Recent developments with 1,2,4-trioxane- type artemisinin analogues

Current Organic Chemistry

Volumn 7, Issue 12, 2003, Pages 1231-1255

  Bez, G ^a   Kalita, B ^a   Sarmah, P ^a   Barua, N C ^a   Dutta, D K ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL CHEMISTRY; MOLECULAR GRAPHICS; MOLECULES; PHARMACODYNAMICS; SYNTHESIS (CHEMICAL);

ANTIMALARIAL DRUG; ARTEMISININ; ARTEMISININ ANALOGS; ENDOPEROXIDES; MECHANISM OF ACTION; PHARMACOPHORES; SESQUITERPENE LACTONES; SIMPLE++; TOTAL SYNTHESIS; TRIOXANE;

TOXICITY;

1,2,3 TRIOXANE; 1,2,4 TRIOXANE DERIVATIVE; 1,2,4 TRIOXEPANE DERIVATIVE; 1,2,5 TRIOSASPIRO[5.5]UNDECANE; 12 METHOXYTRIOXANE DERIVATIVE; 12 O TRIMETHYLSILYL DEHYDROARTEMISININ DERIVATIVE; 2,3 DESETHANO 12 DEOXOARTEMISININ DERIVATIVE; 3BETA HYDROXYARTEMISININ; 3BETA HYDROXYDIHYDROARTEMISINIC ACID; 4,5 SECOARTEMISININ; 5 (9 ANTHRYLAMINO) 1,2,4 TRIOXANE; 5 NOE 4,5 SECOARTEMISININ; 6,7,10 TRIOXASPIRO[4.5]DECANE; 8A,9 SECOARTEMISININ; ANTIMALARIAL AGENT; ARTEETHER; ARTELINIC ACID; ARTEMETHER; ARTEMISININ; ARTEMISININ DERIVATIVE; ARTESUNATE; CHLOROQUINE; DEHYDROARTEMISININ DERIVATIVE; DEOXOARTEMISININ DERIVATIVE; DESETHANOARTEMISININ DERIVATIVE; DIHYDROARTEMISININ DERIVATIVE; FLUOROBENZYL ETHER TRIOXANE; MONOFLUOROOLEFIN; QUININE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIMALARIAL ACTIVITY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; MALARIA; NONHUMAN; PHARMACOPHORE; PLASMODIUM FALCIPARUM; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW;

EID: 0038607734     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486549     Document Type: Review

References (172)

