Carbazoles and Acridines

Heterocycles in Natural Product Synthesis

Volumn , Issue , 2011, Pages 341-376

  Gruner, Konstanze K ^a   Knölker, Hans Joachim ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Acridines; Acridones; Carbazoles; Heterocycles; Natural products; Synthesis

Indexed keywords

EID: 84884090489     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634880.ch10     Document Type: Chapter

References (245)

1. Knölker, H.-J. and Reddy, K.R. (2002) Isolation and synthesis of biologically active carbazole alkaloids. Chem. Rev., 102 (11), 4303-4428
2. Knölker, H.-J. (2004) Synthesis of biologically active carbazole alkaloids using organometallic chemistry. Curr. Org. Synth., 1 (4), 309-331
3. Knölker, H.-J. (2005) Occurrence, biological activity, and convergent organometallic synthesis of carbazole alkaloids. Top. Curr. Chem., 244, 115-148
4. Knölker, H.-J. and Reddy, K.R. (2008) Chemistry and biology of carbazole alkaloids, in The Alkaloids, vol. 65, (ed. G.A. Cordell), Academic Press, Amsterdam, The Netherlands, pp. 1-430
5. Knölker, H.-J. (2009) Synthesis of biologically active carbazole alkaloids using selective transition metal-catalyzed coupling reactions. Chem. Lett., 38 (1), 8-13
6. Mo, C.-J., Shin-ya, K., Furihata, K., Furihata, K., Shimazu, A., Hayakawa, Y. and Seto, H. (1990) Isolation and structural elucidation of antioxidative agents, antiostatins A 1 to A 4 and B 2 to B 5. J. Antibiot., 43 (10), 1337-1340
7. Knott, K.E., Auschill, S., Jäger, A. and Knölker, H.-J. (2009) First total synthesis of the whole series of the antiostatins A and B. Chem. Commun., (12), 1467-1469
8. Alayrac, C., Schollmeyer, D. and Witulski, B. (2009) First total synthesis of antiostatin A1, a potent carbazole -based naturally occurring antioxidant. Chem. Commun., (12), 1464-1466
9. Steglich, W. (1989) Slime moulds (Myxomycetes) as a source of new biologically active metabolites. Pure Appl. Chem., 61 (3), 281-288
10. Gill, M. and Steglich, W. (1987) Pigments of fungi (macromycetes), in Progress in the Chemistry of Organic Natural Products, vol. 51, (eds W. Herz, H. Grisebach, G.W. Kirby and C. Tamm), Springer-Verlag, Wien, Austria, pp. 216-286
11. Kopanski, L., Li, G.-R., Besl, H. and Steglich, W. (1982) Naphthochinon -Farbstoffe aus den Schleimpilzen Trichia fl orimis und Metatrichia vesparium (Myxomycetes). Liebigs Ann. Chem., (9), 1722-1729
12. Gribble, G.W. and Berthel, S.J. (1992) Synthetic approaches to indolo[2,3-a] carbazole alkaloids. Syntheses of arcyriafl avin A and AT2433-B aglycone. Tetrahedron, 48 (41), 8869-8880
13. Harris, W., Hill, C.H., Keech, E. and Malsher, P. (1993) Oxidative cyclizations with palladium acetate. A short synthesis of staurosporine aglycone. Tetrahedron Lett., 34 (51), 8361-8364
14. Bergman, J., Koch, E. and Pelcman, B. (2000) Coupling reactions of indole-3 -acetic acid derivatives. Synthesis of arcyriafl avin A. J. Chem. Soc. Perkin Trans. 1, (16), 2609-2614
15. Hughes, I. and Raphael, R.A. (1983) Synthesis of arcyriafl avin B. Tetrahedron Lett., 24 (13), 1441-1444
16. Ohkubo, M., Nishimura, T., Jona, H., Honma, T. and Morishima, H. (1996) Practical synthesis of indolopyrrolocarbazoles. Tetrahedron, 52 (24), 8099-8112
17. Rickards, R.W., Rothschild, J.M., Willis, A.C., de Chazal, N.M., Kirk, J., Kirk, K., Saliba, K.J. and Smith, G.D. (1999) Calothrixins A and B, novel pentacyclic metabolites from Calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells. Tetrahedron, 55 (47), 13513-13520
18. Kelly, T.R., Zhao, Y., Cavero, M. and Torneiro, M. (2000) Synthesis of the potent antimalarials calothrixin A and B. Org. Lett., 2 (23), 3735-3737
19. Bernardo, P.H., Chai, C.L.L. and Elix, J.A. (2002) A simple and concise route to calothrixin B. Tetrahedron Lett., 43 (16), 2939-2940
20. Bernardo, P.H. and Chai, C.L.L. (2003) Friedel-Crafts acylation and metalation strategies in the synthesis of calothrixins A and B. J. Org. Chem., 68 (23), 8906-8909
21. Sissouma, D., Collet, S.C. and Guingant, A.Y. (2004) A synthesis of calothrixin B. Synlett, (14), 2612-2614
22. Bernardo, P.H., Chai, C.L.L., Heath, G.A., Mahon, P.J., Smith, G.D., Waring, P. and Wilkes, B.A. (2004) Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones. J. Med. Chem., 47 (20), 4958-4963
23. Tohyama, S., Choshi, T., Matsumoto, K., Yamabuki, A., Ikegata, K., Nobuhiro, J. and Hibino, S. (2005) A new total synthesis of an indolo[3,2-j] phenanthridine alkaloid calothrixin B. Tetrahedron Lett., 46 (32), 5263-5264
24. Bennasar, M.L., Roca, T. and Ferrando, F. (2006) A new radical-based route to calothrixin B. Org. Lett., 8 (4), 561-564
25. Yamabuki, A., Fujinawa, H., Choshi, T., Tohyama, S., Matsumoto, K., Ohmura, K., Nobuhiro, J. and Hibino, S. (2006) A biomimetic synthesis of the indolo[3,2-j] phenanthridine alkaloid, calothrixin B. Tetrahedron Lett., 47 (33), 5859-5861
26. Sissouma, D., Maingot, L., Collet, S. and Guingant, A. (2006) Concise and effi cient synthesis of calothrixin B. J. Org. Chem., 71 (22), 8384-8389
27. Sperry, J., McErlean, C.S.P., Slawin, A.M.Z. and Moody, C.J. (2007) A biomimetic synthesis of calothrixin B. Tetrahedron Lett., 48 (2), 231-234
28. Kato, S., Kawai, H., Kawasaki, T., Toda, Y., Urata, T. and Hayakawa, Y. (1989) Studies on free radical scavenging substances from microorganisms I. Carazostatin, a new free radical scavenger produced by Streptomyces. J. Antibiot., 42 (12), 1879-1881
29. Kato, S., Kawasaki, T., Urata, T. and Mochizuki, J. (1993) In vitro and ex vivo free radical scavenging activities of carazostatin, carbazomycin B and their derivatives. J. Antibiot., 46 (12), 1859-1865
