The Marine Bromotyrosine Derivatives

Alkaloids: Chemistry and Biology

Volumn 61, Issue , 2005, Pages 59-262

  Peng, Jiangnan ^a   Li, Jing ^a   Hamann, Mark T ^a  

^a Chemistry Biochemistry   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BROMOTYROSINE; CALCIUM CHANNEL; DRUG DERIVATIVE; TYROSINE;

ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HUMAN; METABOLISM; REVIEW; SPECTROSCOPY; SPONGE (PORIFERA);

ALKALOIDS; ANIMALS; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CALCIUM CHANNELS; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORIFERA; SPECTRUM ANALYSIS; TYROSINE;

EID: 25144498632     PISSN: 10994831     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1099-4831(05)61002-4     Document Type: Article

References (313)

1. Morner C.T. Z. Physiol. Chem. 88 (1913) 138
2. Sharma G.M., and Burkholder P.R. J. Antibiotics, Ser. A. 20 (1967) 200
3. Sharma G.M., and Burkholder P.R. Tetrahedron Lett. (1967) 4147
4. Sharma G.M., Vigand B., and Burkholder P.R. J. Org. Chem. 35 (1970) 2823
5. Anderson R.J., and Faulkner D.J. Tetrahedron Lett. (1973) 1175
6. D. J. Faulkner and C. M. Ireland, NATO Conference Series IV: Marine Sciences 1 (Mar. Nat. Prod. Chem.), 23 (1977), CAN 88:19210.
7. Kernan M.R., Cambie R.C., and Bergquist P.R. J. Nat. Prod. 53 (1990) 720
8. Aydogmus Z., Ersoy N., and Imre S. Turk. J. Chem. 23 (1999) 339
9. D'Ambrosio M., Guerriero A., and Pietra F. Helv. Chim. Acta 67 (1984) 1484
10. D'Ambrosio M., Guerriero A., De Clauser R., De Stanchina G., and Pietra F. Experientia 39 (1983) 1091
11. Capon R.J., and MacLeod J.K. J. Chem. 40 (1987) 341
12. J. Peng and M. T. Hamann, Unpublished material.
13. Daly J.W., Jerina D.M., and Witkop D. Experientia 28 (1972) 1129
14. Fattorusso E., Minale L., and Sodano G. J. Chem. Soc., Chem. Commun. (1970) 751
15. Fattorusso E., Minale L., and Sodano G. J. Chem. Soc., Perkin Trans. 1 1 (1972) 16
16. Fulmor W., Van Lear G.E., Morton G.O., and Mills R.O. Tetrahedron Lett. (1970) 4551
17. Mazzarella L., and Puliti R. Gazz. Chim. Ital. 102 (1972) 39
18. Cosulich D.B., and Lovell F.M. J. Chem. Soc., Chem. Commun. (1971) 397
19. Minale L., Sodano G., Chan W.R., and Chen A.M. J. Chem. Soc., Chem. Comm. (1972) 674
20. Norte M., and Fernandez J.J. Tetrahedron Lett. 28 (1987) 1693
21. Norte M., Rodriguez M.L., Fernandez J.J., Eguren L., and Estrada D.M. Tetrahedron 44 (1988) 4973
22. D'Ambrosio M., Guerriero A., Traldi P., and Pietra F. Tetrahedron Lett. 23 (1982) 4403
23. Guerriero A., D'Ambrosio M., Traldi P., and Pietra F. Naturwissenschaften 71 (1984) 425
24. D'Ambrosio M., Mealli C., Guerriero A., and Pietra F. Helv. Chim. Acta 68 (1985) 1453
25. D'Ambrosio M., Geurreiro A., and Pietra F. Comp. Biochem. Physiol. 83 (1986) 309
26. Krejcarek G.E., White R.H., Hager L.P., McClure W.O., Johnson R.D., Rinehart K.L., McMillan J.A., Paul I.C., Shaw P.D., and Brusca R.C. Tetrahedron Lett. (1975) 507
27. Yasunohu K., Tanaka T., Knox W.E., and Mason H.S. Fed. Proc. Am. Soc. Exp. Biol. 17 (1985) 340
28. Chang C.W.J., and Weinheimer A.J. Tetrahedron Lett. (1977) 4005
29. Kelecom A., and Kannengiesser G.J. Anais da Academia Brasileira de Ciencias 51 (1979) 639
30. Encarnacion R.D., Sandoval E., Malmstrom J., and Christophersen C. J. Nat. Prod. 63 (2000) 874
31. Chib J.S., Stempien M.F., Mierzwa R.A., Ruggieri G.D., and Nigrelli R.F. J. Pharm. Sci. 67 (1978) 264
32. Venkateswarlu Y., and Chavakula R. J. Nat. Prod. 58 (1995) 1087
33. Ciminiello P., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 58 (1995) 689
34. Hunt S., and Breuer S.W. Biochim. Biophys. Acta 252 (1971) 401
35. Albrizio S., Ciminiello P., Fattorusso E., Magno S., and Pansini M. Tetrahedron 50 (1994) 783
