain. Chem. Biodiv., 2007, 4(7), 1508-1519.
140. Sawyer, J.S.; Schmittling, E.A.; Palkowitz, J.A.; Smith, W.J., Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride-Alumina and 18-Crown-6: Expansion of Scope and Utility. J. Org. Chem., 1998, 63(18), 6338-6343.
141. Rewcastle, G.W.; Atwell, G.J.; Baguley, B.C.; Calveley, S.B.; Denny, W.A., Potential Antitumor Agents. 58. Synthesis and Structure-Activity Relationships of Substituted Xanthenone-4-acetic Acids Active against the Colon 38 Tumor in Vivo. J. Med. Chem., 1989, 32(4), 793-799.
142. Berman, E.M.; Showalter, H.D.H., Trimethylsilyl polyphosphate for intramolecular Friedel-Crafts cyclizations. J. Org. Chem, 1989, 54(23), 5642-5644.
143. Allen, F.L.; Koch, P.; Suschitzky, H., Heterocyclic fluorine compounds III: Monofluoroxanthones. Tetrahedron, 1959, 6(4), 315-318.
144. Agranat, I.; Tapuhi, Y., Dynamic stereochemistry and steric effects in overcrowded ethylenes. Conformational behavior of dixanthylenes. J. Am. Chem. Soc., 1979, 101(3), 665-671.
145. Goldberg, A.A.; Wragg, A.H., Xanthones: cyclisation of 3-substituted 2-carboxydiphenyl ethers. J. Chem. Soc., 1958, 4227-4234.
146. Davies, J.S.H.; Lamb, F.; Suschitzky, H., Studies in the xanthone series. Part II. Preparation and reactions of 1-formyl-2-hydroxyxanthone. J. Chem. Soc., 1958, 1790-1793.
147. Olah, G.A.; Mathew, T.; Farnia, M.; Prakash, G.K.S., Nafion-H Catalysed Intramolecular Friedel-Crafts Acylation: Formation of Cyclic Ketones and Related Heterocycles. Synlett, 1999, 7, 1067.
148. Lan, K.; Fen, S.; Shan, Z.X., Synthesis of aromatic cycloketones via intramolecular Friedel-Crafts acylation catalyzed by heteropoly acids. Aust. J. Chem., 2007, 60(1), 80-82.
149. 3/TfOH Cocatalyzed Synthesis of Xanthones and Thioxanthones by Intramolecular Friedel-Crafts Reaction under Solvent-Free Conditions. Heterocycles, 2011, 83(4), 855-866.
150. Familoni, O.B.; Ionica, I.; Bower, J.F.; Snieckus, V., Intramolecular Anionic Friedel-Crafts Equivalents. A General Regiospecific Route to Substituted and Naturally Occurring Xanthen-9-ones. Synlett, 1997, 9, 1081-1083.
151. Gales, L.; Sousa, M.E.; Pinto, M.M.M.; Kijjoa, A.; Damas, A.M., Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether intermediates leading to 1,2-dimethoxyxanthone. Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2001, 57(Part 11), 1319-1323.
152. Granoth, L.; Segall, Y.; Kalir, A., Friedel-Crafts Acylation-Cyclisation Reactions of 3-Bromophenyl Ethers with Phosphorus Trichloride and Oxalyl Chloride to give the Corresponding Phenoxaphosphine and Xanthen-9-one Derivatives. J. Chem. Soc., Perkin Trans. I, 1973, 1972-1974.
153. Granoth, I.; Kali, A., Synthesis, Reactivity, and Spectral Properties of 2,7-Difluoro-9-chloromethylenexanthene. Isoelectronicity with Heptafulvene Derivatives J. Org. Chem, 1973, 38(4), 841-843.
154. Granoth, I.; Gradovski, L.; Alkabets, R., Synthesis of Heterofulvenes-Derivatives of 9-Alkylenexanthenes by the Friedel-Crafts Reaction, Accompanied by Halide Exchange. J. Org. Chem, 1975, 40(16), 2304-2307.