1. White, N.J. J. Antimicro. Chemether, 1992, 30, 571.
2. World Health Organisation, Practical Chemotherapy of Malarias Report of a WHO Scientific Group, Geneva, WHO, 1990.
3. Kozarsky, P.E.; Lober, H.O. Curr. Opin. Infect. Dis. 1994, 701.
4. News from the WHO Division of Control of Tropical Disease, TDR News 1994, 46, 5.
5. Foley, M.; Tilley, L. Int. J. Parasitol. 1997, 27, 213.
6. Bordoloi, M.J.; Shukla, V.S.; Nath, S.C.; Sharma, R.P. Phytochemistry, 1989, 28, 2007.
7. Lin, J. M.; Ni, M-Y, Y-; Tou, Y.-Y.; Wa, Z.-H.; Wu, Y.-L.; Chou, W.-S. Acta Chim. Sinica, 1979, 37, 129.
8. Klayman, D.L. Science, 1985, 228, 1049.
9. Butter, A.R.; Wu, Y.L. Chem. Soc. Rev., 1992, 85.
10. (a) Mei-Y., Z.; Land-Na, L. Tetrahedron, 1983, 39, 2942.
11. (b) Klayman, D.L. Science, 1985, 50, 1994;
12. (d) Wolfgang, J. Synform, 1986, 4, 34;
13. (e) Zhou, W.S.; Xu, X. Staud. Nat. Prod. Chem., 1989, 3, 495.
14. Roth, R.J.; Acton, N. J. Nat. Prod., 1989, 52, 1189.
15. Haynes, A.K.; Vonwiller, S.C. J. Chem. Soc. Chem. Commun., 1990, 451.
16. Ye, B.; Wu, Y.-L. J. Chem. Soc. Chem. Commun., 1990, 726.
17. Roth, R.J.; Acton, N. J. Chem. Educ., 1991, 68, 612.
18. Lansbury, P.T.; Nowak, D.M. Tetrahedron Lett., 1992, 33, 1029.
19. Schmidt, G.; Hofheinz, W. J. Am. Chem. Soc., 1983, 105, 624.
20. Zhou, W.S. Pure & Appl. Chem., 1986, 58, 817.
21. Xu, X.-X.; Zhu, J.; Huang, D.-Z.; Zhou, W.-S. Tetrahedron, 1986, 42, 819.
22. Avery, M.M.A.; Jennings-White, C.; Chong, W.K.M. Tetrahedron Lett., 1987, 28, 4629.
23. Robindranathan, T.; Kumar, M.A.; Chong, W.K.M. Tetrahedron Lett., 1990, 31, 755.
24. Zaman, S.S.; Sharma, R.P. Heterocycles, 1991, 32, 1593.
25. Avery, M.A.; Chong, W.K.M.; Jennings-White, C. J Am Chem Soc., 1992, 114, 974.
26. China Co-operative Research Group on Qinghouso and its derivative as anti-malarial. J. Tradit. Chin. Med., 1982, 2, 9.
27. China Co-operative Research Group on Qinghouso and its derivative as anti-malarial, J. Tradit. Chin. Med., 1982, 2, 45.
28. China Co-operative Research Group on Qinghouso and its derivatives as antimalarials, J. Tradit. Chin. Med., 1982, 2, 25.
29. Lee, I.S.; Mufford, C.D. Pharmacol Ther, 1990, 48, 345.
30. Wong, T.; Xu, R. J. Tradit. Chin. Med., 1985, 5, 240.
31. Lin, J.A.; Klaymann, D.L.; Milhouse, W.K. J. Med. Chem., 1987, 30, 447.
32. Yang, Q.; Shi, W.; Li, R. J. Gan, Tradit. Chem. Med., 1982, 2, 99.
33. a) Jefford, W.C.; Kohmoto, S.; Boukouvalas, J.; Burger, U. J. Am. Chem. Soc., 1983, 105, 6498.
34. b) Kepler, J.A.; Philip, A.; Lee, Y.W.; Morey, M.C.; Caroll, F.I. J. Med., Chem., 1988, 31, 713;
35. c) Nojima, M.; Kasabayaski, S. J. Chem. Soc., Perkin Trans I., 1998, 31, 713
36. d) Avery, M.A.; Jenning-White, C.; Chong, W.K.M. J. Org. Chem., 1989, 54, 1792
37. e) Singh, C. Tetrahedron Lett., 1990, 31, 6901
38. f) Bloodworth, A.J.; Saha, A. J. Chem. Soc. Chem. Commun., 1991, 947
39. g) Posner, G.H.; Oh, C.H.; Milhouse, W. Tetrahedron Lett., 1991, 32, 4235
40. h) Bunnelle, W.H.; Isbell, T.A.; Bernes, C.L.; Qualls, S. J. Am. Chem. Soc., 1991, 113, 8168
41. i) Jefford, C.W. Chem. Soc. Rev., 1993, 22, 59.
42. j) Singh, C. Ind. J. Chem., 1993, 32B, 291.
43. k) Bloodworth, A.J.; Johnson, K.A. Tetrahedron Lett., 1994, 35, 8057.
44. Lee, K.H.; Furukawa, H.; Huang, E.S. J. Med. Chem., 1972, 15, 609.