36. Gao H.-F., Kelly M., and Hamann M.T. Tetrahedron 55 (1999) 9717
37. Hollenbeak K.H., Schmitz F.J., Kaul P.N., and Kulkarni S.K. Drugs Food Sea: Myth or Reality (1978) 81
38. Ciminiello P., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 57 (1994) 1564
39. Ciminiello P., Dell'Aversano S., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 63 (2000) 263
40. Wagoner R.M.V., Jompa J., Tahir A., and Ireland C.M. J. Nat. Prod. 62 (1999) 794
41. Pettit G.R., Butler M.S., Williams M.D., Filiatrault M.J., and Pettit R.K. J. Nat. Prod. 59 (1996) 927
42. Hamann M.T., Scheuer P.J., and Kelly-Borges M. J. Org. Chem. 58 (1993) 6565
43. Ross S.A., Weete J.D., Schinazi R.F., Wirtz S.S., Tharnish P., Scheuer P.J., and Hamann M.T. J. Nat. Prod. 63 (2000) 501
44. Xynas R., and Capon R.J. Aust. J. Chem. 42 (1989) 1427
45. Tsuda M., Shigemori H., Ishibashi M., and Kobayashi J. J. Nat. Prod. 55 (1992) 1325
46. Venkateswarlu, Venkatesham U., and Rao M.R. J. Nat. Prod. 62 (1999) 893
47. Venkateswarlu Y., Rao M.R., and Venkatesham U. J Nat. Prod. 61 (1998) 1388
48. Rao M.R., Venkatesham U., and Venkateswarlu Y. Ind. J. Chem. 38B (1999) 1301
49. Tsukamoto S., Kato H., Hirota H., and Fusetani N. J. Org. Chem. 61 (1996) 2936
50. Fu X., and Schmitz F.J. J. Nat. Prod. 62 (1999) 1072
51. Tsuda M., Endo T., Watanabe K., Fromont J., and Kobayashi J. J. Nat. Prod. 65 (2002) 1670
52. Faulkner D.J. Nat. Prod. Rep 18 (2001) 1
53. Kassuklke K.E., and Faulkner D.J. Tetrahedron 47 (1991) 1809
54. Borders B., Morton G.O., and Wetzel E.R. Tetrahedron Lett. (1974) 2709
55. Makarieva T.N., Stonik V.A., Alcolado P., and Elyakov Y.B. Comp. Biochem. Physiol. 68B (1981) 481
56. Fattorusso E., Minale L., Sodano G., Moody K., and Thomson R.H. J. Chem. Soc., Chem. Commun. (1970) 752
57. Fattorusso E., Minale L., Moody K., Sodano G., and Thomson R.H. Gazz. Chim. Ital. 101 (1971) 61
58. Moody K.R.H., Thomson E., Fattorusso L., and Minale G.S. J. Chem. Soc., Perkin Trans. 1 10 (1972) 18
59. Minale L. Pure Appl. Chem. 48 (1976) 7
60. McMillan J.A., Paul I.C., Goo Y.M., Rinehart K.L., Krueger W.C., and Pschigoda L.M. Tetrahedron Lett. 22 (1981) 39
61. Ciminiello P., Costantino V., Fattorusso E., Magno S., Mangoni A., and Pansini M. J. Nat. Prod. 57 (1994) 705
62. Gunasekera M., and Gunasekera S.P. J. Nat. Prod. 52 (1989) 753
63. Kernan M.R., Cambie R.C., and Bergquis P.R. J. Nat. Prod. 53 (1990) 615
64. Acosta A.L., and Rodriguez A.D. J. Nat. Prod. 55 (1992) 1007
65. Ciminiello P., Fattorusso E., Forino M., Magno S., and Pansini M. Tetrahedron 53 (1997) 6565
66. Saeki B.M., Granato A.C., Berlinck R.G.S., Magalhaes A., Schefer A.B., Ferreira A.G., Pinheiro U.S., and Hajdu E. J. Nat. Prod. 65 (2002) 796
67. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., Carrano L., and Pansini M. Tetrahedron 52 (1996) 9863
68. Gopichand Y., and Schmitz F.J. Tetrahedron Lett. (1979) 3921
69. Cimino G., De S., De Rosa S., De Stefano S., Self R., and Sodano G. Tetrahedron Lett. 24 (1983) 3029
70. König G.M., and Wright A.D. Heterocycles 36 (1993) 1351
71. Gunasekera S.P., and Cross S.S. J. Nat. Prod. 55 (1992) 509
72. Mancini I., Guella G., Laboute P., Debitus C., and Pietra F. J. Chem. Soc., Perkin Trans. 1 (1993) 3121
73. Compagnone R.S., Avila R., Suarez A.I., Abrams O.V., Rangel H.R., Arvelo F., Pina I.C., and Merentes E. J. Nat. Prod. 62 (1999) 1443
74. Kijjoa A., Watanadilok R., Sonchaeng P., Silva A.M.S., and Eaton G. Z. Naturforsch. 56c (2001) 1116
75. Takada N., Watanabe R., Suenaga K., Yamada K., Ueda K., Kita M., and Uemura D. Tetrahedron Lett. 42 (2001) 5265
76. D. Uemura, A. Takada, K. Suenaga, K. Yamada, and R. Watanabe, Jpn. Kokai Tokkyo Koho 8 pp. CODEN: JKXXAF JP 2002338554 A2 20021127. Application: JP 2001-144150 20010515 (2002).