155. Martin, N.H.; Clary, R.T.; Fudala, L.D.; Hyde, R.D.; Jackson, E.P.; Vehling, J.M.; O'Conner, F.; Pennington, G.A.; Piner, R.T., Synthesis and Spectra of subtituted 9-chloromethylenexanthenes, their corresponding xanthones, and related minor products J. Elisha Mitchell Sci. Soc., 1992, 108(3), 102-110.
156. Suau, R.; Rico, R.; López-Romero, J.M.; Nájera, F.; Ruiz, A.; Ortiz-López, F.J., Synthesis of 3,4-dioxocularine and aristocularine alkaloids in a convergent route from aryloxy-phenyl acetamides involving oxalyl chloride-Lewis Acid ARKIVOC, 2002, V, 62-72.
157. Zhang, W.C.; Wu, S.L.; Zhang, Z.G.; Yennawar, H.M.; Zhang, X.M., Practical synthesis of chiral 9,9 '-spirobixanthene-1,1 '-diol. Org. Biomol. Chem., 2006, 4(24), 4474-4477.
158. Vitale, A.A.; Romanelli, G.P.; Autino, J.C.; Pomilio, A.B., A Novel Route for the Preparation of Xanthones and Chromanones. J. Chem. Res., Synop., 1994(2), 82-84.
159. Zhang, H.; Shi, R.; Gan, P.; Liu, C.; Ding, A.; Wang, Q.; Lei, A., Palladium-Catalyzed Oxidative Double C-H Functionalization/Carbonylation for the Synthesis of Xanthones. Angew. Chem. Int. Ed., 2012, 41(21), 5204-5207.
160. Wang, P.; Rao, H.; Hua, R.; Li, C.-J., Rhodium-Catalyzed Xanthone Formation from 2-Aryloxybenzaldehydes via Cross-Dehydrogenative Coupling (CDC). Org. Lett., 2012, 14(3), 902-905.
161. Yang, J.; Dong, C.; Li, H.; Li, H.; Li, Y., Iron-catalyzed one-pot reactions of o-aryloxybenzaldehydes to xanthones. Chin. Sci. Bull., 2012, 57(19), 2364-2367.
162. Hauser, F.M.; Hewawasam, P.; Baghdanov, V.M., Regiospecific Preparation of the Benz[b]xanthen-12-one Ring System: Total Synthesis of Bikaverin. J. Org. Chem, 1988, 53(1), 224-226.
163. Cremins, P.J.; Saengchantara, S.T.; Wallace, T.W., Cycloadditions of substituted benzopyran-4-ones to electron-rich dienes: a new route to xanthone derivatives. Tetrahedron, 1987, 43(13), 3075-3082.
164. Sandulache, A.; Silva, A.M.S.; Cavaleiro, J.A.S., Diels-Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane. Tetrahedron, 2002, 58(1), 105-114.
165. Sandulache, A.; Silva, A.M.S.; Cavaleiro, J.A.S., New Benzo[b]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho-Benzoquinodimethanes. Monatsh. Chem., 2003, 134(4), 551-563.
166. Pinto, D.; Silva, A.M.S.; Brito, C.M.; Sandulache, A.; Carrillo, J.R.; Prieto, P.; Diaz-Ortiz, A.; de la Hoz, A.; Cavaleiro, J.A.S., Reactivity of 3-styrylchromones as dienes in Diels-Alder reactions under microwave irradiation: A new synthesis of xanthones. Eur. J. Org. Chem., 2005(14), 2973-2986.
167. Dang, A.T.; Miller, D.O.; Dawe, L.N.; Bodwell, G.J., Electron-deficient dienes. 5. An inverse-electron-demand Diels-Alder approach to 2-substituted 4-methoxyxanthones and 3,4-dimethoxyxanthones. Org. Lett., 2008, 10(2), 233-236.
168. Tatsuta, K.; Kasai, S.; Amano, Y.; Yamaguchi, T.; Seki, M.; Hosokawa, S., The First Total Synthesis of Vinaxanthone, a Fungus Metabolite Possessing Multiple Bioactivities. Chem. Lett., 2007, 36(1), 10-11.
169. Zhao, L.; Xie, F.; Cheng, G.; Hu, Y., A Base-Promoted Tandem Reaction of 3-(1-Alkynyl)chromones with 1,3-Dicarbonyl Compounds: An Efficient Approach to Functional Xanthones. Angew. Chem. Int. Ed., 2009, 48(35), 6520-6523.