30. Knölker, H.-J. and Hopfmann, T. (1995) Total synthesis of the naturally occurring free radical scavenger carazostatin. Synlett, (9), 981-983
31. Choshi, T., Sada, T., Fujimoto, H., Nagayama, C., Sugino, E. and Hibino, S. (1996) Total syntheses of carazostatin and hyellazole by allene-mediated electrocyclic reaction. Tetrahedron Lett., 37 (15), 2593-2596
32. Choshi, T., Sada, T., Fujimoto, H., Nagayama, C., Sugino, E. and Hibino, S. (1997) Total syntheses of carazostatin, hyellazole, and carbazoquinocins B-F. J. Org. Chem., 62 (8), 2535-2543
33. Knölker, H.-J. and Hopfmann, T. (2002) Iron-mediated synthesis of carazostatin, a free radical scavenger from Streptomyces chromofuscus, and O -methylcarazostatin. Tetrahedron, 58 (44), 8937-8945
34. Pacher, T., Bacher, M., Hofer, O. and Greger, H. (2001) Stress induced carbazole phytoalexins in Glycosmis species. Phytochemistry, 58 (1), 129-135
35. Schmidt, M. and Knölker, H.-J. (2009) Palladium-catalyzed approach to 2,6-dioxygenated carbazole alkaloids-fi rst total synthesis of the phytoalexin carbalexin C. Synlett, (15), 2421-2424
36. Kotoda, N., Shin-ya, K., Furihata, K., Hayakawa, Y. and Seto, H. (1997) Isolation and structure elucidation of novel neuronal cell protecting substances, carbazomadurins A and B produced by Actinomadura madurae. J. Antibiot., 50 (9), 770-772
37. Knöll, J. and Knölker, H.-J. (2006) First total synthesis and assignment of the absolute confi guration of the neuronal cell protecting alkaloid carbazomadurin B. Synlett, (4), 651-653
38. Knölker, H.-J. and Knöll, J. (2003) First total synthesis of the neuronal cell protecting carbazole alkaloid carbazomadurin A by sequential transition metal-catalyzed reactions. Chem. Commun., (10), 1170-1171
39. Hieda, Y., Choshi, T., Kishida, S., Fujioka, H. and Hibino, S. (2010) A novel total synthesis of the bioactive poly-substituted carbazole alkaloid carbazomadurin A. Tetrahedron Lett., 51 (27), 3593-3596
40. Sakano, K.-I., Ishimaru, K. and Nakamura, S. (1980) New antibiotics, carbazomycins A and B I. Fermentation, extraction, purifi cation and physico -chemical and biological properties. J. Antibiot., 33 (7), 683-689
41. Sakano, K.-I. and Nakamura, S. (1980) New antibiotics, carbazomycins A and B II. Structural elucidation. J. Antibiot., 33 (9), 961-966
42. Kaneda, M., Sakano, K.-I., Nakamura, S., Kushi, Y. and Iitaka, Y. (1981) The structure of carbazomycin B. Heterocycles, 15 (2), 993-998
43. Naid, T., Kitahara, T., Kaneda, M. and Nakamura, S. (1987) Carbazomycins C, D, E and F., minor components of the carbazomycin complex. J. Antibiot., 40 (2), 157-164
44. Kaneda, M., Naid, T., Kitahara, T., Nakamura, S., Hirata, T. and Suga, T. (1988) Carbazomycins G and H, novel carbazomycin congeners containing a quinol moiety. J. Antibiot., 41 (5), 602-608
45. Kondo, S., Katayama, M. and Marumo, S. (1986) Carbazomycinal and 6-methoxycarbazomycinal as aerial mycelium formation inhibitory substances of Streptoverticillium species. J. Antibiot., 39 (5), 727-730
46. Hook, D.J., Yacobucci, J.J., O'Connor, S., Lee, M., Kerns, E., Krishnan, B., Matson, J. and Hesler, G. (1990) Identifi cation of the inhibitory activity of carbazomycins B and C against 5-lipoxygenase, a new activity for these compounds. J. Antibiot., 43 (10), 1347-1348
47. Knölker, H.-J., Bauermeister, M., Bläser, D., Boese, R. and Pannek, J.-B. (1989) Highly selective oxidations of Fe(CO) 3 -cyclohexadiene complexes: synthesis of 4b,8a-dihydrocarbazol-3-ones and the fi rst total synthesis of carbazomycin A. Angew. Chem., 101 (2), 225-227. Angew. Chem. Int. Ed. Engl. 28 (2), 223-225
48. Knölker, H.-J. (1992) Iron-mediated synthesis of heterocyclic ring systems and applications in alkaloid chemistry. Synlett, (5), 371-387
49. Moody, C.J. and Shah, P. (1989) Synthesis of the carbazole alkaloids carbazomycin A and B and hyellazole. J. Chem. Soc. Perkin Trans. 1, (2), 376-377
50. Knölker, H.-J. and Bauermeister, M. (1989) Transition metal-diene complexes in organic synthesis, Part 2. The total synthesis of the carbazole antibiotic carbazomycin B and an improved route to carbazomycin A. J. Chem. Soc. Chem. Commun., (19), 1468-1470
51. Knölker, H.-J. and Bauermeister, M. (1993) Transition metal-diene complexes in organic synthesis. Part 15. Iron -mediated total synthesis of carbazomycin A and B. Helv. Chim. Acta, 76 (7), 2500-2514
52. Knölker, H.-J. and Fröhner, W. (1999) Improved total syntheses of the antibiotic alkaloids carbazomycin A and B. Tetrahedron Lett., 40 (38), 6915-6918
53. Clive, D.L.J., Etkin, N., Joseph, T. and Lown, J.W. (1993) Synthesis of carbazomycin B. J. Org. Chem., 58 (9), 2442-2445
54. Beccalli, E.M., Marchesini, A. and Pilati, T. (1996) Diels-Alder reactions of (Z)-ethyl 3-[(1-ethoxycarbonyloxy-2 -methoxy)ethenyl]-2-(ethoxycarbonyloxy) -indole-1-carboxylate. Synthesis of the carbazole alkaloid carbazomycin B. Tetrahedron, 52 (8), 3029-3036
55. Crich, D. and Rumthao, S. (2004) Synthesis of carbazomycin B by radical arylation of benzene. Tetrahedron, 60 (7), 1513-1516
56. Knölker, H.-J. and Schlechtingen, G. (1997) First total synthesis of carbazomycin C and D. J. Chem. Soc. Perkin Trans. 1, (4), 349-350
57. Knölker, H.-J. and Bauermeister, M. (1991) First total synthesis of carbazomycinal. Heterocycles, 32 (12), 2443-2450
58. Knölker, H.-J. and Fröhner, W. (1997) First total synthesis of carbazomycin G and H. Tetrahedron Lett., 38 (23), 4051-4054
59. Knölker, H.-J. and Fröhner, W. (1998) Palladium-catalyzed total synthesis of the antibiotic carbazole alkaloids carbazomycin G and H. J. Chem. Soc. Perkin Trans. 1, (2), 173-175