77. Ciminiello P., Dell'Aversano C., Fattorusso E., and Magno S. Eur. J. Org. Chem. (2001) 55
78. Okamoto Y., Ojika M., Kato S., and Sakagami Y. Tetrahedron 56 (2000) 5813
79. Kobayashi J., Honma K., Sasaki T., and Tsuda M. Chem. Pharm. Bull. 43 (1995) 403
80. Aiello A., Fattorusso E., Menna M., and Pansini M. Biochem. Syst. & Ecol. 23 (1995) 377
81. Longeon A., Guyot M., and Vacelet J. Experientia 46 (1990) 548
82. James D.M., Kunze H.B., and Faulkner D.J. J. Nat. Prod. 54 (1991) 1137
83. Rodríguez A.D., and Pina I.C. J. Nat. Prod. 56 (1993) 907
84. Kobayashi J., Tsuda M., Agemi K., Shigemori H., Ishibashi M., Sasaki T., and Mikami Y. Tetrahedron 47 (1991) 6617
85. Kobayashi J., Tsuda M., Agemi K., Honma K., Shigemori H., Ishibashi M., and Sasaki T. Peptide Chem. 1995 (1996) 197
86. Tabudravu J.N., and Jaspars M. J. Nat. Prod. 65 (2002) 1798
87. Assmann M., Wray V., Van Soest R.W.M., and Proksch P. Z. Naturforsch. 53 (1998) 398
88. Fendert T., Wray V., Van Soest R.W.M., and Proksch P. Z. Naturforsch. 54c (1999) 246
89. Benharref A., and Païs M. J. Nat. Prod. 59 (1996) 177
90. Nicholas G.M., Newton G.L., Fahey R.C., and Bewley C.A. Organic Lett. 3 (2001) 1543
91. Nakamura H., Wu H., Kobayashi J., Nakamura Y., Ohizumi Y., and Hirata Y. Tetrahedron Lett. 26 (1985) 4517
92. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 62 (1999) 590
93. Kashman Y., Groweiss A., Carmely S., Kinamoni Z., Czarkie D., and Rotem M. Pure Appl. Chem. 54 (1982) 1995
94. Roll D.M., Chang C.W.J., Scheuer P.J., Gray G.A., Shoolery J.N., Matsumoto G.K., Van Duyne G.D., and Clardy J. J. Am. Chem. Soc. 107 (1985) 2916
95. Copp B.R., Ireland C.M., and Barrows L.R. J. Nat. Prod. 55 (1992) 822
96. Ichiba T., Scheuer P.J., and Kelly-Borges M. J. Org. Chem. 58 (1993) 4149
97. Liu S., Fu X., Schmitz F.J., and Kelly-Borges M. J. Nat. Prod. 60 (1997) 614
98. Tsukamoto S., Kato H., Hirota H., and Fusetani N. Tetrahedron 52 (1996) 8181
99. Litaudon M., and Guyot M. Tetrahedron Lett. 27 (1986) 4455
100. Thirionet I., Daloze D., and Braekman J.C. Nat. Prod. Lett. 12 (1998) 209
101. Mierzwa R., King A., Conover M.A., Tozzi S., Puar M.S., Patel M., and Coval S.J. J. Nat. Prod. 57 (1994) 175
102. Wu H., Nakamura H., Kobayashi J., Ohizumi Y., and Hirata Y. Experientia 42 (1986) 855
103. Kobayashi J., Honma K., Tsuda M., and Kosaka T. J. Nat. Prod. 58 (1995) 467
104. Ishibashi M., Tsuda M., Ohizumi Y., Sasaki T., and Kobayashi J. Experientia 47 (1991) 299
105. Tsuda M., Shigemori H., Ishibashi M., and Kobayashi J. Tetrahedron Lett. 33 (1992) 2597
106. Sakota N., Okita K., and Matsui Y. Bull. Soc. Jap. 43 (1970) 1138
107. Arabshahi L., and Schmitz F.J. J. Org. Chem. 52 (1987) 3584
108. Quinoa E., and Crews P. Tetrahedron Lett. 28 (1987) 3229
109. Rodriguez A.D., Akee R.K., and Scheuer P.J. Tetrahedron Lett. 28 (1987) 4989
110. Jimenez C., and Crews P. Tetrahedron 47 (1991) 2097
111. He H., Faulkner J.D., Shumsky J.S., Hong K., and Clardy J. J. Org. Chem. 54 (1989) 2511
112. Pina I.C., Gautschi J.T., Wang G., Sanders M.L., Schmitz F.J., France D., Cornell-Kennon S., Sambucetti L.C., Remiszewski S.W., Perez L.B., Bair K.W., and Crews P. J. Org. Chem. 68 (2003) 3866
113. Dumdei E., and Andersen R.J. J. Nat. Prod. 56 (1993) 792
114. Shin J., Lee H.-S., Seo Y., Rho J.-R., Cho K.W., and Paul V.J. Tetrahedron 56 (2000) 9071
115. Manes L.V., Crews P., Kernan M.P., Faulkner D.J., Fronczek F.R., and Gandour R.D. J. Org. Chem. 53 (1988) 570
116. Wright A.E., McCarthy P.J., and Schulte G.K. J. Org. Chem. 54 (1989) 3472
117. Park Y., Liu Y., Hong J., Lee C., Cho H., Kim D.-K., Im K.S., and Jung J.H. J. Nat. Prod. 66 (2003) 1495