170. Xie, F.; Pan, X.; Lin, S.; Hu, Y., A base-promoted desalicyloylative dimerization of 3-(1-alkynyl)chromones: An unusual approach to 2-alkynyl xanthones. Org. Biomol. Chem., 2010, 8(6), 1378-1381.
171. Liu, Y.; Huang, L.; Xie, F.; Hu, Y., Base-Promoted One-Pot Tandem Reaction of 3-(1-Alkynyl)chromones under Microwave Irradiation to Functionalized Amino-Substituted Xanthones. J. Org. Chem, 2010, 75(18), 6304-6307.
172. Sammes, P.G.; Wallace, T.W., Photochemical Reactions. Part V. Photoinduced Cyclizations of 3-Aroylchromones. J. Chem. Soc., Perkin Trans. I, 1975, 1845-1849.
173. Terzidis, M.A.; Tsiaras, V.G.; Stephanidou-Stephanatou, J.; Tsoleridis, C.A., Organocatalyzed Reactions Involving 3-Formylchromones and Acetylenedicarboxylates: Efficient Synthesis of Functionalized Benzophenones and Polysubstituted Xanthones. Synthesis, 2011(1), 97-103.
174. Ghosh, C.K.; Bhattachatyya, S.; Patra, A., Unusual condensation of 2-(2-dimethylaminovinyl)-1-benzopyran-4-one with dimethyl acetylenedicarboxylate: formation of 2,3-bis(methoxycarbonyl)xanthen-9-one. J. Chem. Soc., Perkin Trans. I, 1997(15), 2167-2168.
175. Ghosh, C.K.; Bhattachatyya, S.; Ghosh, C.; Patra, A., Benzopyrans. Part 41. Reactions of 2-(2-dimethylaminovinyl)-1-benzopyran-4-ones with various dienophiles. J. Chem. Soc., Perkin Trans. I, 1999(20), 3005-3013.
176. Kelkar, A.S.; Letcher, R.M.; Cheung, K.-K.; Chiu, K.-F.; Brown, G.D., Synthesis of C-ring substituted xanthones from the [4 + 2] cycloaddition reaction of vinylchromones and acyclic enamines. J. Chem. Soc., Perkin Trans. I, 2000(22), 3732-3741.
177. Silva, A.M.S.; Pinto, D.C.G.A.; Tavares, H.R.; Cavaleiro, J.A.S.; Jimeno, M.L.; Elguero, J., Novel (E)-and (Z)-2-Styrylchromones from (E, E)-2'-Hydroxycinnamylideneacetophenones-Xanthones from Daylight Photooxidative Cyclization of (E)-2-Styrylchromones Eur. J. Org. Chem., 1998(9), 2031-2038.
178. Santos, C.M.M.; Silva, A.M.S.; Cavaleiro, J.A.S., New synthesis of 2,3-diarylxanthones. Synlett, 2005(20), 3095-3098.
179. Santos, C.M.A.; Silva, A.M.S.; Cavaleiro, J.A.S., A novel and efficient route for the synthesis of hydroxylated 2,3-diarylxanthones. Synlett, 2007(20), 3113-3116.
180. Santos, C.M.M.; Silva, A.M.S.; Cavaleiro, J.A.S., Efficient syntheses of new polyhydroxylated 2,3-diaryl-9H-xanthen-9-ones. Eur. J. Org. Chem., 2009(16), 2642-2660.
181. Xie, F.; Chen, H.; Hu, Y., Efficient Construction of a 3C-Xanthone-Linked 3C-Chromone Scaffold by Novel Double Michael Additions and Cyclizations. Org. Lett., 2010, 12(13), 3086-3089.
182. Gong, J.; Xie, F.; Chen, H.; Hu, Y., An efficient approach to functionalized benzo[a]xanthones through reactions of 2-methyl-3-(1-alkynyl)chromones with electron-deficient chromone-fused dienes. Org. Lett., 2010, 12(17), 3848-3851.
183. Gong, J.; Xie, F.; Ren, W.; Chen, H.; Hu, Y., Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes. Org. Biomol. Chem., 2012, 10(3), 486-489.
