Aaptamine and related products. Their isolation, chemical syntheses, and biological activity

Tetrahedron

Volumn 65, Issue 22, 2009, Pages 4257-4282

  Larghi, Enrique L ^a   Bohn, María L ^a   Kaufman, Teodoro S ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

1H Benzo de 1,6 naphthyridines; Aaptamine; Bioactive compounds; Natural product synthesis; Sponge alkaloids

Indexed keywords

1 METHYL 8 DEMETHYLAAPTAMINE; 2,3 DIHYDRO 9 DEMETHYLAAPTAMINE; 2,3 DIHYDROAAPTAMINE; 2,3,3A,4,5,6 HEXAHYDROAAPTAMINE; 3,4 DIMETHOXY 2 NITRO 6 (TRIMETHYLSILYLETHENYL)BENZONITRILE; 4 CHLOROQUINOLINE DERIVATIVE; 5,6 DIHYDROAAPTAMINE; 6 BROMO 4 HYDROXY 3 METHOXY 2 NITROBENZALDEHYDE; 6,7 DIMETHOXY 8 NITRO 1(2H) ISOQUINOLONE; 8 DEMETHYLAAPTAMINE; 8,9 BISDEMETHYLAAPTAMINE; 8H 5,8 DIAZABENZ[CD]AZULENE ALKALOID AAPTOSINE; 9 DEMETHYLAAPTAMINE; AAPTAMINE; AAPTAMINOID DERIVATIVE; AAPTOSAMINE; BISDEMETHYLAAPTAMINE; BISDEMETHYLAAPTAMINE 9 O SULFATE; BROMO NITROBENZALDEHYDE; BROMO NITROBENZONITRILE; DEMETHOXYAAPTAMINE; ISOAAPTAMINE; LIHOUIDINE; NECATORIN; NYSTATIN; PYRROLOQUINOLINE; QUINOLINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; TRICYCLIC AZAKYNURENIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADRENERGIC ACTIVITY; ANTICONVULSANT ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIVIRAL ACTIVITY; BIOLOGICAL ACTIVITY; BIOSYNTHESIS; CYTOTOXICITY; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC 50; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; REVIEW; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

EID: 65249127970     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.027     Document Type: Review

References (276)

1. Battershill C., Jaspars M., and Long P. Biologist 52 (2005) 107-114
2. Amsler C.D., Iken K.B., McClintock J.B., and Baker B.J. Secondary Metabolites from Antarctic Marine Organisms and their Ecological Implications. In: McClintock J.B., and Baker J.B. (Eds). Marine Chemical Ecology (2001), CRC, Boca Raton, FL 267-300
3. Blunt J.W., Copp B.R., Hu W.P., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 24 (2007) 31-86
4. Lindquist N. J. Chem. Ecol. 28 (2002) 1987-2000
5. Paul V.J. Chemical Defenses of Benthic Marine Invertebrates. In: Paul V.J. (Ed). Ecological Roles of Marine Natural Products (1992), Cornell University Press, Ithaca, NY 164-188
6. Pawlik J.R. Oceanogr. Mar. Biol. Annu. Rev. 30 (1992) 273-335
7. Stachowicz J.J., and Lindquist N. Mar. Ecol. Prog. Ser. 155 (1997) 115-126
8. National Research Council. Marine Biotechnology in the Twenty-first Century: Problems, Promise and Products (2002), National Academy, Washington, D.C.
9. Gustafson K.R., Oku N., and Milanowski D.J. Curr. Med. Chem. Anti-Infect.Agents 3 (2004) 233-249
10. Arif J.M., Al-Hazzani A.A., Kunhi M., and Al-Khodairy F. J. Biomed. Biotechnol. 2 (2004) 93-98
11. Ireland C.M., Copp B.R., Forster M.P., McDonald L.A., Radisky D.C., and Swersey J.C. Biomedical Potential of Marine Natural Products. In: Attaway D., and Zaborsky O.R. (Eds). Pharmaceutical and Bioactive Natural Products, Marine Biotechnology (1993), Plenum, New York, NY 1-30
12. García-Fernández L.F., Reyes F., and Sánchez-Puelles J.M. Pharm. News 9 (2002) 495-501
13. Faulkner D.J. Anton. Van Leeuw. Int. J. Gen. Mol. Microbiol. 77 (2000) 135-145
14. Amador M.L., Jimeno J., Paz-Ares L., Cortes-Funes H., and Hidalgo M. Ann. Oncol. 14 (2003) 1607-1615
15. Haefner B. Drug Discov. Today 8 (2003) 536-544
16. Faulkner D.J. Nat. Prod. Rep. 15 (1998) 113-158
17. Munro M.H.G., Blunt J.W., Dumdei E.J., Hickford S.J.H., Lill R.E., Li S.X., Battershill C.N., and Duckworth A.R. J. Biotechnol. 70 (1999) 15-25