60. Knölker, H.-J., Fröhner, W. and Reddy, K.R. (2003) Iron-mediated synthesis of carbazomycin G and carbazomycin H, the fi rst carbazole-1,4-quinol alkaloids from Streptoverticillium ehimense. Eur. J. Org. Chem., (4), 740-746
61. Hagiwara, H., Choshi, T., Fujimoto, H., Sugino, E. and Hibino, S. (2000) A novel total synthesis of antibiotic carbazole alkaloid carbazomycin G. Tetrahedron, 56 (32), 5807-5811
62. Shin-ya, K., Tanaka, M., Furihata, K., Hayakawa, Y. and Seto, H. (1993) Structure of carquinostatin A, a new neuronal cell protecting substance produced by Streptomyces exfoliatus. Tetrahedron Lett., 34 (31), 4943-4944
63. Knölker, H.-J. and Fröhner, W. (1997) First total synthesis of the neuronal cell protecting substance (±)-carquinostatin A via iron-and nickel-mediated coupling reactions. Synlett, (9), 1108-1110
64. Knölker, H.-J., Baum, E. and Reddy, K.R. (2000) First enantioselective total synthesis of the potent neuronal cell protecting substance carquinostatin A from (R)-propene oxide. Tetrahedron Lett., 41 (8), 1171-1174
65. Cardellina, J.H., Kirkup, M.P., Moore, R.E., Mynderse, J.S., Seff, K. and Simmons, C.J. (1979) Hyellazole and chlorohyellazole, two novel carbazoles from the blue-green alga Hyella caespitosa born. et fl ah. Tetrahedron Lett., 20 (51), 4915-4916
66. Kano, S., Sugino, E., Shibuya, S. and Hibino, S. (1981) Synthesis of carbazole alkaloids hyellazole and 6-chlorohyellazole. J. Org. Chem., 46 (19), 3856-3859
67. Beccalli, E.M., Marchesini, A. and Pilati, T. (1994) Synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole and related derivatives. J. Chem. Soc. Perkin Trans. 1 (5), 579-586
68. Duval, E. and Cuny, G.D. (2004) Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives. Tetrahedron Lett., 45 (28), 5411-5413
69. Knölker, H.-J., Fröhner, W. and Heinrich, R. (2004) Total synthesis of the marine alkaloid 6-chlorohyellazole. Synlett, (15), 2705-2708
70. Chakraborty, A., Chowdhury, B.K. and Bhattacharyya, P. (1995) Clausenol and clausenine-two carbazole alkaloids from Clausena anisata. Phytochemistry, 40 (1), 295-298
71. Lin, G. and Zhang, A. (1999) The fi rst synthesis of optically pure biscarbazoles and determination of their absolute confi gurations. Tetrahedron Lett., 40 (2), 341-344
72. Börger, C. and Knölker, H.-J. (2008) A general approach to 1,6-dioxygenated carbazole alkaloids-fi rst total synthesis of clausine G, clausine I, and clausine Z. Synlett, (11), 1698-1702
73. Wu, T.-S., Huang, S.-C., Wu, P.-L. and Teng, C.-M. (1996) Carbazole alkaloids from Clausena excavata and their biological activity. Phytochemistry, 43 (1), 133-140
74. Wu, T.-S., Huang, S.-C. and Wu, P.-L. (1996) Carbazole alkaloids from stem bark of Clausena excavata. Phytochemistry, 43 (6), 1427-1429
75. Ito, C., Katsuno, S., Ohta, H., Omura, M., Kajiura, I. and Furukawa, H. (1997) Constituents of Clausena excavata. Isolation and structural elucidation of new carbazole alkaloids. Chem. Pharm. Bull., 45 (1), 48-52
76. Kongkathip, B., Kongkathip, N., Sunthitikawinsakul, A., Napaswat, C. and Yoosook, C. (2005) Anti-HIV-1 constitutes from Clausena excavata: Part II. Carbazoles and a pyranocoumarin. Phytother. Res., 19 (8), 728-731
77. Sunthitikawinsakul, A., Kongkathip, N., Kongkathip, B., Phonnakhu, S., Daly, J.W., Spande, T.F., Nimit, Y. and Rochanaruangrai, S. (2003) Coumarins and carbazoles from Clausena excavata exhibited antimycobacterial and antifungal activities. Planta Med., 69 (2), 155-157
78. Choi, T.A., Czerwonka, R., Fröhner, W., Krahl, M.P., Reddy, K.R., Franzblau, S.G. and Knölker, H.-J. (2006) Synthesis and activity of carbazole derivatives against Mycobacterium tuberculosis. ChemMedChem, 1 (8), 812-815
79. Choi, T.A., Czerwonka, R., Forke, R., Jäger, A., Knöll, J., Krahl, M.P., Krause, T., Reddy, K.R., Franzblau, S.G. and Knölker, H.-J. (2008) Synthesis and pharmacological potential of carbazoles. Med. Chem. Res., 17 (2-7), 374-385
80. Kataeva, O., Krahl, M.P. and Knölker, H.-J. (2005) First total synthesis of the biologically active 2,7-dioxygenated tricyclic carbazole alkaloids 7-methoxy -O-methylmukonal, clausine H (clauszoline-C), clausine K (clauszoline-J) and clausine O. Org. Biomol. Chem., 3 (17), 3099-3101
81. Wu, T.-S., Huang, S.-C., Lai, J.-S., Teng, C.-M., Ko, F.-N. and Kuoh, C.-S. (1993) Chemical and antiplatelet aggregative investigation of the leaves of Clausena excavata. Phytochemistry, 32 (2), 449-451
82. Forke, R., Jäger, A. and Knölker, H.-J. (2008) First total synthesis of clausine L and pityriazole, a metabolite of the human pathogenic yeast Malassezia furfur. Org. Biomol. Chem., 6 (14), 2481-2483
83. Forke, R., Krahl, M.P., Däbritz, F., Jäger, A. and Knölker, H.-J. (2008) An effi cient palladium-catalyzed route to 2-oxygenated and 2,7-dioxygenated carbazole alkaloids-total synthesis of 2-methoxy-3-methylcarbazole, glycosinine, clausine L, mukonidine, and clausine V. Synlett, (12), 1870-1876
84. Potterat, O., Puder, C., Bolek, W., Wagner, K., Ke, C., Ye, Y. and Gillardon, F. (2005) Clausine Z, a new carbazole alkaloid from Clausena excavata with inhibitory activity on CDK5. Pharmazie, 60 (8), 637-639
85. Furukawa, H., Wu, T.-S. and Kuoh, C.-S. (1985) Dihydroxygirinimbine, a new carbazole alkaloid from Murraya euchrestifolia. Heterocycles, 23 (6), 1391-1393
86. Gruner, K.K., Hopfmann, T., Matsumoto, K., Jäger, A., Katsuki, T. and Knölker, H.-J. (2011) Effi cient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids-fi rst total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, fi rst asymmetric synthesis and assignment of the absolute confi guration of (-)-trans -dihydroxygirinimbine. Org. Biomol. Chem., 9 (7), 2057-2061