184. Ghosh, C.K.; Bhattacharyya, A.; Bandyopadhyay, C., Base Catalysed Deacylative Dimerisation of 3-Acetylchromenone: a Facile Diels-Alder Reaction. J. Chem. Soc., Chem. Commun., 1984(20), 1319-1320.
185. Ghosh, C.K.; Sahana, S., Benzopyrans. Part 30. Synthesis of Substituted Xanthones from 3-Acyl-2-methyl-1-benzopyran-4-ones. Tetrahedron, 1993, 49(19), 4127-4134.
186. Hauser, F.M.; Dorsch, W.A., A New Regiospecific Preparation of Xanthones. Org. Lett., 2003, 5(20), 3753-3754.
187. Rocha, D.H.A.; Pinto, D.C.G.A.; Silva, A.M.S.; Patonay, T.; Cavaleiro, J.A.S., A New Synthesis of 5-Arylbenzo[c]xanthones from Photoinduced Electrocyclisation and Oxidation of (E)-3-Styrylflavones. Synlett, 2012, 23(4), 559-564.
188. Gabbutt, C.D.; Hepworth, J.D.; Urquhart, M.W.J.; Miguel, L.M.V.d., Acid catalysed rearrangements of 1-hydroxy-2,3,4,4a-tetrahydro-9H-xanthen-9-ones: synthesis and cycloaddition reactions of 3,4-dihydro-9H-xanthen-9-ones. J. Chem. Soc., Perkin Trans. I, 1998(9), 1547-1553.
189. Xu, F.; Cao, X.; Cao, Z.; Zou, L., A new method for the preparation of 2,3-cycloalkeno-5,6-cycloalkeno-4H-pyran-4-ones. Tetrahedron Lett., 2000, 41(52), 10257-10261.
190. Paquette, L.A.; Stucki, H., A New General Approach to the Synthesis of Oxygen-Containing Heterocycles by Virtue of Hydroxyl Neighboring Group Participation. The Condensation of Enamines with Salicylaldehydes. J. Org. Chem, 1966, 31(4), 1232-1235.
191. Croisy-Delcey, M.; Croisy, A.; Mousset, S.; Letourneur, M.; Bisagni, E.; Jacquemin-Sablon, A.; Pierred, J., Genistein analogues: effects on epidermal growth factor receptor tyrosine kinase and on stress-activated pathways Biomed. Pharmacother., 1997, 51(6-7), 286-294.
192. Letcher, R.M.; Yue, T.-Y.; Chiu, K.-F.; Kelkar, A.S.; Cheung, K.-K., The synthesis of various cycloalkana[d]xanthones and conversion of the cyclohexa-analogue to a 7,7a-dimethylcyclohexa[d]xanthene. J. Chem. Soc., Perkin Trans. I, 1998(19), 3267-3276.
193. Brito, C.M.; Pinto, D.; Silva, A.M.S.; Silva, A.M.G.; Tome, A.C.; Cavaleiro, J.A.S., Diels-Alder reactions of 2 '-hydroxychalcones with orthobenzoquino-dimethane: A new synthesis of 3-aryl-2-naphthyl 2-hydroxyphenyl ketones. Eur. J. Org. Chem., 2006(11), 2558-2569.
194. Sun, L.; Liebeskind, L.S., Novel Constrution of Highly-Substituted Xanthones. J. Am. Chem. Soc., 1996, 118(49), 12473-12474.
195. Sun, L.; Liebeskind, L.S., The Regiospecific Synthesis of Angularly-Fused Xanthones via the Benzannulation of 1,2-Adducts Derived from 3-(o-Amsoyl)-4-substituted Cyclobutenediones and Their Dithianyl Derivatives. Tetrahedron, 1997, 38(21), 3663-3666.
196. Nichols, A.L.; Zhang, P.; Martin, S.F., General and Expedient Synthesis of 1,4-Dioxygenated Xanthones. Org. Lett., 2011, 13(17), 4696-4699.
197. Xu, W.Z.; Huang, Z.T.; Zheng, Q.Y., Synthesis of benzo[c]xanthones from 2-benzylidene-1-tetralones by the ultraviolet radiation-mediated tandem reaction. J. Org. Chem, 2008, 73(14), 5606-5608.