18. Dembitsky V.M., Gloriozova T.A., and Poroikov V.V. Mini-Rev. Med. Chem. 5 (2005) 319-336
19. Kim J., and Park E.J. Curr. Med. Chem. Anti-Cancer Agents 2 (2002) 485-537
20. Erpenbeck D., and van Soest R.W.M. Mar. Biotechnol. 9 (2007) 2-19
21. Nakao Y., Kawatsu S., Okamoto C., Okamoto M., Matsumoto Y., Matsunaga S., van Soest R.W.M., and Fusetani N. J. Nat. Prod. 71 (2008) 469-472
22. Bretting H., Kabat E.A., Liao J., and Pereira M.E.A. Biochemistry 15 (1976) 5029-5038
23. Edrada R.A., Proksch P., Wray V., Witte L., Muller W.E.G., and Van Soest R.W.M. J. Nat. Prod. 59 (1996) 1056-1060
24. Shen Y.C., Lo K.L., Kuo Y.H., and Chakraborty R. Chin. Pharm. J. 54 (2002) 207-213
25. Bourguet-Kondracki M.L., Rakotoarisoa M.T., Martin M.T., and Guyot M. Tetrahedron Lett. 33 (1992) 225-226
26. Jimenez C., and Crews P. J. Nat. Prod. 53 (1990) 978-982
27. Quiñoa E., Kho E., Manes L.V., and Crews P. J. Org. Chem. 51 (1986) 4260-4264
28. Iguchi K., Fujita M., Nagaoka H., Mitome H., and Yamada Y. Tetrahedron Lett. 34 (1993) 6277-6280
29. Lerch M.L., and Faulkner D.J. Tetrahedron 57 (2001) 4091-4094
30. Tsukamoto S., Takahashi M., Matsunaga S., Fusetani N., and van Soest R.W.M. J. Nat. Prod. 63 (2000) 682-684
31. Iwagawa T., Kaneko M., Okamura H., Nakatani M., and van Soest R.W.M. J. Nat. Prod. 63 (2000) 1310-1311
32. Tasdemir D., Marshall K.M., Mangalindan G.C., Concepcion G.P., Barrows L.R., Harper M.K., and Ireland C.M. J. Org. Chem. 66 (2001) 3246-3248
33. De Guzman F.S., Carte B., Troupe N., Faulkner D.J., Harper M.K., Concepcion G.P., Mangalindan G.C., Matsumoto S.S., Barrows L.R., and Ireland C.M. J. Org. Chem. 64 (1999) 1400-1402
34. Shin J., Seo Y., Rho J.R., Baek E., Kwon B.M., Jeong T.-S., and Bok S.-H. J. Org. Chem. 60 (1995) 7582-7588
35. Barnathan G., Kornprobst J.M., Doumenq P., Miralles J., and Boury-Esnault N. J. Nat. Prod. 56 (1993) 2104-2113
36. Lee H.-S., Ahn J.-W., Lee Y.-H., Rho J.-R., and Shin J. J. Nat. Prod. 67 (2004) 672-674
37. Tanaka C., Tanaka J., Bolland R.F., Marriott G., and Higa T. Tetrahedron 62 (2006) 3536-3542
38. Díaz-Marrero A.R., Brito I., Dorta E., Cueto M., San-Martín A., and Darias J. Tetrahedron Lett. 44 (2003) 5939-5942
39. Kijoa A., and Sawangwong P. Mar. Drugs 2 (2004) 73-82
40. Kobayashi J., Zeng C.-M., Ishibashi M., and Sasaki T. J. Nat. Prod. 56 (1993) 436-439
41. König G.M., Wright A.D., and Sticher O. J. Nat. Prod. 55 (1992) 174-178
42. Gauvin A., Smadja J., Aknin M., Faure R., and Gaydou E.M. Can. J. Chem. 78 (2000) 986-992
43. Inaba K., Sato H., Tsuda M., and Kobayashi J. J. Nat. Prod. 61 (1998) 693-695
44. Capon R.J., Skene C., Vuong D., Lacey E., Gil J.H., Heiland K., and Friedel T. J. Nat. Prod. 65 (2002) 368-370
45. Prinsep M.R., Blunt J.W., and Munro M.H.G. J. Nat. Prod. 57 (1994) 1557-1559
46. Kobayashi J., Kanda F., Ishibashi M., and Shigemori H. J. Org. Chem. 56 (1991) 4574-4576
47. Gao H., Kelly M., and Hamann M.T. Tetrahedron 55 (1999) 9717-9726
48. Hirano K., Tsuda M., Watanabe K., Fromont J., and Kobayashi J. Tetrahedron 56 (2000) 8107-8110
49. Tsuda M., Sakuma Y., and Kobayashi J. J. Nat. Prod. 64 (2001) 980-982
50. Debitus C., Guella G., Mancini I., Waikedre J., Guemas J., Nicolas J.I., and Pietra F. J. Mar. Biotechnol. 6 (1998) 136-141
51. Rao M.R., Venkatesham U., Sridevi K.V., and Venkateswarlu Y. Indian J. Chem. 39 (2000) 723-733
52. Abou-Shoer M.I., Shaala L.A., Youssef D.T.A., Badr J.M., and Habib A.-A.M. J. Nat. Prod. 71 (2008) 1464-1467
53. Anderson I. New Scientist 148 (1995) 5
54. Duckworth A.R., Battershill C.N., Schiel D.R., and Bergquist P.R. Mem. Queensland Mus. 44 (1999) 155-159