87. Knölker, H.-J. and Hofmann, C. (1996) Molybdenum-mediated total synthesis of girinimbine, murrayacine, and dihydroxygirinimbine. T etrahedron Lett., 37 (44), 7947-7950
88. Goodwin, S., Smith, A.F. and Horning, E.C. (1959) Alkaloids of Ochrosia elliptica Labill. J. Am. Chem. Soc., 81 (8), 1903-1908
89. Stiborová, M., Bieler, C.A., Wiessler, M. and Frei, E. (2001) The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem. Pharmacol., 62 (12), 1675-1684
90. Sainsbury, M. (1977) The synthesis of 6 H-pyrido[4,3-b]carbazoles. Synthesis, (7), 437-448
91. Suffness, M. and Cordell, G.A. (1985) Antitumor alkaloids; XI. Ellipticine, in The Alkaloids (ed. A. Brossi), Academic Press, New York, USA, p. 89
92. Suffness, M. and Cordell, G.A. (1985) Antitumor alkaloids; XI. Ellipticine, in The Alkaloids (ed. A. Brossi), Academic Press, New York, USA, p. 304
93. Hibino, S. and Sugino, E. (1990) Synthesis of ellipticine and olivacine by the thermal electrocyclic reaction via pyridine 3,4-quinodimethane intermediates. J. Heterocycl. Chem., 27 (6), 1751-1755
94. Ho, T.-L. and Hsieh, S.-Y. (2006) Regioselective synthesis of ellipticine. Helv. Chim. Acta, 89 (1), 111-116
95. Konakahara, T., Kiran, Y.B., Okuno, Y., Ikeda, R. and Sakai, N. (2010) An expedient synthesis of ellipticine via Suzuki-Miyaura coupling. Tetrahedron Lett., 51 (17), 2335-2338
96. Nihei, Y., Yamamoto, H., Hasegawa, M., Hanada, M., Fukagawa, Y. and Oki, T. (1993) Epocarbazolines A and B, novel 5-lipoxygenase inhibitors taxonomy, fermentation, isolation, structures, and biological activities. J. Antibiot., 46 (1), 25-33
97. Knöll, J. and Knölker, H.-J. (2006) First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (-)-epocarbazolin A via Shi epoxidation. Tetrahedron Lett., 47 (34), 6079-6082
98. Wu, T.-S., Wang, M.-L. and Wu, P.-L. (1996) Seasonal variations of carbazole alkaloids in Murraya euchrestifolia. Phytochemistry, 43 (4), 785-789
99. Gruner, K.K. and Knölker, H.-J. (2008) Palladium-catalyzed total synthesis of euchrestifoline using a one-pot Wacker oxidation and double aromatic C-H bond activation. Org. Biomol. Chem., 6 (21), 3902-3904
100. Kumar, V., Reisch, J. and Wickramasinghe, A. (1989) Glycomaurin and glycomaurrol, new carbazole alkaloids from Glycosmis mauritiana (Rutaceae). Bark. Aust. J. Chem., 42 (8), 1375-1379
101. Ito, C. and Furukawa, H. (1990) New carbazole alkaloids from Murraya euchrestifolia Hayata. Chem. Pharm. Bull., 38 (6), 1548-1550
102. Lebold, T.P. and Kerr, M.A. (2007) Total synthesis of eustifolines A-D and glycomaurrol via a divergent Diels-Alder strategy. Org. Lett., 9 (10), 1883-1886
103. Forke, R., Krahl, M.P., Krause, T., Schlechtingen, G. and Knölker, H.-J. (2007) First total synthesis of methyl 6-methoxycarbazole-3-carboxylate, glycomaurrol, the anti-TB active micromeline, and the furo[2,3-c] carbazole alkaloid eustifoline-D. Synlett, (2), 268-272
104. Wu, T.-S., Huang, S.-C. and Wu, P.-L. (1997) Pyrano-and furocarbazole alkaloids from the root bark of Clausena excavata. Heterocycles, 45 (5), 969-973
105. Knölker, H.-J. and Krahl, M.P. (2004) First total synthesis of furoclausine-A. Synlett, (3), 528-530
106. Knölker, H.-J. and Fröhner, W. (1996) First total synthesis of furostifoline. Tetrahedron Lett., 37 (51), 9183-9186
107. Hagiwara, H., Choshi, T., Fujimoto, H., Sugino, E. and Hibino, S. (1998) New syntheses of murrayaquinone A and furostifoline. Chem. Pharm. Bull., 46 (12), 1948-1949
108. Hagiwara, H., Choshi, T., Nobuhiro, J., Fujimoto, H., Sugino, E. and Hibino, S. (2001) Novel syntheses of murrayaquinone A and furostifoline through 4-oxygenated carbazoles by allene-mediated electrocyclic reactions starting from 2-chloroindole-3-carbaldehyde. Chem. Pharm. Bull., 49 (7), 881-886
109. Beccalli, E.M., Clerici, F. and Marchesini, A. (1998) A new synthesis of furostifoline. Tetrahedron, 54 (38), 11675-11682
110. Soós, T., Timári, G. and Hajós, G. (1999) A concise synthesis of furostifoline. Tetrahedron Lett., 40 (49), 8607-8609
111. Knölker, H.-J. and Fröhner, W. (2000) Convergent iron-mediated syntheses of the furo[3,2-a]carbazole alkaloid furostifoline. Synthesis, (14), 2131-2136
112. Yasuhara, A., Suzuki, N. and Sakamoto, T. (2002) A concise synthesis of furostifoline by tetrabutylammonium fl uoride-promoted indole ring formation. Chem. Pharm. Bull., 50 (1), 143-145
113. Fröhner, W., Krahl, M.P., Reddy, K.R. and Knölker, H.-J. (2004) Synthetic routes to naturally occurring furocarbazoles. Heterocycles, 63 (10), 2393-2407
114. Chakraborty, D.P., Barman, B.K. and Bose, P.K. (1964) On the structure of girinimbine, a pyrano-carbazole derivative, isolated from Murraya koenigii Spreng. Sci. Cult., 30 (9), 445
115. Joshi, B.S., Kamat, V.N. and Gawad, D.H. (1970) On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine. Tetrahedron, 26 (5), 1475-1482
116. Chakraborty, D.P. and Roy, S. (2003) Carbazole alkaloids IV., in Progress in the Chemistry of Organic Natural Products (eds W. Herz, H. Grisebach, G.W. Kirby, W. Steglich and C. Tamm), Springer-Verlag, Wien, Austria, pp. 125-230
117. Cui, C.-B., Yan, S.-Y., Cai, B. and Yao, X.-S. (2002) Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena Dunniana Levl. J. Asian Nat. Prod. Res., 4 (4), 233-241
118. Kano, S., Sugino, E. and Hibino, S. (1980) Synthesis of the carbazole alkaloid hyellazole. J. Chem. Soc. Chem. Commun., (24), 1241-1242
119. Takano, S., Suzuki, Y. and Ogasawara, K. (1981) A simple synthesis of the blue-green alga alkaloid, hyellazole. Heterocycles, 16 (9), 1479-1480
120. Kawasaki, T., Nonaka, Y. and Sakamoto, M. (1989) A new effi cient synthesis of the 3-methoxycarbazole alkaloid hyellazole. J. Chem. Soc. Chem. Commun., (1), 43-44