198. Ma, S.M.; Zhan, J.; Watanabe, K.; Xie, X.; Zhang, W.; Wang, C.C.; Tang, Y., Enzymatic synthesis of aromatic polyketides using PKS4 from Gibberella fujikuroi. J. Am. Chem. Soc., 2007, 129(35), 10642-10643.
199. Einhorn, C.; Einhorn, J.; Marcadal, C.; Pierre, J.-L., Oxidation of organic substrates by molecular oxygen mediated by N-hydroxyphthalimide (NHPI) and acetaldehyde. Chem. Comm., 1997(5), 447-448.
200. Matsushita, T.; Ebitani, K.; Kaneda, K., Highly efficient oxidation of alcohols and aromatic compounds catalysed by the Ru-Co-Al hydrotalcite in the presence of molecular oxygen. Chem. Comm., 1999(3), 265-266.
201. Oliveira, A.M.A.G.; Oliveira-Campos, A.M.F.; Rodrigues, L.M.; Raposo, M.M.M.; Machado, A.E.H.; Nascimento, M.S.J.; Nazareth, N.; Pinto, M., Synthesis and Antitumor Evaluation of Benzopsoralen Analogues. Chem. Biodiv., 2007, 4(5), 980-990.
202. Ochiai, M.; Ito, T.; Takahashi, H.; Nakanishi, A.; Toyonari, M.; Sueda, T.; Goto, S.; Shiro, M., Hypervalent (tert-Butylperoxy)iodanes Generate Iodine-Centered Radicals at Room Temperature in Solution: Oxidation and Deprotection of Benzyl and Allyl Ethers, and Evidence for Generation of ROxy Carbon Radicals. J. Am. Chem. Soc., 1996, 118(33), 7716-7730.
203. El-Abbady, A.M.; Ayoub, S.; Badda, F.G., b-Aroylpropionic Acids. Part XVI. The Conversion of y-Oxo-y-2-xanthenylbutyric Acid into 2,3-Benxoxanthone J. Chem. Soc., 1960, 2556-2559.
204. Oussaid, A.; Loupy, A., Selective Oxidation of Arenes in Dry Media under Focused Microwaves. J. Chem. Res., Synop., 1997(9), 342-343.
205. Noureldin, N.A.; Zhao, D.; Lee, D.G., Heterogeneous Permanganate Oxidations. 7. The Oxidation of Aliphatic Side Chains. J. Org. Chem., 1997, 62(25), 8767-8772.
206. Shaabani, A.; Lee, D.G., Solvent free permanganate oxidations. Tetrahedron Lett., 2001, 42(34), 5833-5836.
207. Bovicelli, P.; Sanetti, A.; Bernini, R., Oxyfuncuonalisation of Activated Methylenes by Dimethyldioxirane: an Easy Conversion of Isochromans into Isocoumarins Tetrahedron, 1997, 53(28), 9755-9760.
208. Kondedeshmukhab, R.S.; Paradkara, M.V., Synthesis of Linear Pyranoxanthones Synth. Commun., 1994, 24(5), 659-664.
209. Barton, D.H.R.; Wang, T.-L., Novel allylic oxidation reagents Tetrahedron Lett., 1994, 35(29), 5149-5152.
210. Kraus, G.A.; Liu, F., Synthesis of polyhydroxylated xanthones via acyl radical cyclizations. Tetrahedron Lett., 2012, 53(11), 111-114.
211. Szajnman, S.H.; Yan, W.; Bailey, B.N.; Docampo, R.; Elhalem, E.; Rodriguez, J.B., Design and Synthesis of Aryloxyethyl Thiocyanate Derivatives as Potent Inhibitors of Trypanosoma cruzi Proliferation. J. Med. Chem., 2000, 43(9), 1826-1840.
212. 13C NMR Chemical Shifts. Arch. Pharm., 1998, 331(5), 177-192.
213. Gardikis, Y.; Tsoungas, P.G.; Potamitis, C.; Zervou, M.; Cordopatis, P., Xanthones in Heterocyclic Synthesis, an Eficient Route or the Synthesis of C3-o-Hydroxyaryl Substituted 1,2-Benzisoxazoles adn their N-Oxides, Potential Scaffolds for Angiotensin(II) Antagonist Hybrid Peptides. Heterocycles, 2011, 83(5), 1077-1091.