55. de Voogd, N. J. Ph.D. Thesis, University of Amsterdam, 2005;
56. Müller W.E.G., Grebenjuk V.A., Le Pennec G., Schroder H.C., Brummer F., Hentschel U., Müller I.M., and Breter H.J. Mar. Biotechnol. 6 (2004) 105-117
57. Garson M.J., Flowers A.E., Webb R.I., Charan R.D., and McCaffrey E.J. Cell Tissue Res. 293 (1998) 365-373
58. Sipkema D., Osinga R., Schatton W., Mendola D., Tramper J., and Wijffels R.H. Biotechnol. Bioeng. 90 (2005) 201-222
59. Efros L.S., Ezhova L.A., Zakhs E.R., and Treiger V.M. Chem. Heterocycl. Compd. 8 (1972) 180-182
60. Chem. Abstr. 76 (1972) 146868
61. Fugmann B., Steffan B., and Steglich W. Tetrahedron Lett. 25 (1984) 3575-3578
62. Klamann J.-D., Fugmann B., and Steglich W.P. Phytochemistry 28 (1989) 3519-3522
63. See also:
64. Suortti T., von Wright A., and Koskinen A. Phytochemistry 22 (1983) 2873-2874
65. Suortti T., and von Wright A. J. Chromatogr. 255 (1983) 529-532
66. Gill M., and Steglich W. Prog. Chem. Org. Nat. Prod. 51 (1987) 1-317
67. Nakamura H., Kobayashi J., Ohizumi Y., and Hirata Y. Tetrahedron Lett. 23 (1982) 5555-5558
68. Nakamura H., Kobayashi J., Ohizumi Y., and Hirata Y. J. Chem. Soc., Perkin Trans. 1 (1987) 173-176
69. Fedoreev S.A., Prokof'eva N.G., Denisenko V.A., and Rebachuk N.M. Pharm. Chem. J. (USSR) 22 (1988) 615-618
70. Chem. Abstr. 109 (1988) 183140
71. Bergquist P.R., Cambie R.C., and Kernan M.R. Biochem. Syst. Ecol. 19 (1991) 289-290
72. Kashman Y., Rudi A., Hirsch S., Isaacs S., Green D., Blasberger D., and Camely S. New J. Chem. 14 (1990) 729-740
73. Rudi A., and Kashman Y. Tetrahedron Lett. 34 (1993) 4683-4684
74. Park S.K., Kim S.S., Park J.D., Hong J.S., and Kim I.K. J. Korean Chem. Soc. 39 (1995) 559-563
75. Park S.K., Kim T.J., and Cho H.-W. Anal. Sci. Technol. 9 (1996) 355-363
76. Shen Y.C., Chein C.C., Hsieh P.W., and Duh C.Y. J. Fish. Soc. Taiwan 24 (1997) 117-125
77. Xu, L. Ph.D. Thesis, University of British Columbia, 2000.
78. Tinto W.F. Heterocycles 48 (1998) 2089-2093
79. Bobzin S.C., Yang S., and Kasten T.P. J. Chromatogr., B 748 (2000) 259-267
80. Bobzin S.C., Yang S., and Kasten T. J. Ind. Microbiol. Biotechnol. 25 (2000) 342-345
81. Coutinho A.F., Chanas B., Souza T.M.L., Frugulhetti I.C.P.P., and Epifanio R.A. Heterocycles 57 (2002) 1265-1272
82. Calcul L., Longeon A., Al Mourabit A., Guyot M., and Bourguet-Kondracki M.-L. Tetrahedron 59 (2003) 6539-6544
83. Makarchenko, A. E.; Utkina, N.K. Antiradical Activity of Alkaloids from Marine Sponges International. Conference on Natural Products and Physiologically Active Substances (ICNPAS-2004). Novosibirsk, Russia, Sep 12-17, 2004.
84. Granato A.C., Berlinck R.G.S., Magalhães A., Schefer A.B., Ferreira A.G., de Sanctis B., de Freitas J.C., Hajdu E., and Migotto E. Quim. Nova 23 (2000) 594-599
85. Berlinck R.G.S., Hajdu E., da Rocha R.M., de Oliveira J.H.H.L., Hernández I.L.C., Seleghim M.H.R., Granato A.C., de Almeida E.V.R., Nuñez C.V., Muricy G., Peixinho S., Pessoa C., Moraes M.O., Cavalcanti B.C., Nascimento G.G.F., Thiemann O., Silva M., Souza A.O., Silva C.L., and Minarini P.R.R. J. Nat. Prod. 67 (2004) 510-522
86. For a discussion on the molecular systematics of sponges, see:. Borchiellini B., Chombard C., Lafay B., and Boury-Esnault N. Hydrobiologia 420 (2000) 15-27
87. Pettit G.R., Hoffmann H., McNulty J., Higgs K.C., Murphy A., Molloy D.J., Herald D.L., Williams M.D., Pettit R.K., Doubek D.L., Hooper J.N.A., Albright L., Schmidt J.M., Chapuis J.C., and Tackett L.P. J. Nat. Prod. 67 (2004) 506-509
88. Herlt A., Mander L., Rombang W., Rumampuk R., Soemitro S., Steglich W., Tariganc P., and von Nussbaum F. Tetrahedron 60 (2004) 6101-6104