121. Danheiser, R.L., Brisbois, R.G., Kowalczyk, J.J. and Miller, R.F. (1990) An annulation method for the synthesis of highly substituted polycyclic aromatic and heteroaromatic compounds. J. Am. Chem. Soc., 112 (8), 3093-3100
122. Kawasaki, K., Nonaka, Y., Akahane, M., Maeda, N. and Sakamoto, M. (1993) New approach to 3-oxygenated carbazoles. Synthesis of hyellazole and 4-deoxycarbazomycin B. J. Chem. Soc. Perkin Trans. 1, (15), 1777-1781
123. Knölker, H.-J., Baum, E. and Hopfmann, T. (1995) Total synthesis of the marine alkaloid hyellazole. Tetrahedron Lett., 36 (30), 5339-5342
124. Knölker, H.-J., Baum, E. and Hopfmann, T. (1999) Iron-mediated synthesis of hyellazole and isohyellazole. T etrahedron, 55 (34), 10391-10412
125. Witulski, B. and Alayrac, C. (2002) A highly effi cient and fl exible synthesis of substituted carbazoles by rhodium -catalyzed inter-and intramolecular alkyne cyclotrimerizations. Angew. Chem., 114 (17), 3415-3418. Angew. Chem. Int. Ed. 41 (17), 3281-3284
126. Shin-Ya, K., Shimizu, S., Kunigami, T., Furihata, K., Furihata, K. and Seto, H. (1995) A new neuronal cell protecting substance, lavanduquinocin, produced by Streptomyces viridochromogenes. J. Antibiot., 48 (7), 574-578
127. Knölker, H.-J. and Fröhner, W. (1998) First total synthesis of the potent neuronal cell protecting substance (±)-lavanduquinocin via iron-and nickel-mediated coupling reactions. Tetrahedron Lett., 39 (17), 2537-2540
128. Knölker, H.-J., Baum, E. and Reddy, K.R. (2000) First enantioselective total synthesis of lavanduquinocin, a potent neuronal cell protecting substance from Streptomyces viridochromogenes. Chirality, 12 (5-6), 526-528
129. Ma, C., Case, R.J., Wang, Y., Zhang, H.-J., Tan, G.T., Hung, N.V., Cuong, N.M., Franzblau, S.G., Soejarto, D.D., Fong, H.H.S. and Pauli, G.F. (2005) Anti-tuberculosis constituents from the stem bark of Micromelum hirsutum. Planta Med., 71 (3), 261-267
130. Chakraborty, D.P., Roy, S. and Guha, R. (1978) Structure of mukonidine. J. Indian Chem. Soc., 55 (11), 1114-1115
131. Knölker, H.-J. and Wolpert, M. (1997) Cyclization of tricarbonyliron complexes by oxygen to 4a,9a-dihydro-9 H -carbazoles: application to the synthesis of mukonine, mukonidine, and pyrido[3,2,1-jk]carbazoles. Tetrahedron Lett., 38 (4), 533-536
132. Knölker, H.-J. and Wolpert, M. (2003) Iron-mediated total synthesis of mukonine and mukonidine by oxidative cyclization with air as the oxidizing agent. Tetrahedron, 59 (28), 5317-5322
133. Chakraborty, D.P. and Das, K.C. (1968) Structure of murrayacine. Chem. Commun., (16), 967-969
134. Chakraborty, D.P., Das, K.C. and Chowdhury, B.K. (1971) Chemical taxonomy. XXVI. Structure of murrayacine. J. Org. Chem., 36 (5), 725-727
135. Ray, S. and Chakraborty, D.P. (1976) Murrayacine from Clausena heptaphylla. Phytochemistry, 15 (2), 356-356
136. Das, K.C., Chakraborty, D.P. and Bose, P.K. (1965) Antifungal activity of some constituents of Murraya koenigii Spreng. Experientia, 21 (6), 340
137. Chakraborty, D.P., Barman, B.K. and Bose, P.K. (1965) On the constitution of murrayanine, a carbazole derivative isolated from Murraya koenigii Spreng. Tetrahedron, 21 (2), 681-685
138. Bhattacharyya, P. and Chakraborty, D.P. (1973) Murrayanine and dentatin from Clausena heptaphylla. Phytochemistry, 12 (7), 1831-1832
139. Cuong, N.M., Hung, T.Q., Sung, T.V. and Taylor, W.C. (2004) A new dimeric carbazole alkaloid from Glycosmis stenocarpa roots. Chem. Pharm. Bull., 52 (10), 1175-1178
140. Knölker, H.-J. and Bauermeister, M. (1990) Iron-mediated total synthesis of the cytotoxic carbazole koenoline and related alkaloids. J. Chem. Soc. Chem. Commun., (9), 664-665
141. Knölker, H.-J. and Bauermeister, M. (1993) Iron-mediated total synthesis of 1-oxygenated carbazole alkaloids. Tetrahedron, 49 (48), 11221-11236
142. Benavides, A., Peralta, J., Delgado, F. and Tamariz, J. (2004) Total synthesis of the natural carbazoles murrayanine and murrayafoline A, based on the regioselective Diels-Alder addition of exo-2-oxazolidinone dienes. Synthesis, (15), 2499-2504
143. Kato, S., Shindo, K., Kataoka, Y., Yamagishi, Y. and Mochizuki, J. (1991) Studies on free radical scavenging substances from microorganisms II. Neocarazostatins A, B and C, novel free radical scavengers. J. Antibiot., 44 (8), 903-907
144. Czerwonka, R., Reddy, K.R., Baum, E. and Knölker, H.-J. (2006) First enantioselective total synthesis of neocarazostatin B, determination of its absolute confi guration and transformation into carquinostatin A. Chem. Commun., (7), 711-713
145. Knölker, H.-J., Fröhner, W. and Wagner, A. (1998) First total synthesis of the free radical scavenger (±)-neocarazostatin B via iron-and nickel-mediated coupling reactions. T etrahedron Lett., 39 (19), 2947-2950
146. Azoug, M., Loukaci, A., Richard, B., Nuzillard, J.-M., Moreti, C., Zèches -Hanrot, M. and Le Men-Olivier, L. (1995) Alkaloids from stem bark and leaves of Peschiera buchtieni. Phytochemistry, 39 (5), 1223-1228
147. Wittwer, H. and Schmutz, J. (1960) Die Synthese von Olivacin, Dihydro-olivacin, Tetrahydro-olivacin, N-Methyl -tetrahydro-olivacin, und die Konstitution von u-Alkaloid D. Helv. Chim. Acta, 43 (3), 793-799
148. Yokoyama, Y., Okuyama, N., Iwadate, S., Momoi, T. and Murakami, Y. (1990) Synthetic studies of indoles and related compounds, Part 22. The Vilsmeier -Haak reaction of N-benzyl-1,2,3,4 -tetrahydrocarbazoles and its synthetic application to olivacine and ellipticine. J. Chem. Soc. Perkin Trans. 1, (11), 1319-1329
149. Gribble, G.W., Saulnier, M.G., Obaza-Nutaitis, J.A. and Ketcha, D.M. (1992) A versatile and effi cient construction of the 6 H-pyrido[4,3-b] carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs. J. Org. Chem., 57 (22), 5891-5899