118. Jurek J., Yoshida W.Y., Scheuer P.J., and Kelly-Borges M. J. Nat. Prod. 56 (1993) 1609
119. Pakrashi S.C., Achari B., Dutta P.K., Chakrabarti A.K., Giri C., Saha S., and Basa S. Tetrahedron 50 (1994) 12009
120. Pakrashi S.C., Achari B., Dutta P.K., Chakrabarti A.K., Giri C., Saha S., and Basa S. Tetrahedron 50 (1994) 12783
121. Yagi H., Matsunaga S., and Fusetani N. Tetrahedron 49 (1993) 3749
122. Goud T.V., Srinivasulu M., Reddy V.L.N., Reddy A.V., Rao T.P., Kumar D.S., Murty U.S., and Venkateswarlu Y. Chem. & Pharm. Bull. 51 (2003) 990
123. Fusetani N., Masuda Y., Nakao Y., Matsunaga S., and Van Soest R.W.M. Tetrahedron 57 (2001) 7507
124. Kernan M.R., Cambie R.C., and Bergquist P.R. J. Nat. Prod. 53 (1990) 720
125. Evan T., Rudi A., Ilan M., and Kashman Y. J. Nat. Prod. 64 (2001) 226
126. Tsuda M., Sakuma Y., and Kobayashi J. J. Nat. Prod. 64 (2001) 980
127. Carroll A.R., Bowden B.F., and Coll J.C. Aust. J. Chem. 46 (1993) 825
128. Kazlauskas R., Lidgard R.O., Murphy P.T., and Wells R.J. Tetrahedron Lett. 21 (1980) 2277
129. Kazlauskas R., Lidgard R.O., Murphy P.T., Wells R.J., and Blount J.F. Aust. J. Chem. 34 (1981) 765
130. Franklin M.A., Penn S.G., Lebrilla C.B., Lam T.H., Pessah I.N., and Molinski T.F. J. Nat. Prods. 59 (1996) 1121
131. Butler M.S., Lim T.K., Capon R.J., and Hammond L.S. Aust. J. Chem. 44 (1991) 287
132. Pordesimo E.O., and Schmitz F.J. J. Org. Chem. 55 (1990) 4704
133. Carney J.R., Scheuer P.J., and Kelly-Borges M. J. Nat. Prod. 56 (1993) 153
134. Dexter A.F., Garson M.J., and Hemling M.E. J. Nat. Prod. 56 (1993) 56
135. Park S.K., Jurek J., Carney J.R., and Scheuer P.J. J. Nat. Prod. 57 (1994) 407
136. Park S.K., Park H., and Scheuer P.J. Bull. Kor. Chem. Soc. 5 (1994) 534
137. Park S.K., Ryu J.K., and Scheuer P.J. Bull. Kor. Chem. Soc. 16 (1995) 677
138. Jaspars M., Rali T., Laney M., Schatzman R.C., Diaz M.C., Schmitz F.J., Pordesimo E.O., and Crews P. Tetrahedron 50 (1994) 7367
139. Mack M.M., Molinski T.F., Buck E.D., and Pessah I.N. J. Biol. Chem. 269 (1994) 23236
140. Coll J.C., Kearns P.S., Rideout J.A., and Sankar V. J. Nat. Prod. 65 (2002) 753
141. Gulavita N.K., Wright A.E., McCarthy P.J., Pomponi S.A., Kelly-Borges M., Chin M., and Sills M.A. J. Nat. Prod. 56 (1993) 1613
142. Miao S., Andersen R.J., and Allen T.M. J. Nat. Prod. 53 (1990) 1441
143. Pettit G.R., Butler M.S., Bass C.G., Doubek D.L., Williams M.D., Schmidt J.M., Pettit R.K., Hooper J.N.A., Tackett L.P., and Filliatrault M.J. J. Nat. Prod. 58 (1995) 680
144. Trost B.M., Belletire J.L., Godleski S., McDougal P.G., Balkovec J.M., Baldwin J.J., Christy M.E., Ponticello G.S., Varga S.L., and Springer J.P. J. Org. Chem. 51 (1986) 2370
145. Mcdonald L.A., Swersey J.C., Ireland C.M., Carroll A.R., Coll J.C., Bowden B.F., Fairchild C.R., and Cornell L. Tetrahedron 51 (1995) 5237
146. Costantino V., Fattorusso E., Mangoni A., and Pansini M. J. Nat. Prod. 57 (1994) 1552
147. Bergwuist R.P., and Wells R.J. In: Scheuer P.J. (Ed). Marine Natural Products: Chemical and Biological Perspectives V (1983), Academic Press, New York 12-22
148. Neidleman S.L., and Geigeert J. Biohalogenation: Principles, Basic Roles, and Applications (1986), Ellis Horwood Ltd., Chichester, UK 46-47
149. Kaestner A. Invertebrate Zoology I (1967), Wiley Interscience, New York 24
150. Gulavita N.K., Pomponi S.A., and Wright A.E. J. Nat. Prod. 58 (1995) 954
151. Manzo E., Van Soest R., Matainaho L., Roberge M., and Andersen R.J. Org. Lett. 5 (2003) 4591
152. Hirano K., Kubota T., Tsuda M., Watanabe K., Fromont J., and Kobayashi J. Tetrahedron 56 (2000) 8107
153. Lindquist N., and Fenical W. Tetrahedron Lett. 31 (1990) 2521