89. Pedpradab, S. Ph.D. Thesis, University of Düsseldorf, 2005.
90. Aoki S., Kong D., Suna H., Sowa Y., Sakai T., Setiawan A., and Kobayashi M. Biochem. Biophys. Res. Commun. 342 (2006) 101-106
91. Diers J.A., Bowling J.J., Duke S.O., Wahyuono S., Kelly M., and Hamann M.T. Mar. Biol. 8 (2006) 366-372
92. Diers J.A., Ivey K.D., El-Alfy A., Shaikh J., Wang J., Kochanowska A.J., Stoker J.F., Hamann M.T., and Matsumoto R.R. Pharmacol. Biochem. Behav. 89 (2008) 46-53
93. Jang K.H., Chung S.-C., Shin J., Lee S.-H., Kim T.-I., Lee H.-S., and Oh K.-B. Bioorg. Med. Chem. Lett. 17 (2007) 5366-5369
94. Shaari K., Ling K.C., Rashid Z.M., Jean T.P., Abas F., Raof S.M., Zainal Z., Lajis N.H., Mohamad H., and Ali A.M. Mar. Drugs 7 (2009) 1-8
95. Anderson, M. A.; Enticknap, J. J.; Hamann, M. T.; Hill, R. T. Characterization of the Microbial Communities in an Aaptamine-producing Marine Sponge, Aaptos sp. International Marine Biotechnology Conference. St. John's, Newfoundland & Labrador, Canada, 2005; C10.008.
96. Bowden B.F., McCool B.J., and Willis R.H. J. Org. Chem. 69 (2004) 7791-7793
97. Feldman K.S., and Coca A. Tetrahedron Lett. 49 (2008) 2136-2138
98. Baldwin J.E., Claridge T.D.W., Cushaw A.J., Heupel F.A., Lee V., Spring D.R., Whitehead R.C., Boughtflower R.J., Mutton I.M., and Upton R.J. Angew. Chem., Int. Ed. 37 (1998) 2661-2663
99. Balczewski P., Kieran M., Mallon J., Street J.D., and Joule J.A. J. Chem. Soc., Perkin Trans. 1 (1990) 3193-3199
100. Steglich et al. followed an analogous biomimetic pathway, starting from 2-aminobenzaldehyde and tyrosine in the synthesis of necatorone (first isolated as necatorine), see: von Nussbaum, F.; Eizenhöfer, T.; Klamann, J.-D.; Spiteller, P.; Heinrich, M.; Steglich, W., unpublished results;
101. Hilger C.S., Fugmann B., and Steglich W. Tetrahedron Lett. 26 (1985) 5975-5978
102. Bross, M.; Hilger, C. S.; Klamann, J. D.; Schoneseiffen, J.; Steglich, W.; Sterner, O. 4th International Conference, Chemistry and Biotechnology of Biologically Active Natural Products, Budapest, 1987; Symposium Papers, p. 381;
103. Steglich, W. The Colorful Chemistry of Mushrooms and Marine Animals. International Conference on Natural Products and Physiologically Active Substances (ICNPAS-2004), Novosibirsk, Russian, Sep 12-17, 2004.
104. Kashman, Y.; Koren-Goldshlager, G.; García Gravalos, M. D. World Pat. WO 00/20411, 2000;
105. Chem. Abstr. 132 (2000) 260678
106. Heinrich M.R., Steglich W., Banwell M.G., and Kashman Y. Tetrahedron 59 (2003) 9239-9247
107. Usuki Y., Hirakawa H., Goto K., and Iio H. Tetrahedron: Asymmetry 12 (2001) 3293-3296
108. Banwell M.G., Bray A.M., Edwards A.J., and Wong D.J. New J. Chem. 25 (2001) 1347-1350
109. Banwell M.G., Bray A.M., Edwards A.J., and Wong V. J. Chem. Soc., Perkin Trans. 1 (2002) 1340-1343
110. Zheng J.-F., Jin L.-R., and Huang P.-Q. Org. Lett. 6 (2004) 1139-1142
111. Fürstner A., Krause H., and Thiel O.R. Tetrahedron 58 (2002) 6373-6380
112. Pelletier J.C., and Cava M.P. Tetrahedron Lett. 26 (1985) 1259-1260
113. Pelletier J.C., and Cava M.P. J. Org. Chem. 52 (1987) 616-622
114. Brossi A., Dolan L.A., and Teitel S. Org. Synth. 56 (1977) 3-7
115. Brossi A., O' Brien J., and Teitel S. Org. Prep. Proced. Int. 2 (1970) 281-283
116. Ingold C.K. Structure and Mechanism in Organic Chemistry. 2nd ed. (1969), Cornell University, Ithaca, NY p 337