150. Miki, Y., Tsuzaki, Y., Hibino, H. and Aoki, Y. (2004) Synthesis of 3-methoxyolivacine and olivacine by Friedel-Crafts reaction of indole-2,3 -dicarboxylic anhydride with 2,4,6-trimethoxypyridine. Synlett, (12), 2206-2208
151. Irlinger, B., Bartsch, A., Krämer, H.-J., Mayser, P. and Steglich, W. (2005) New tryptophan metabolites from cultures of the lipophilic yeast Malassezia furfur. Helv. Chim. Acta, 88 (6), 1472-1484
152. Nettleton, D.E., Doyle, T.W., Krishnan, B., Matsumoto, G.K. and Clardy, J. (1985) Isolation and structure of rebeccamycin-a new antitumor antibiotic from Nocardia aerocoligenes. Tetrahedron Lett., 26 (34), 4011-4014
153. Bush, J.A., Long, B.H., Catino, J.J., Bradner, W.T. and Tomita, K. (1987) Production and biological activity of rebeccamycin, a novel antitumor agent. J. Antibiot., 40 (5), 668-678
154. Kaneko, T., Wong, H., Okamoto, K.T. and Clardy, J. (1985) Two synthetic approaches to rebeccamycin. Tetrahedron Lett., 26 (34), 4015-4018
155. Gallant, M., Link, J.T. and Danishefsky, S.J. (1993) A stereoselective synthesis of indole-β-N-glycosides: an application to the synthesis of rebeccamycin. J. Org. Chem., 58 (2), 343-349
156. Faul, M.M., Winneroski, L.L. and Krumrich, C.A. (1999) Synthesis of rebeccamycin and 11-dechlororebeccamycin. J. Org. Chem., 64 (7), 2465-2470
157. Wang, J., Rosingana, M., Watson, D.J., Dowdy, E.D., Discordia, R.P., Soundarajan, N. and Li, W.-S. (2001) Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker -type catalytic system. Tetrahedron Lett., 42 (51), 8935-8937
158. Meragelman, K.M., McKee, T.C. and Boyd, M.R. (2000) Siamenol, a new carbazole alkaloid from Murraya siamensis. J. Nat. Prod., 63 (3), 427-428
159. Krahl, M.P., Jäger, A., Krause, T. and Knölker, H.-J. (2006) First total synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7 -hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly effi cient palladium -catalyzed approach. Org. Biomol. Chem., 4 (17), 3215-3219
160. Naffziger, M.R., Ashburn, B.O., Perkins, J.R. and Carter, R.G. (2007) Diels-Alder approach for the construction of halogenated, o-nitro biaryl templates and application to the total synthesis of the anti-HIV agent siamenol. J. Org. Chem., 72 (26), 9857-9865
161. Omura, S., Iwai, Y., Hirano, A., Nakagawa, A., Awaya, J., Tsuchiya, H., Takahashi, Y. and Masuma, R. (1977) A new alkaloid AM-2282 of Streptomyces origin. Taxonomy, fermentation, isolation and preliminary characterization. J. Antibiot., 30 (4), 275-282
162. Funato, N., Takayanagi, H., Konda, Y., Toda, Y., Harigaya, Y., Iwai, Y. and Omura, S. (1994) Absolute confi guration of staurosporine by X-ray analysis. Tetrahedron Lett., 35 (8), 1251-1254
163. Omura, S., Sasaki, Y., Iwai, Y. and Takeshima, H. (1995) Staurosporine, a potential important gift from a microorganism. J. Antibiot., 48 (7), 535-548
164. Link, J.T., Raghavan, S. and Danishefsky, S.J. (1995) First total synthesis of staurosporine and ent-staurosporine. J. Am. Chem. Soc., 117 (1), 552-553
165. Link, J.T., Raghavan, S., Gallant, M., Danishefsky, S.J., Chou, T.C. and Ballas, L.M. (1996) Staurosporine and ent-staurosporine: the fi rst total syntheses, prospects for a regioselective approach, and activity profi les. J. Am. Chem. Soc., 118 (12), 2825-2842
166. Wood, J.L., Stoltz, B.M. and Goodman, S.N. (1996) Total synthesis of (+)-RK -286c, (+)-MLR-52, (+)-staurosporine, and (+)-K252a. J. Am. Chem. Soc., 118 (43), 10656-10657
167. Wood, J.L., Stoltz, B.M., Goodman, S.N. and Onwueme, K. (1997) Design and implementation of an effi cient synthetic approach to pyranosylated indolocarbazoles: total synthesis of (+)-RK286c, (+)-MLR-52, (+)-staurosporine, and (-)-TAN-1030a. J. Am. Chem. Soc., 119 (41), 9652-9661
168. Nakanishi, S., Matsuda, Y., Iwahashi, K. and Kase, H. (1986) K-252b, c and d, potent inhibitors of protein kinase C from microbial origin. J. Antibiot., 39 (8), 1066-1071
169. Yasuzawa, T., Iida, T., Yoshida, M., Hirayama, N., Takahashi, M., Shirahata, K. and Sano, H. (1986) The structures of the novel protein kinase C inhibitors K-252a, b, c and d. J. Antibiot., 39 (8), 1072-1078
170. Horton, P.A., Longley, R.E., McConnell, O.J. and Ballas, L.M. (1994) Staurosporine aglycon (K252-c) and arcyriafl avin A from marine ascidian Eudistoma sp. Experientia, 50 (9), 843-845
171. Sarstedt, B. and Winterfeldt, E. (1983) Reactions with indole derivatives, XLVIII. A simple synthesis of the staurosporine aglycon. Heterocycles, 20 (3), 469-476
172. Moody, C.J. and Rahimtoola, K.F. (1990) Synthesis of the staurosporine aglycone. J. Chem. Soc. Chem. Commun., (23), 1667-1668
173. Hughes, I., Nolan, W.P. and Raphael, R.A. (1990) Synthesis of the indolo[2,3-a] carbazole natural products staurosporinone and arcyriafl avin B. J. Chem. Soc. Perkin Trans. 1, (9), 2475-2480
174. Moody, C.J., Rahimtoola, K.F., Porter, B. and Ross, B.C. (1992) Synthesis of the staurosporine aglycon. J. Org. Chem., 57 (7), 2105-2114
175. Faul, M.M., Sullivan, K.A. and Winneroski, L.L. (1995) A general approach to the synthesis of bisindolylmaleimides: synthesis of staurosporine aglycone. Synthesis, (12), 1511-1516
176. Mahboobi, S., Eibler, E., Koller, M., Kumar, K.C.S., Popp, A. and Schollmeyer, D. (1999) Synthesis of pyrrolidin-2-ones and of staurosporine aglycon (K-252c) by intermolecular Michael reaction. J. Org. Chem., 64 (13), 4697-4704
177. Gaudêncio, S.P., Santos, M.M.M., Lobo, A.M. and Prabhakar, S. (2003) A short synthesis of staurosporinone (K-252c). Tetrahedron Lett., 44 (12), 2577-2578