154. Bobzin S.C., and Faulkner D.J. J. Org. Chem 56 (1991) 4403
155. Kijjoa A., Watanadilok R., Sonchaeng P., Sawangwong P., Pedro M., Nascimento M.S.J., Silva A.M.S., Eaton G., and Herz W. Z. Naturforsch 57c (2002) 732
156. Zabriskie T.M., Klocke J.A., Ireland C.M., Marcus A.H., Molinski T.F., Faulkner D.J., Xu C., and Clardy J.C. J. Am. Chem. Soc. 108 (1986) 3123
157. Crews P., Manes L.V., and Boehler M. Tetrahedron Lett. 27 (1986) 2797
158. Chan W.R., Tinto W.F., Manchand P.S., and Todaro L.J. J. Org. Chem. 52 (1987) 3091
159. de Silva E.D., Andersen R.J., and Allen T.M. Tetrahedron Lett. 31 (1990) 489
160. Coleman J.E., de Silva E.D., Kong F., Andersen R.J., and Allen T.M. Tetrahedron 51 (1995) 10653
161. Tinto W.F., Lough A.J., McLean S., Reynolds W.F., Yu M., and Chan W.R. Tetrahedron 54 (1998) 4451
162. Talpir R., Benayahu Y., Kashman Y., Pannell L., and Schleyer M. Tetrahedron Lett. 35 (1994) 4453
163. D'Auria M.V., Paloma L.G., Minale L., Zampella A., Debitus C., and Perez J. J. Nat. Prod. 58 (1995) 121
164. Coleman J.E., Soest R.V., and Andersen R.J. J. Nat. Prod. 62 (1999) 1137
165. Jansen R., Kunze B., Reichenbach H., and Hoefle G. Liebigs Ann. (1996) 285
166. Kunze B., Jansen R., Sasse F., Hoefle G., and Reichenbach H. J. Antibiot. 48 (1995) 1262
167. Rudi A., Goldberg I., Stein Z., Frolow F., Benayahu Y., Schleyer M., and Kashman Y. J. Org. Chem. 59 (1994) 999
168. Rudi A., Evan T., Aknin M., and Kashman Y. J. Nat. Prod. 63 (2000) 832
169. Andersen R.J., Faulkner D.J., He C.H., Van Duyne G.D., and Clardy J. J. Am. Chem. Soc. 107 (1985) 5492
170. Lindquist N., Fenical W., Van Duyne G.D., and Clardy J. J. Org. Chem. 53 (1988) 4570
171. Carroll A.R., Bowden B.F., and Coll J.C. Aust. J. Chem. 46 (1993) 489
172. Leete E. Techniques of Organic Chemistry XI, Part I (1963), Wiley Interscience Publishers, New York 437
173. Kasperek G.J., Bruice T.C., Yagi H., Kaubisch N., and Jerina D.M. J. Am. Chem. Soc. 94 (1972) 7876
174. Stowe B.B. Progress in the Chemistry of Organic Natural Products 17 (1959), Springer, Vienna 248
175. De Rosa M., Minale L., and Sodano G. Comp. Biochem. Physiol. 45 (1973) 883
176. Tymiak A.A., and Rinehart K.L. J. Am. Chem. Soc. 103 (1981) 6763
177. Weiss U.U., and Edward J.M. The Biosynthesis of Aromatic Compounds (1980), Wiley, New York 144
178. Nozaki M. Top. Curr. Chem. 78 (1975) 145
179. Saito I., Chujo Y., Shimazu H., Yamane M., Matsuura T., and Cahnmann H.J. J. Am. Chem. Soc. 97 (1975) 5272
180. Ahmad A., and Spenser I.D. Can. J. Chem. 39 (1961) 1340
181. Tapper B.A., Conn E.E., and Butler G.W. Arch. Biochem. Biophys. 119 (1967) 593
182. Bicchierini N., Cavazza M., Nucci L., Pergola F., and Pietra F. Tetrahedron Lett. 32 (1991) 4039
183. Cimino G., DeStefano S., and Minale L. Experientia 31 (1975) 756
184. Carney J.R., and Rinehart K.L. J. Nat. Prod. 58 (1995) 971
185. Goo Y.M. Diss. Abstr. Int. B 41 (1980) 569
186. Cavazza M., Guella G., Nucci L., Pergola F., Bicchierini N., and Pietra F. J. Chem., Soc. Perkin Trans. 1 (1993) 3117
187. a) A. Rieker, in "Methoden der Organischen Chimie (Houben-Weyl)" Band VII-3b, (G. Thieme Verlag, ed.), p. 524. Stuttgart, 1979; b)"Rodd's Chemistry of Carbon Compounds", Part III A Supplement, (S. Coffy, Elsevier, AÁmsterdam), p. 174 (1983)
188. a) D. H. R. Barton, Proc. Chem. Soc. 293 (1963); b) A. I. Scott, Quart. Rev. 19, 1 (1965); c) S. Natori, in "Natural Products Chemistry", (K. Nakanishi, T. Goto, S. Ito, S. Natori, and S. Nozoe, ed), Vol. 2 p. 182. Kodanska Ltd., Academic Press, New York, (1975); d) T. A. Geissman and G. Crout, "Organic Chemistry of Secondary Plant Metabolism", p. 383. Freeman, Cooper & Company, San Francisco, (1969).