117. Pelletier J.C., and Cava M.P. Synthesis (1987) 474-477
118. Sakamoto T., Miura N., Kondo Y., and Yamanaka H. Chem. Pharm. Bull. 34 (1986) 2760-2765
119. Raiford L.C., and Stoesser W.C. J. Am. Chem. Soc. 50 (1927) 2556-2563
120. Sakamoto T., Kondo Y., and Yamanaka H. Chem. Pharm. Bull. 33 (1985) 626-633
121. Bassoli A., Maddinelli G., Rindone B., Tollari S., and Chioccara F. J. Chem. Soc., Chem. Commun. (1987) 150-151
122. Bradsher C.K., and Dutta W.L. J. Org. Chem. 26 (1961) 2231-2234
123. Isomura K., Okada M., and Taniguchi H. Tetrahedron Lett. 10 (1969) 4073-4076
124. Kikugawa Y., and Kawase M. J. Chem. Soc., Chem. Commun. (1991) 1354-1355
125. Kawase M., Kitamura Y., and Kikugawa Y. J. Org. Chem. 54 (1989) 3394-3403
126. Maryanoff B.E., Parvez M., and Olofson R.A. J. Org. Chem. 55 (1990) 760-764
127. Lenz G.R. J. Org. Chem. 53 (1988) 5791-5793
128. Balczewski P., Kieran M., Mallon J., Street J.D., and Joule J.A. Tetrahedron Lett. 31 (1990) 569-572
129. Larghi E.L., and Kaufman T.S. Tetrahedron Lett. 38 (1997) 3159-3162
130. Rozwadowska M.D., and Brozda D. Pharmazie 39 (1984) 387-388
131. Kaiser E., and Knutson P. Synthesis (1978) 148-150
132. Meghani P., Street J.D., and Joule J.A. J. Chem. Soc., Chem. Commun. (1987) 1406-1407
133. Kawase M., Sinhababu A.K., and Borchardt R.T. J. Heterocycl. Chem. 24 (1987) 1499-1501
134. Brown R.K. Chemistry of Heterocyclic Compounds. In: Houlihan W.J. (Ed). Indoles. Part One Vol. 25 (1972), Wiley, New York, NY 479 Chapter 11
135. Nagarajan K., and Rodrigues P.J. Indian J. Chem. 33B (1994) 1115-1118
136. Nagarajan K., and Rodrigues P.J. J. Chem. Res., Synop. (1993) 336-337
137. Molina P., Vidal A., and Barquero I. Synthesis (1996) 1199-1202
138. Fresneda P.M., and Molina P. Synlett (1994) 1-17
139. Pommier A., Kocienski P., and Pons J.M. J. Chem. Soc., Perkin Trans. 1 (1998) 2105-2118
140. Kelly T.R., and Maguire M.P. Tetrahedron 41 (1985) 3033-3036
141. Mori S., Aoyama T., and Shioiri T. Tetrahedron Lett. 25 (1984) 429-432
142. Heindel N.D., Kennewel V., and Fish V.B. J. Heterocycl. Chem. 6 (1969) 77-81
143. Craig Jr. J.C., and Pearson D.E. J. Heterocycl. Chem. 6 (1968) 631-637
144. Kametani T., and Fukumoto K. In: Grethe G. (Ed). Isoquinolines, Part I (1981), Wiley, New York, NY 218
145. For other routes to 1H-pyrrolo[3,2-c]quinolines, see:
146. Parrick J., and Wilcox R. J. Chem. Soc., Perkin Trans. 1 (1976) 2121-2125
147. Khan M.A., and da Rocha J.F. J. Heterocycl. Chem. 15 (1978) 913-921
148. Olah, G. A. U.S. Patent 3,708,553, 1973.
149. Fixler N., Demeunynck M., and Lhomme J. Synth. Commun. 27 (1997) 2311-2324
150. Andrew R.G., and Raphael R.A. Tetrahedron 43 (1987) 4803-4816
151. McKillop A., Fiaud J.-C., and Rug R.P. Tetrahedron 30 (1974) 1379-1382
152. Ono N., Yanai T., and Kaji A. J. Chem. Soc., Chem. Commun. (1986) 1040-1041
153. Slotta K.H., and Szyska G. Chem. Ber. 68 (1935) 184-192
154. Rawal V.H., Rao J.A., and Cava M.P. Tetrahedron Lett. 26 (1985) 4275-4278
155. Cassis R., Tapia R., and Valderrama J.A. Synth. Commun. 15 (1985) 125-133
156. Vorbrüggen H., and Krolikiewicz K. Chem. Ber. 117 (1984) 1523-1541
157. Nishikawa S., Kumazawa Z., Kashinura N., Maki S., and Nishikimi Y. Agric. Biol. Chem. 50 (1986) 495-497
158. Vorbrüggen H. Acc. Chem. Res. 28 (1995) 509-520
159. Kano S., Sugino E., Shibuya S., and Hibino S. J. Chem. Soc., Chem. Commun. (1980) 1241-1242