178. Bonjouklian, R., Smitka, T.A., Doolin, L.E., Molloy, R.M., Debono, M.,
179. Kuethe, J.T., Wong, A. and Davies, I.W. (2003) Effective strategy for the preparation of indolocarbazole aglycons and glycosides: total synthesis of tjipanazoles B, D, E, and I. Org. Lett., 5 (20), 3721-3723
180. Gilbert, E.J., Ziller, J.W. and Van Vranken, D.L. (1997) Cyclizations of unsymmetrical bis-1,2-(3-indolyl) ethanes: synthesis of (-)-tjipanazole F1. Tetrahedron, 53 (48), 16553-16564
181. Gilbert, E.J. and Van Vranken, D.L. (1996) Control of dissymmetry in the synthesis of (+)-tjipanazole F2. J. Am. Chem. Soc., 118 (23), 5500-5501
182. Chakraborty, D.P. (1977) Carbazole alkaloids, in Progress in the Chemistry of Organic Natural Products, vol. 34, (eds W. Herz, H. Griesebach and G.W. Kirby), Springer, Wien, Austria, pp. 299-371
183. Iwaki, T., Yasuhara, A. and Sakamoto, T. (1999) Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction. J. Chem. Soc. Perkin Trans. 1, (11), 1505-1510
184. Bedford, R.B. and Cazin, C.S.J. (2002) A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation. Chem. Commun., (20), 2310-2311
185. Ackermann, L. and Althammer, A. (2007) Domino N-H/C-H bond activation: palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes. Angew. Chem., 119 (10), 1652-1654. Angew. Chem. Int. Ed. 46 (10), 1627-1629
186. Knölker, H.-J. (2000) Effi cient synthesis of tricarbonyliron-diene complexes-development of an asymmetric catalytic complexation. Chem. Rev., 100 (8), 2941-2962
187. Chakraborty, D.P. and Islam, A. (1971) Synthesis of girinimbine. J. Indian Chem. Soc., 48 (1), 91-92
188. Leino, R., Luttikhedde, H.J.G., Lehtonen, A., Sillanpää, R., Penninkangas, A., Strandé n, J., Mattinen, J. and Näsman, J.H. (1998) Bis[2-(tert-butyldimethylsiloxy)-4,7 -dimethylindenyl]zirconium dichloride: synthesis, torsional isomerism and olefi n polymerization catalysis. J. Organomet. Chem., 558 (1-2), 171-179
189. Reddy, G.M., Chen, S.-Y. and Uang, B.-J. (2003) A facile synthesis of indolo[2,3-a] pyrrolo[3,4-c]carbazoles via oxidative photocyclization of bisindolylmaleimides. Synthesis, (4), 497-500
190. Graebe, C. and Caro, H. (1870) Ueber Acridin. Ber. Dtsch. Chem. Ges., 3 (2), 746-747
191. Hughes, G.K., Lahey, F.N., Price, G.R. and Webb, L.J. (1948) Alkaloids of the Australian rutaceae. Nature, 162 (4110), 223-224
192. Michael, J.P. (2008) Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 25 (1), 166-187
193. Michael, J.P. (2007) Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 24 (1), 223-246
194. Skaltsounis, A.L., Mitaku, S. and Tillequin, F. (2000) Acridone alkaloids, in The Alkaloids, vol. 54, (ed. G.A. Cordell), Academic Press, Amsterdam, The Netherlands, pp. 259-377
195. Demeunynck, M., Charmantray, F. and Martelli, A. (2001) Interest of acridine derivatives in the anticancer chemotherapy. Curr. Pharm. Des., 7 (17), 1703
196. Denny, W.A. (2004) Chemotherapeutic effects of acridine derivatives. Med. Chem. Rev, 1 (3), 257-266
197. Belmont, P., Bosson, J., Godet, T. and Tiano, M. (2007) Acridine and acridone derivatives, anticancer properties and synthetic methods: where are we now ? Anticancer Agents Med. Chem., 7 (2), 139-169
198. Michael, J.P. (2001) Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 18 (5), 543-559
199. Michael, J.P. (2005) Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 22 (5), 627-646
200. Tillequin, F. (2007) Rutaceous alkaloids as models for the design of novel antitumor drugs. Phytochem. Rev., 6 (1), 65-79
201. Beck, J.R., Booher, R.N., Brown, A.C., Kwok, R. and Pohland, A. (1967) Synthesis of acronycine. J. Am. Chem. Soc., 89 (15), 3934-3935
202. Loughhead, D.G. (1990) Synthesis of des-N-methylacronycine and acronycine. J. Org. Chem., 55 (7), 2245-2246
203. Anand, R.C. and Selvapalam, N. (1996) A practical regiospecifi c approach towards acronycine and related alkaloids. Chem. Commun., (2), 199-200
204. Lasnitzki, T. and Wilkinson, J.H. (1948) The effect of acridine derivatives on the growth and mitosis of cells in vitro. Br. J. Cancer, 2 (4), 369-375
205. Sebestík, J., Hlavácek, J. and Stibor, I. (2007) A role of the 9-aminoacridines and their conjugates in a life science. Curr. Protein Pept. Sci., 8 (5), 471-483
206. Schmitz, F.J., Agarwal, S.K., Gunasekera, S.P., Schmidt, P.G. and Shoolery, J.N. (1983) Amphimedine, new aromatic alkaloid from a pacifi c sponge, Amphimedon sp. Carbon connectivity determination from natural abundance 13 C-13 C coupling constants. J. Am. Chem. Soc., 105 (14), 4835-4836
207. Marshall, K.M. and Barrows, L.R. (2004) Biological activities of pyridoacridines. Nat. Prod. Rep., 21 (6), 731-751
208. Echavarren, A.M. and Stille, J.K. (1988) Total synthesis of amphimedine. J. Am. Chem. Soc., 110 (12), 4051-4053
209. Nakahara, S., Tanaka, Y. and Kubo, A. (1996) Total synthesis of amphimedine. H eterocycles, 43 (10), 2113-2123
210. Nakahara, S., Tanaka, Y. and Kubo, A. (1993) Total synthesis of eilatin. Heterocycles, 36 (5), 1139-1144
211. Horstmann, M.A., Hassenpfl ug, W.A., zur Stadt, U., Escherich, G., Janka, G. and Kabisch, H. (2005) Amsacrine combined with etoposide and high-dose methylprednisolone as salvage therapy in acute lymphoblastic leukemia in children. H aematologica, 90 (12), 1701-1703
212. Cain, B.F., Atwell, G.J. and Denny, W.A. (1975) Potential antitumor agents. 16. 4'-(Acridin-9-ylamino)methanesulfon -anilides. J. Med. Chem., 18 (11), 1110-1117
213. Ito, C., Kondo, Y., Rao, K.S., Tokuda, H., Nishino, H. and Furukawa, H. (1999) Chemical constituents of Glycosmis pentaphylla. Isolation of a novel naphtoquinone and a new acridone alkaloid. Chem. Pharm. Bull., 47 (11), 1579-1581