189. Cavazza M., Guella G., Nucci L., Pergola F., Bicchierini N., and Pietra F. J. Chem. Soc., Perkin Trans. 1 (1993) 3117
190. Cavazza M., Guella G., Nucci L., Pergola F., Bicchierini N., and Pietra F. J. Chem. Soc., Perkin Trans. 1 (1995) 1199
191. Vogel E., and Günther H. Angew. Chem., Int. Ed. Engl. 6 (1967) 385
192. Neuss N., Nagarajan R., Molly B.B., and Huckstep L.L. Tetrahedron Lett. (1968) 4467
193. Brannon D.R.M.J.A., Molloy B.B., and Day W.A. Biochem. Biophys. Res. Commun. 43 (1971) 588
194. Johnson T.B., and Bengis R. J. Am. Chem. Soc. 34 (1912) 1061
195. Fisher A., and Henderson G.N. Tetrahedron Lett. 24 (1983) 131
196. Andersen R.J., and Faulkner D.J. J. Am. Chem. Soc. 94 (1975) 936
197. Schoenfeld R.C., and Ganem B. Tetrahedron Lett. 39 (1998) 4147
198. Schoenfeld R.C., Lumb J.P., Fantini J., and Ganem B. Bioorg. Med. Chem. Lett. 10 (2000) 2679
199. Schoenfeld R.C., Conova S., Rittschof D., and Ganem B. Bioorg. Med. Chem. Lett. 12 (2002) 823
200. Hoshino O., Murakata M., and Yamada K. Bioorg. Med. Chem. Lett. 2 (1992) 1561
201. Nicolaou K.C., Hughes R., Pfefferkorn J.A., Barluenga S., and Roecker A.J. Chem. Eur. J. 7 (2001) 4280
202. Lehn J.-M. Chem. Eur. J. 5 (1999) 2455
203. Otto S., Furlan R.L.E., and Sanders J.K.M. J. Am. Soc. Chem. 122 (2001) 12063
204. Lees W.J., and Whitesides G.M. J. Org. Chem. 58 (1993) 642
205. Boehlow T.R., Harburn J.J., and Spilling C.D. J. Org. Chem. 66 (2001) 3111
206. Forrester A.R., Thomson R.H., and Woo S.-O. J. Chem. Soc., Perkin Trans. 1 (1975) 2340
207. Forrester A.R., Thomson R.H., and Woo S.-O. J. Chem. Soc., Chem. Comm. (1973) 604
208. Forrester A.R., Thomson R.H., and Woo S.-O. J. Chem. Soc., Perkin Trans. 1 (1975) 2348
209. Boehlow T.R., and Spilling C.D. Nat. Prod. Lett. 7 (1995) 1
210. Conte V., Furi F.D., and Moro S. Tetrahedron Lett. 35 (1994) 7429
211. Noda H., Niwa M., and Yamamura S. Tetrahedron Lett. 22 (1981) 3247
212. Kacan M., Koyuncu D., and McKillop A. J. Chem. Soc., Perkin Trans. 1 (1993) 1771
213. Nishiyama S., and Yamamura S. Tetrahedron Lett. 24 (1983) 3351
214. Murakata M., Yamada K., and Hocino O. Tetrahedron 52 (1996) 14713
215. Murakata M., Tamura M., and Hoshino O. J. Org. Chem. 62 (1997) 4428
216. Forrester A.R., Thomson R.H., and Woo S.-O. Justus Liebigs Ann. Chem. (1978) 66
217. Nishiyama S., and Yamamura S. Bull. Chem. Soc. Jap. 58 (1985) 3453
218. Wasserman H.H., Ennis D.W., Power P.L., and Mitchell J.R. J. Org. Chem. 58 (1993) 4785
219. Wasserman H.H., and Ho W.B. J. Org. Chem. 59 (1994) 4364
220. Wasserman H.H., and Peterson A.K. Tetrahedron Lett. 38 (1997) 953
221. Wasserman H.H., and Peterson A.K. J. Org. Chem. 62 (1997) 8972
222. Wasserman H.H., and Wang J. J. Org. Chem. 63 (1998) 5581
223. Murakata M., Yamada K., and Hoshino O. Heterocycles 47 (1998) 921
224. Winterfeldt E. Chem. Rev. 93 (1993) 827
225. Borm C., Meibom D., and Winterfeldt E. Chem. Commun. (1996) 887
226. Winterfeldt E., Borm C., and Nerenz F. Advances in Asymmetric Synthesis 2 (1997) 1
227. P. G. Jones, H. Weinmann, and E. Winterfelt, Angew. Chem. 107, 489 (1995); Angew. Chem. Int. Ed. 34, 448 (1995).
228. Beil W., Jones P.G., Nerenz F., and Winterfeldt E. Tetrahedron 54 (1998) 7273
229. Goldenstein K., Fendert T., Proksch P., and Winterfeldt E. Tetrahedron 56 (2000) 4173
230. Noda H., Niwa M., and Yamamura S. Tetrahedron Lett. 22 (1981) 3247
231. Nishiyama S., Suzuki T., and Yamamura S. Chem. Lett. (1982) 1851
232. Nishiyama S., and Yamamura S. Tetrahedron Lett. 23 (1982) 1281
233. Nishiyama S., and Yamamura S. Tetrahedron Lett. 23 (1982) 3699
234. Guo Z.W., Machiya K., Salamonczyk G.M., and Sih C.J. J. Org. Chem. 63 (1998) 4269
235. Guo Z.W., Salamonczyk G.M., Han K., Machiya K., and Sih C.J. J. Org. Chem. 62 (1997) 6700
236. E. A. Couladouros, V. I. Moutsos, and E. N. Pitsinos, ARKIVOC (Gainesville, FL, United States) 92 (2003). http://www.arkat-usa.org/ark/journal/2003/General_Part(xv)/AV-910A/910A. pdf.