160. Kano S., Sugino E., Shibuya S., and Hibino S. J. Org. Chem. 46 (1981) 3856-3859
161. Kano S., Sugino E., Shibuya S., and Hibino S. J. Org. Chem. 46 (1981) 2979-2981
162. Kano S., Sugino E., and Hibino S. Heterocycles 19 (1982) 1673-1675
163. Kano S., Muchizuki N., Hibino S., and Shibuya S. J. Org. Chem. 47 (1982) 3566-3569 and related references cited therein
164. Moskal J., van Stralen R., Postma D., and van Leusen A.M. Tetrahedron Lett. 27 (1986) 2173-2176
165. Moskal J., and van Leusen A.M. J. Org. Chem. 51 (1986) 4131-4139
166. Hibino S., Sugino E., Choshi T., and Sato K. J. Chem. Soc., Perkin Trans. 1 (1988) 2429-2432
167. For a review, see:. Sugino E., Choshi T., and Hibino S. Heterocycles 50 (1999) 543-559
168. Hibino S., Kano S., Mochizuki N., and Sugino E. J. Org. Chem. 49 (1984) 5006-5008
169. Hibino S., Sugino E., Yamochi T., Kuwata M., Hashimoto H., Sato K., Amanuma F., and Karasawa Y. Chem. Pharm. Bull. 35 (1987) 2261-2265
170. Hibino S., and Sugino E. Heterocycles 26 (1987) 1883-1889
171. Kuwabara N., Hayashi H., Hiramatsu N., Choshi T., Sugino E., and Hibino S. Chem. Pharm. Bull. 47 (1999) 1805-1807
172. Koshi K., and Shimizu M. Chem. Pharm. Bull. 16 (1968) 2343-2350
173. Sato M., Yoneda N., Katagiri N., Watanabe H., and Kaneko C. Synthesis (1986) 672-674
174. Shepherd R.G., and Fedrick J.L. Adv. Heterocycl. Chem. 4 (1965) 145-423
175. Vorbrüggen H. Adv. Heterocycl. Chem. 49 (1990) 117-192
176. Walz A.J., and Sundberg R.J. J. Org. Chem. 65 (2000) 8001-8010
177. Jones G. Quinolines, Part I, The Chemistry of Heterocyclic Compounds Vol. 32 (1978), Wiley, New York, NY 139-150
178. Reitsema R.H. Chem. Rev. 48 (1948) 43-68
179. Fernandez R., Gasch C., Gomez-Sanchez A., and Vilchez J.E. Tetrahedron Lett. 32 (1991) 3225-3228
180. Ram S., and Ehrenkaufer R.E. Tetrahedron Lett. 25 (1984) 3415-3418
181. Gordon H.J., Martin J.C., and McNab H. J. Chem. Soc., Chem. Commun. (1983) 957-958
182. Briehl H., Lukosh A., and Wentrup C. J. Org. Chem. 49 (1984) 2772-2779
183. Larghi E.L., Obrist B.V., and Kaufman T.S. Tetrahedron 64 (2008) 5236-5245
184. Shioiri T., Ninomiya K., and Yamada S. J. Am. Chem. Soc. 94 (1972) 6203-6205
185. Ninomiya K., Shioiri T., and Yamada S. Tetrahedron 30 (1974) 2151-2157
186. Poondra R.R., Fischer P.M., and Turner N.J. J. Org. Chem. 69 (2004) 6920-6922
187. Pinnick H.W., Brown S.P., McLean E.A., and Zoller III L.W. J. Org. Chem. 46 (1981) 3758-3760
188. Fillion E., and Fischlock D. J. Am. Chem. Soc. 127 (2005) 13144-13145
189. Kasiotis K.M., Fokialakis N., and Haroutounian S.A. Synthesis (2006) 1791-1802
190. Bell F., and Millar A.S. J. Chem. Soc. C (1966) 375-376
191. Chackal S., Houssin R., and Hénichart J.-P. J. Org. Chem. 67 (2002) 3502-3505
192. Kaufman T.S. J. Chem. Soc., Perkin Trans. 1 (1993) 403-404
193. Kaufman T.S. Synth. Commun. 22 (1992) 1913-1921
194. Bianchi D.A., and Kaufman T.S. ARKIVOC x (2003) 178-188
195. Schön I. Chem. Rev. 84 (1984) 287-297
196. Tarbell D.S., Yamamoto Y., and Pope B.M. Proc. Natl. Acad. Sci. U.S.A. 69 (1972) 730-732
197. Lansbury P.T., and Mancuso N.R. Tetrahedron Lett. 6 (1965) 2445-2450
198. Fikes L.E., and Shechter H. J. Org. Chem. 44 (1979) 741-744
199. von Nussbaum F., Schumann S., and Steglich W. Tetrahedron 57 (2001) 2331-2335
200. Fugmann, B. Ph.D. Thesis, University of Bohn, 1985;
201. von Nussbaum, F. Ph.D. Thesis, University of Munich, 1998.