214. Reisch, J., Szendrei, K., Novak, I. and Minker, E. (1972) Vorkommen und biologische Wirkung von Acridon -Derivaten. Scientia Pharmaceutica, 40 (3), 161-178
215. Michael, J.P. (2000) Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 17 (6), 603-620
216. Tringali, C., Spatafora, C., Calì, V. and Simmonds, M.S.J. (2001) Antifeedant constituents from Fagara macrophylla. Fitoterapia, 72 (5), 538-543
217. Réthy, B., Zupkó, I., Minorics, R., Hohmann, J., Ocsovszki, I. and Falkay, G. (2007) Investigation of cytotoxic activity on human cancer cell lines of arborinine and furanoacridones isolated from Ruta graveolens. Planta Med., 73 (1), 41-48
218. Govindachari, T.R., Viswanathan, N., Pai, B.R., Ramachandran, V.N. and Subramaniam, P.S. (1970) Alkaloids of Atalantia monophylla Correa. Tetrahedron, 26 (12), 2905-2910
219. Bahar, M.H., Shringarpure, J.D., Kulkarni, G.H. and Sabata, B.K. (1982) Structure and synthesis of atalaphylline and related alkaloids. Phytochemistry, 21 (11), 2729-2731
220. Wu, T.-S. and Chen, C.-M. (2000) Acridone Alkaloids from the root bark of Severinia buxifolia in Hainan. Chem. Pharm. Bull., 48 (1), 85-90
221. Chou, T.-C., Tzeng, C.-C., Wu, T.-S., Watanabe, K.A. and Su, T.-L. (1989) Inhibition of cell growth and macromolecule biosynthesis of human promyelocytic leukemic cells by acridone alkaloids. Phytother. Res., 3 (6), 237-242
222. Kawaii, S., Tomono, Y., Katase, E., Ogawa, K., Yano, M., Takemura, Y., Ju-ichi, M., Ito, C. and Furukawa, H. (1999) Acridones as inducers of HL-60 cell differentiation. Leuk. Res., 23 (3), 263-269
223. Ramesh, K. and Kapil, R.S. (1986) Synthesis of acridone alkaloids: glycocitrine-I, N-methylatalaphylline, atalaphyllidine, 11-hydroxyacronycine and 11-hydroxynoracronycine. Indian J. Chem. Sect. B, 25 (7), 684-687
224. Wu, T.-S., Furukawa, H. and Kuoh, C.-S. (1982) Acridone alkaloids IV. Structures of four new acridone alkaloids from Glycosmis citrifolia (Willd.) Lindl. Heterocycles, 19 (6), 1047-1051
225. Su, T.-L., Dziewiszek, K. and Wu, T.-S. (1991) Synthesis of glyfoline, a constituent of glycosmis citrifolia (Willd.) Lindl. and a potential anticancer agent. Tetrahedron Lett., 32 (12), 1541-1544
226. Su, T.L., Kohler, B., Chou, T.C., Chun, M.W. and Watanabe, K.A. (1992) Synthesis of the acridone alkaloids, glyfoline and congeners. Structure -activity relationship studies of cytotoxic acridones. J. Med. Chem., 35 (14), 2703-2710
227. Mietzsch, F. and Mauss, H. (1934) Gegen Malaria wirksame Acridinverbindungen. Angew. Chem., 47 (37), 633-636
228. Coatney, G.R. and Greenberg, J. (1952) The use of antiobiotics in the treatment of malaria. Ann. N. Y. Acad. Sci., 55 (6), 1075-1081
229. Colledge, L., Drummond, H., Worthington, R.T., McNee, J.W., Sladden, A.F. and McCartney, J.E. (1917) A report on the treatment of a series of recently infl icted war wounds with 'profl avine'. Lancet, 190 (4914), 676-677
230. Benda, L. (1912) Über das 3.6-Diamino -acridin. Ber. Dtsch. Chem. Ges., 45 (2), 1787-1799
231. Reisch, J., Szendrei, K., Minker, E. and Novak, I. (1967) Chemistry of natural substances. XVI. Rutacridone from Ruta graveolens. Acta Pharm. Suec., 4 (4), 265-266
232. Meepagala, K.M., Schrader, K.K., Wedge, D.E. and Duke, S.O. (2005) Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs. Phytochemistry, 66 (22), 2689-2695
233. Mester, I., Reisch, J., Rózsa, S. and Szendrei, K. (1981) Synthesis of (±)-rutacridone. Heterocycles, 16 (1), 77-79
234. McKenna, M.T., Proctor, G.R., Young, L.C. and Harvey, A.L. (1997) Novel tacrine analogues for potential use against Alzheimer's disease: potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors. J. Med. Chem., 40 (22), 3516-3523
235. Carlier, P.R., Chow, E.S.H., Han, Y., Liu, J., Yazal, J.E. and Pang, Y.-P. (1999) Heterodimeric tacrine-based acetylcholinesterase inhibitors: investigating ligand-peripheral site interactions. J. Med. Chem., 42 (20), 4225-4231
236. Lahiri, D.K., Farlow, M.R. and Sambamurti, K. (1998) The secretion of amyloid β-peptides is inhibited in the tacrine-treated human neuroblastoma cells. Mol. Brain Res., 62 (2), 131-140
237. Albert, A. and Gledhill, W. (1945) Improved syntheses of aminoacridines. Part IV. Substituted 5-aminoacridines. J. Soc. Chem. Ind., 64, 169-172
238. Moore, J.A. and Kornreich, L.D. (1963) A direct synthesis of 4-aminoquinolines. Tetrahedron Lett., 4 (20), 1277-1281
239. Pegel, K.H. and Wright, W.G. (1969) South african plant extractives Part II. Alkaloids of Teclea natalensis. J. Chem. Soc.(C), (18), 2327-2329
240. Rasoanaivo, P., Federici, E., Palazzino, G. and Galeffi, C. (1999) Acridones of Vepris sclerophylla: their 13 C-NMR data. Fitoterapia, 70 (6), 625-627
241. Ramachandran, V.N., Pai, B.R. and Santhanam, R. (1972) Synthesis of tecleanthine. I ndian J. Chem., 10 (1), 14-15
242. Hughes, G.K., Neill, K.G. and Ritchie, E. (1952) Alkaloids of the Australian rutaceae: Evodia xanthoxyloides F. Muell. II. Isolation of the alkaloids from the leaves. Aust. J. Sci. Res., 5 (2), 401-405
243. Cannon, J.R., Hughes, G.K., Neill, K.G. and Ritchie, E. (1952) Alkaloids of the Australian Rutaceae: Evodia xanthoxyloide s F. Muell. III. The structures of the coloured alkaloids, Evoxanthidine, Xanthevodine and Xanthoxoline. A ust. J. Sci. Res., 5 (2), 406-411
244. Chourpa, I., Morjani, H., Riou, J.-F. and Manfait, M. (1996) Intracellular molecular interactions of antitumor drug amsacrine (m-AMSA) as revealed by surface-enhanced Raman spectroscopy. F EBS Lett., 397 (1), 61-64
245. Cain, B.F., Seelye, R.N. and Atwell, G.J. (1974) Potential antitumor agents. 14. Acridylmethanesulfonanilides. J. Med. Chem., 17 (9), 922-930.