237. Couladouros E.A., and Moutsos V.I. Tetrahedron Lett. 40 (1999) 7027
238. Couladouros E.A., and Moutsos V.I. Tetrahedron Lett. 40 (1999) 7023
239. Carreno M.C., Ruano J.G., Sanz G., Toledo M.A., and Urbano A. J. Org. Chem. 60 (1995) 5328
240. Bailey K.L., and Molinski T.F. J. Org. Chem. 64 (1999) 2500
241. Bailey K.L., and Molinski T.F. Tetrahedron Lett. 43 (2002) 9657
242. Masuno M.N., and Molinski T.F. J. Nat. Prod. 66 (2003) 112
243. Leone-Stumpf D., and Lindel T. Chem. Eur. J. 7 (2001) 3961
244. Leone-Stumpf D., and Lindel T. Eur. J. Org. Chem. (2003) 1853
245. Andreas K.T., Caroline R., and Wolfgang S. Org. Lett. 4 (2002) 3287
246. Grieco P.A., Hon Y.S., and Perez-Medrano A. J. Am. Chem. Soc. 110 (1988) 1630
247. Chan W.R., Tinto W.F., Manchand P.S., and Todaro L.J. J. Org. Chem. 52 (1987) 3091
248. Grieco P.A., and Perez-Medrano A.A. Tetrahedron Lett. 29 (1988) 4225
249. Irreland C.M., Molinski T.F., Roll D.M., Zabriskie T.M., Mckee T.C., Swersey J.C., and Foster M.P. In: Scheuer P.J. (Ed). Bioorganic Marine Chemistry 3 (1989), Springer-Verlag, New York 1
250. Shield L.S., and Rinehart Jr. K.L. Antibiotics. Isolation, Separation and Purification (1978), Elsevier, New York 309
251. Hashimoto Y. Marine Toxins and Other Bioactive Marine Metabolites (1976), Japan Scientific Societies Press, Tokyo 245
252. Teeyapant R., Woerdenbag H.J., Kreis P., Hacker J., Wray V., Witte L., and Proksch P. Z. Naturforsch. 48c (1993) 939
253. Peng J., Shen X., El Sayed K.A., Dunbar D.C., Perry T.L., Wilkins S.P., and Hamann M.T. J. Food Agr. Chem. 51 (2003) 2246
254. Encarnacion-Dimayuga R., Ramirez M.R., and Luna-Herrera J. Pharm. Bio. 41 (2003) 384
255. El Sayed K.A., Bartyzel P., Shen X., Perry T.L., Zjawiony J.K., and Hamann M.T. Tetrahedron 56 (2000) 949
256. Nicolaou K.C., Hughes R., Pfefferkorn J.A., Barluenga S., and Roecker A.J. Chem. Eur. J. 7 (2001) 4280
257. Nicolaou K.C., Hughes R., Pfefferkorn J.A., and Barluenga S. Chem. Eur. J. 7 (2001) 4280
258. Kim D., Lee II.S., Jung J.H., and Yang S.II. Arch. Pharm. Res. 22 (1999) 25
259. Burkholder P.R. In: Jones O.A., and Endean R. (Eds). Biology and Geology of Coral Reefs (1973), Academic Press, New York 117
260. Breakman J.C., and Daloze D. Pure Appl. Chem. 58 (1986) 357
261. MaCaffrey E.J., and Endean R. Mar. Biol. 89 (1985) 1
262. Weiss B., Ebel R., Elbraechter M., Kirchner M., and Proksch P. Biochem. System. Ecol. 24 (1996) 1
263. Bulich A.A., Ker-Kong T., and Scheibner G. J. Bioluminesc. Chemoluminesc. 5 (1990) 71
264. Lawton L.A., Campbell D.L., and Beattie K.A. Lett. Appl. Microbiol. 11 (1990) 205
265. Teeyapant R., Kreis P., Wray V., Witte L., and Proksch P. Z. Naturforsch. 48c (1993) 640
266. Proksch P. Dtsch. Apoth. Ztg. 134 (1994) 5069
267. Kreuter M.H., Bernd A., Holzmann H., Müller-Klieser W., Maidhof A., Weiβmann N., Kljajic Z., and Batel R. Z. Naturforsch. 44c (1989) 680
268. W. E. G. Müeller and M. H. Kreuter, Ger. Offen. CODEN: GWXXBX DE 3737108 A1 19890511, (1989). CAN 112:91780.
269. Müller W.E.G., Rohde H.J., Beyer R., Maidhof A., Bachmann M., Taschner H., and Zahn R.K. Cancer Res. 35 (1975) 2160
270. Müller W.E.G., Zahn R.K., Maidhof A., Beyer R., and Arendes J. Chem.-Biol. Interact. 23 (1978) 141
271. Müller W.E.G., Maidhof A., Arendes J., Geurtsen W., Zahn R.K., and Schmidseder R. Cancer Res. 39 (1979) 3768
272. Müller W.E.G., Obermeier J., Maidhof A., and Zahn R.K. Chem.-Biol. Interact. 8 (1974) 183
273. Oda Y., Nakamura S., Oki I., Kato T., and Shinagawa H. Mut. Res. 147 (1985) 219
274. Corbett T.H., Leopold W.R., Dykes D.J., Roberts B.J., Griswold D.P., and Schabel F.W. Cancer Res. 42 (1982) 1707
275. Kreuter M.H., Leake R.E., Rinaldi F., Mueller-Klieser W., Maidhof A., Mueller W.E.G., and Schroeder H.C. Comp. Biochem. Physiol. B Comp. Biochem. 97 (1990) 151
276. Pepinsky R.B., and Sinclair L.K. Nature, Lond. 321 (1986) 81