202. Ballini R., Bosica G., and Forconi P. Tetrahedron 52 (1996) 1677-1684
203. Nose A., and Kudo T. Chem. Pharm. Bull. 29 (1981) 1159-1161
204. Pettit G.R., and Lippert III J.W. Anti-Cancer Drug Des. 15 (2000) 203-216
205. Silverberg L.J., Dillon J.L., and Vemishetti P. Tetrahedron Lett. 37 (1996) 771-774
206. Pettit G.R., Rhodes M.R., Herald D.L., Chaplin D.J., Stratford M., Hamel E., Pettit R.K., Chapuis J.-C., and Oliva D. Anti-Cancer Drug Des. 13 (1998) 981-993
207. Lazar S., and Guillaumet G. Synth. Commun. 22 (1992) 923-931
208. Pettit G.R., Hoffmann H., Herald D.L., Blumberg P.M., Hamel E., Schmidt J.M., Chang Y., Pettit R.K., Lewin N.E., and Pearce L.V. J. Med. Chem. 47 (2004) 1775-1782
209. Pettit G.R., Hoffmann H., Herald D.L., McNulty J., Murphy A., Higgs K.C., Hamel E., Lewin N.E., Pearce L.V., Blumberg P.M., Pettit R.K., and Knight J.C. J. Org. Chem. 69 (2004) 2251-2256
210. Mitscher L.A., Bathala M.S., and Beal J.L. J. Chem. Soc. (D) Chem. Commun (1971) 1040
211. Psotova J., Ducher L., Ulrichova J., and Waltierova D. Chem. Listy 90 (1996) 613-614
212. Del Poeta M., Chen S.-F., Von Hoff D., Dykstra C.C., Wani M.C., Manikumar G., Heitman J., Wall M.E., and Perfect J.R. Antimicrob. Agents Chemother. 43 (1999) 2862-2868
213. Murphy W.S., and Bertrand M. J. Chem. Soc., Perkin Trans. 1 (1998) 4115-4119
214. Shen Y.-C., Lin T.S., Sheu J.-H., and Duh C.-H. J. Nat. Prod. 62 (1999) 1264-1267
215. Bowling J.J., Pennaka H.K., Ivey K., Wahyuono S., Kelly M., Schinazi R.F., Valeriote F.A., Graves D.E., and Hamann M.T. Chem. Biol. Drug Des. 71 (2008) 205-215
216. Gul W., Hammond N.L., Yousaf M., Bowling J.J., Schinazi R.F., Wirtz S.S., Andrews G.C., Cuevas C., and Hamann M.T. Bioorg. Med. Chem. 14 (2006) 8495-8505
217. Pelletier, J. C.; Cava, M. P. Book of Abstracts, 188th Meeting of the American Chemical Society, Philadelphia, 1984; ACS: Washington, DC; Abstract ORGN 63.
218. Eckhart E. Magy. Kem. Folyoirat 70 (1964) 296-299
219. Chem. Abstr. 61 (1964) 13355e
220. Sakane K., Terayama K., Haruki E., Imoto E., and Otsuji Y. Nippon Kagaku Kaishi (1974) 1535-1538
221. Chem. Abstr. 81 (1974) 120392y
222. Gololobov Y.G., and Kasukhin L.F. Tetrahedron 48 (1992) 1353-1406
223. Gusar N.I. Russ. Chem. Rev. (Engl. Transl.) 60 (1991) 146-161
224. Barluenga J., and Palacios F. Org. Prep. Proced. Int. 23 (1991) 1-65
225. Eguchi S., Matsushita Y., and Yamashita K.F. Org. Prep. Proced. Int. 24 (1992) 209-244
226. Molina P., and Vilaplana M.J. Synthesis (1994) 1197-2018
227. Molina P., Alajarb M., and Vidal A. J. Org. Chem. 57 (1992) 6703-6711
228. Sinhababu A.K., and Borchardt R.T. J. Org. Chem. 48 (1983) 1941-1944
229. Wolfe J.P., Wagaw S., and Buchwald S.L. J. Am. Chem. Soc. 118 (1996) 7215-7216
230. Harrison B.L., Baron B.M., Cousino D.M., and McDonald I.A. J. Med. Chem. 33 (1990) 3130-3132
231. Heindel N.D., Bechara I.S., Kennewell J.M., Ohnmacht C.J., Lemke S.M., and Lemke T.F. J. Med. Chem. 11 (1968) 1218-1221
232. Hume W.E., and Nagata R. Synlett (1997) 473-474
233. Krolski M.E., Renaldo A.F., Rudisill D.E., and Stille J.K. J. Org. Chem. 53 (1988) 1170-1176
234. Larock R.C., Hoightower T.R., Hasvold L.A., and Peterson K.P. J. Org. Chem. 61 (1996) 3584-3585
235. Torres J.C., Pilli R.A., Vargas M.D., Violante F.A., Garden S.J., and Pinto A.C. Tetrahedron 58 (2002) 4487-4492
236. Guram A., Rennels R., and Buchwald S. Angew. Chem., Int. Ed. Engl. 34 (1995) 1348-1350
237. Louie J., and Hartwig J. Tetrahedron Lett. 36 (1995) 3609-3612
238. Breimer L.H. Mol. Carcinog. 3 (1990) 188-197
239. Cerutti P.A. Science 227 (1985) 375-380
240. Takamatsu S., Hodges T.W., Rajbhandari I., Gerwick W.H., Hamann M.T., and Nagle D.G. J. Nat. Prod. 66 (2003) 605-608
241. Sova V.V., and Fedoreev S.A. Chem. Nat. Compd. 26 (1990) 420-422
242. Ioffina D.I., Volkovitskaya O.E., Gorkin V.Z., Rebachuk N.M., Utkina N.K., and Fedoreev S.A. Chem. Nat. Compd. 24 (1990) 456-458
243. Floquet N., Richez C., Durand P., Maigret B., Badet B., and Badet-Denisot M.A. Bioorg. Med. Chem. Lett. 17 (2007) 1966-1970
244. Nishizawa Y. Nature 334 (1988) 661-665
245. Patil, A. D.; Westley, J. W.; Mattern, M.; Freyer, A. J.; Hofmann, G. A. Aaptamines as Protein Kinase C Inhibitors. PCT Int. Appl. WO 95/0584, 1995.