214. 13C NMR Spectroscopy of Mono-, Di-, Triand Tetrasubstituted Xanthones. Magn. Reson. Chem., 1998, 36(4), 305-309.
215. Pfister, J.R.; Ferraresi, R.W.; Harrison, I.T.; Rooks, W.H.; Roszkowski, A.P.; Horn, A.V.; Fried, J.H., Xanthone-2-carboxylic acids, a new series of antiallergic substances. J. Med. Chem., 1972, 15(10), 1032-1035.
216. Thull, U.; Kneubühler, S.; Testa, B.; Borges, M.F.M.; Pinto, M.M.M., Substituted Xanthones as Selective and Reversible Monoamine Oxidase A (MAO-A) Inhibitors. Pharm. Res., 1993, 10(8), 1187-1190.
217. Garci{dotless}ča, A.; Domi{dotless}čnguez, D., [1]Benzopyrano[2,3,4-i, j]isoquinolines: a new, versatile route from 1-bromoxanthones. Tetrahedron Lett., 2001, 42(31), 5219-5221.
218. Reese, C.B.; Song, Q.; Yan, H., Xanthen-9-ylidene and 2,7-dimethylxanthen-9-ylidene protecting groups. Tetrahedron Lett., 2001, 42(9), 1789-1791.
219. Reese, C.B.; Yan, H., Xanthen-9-ylidene protecting groups in glycerol chemistry. J. Chem. Soc., Perkin Trans. I, 2001(15), 1807-1815.
220. Odrowaz-Sypniewski, M.R.; Tsoungas, P.G.; Varvounis, G.; Cordopatis, P., Xanthone in synthesis: a reactivity profile via directed lithiation of its dimethyl ketal. Tetrahedron Lett., 2009, 50(44), 5981-5983.
221. Szkaradek, N.; Stachura, K.; Waszkielewicz, A.M.; Cegla, M.; Szneler, E.; Marona, H., Synthesis and antimycobacterial assay of some xanthone derivatives. Acta Pol. Pharm., 2008, 65(1), 21-28.
222. Marona, H.; Szkaradek, N.; Kubacka, M.; Bednarski, M.; Filipek, B.; Cegla, M.; Szneler, E., Synthesis and evaluation of some xanthone derivatives for anti-arrhythmic, hypotensive properties and their affinity for adrenergic receptors. Arch. Pharm., 2008, 341(2), 90-98.
223. Marona, H.; Szkaradek, N.; Rapacz, A.; Filipek, B.; Dybała, M.; Siwek, A.; Cegła, M.; Szneler, E., Preliminary evaluation of pharmacological properties of some xanthone derivatives. Bioorg. Med. Chem., 2009, 17(3), 1345-1352.
224. Lin, K.-W.; Fang, S.-C.; Hung, C.-F.; Shieh, B.-J.; Yang, S.-C.; Teng, C.-M.; Lin, C.-N., Synthesis, Antiplatelet and Vasorelaxing Activities of Xanthone Derivatives. Arch. Pharm., 2009, 342(1), 19-26.
225. Marona, H.; Librowski, T.; Cegła, M.; Erdoǧan, C.; žahin, N.O., Antiarrhythmic and antihypertensive activity of some xanthone derivatives. Acta Pol. Pharm., 2008, 65(3), 383-390.
226. Hu, H.G.; Wang, M.J.; Zhao, Q.J.; Yu, S.C.; Liu, C.M.; Wu, Q.Y., Synthesis of mangiferin derivates and study their potent PTP1B inhibitory activity. Chin. Chem. Lett., 2007, 18(11), 1323-1326.
227. Hu, H.-g.; Wang, M.-j.; Zhao, Q.-j.; Liao, H.-l.; Cai, L.-z.; Song, Y.; Zhang, J.; Yu, S.-c.; Wan-sheng Chen; Liu, C.-m.; Wu, Q.-y., Synthesis of Mangiferin derivatives as protein Tyrosine Phosphatase 1B inhibitors. Chem. Nat. Compd., 2007, 43(6), 663-666.