277. Kreuter M.H., Robitzki A., Chang S., Steffen R., Michaelis M., Kljajic Z., Bachmann M., Schroder H.C., and Muller W.E.G. Comp. Biochem. Physiol. C Comp. Pharmacol. 101 (1992) 183
278. Koulman A., Proksch P., Beekman R.A.C.E., Uden W.V., Konings A.W.T., Pedersen J.A., Pras N., and Woerdenbag H.J. J. Nat. Prod. 59 (1996) 591
279. Meister A. Science 220 (1982) 472
280. Arrick B.A., and Nathan C.F. Cancer Res. 44 (1984) 4224
281. Workman P. Oncology Res. 6 (1994) 461
282. Rodriguez-Nieto S., Gonzalez-Iriarte M., Carmona R., Munoz-Chapuli R., Medina M.A., and Quesada A.R. FASEB J. 16 (2002) 261
283. A. R. Quesada, M. A. M. Torres, R. M. Chapuli, and J. L. F. Puentes, "Aeroplysinin-1 and related compounds for the treatment of angiogenic diseases" PCT Int. Appl., pp. 14, CODEN: PIXXD2 WO 2002043718 A2 20020606 (2002)
284. Folkman J. N. Engl. J. Med. 285 (1971) 1182
285. Harris A.L. Recent Results Cancer Res. 152 (1998) 341
286. Paleolog E.M., and Miotla J.M. Angiogenesis 2 (1998) 295
287. Perez L.B., Bair K.W., Karl D., Green M.A., Lamberson C., Remiszewski S.W., and Sambucetti L.C. Proc. 92nd AACR 42 (2001) 927
288. Shim S.S., Lee H.-S., Shin J., and Kwon H.J. Cancer Lett. 203 (2004) 163
289. Layman P.L. Chem. Eng. News, May 1 (1995) 23
290. Pawlik J.R. Chem. Rev. 93 (1993) 191
291. Clare A.S., Rittschof D., Gerhart D.J., and Maki J.S. Invert. Reprod. Dev. 22 (1992) 67
292. Thompson J.E. Mar. Biol. 88 (1985) 23
293. Teeyapan R., and Proksch P. Naturwissenschaften 80 (1993) 369
294. Yamada A., Kitamura H., Yamaguchi K., Fukuzawa S., Kamijima C., Yazawa K., Kuramoto M., Wang G.-Y.-S., Fujitani Y., and Uemura D. Bull. Chem. Soc. Jap. 70 (1997) 3061
295. Diers J.A., Pennaka H.K., Peng J., Bowling J.J., Duke S.O., and Hamann M.T. J. Nat. Prod. 67 (2004)
296. Takito J., Nakamura H., Kobayashi J., Ohizumi Y., Ebisawa K., and Nonomura Y. J. Biol. Chem. 261 (1986) 13861
297. Fang Y.-II., Yokota E., Mabuchi I., Nakamura H., and Ohizumi Y. Biochemistry 36 (1997) 15561
298. Nakamura Y., Kobayashi M., Nakamura H., Wu H., Kobayashi J., and Ohizumi Y. Eur. J. Biochem. 167 (1987) 1
299. E. Nakamura, J. Kobayashi, Y. Nakamura, and Y. Oizumi, "Tyrosine derivatives and salts" Jpn. Kokai Tokkyo Koho CODEN: JKXXAF JP 61130274 A2 19860618 (1986). CAN 107:111799.
300. Takito J., Nakamura H., Kobayashi J., and Ohizumi Y. Biochim. Biophys. Acta 912 (1987) 404
301. Takito J., Ohizumi Y., Nakamura H., Kobayashi J., Ebisawa K., and Nonomura Y. Euro. J. Pharmacol. 142 (1987) 189
302. Yoshida M., Kijima M., Akita M., and Beppu T. J. Biol. Chem. 265 (1990) 17174
303. Kijima M., Yoshida M., Sugita K., Horinouchi S., and Beppu T. J. Biol. Chem. 268 (1993) 22429
304. Remiszewski S.W., Sambucetti L.C., Atadja P., Bair K.W., Cornell W.D., Green M.A., Howell K.L., Jung M., Kwon P., Trogani N., and Walker H. J. Med. Chem. 45 (2002) 753
305. Remiszewski S.W., Sambucetti L.C., Atadja P., Bair K.W., Cesarz D., Chandramouli N., Cheung M., Cornell W., Dean K., Green M.A., Howell K.L., Lassota P., Sorensen E., Sheng T., Taplin F., Trogani N., Versace R., Walker H., and Wood A. Proc.92nd AACR 43 (2002) 740
306. Barre-Sinoussl F., Chermann J.C., Rey F., Nugeyre M.T., Chamarel S., Gruest J., Daguet C., Axler-Blin C., Vezlnet-Brun F., Rozenbaum C., and Monlagnler L. Science 220 (1983) 868
307. Loya S., Rudi A., Kashman Y., and Hizi A. Biochem. J. 344 (1999) 85
308. Chen L., Molinski T.F., and Pessah I.N. J. Biol.Chem. 274 (1999) 32603
309. Gonzalez A., Kirsch W.G., Shirokova N., Pizarro G., Brum G., Pessah I.N., Stern M.D., Cheng H., and Rios E. Proc. Natl. Acad. Sci. 97 (2000) 4380
310. DiJulio D.H., Watson E.L., Pessah I.N., Jacobson K.L., Ott S.M., Buck E.D., and Singh J.C. J. Biol. Chem. 272 (1997) 15687
311. Kotte A., Myers J., Shih N.-Y., Egan R.W., and Clark M.A. Biochem. Biophys. Res. Commun. 168 (1990) 979
312. Trzeciakowski J.P. J. Pharmacol. Exp. Ther. 243 (1987) 874
313. 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., Wirtz S., Tharnish P.M., and Hamann M.T. Mini Rev. Med. Chem. 3 (2003) 451