246. Longley R.E., McConnell O.J., Essich E., and Harmody D. J. Nat. Prod. 56 (1993) 915-920
247. Longley R.E., and Harmody D. J. Antibiot. 44 (1991) 93-102
248. Mazmanian S.K., Liu G., Ton-That H., and Schneewind O. Science 285 (1999) 760-763
249. Mazmanian S.K., Ton-That H., Su K., and Schneewind O. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 2293-2298
250. Mazmanian S.K., Skaar E.P., Gaspar A.H., Humayun M., Gornicki P., Jelenska J., Joachmiak A., Missiakas D.M., and Schneewind O. Science 299 (2003) 906-909
251. Ton-That H., Liu G., Mazmanian S.K., Faull K.F., and Schneewind O. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 12424-12429
252. Mazmanian S.K., Liu G., Lenoy E.R., and Schneewind O. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 5510-5515
253. Souza T.M.L., Abrantes J.L., Epifanio R.A., Fontes C.F.L., and Frugulhetti I.C.P.P. Planta Med. 73 (2007) 200-205
254. Nawawi A., Ma C., Nakamura N., Hattori M., Kurokawa M., and Shiraki K. Biol. Pharm. Bull. 22 (1999) 268-274
255. Gochfeld D.J., El Sayed K.A., Yousaf M., Hu J., Bartyzel P., Dunbar D.C., Wilkins S.P., Zjawiony J.K., Schinazi R.F., Schlueter Wirtz S., Tharnish P.M., and Hamann M.T. Mini-Rev. Med. Chem. 3 (2003) 451-475
256. Seleghim M.H.R., Lira S.P., Kossuga M.H., Batista T., Berlinck R.G.S., Hajdu E., Muricy G., da Rocha R.M., do Nascimento G.G.F., Silva M., Pimenta E.F., Thiemann O.H., Oliva G., Cavalcanti B.C., Pessoa C., de Moraes M.O., Galetti F.C.S., Silva C.L., de Souza A.O., and Peixinho S. Rev. Bras. Farmacogn. 17 (2007) 287-318
257. Bryskier A. Exp. Rev. Anti-infect. Ther. 3 (2005) 505-553
258. Pettit R.K., Weber C.A., Kean M.J., Hoffmann H., Pettit G.R., Tan R., Franks K.S., and Horton M.L. Antimicrob. Agents Chemother. 49 (2005) 2612-2617
259. Arif, J. M.; Kunhi, M.; Siddiqui, Y.; El-Sayed, K.A.; Orabi, K.-Y.; Al-Hazzani, A. A.; Al-Ahdal, M. N.; Al-Khodairy, F. M. DNA Adducts as Bioscreening Tool in Determining Anticancer Potential of Chemically Diverse Marine Compounds, In: Proceedings of the 97th Annual Meeting of the AACR, Orlando, FL, Mar 27-31, 2004.
260. Proc. Am. Assoc. Cancer Res. 45 (2004) Abstract 5489
261. Hollstein A., Sidransky D., Vogelstein B., and Harris C.C. Science 253 (1991) 49-53
262. Vogelstein B., and Kinzler K.W. Cell 70 (1992) 523-526
263. Nakano K., Mizuno T., Sowa Y., Orita T., Yoshino T., Okuyama Y., Fujita T., Ohtani-Fujita N., Matsukawa Y., Tokino T., Yamagishi H., Oka T., Nomura H., and Sakai T. J. Biol. Chem. 272 (1997) 22199-22206
264. Aoki S., Nasu H., Sowa H., Sakai T., and Kobayashi M. J. Pharm. Soc. Jpn. 126 (2006) 6-9
265. Arif J.M., Kunhi M., Siddiqui Y.M., El Sayed K.A., Orabi K.Y., Al-Hazzani A., Al-Ahdal M.N., and Al-Khodairy F.M. Int. J. Cancer Prev. 1 (2004) 259-268
266. Ohizumi Y., Kajiwara A., Nakamura H., and Kobayashi J. J. Pharm. Pharmacol. 36 (1984) 785-786
267. Litvinov V.P., Roman S.V., and Dyachenko V.D. Russ. Chem. Rev. 70 (2001) 299-320
268. Rothman S.M., and Olney J.W. Trends Neurosci. 18 (1995) 57-58
269. Leeson P.D., and Iversen L.L. J. Med. Chem. 37 (1994) 4053-4067
270. Kemp J.A., and Leeson P.D. Trends Pharmacol. Sci. 14 (1993) 20-25
271. Jansen M., and Dannhardt G. Eur. J. Med. Chem. 38 (2003) 661-670
272. Yoneda Y., Suzuki T., Ogita K., and Han D. J. Neurochem. 60 (1993) 634-654
273. Sundberg D.C., Vasishtha N., Zimmerman R.C., and Smith C.M. Selection, Design and Delivery of Environmentally Benign Antifouling Agents. Naval Research Reviews (1998), Office of Naval Research, Arlington, VA pp 51-59
274. Fusetani N. Nat. Prod. Rep. 21 (2004) 94-104
275. Omae I. Chem. Rev. 103 (2003) 3431-3488
276. Ivey K.D., Diers J.A., Shaikh J., Wang J., Stoker J.F., Hamann M.T., and Matsumoto R.R. The Pharmacologist 48 (2006) 160