228. Wang, T.C.; Chen, I.L.; Lu, C.M.; Kuo, D.H.; Liao, C.H., Synthesis, and cytotoxic and antiplatelet activities of oxime-and methyloxime-containing flavone, isoflavone, and xanthone derivatives. Chem. Biodiv., 2005, 2(2), 253-263.
229. Schwaebe, M.K.; Moran, T.J.; Whitten, J.P., Total synthesis of psorospermin. Tetrahedron Lett., 2005, 46(5), 827-829.
230. Kolokythas, G.; Kostakis, I.K.; Pouli, N.; Marakos, P.; Kousidou, O.C.; Tzanakakis, G.N.; Karamanos, N.K., Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells. Eur. J. Med. Chem, 2007, 42(3), 307-319.
231. Dar, A.; Faizi, S.; Naqvi, S.; Roome, T.; Zikr-ur-Rehman, S.; Ali, M.; Firdous, S.; Moin, S.T., Analgesic and antioxidant activity of mangiferin and its derivatives: the structure activity relationship. Biolog. Pharm. Bull., 2005, 28(4), 596-600.
232. Liu, Y.; Ke, Z.; Cui, J.; Chen, W.-H.; Ma, L.; Wang, B., Synthesis, inhibitory activities, and QSAR study of xanthone derivatives as [alpha]-glucosidase inhibitors. Bioorg. Med. Chem., 2008, 16(15), 7185-7192.
233. Rizzo, S.; Cavalli, A.; Ceccarini, L.; Bartolini, M.; Belluti, F.; Bisi, A.; Andrisano, V.; Recanatini, M.; Rampa, A., Structure-Activity Relationships and Binding Mode in the Human Acetylcholinesterase Active Site of Pseudo-Irreversible Inhibitors Related to Xanthostigmine. ChemMedChem, 2009, 4(4), 670-679.
234. Raj, K.; Misra, N.; Pachauri, G.; Sharma, M.; Tamrakar, A.K.; Singh, A.B.; Srivastava, A.K.; Phani Kiran, K.; Narasimha Rao, C.V.; Prubhu, S.R., Novel class of hybrid natural products as antidiabetic agents. Nat. Prod. Rep., 2009, 23(1), 60-69.
235. Castanheiro, R.A.P.; Pinto, M.M.M.; Cravo, S.M.M.; Pinto, D.C.G.A.; Silva, A.M.S.; Kijjoa, A., Improved Methodologies for Synthesis of Prenylated Xanthones by Microwave Irradiation and Combination of Heterogeneous Catalysis (K10 clay) with Microwave Irradiation. Tetrahedron, 2009, 65(19), 3848-3857.
236. Fellows, I.M.; Schwaebe, M.; Dexheimer, T.S.; Vankayalapati, H.; Gleason-Guzman, M.; Whitten, J.P.; Hurley, L.H., Determination of the importance of the stereochemistry of psorospermin in topoisomerase II-induced alkylation of DNA and in vitro and in vivo biological activity. Mol. Cancer Ther., 2005, 4(11), 1729-1739.
237. Xie, H.; Qin, Y.X.; Zhou, Y.L.; Tong, L.J.; Lin, L.P.; Geng, M.Y.; Duan, W.H.; Ding, J., GA3, a new gambogic acid derivative, exhibits potent antitumor activities in vitro via apoptosis-involved mechanisms. Acta Pharm. Sin., 2009, 30(3), 346-354.
238. Mitchell, D.; Wan, P., Formal intramolecular photoredox reactions of phenylbenzophenone, xanthone and fluorenone methanols in aqueous solution. J. Photoch. Photobio. A, 2009, 205(1), 34-43.
239. Miller, E.W.; Albers, A.E.; Pralle, A.; Isacoff, E.Y.; Chang, C.J., Boronatebased fluorescent probes for imaging cellular hydrogen peroxide. J. Am. Chem. Soc., 2005, 127(47), 16652-16659.
240. Li, J.; Hu, M.; Yao, S.Q., Rapid synthesis, screening, and identification of xanthone-And xanthene-based fluorophores using click chemistry. Org. Lett., 2009, 11(14), 3008-3011.