45. Lee, K.H.; Meck, R.; Raintadoshi, C.; Huang, E.S. J. Med. Chem., 1973, 299.
46. Lee, K.H.; Kim, S.H.; Raintadoshi, C.; Huang, E.S. J. Med. Chem., 1975, 59.
47. Lee, K.H.; Ibuka, T.; Simo, D.; Muraoka, O.; Kiyohawa, H.; Hall, I.H.; Kim, H.L. J. Med. Chem., 1981, 24, 924.
48. Waddell, T.G.; Austin, A.M.; Cochran, J.W.; Grerhart, K.G.; Hall, J.H.; Lee, K.H. J. Pharm. Sci., 1979, 68, 715.
49. (a) Lee, K.H.; Huang, H.C.; Huang, E.S.; Furuzaka, H. J. Pharm. Sci., 1972, 61, 629
50. (b) Tani, S.; Fukamiya, N.; Kiyokawa, H.; Masallam, H.A.; Pick, R.P.; Lee, K.H. J. Med. Chem., 1985, 28, 1743
51. (a) Johnan, W. Synform 1986, 4 (1), 34 (Eng)
52. (b) Luo, X.D.; Shen, C.C. Med. Res. Rev. 1987, 7(1), 29 (Eng)
53. (c) Zhou, W. Pure Appl. Chem., 1986, 58 (5), 817 (Eng)
54. (d) Gu, H. Int. Cong. Ser - Excerpta Med. 1987, 750 (Pharmacology), 657 (Eng)
55. (e) Jefford, C.W.; Fero, S.; Moulin, M.C.; Valarde, J.; Jaggi, D.; Kohmoto, S.; Richardson, G.D.; Godoy, J.; Rossier, J.C. NewTrend. Nat. Prod. Chem. 1986; 163 (Eng)
56. (f) Zaman, S.S.; Sharma, R.P. Heterocycle 1991, 32 (8), 1593
57. (g) Webstar, H.K.; Lehnert, E.K. Trans R. Soc. Trop. Med. Hyg. 1994, 88(Suppl. 1), 27 (Eng)
58. (j) Zhou, W.-S.; Xu, X. Acad. Chem. Res., 1994, 27(7), 211 (Eng)
59. (h) Avery, M.A. Adv. Med. Chem., 1999, 4, 125 (Eng)
60. (i) Vromany, J.A.; Mari, A.-G.; Avery, M.A. Curr. Pharm Des. 1999, 5(2), 101 (Eng)
61. (j) Bhattacharya, A.K.; Sharma, R.P. Heterocycles, 1999, 51(7), 1681.
62. China Co-operative Research Group. J. Trad. Chinese Med., 1982, 2, 9.
63. Cao, M.Z.; Hu, S.C.; Li, M.H.; Zhang, S. Nanjing Yaoxueyuan Xuebao, 1982, 18, 53.
64. O'Neill, P.M.; Miller, A.; Bishop, L.P.D.; Stephen, H.; Maggs, J.L.; Ward, S.A.; Roberts, S.M.; Scheinmann, F.; Stachulskii, A.V.; Posner, G.H.; Park, B.K. J. Med. Chem., 2001, 44, 58.
65. Fishwick, J.; McClean, W.G.; Edwards, G.; Ward, S.A. Chem. Biol. Interact., 1995, 96, 263.
66. (a) Grade, J.M.; Aguilar, A.J.; Trotman, K.M.; Brewer, T.G.; Drug. Metab. Dispos., 1998, 26, 313
67. (b) Maggs, J.A.; Bishop, L.P.D.; Edwards, G.; O'Neill, P.M.; Ward, S.A.; Winstanley, P.A.; Park, B.K. Drug. Metab. Dispos., 2000, 28, 209.
68. O'Neill, P.M.; Miller, A.; Ward, A.S.; Park, B.K.; Scheinmann, F.; Stachulskii, A.V. Tetrahedron Lett., 1999, 40, 9129.
69. Lin, A.J.; Li, L.-Q.; Anderson, S.L.; Klayman, J. Med. Chem. 1992, 35, 1639.
70. O'Neill, P.M.; Scheinmann, F.; Stachulski, A.V.; Maggs, J.L.; Park, B.K. J. Med. Chem. 2001, 44, 1467.
71. Maggs, J.L.; Baty, K.T.; Ilett, K.F.; Edwards, G.; Park, B.K. Br. J. Chim. Pharmacol. 1998, 46, 2931.
72. Brown, R.T.; Scheinmann, F.; Stachulski, A.V. J. Chem. Res. (S) 1997, 370.
73. Brown, R.T.; Carter, N.E.; Lumbard, K.W.; Scheinmann, F. Tetrahedron Lett., 1995, 36, 8661.
74. Li, Y.; Zhu, Y.-M.; Jiang, H.-J.; Pan, J.-P.; Wu G.-S. Wu J.-M.; Shi, Y.-L,; Yang, J.-D.; Wu, B.-A. J. Med. Chem. 2000, 43, 1935.
75. Yu, P.L.; Cheng, Y.X.; Li, Y.; Ji, R.Y. Acta Pharm. Sin., 1985, 20, 357.
76. Venugopalan, B.; Karonik, P.J.; Bapat, C.P.; Chatterjee, P.K.; Iyer, N.; Lepcha, D. Eur. J. Med. Chem., 1995, 30, 697.
77. Li, Y.; Lu, D.W.; Zhang, W.B. Chem. Lett., 1993, 4, 99.
78. Li, Y.; Zhang, H.B.; Ya, Y.P. Chin. J. Med. Chem. 1995, 5, 127.
79. Luo, X.-D.; Shen, C.C. Med. Res. Rev. 1987, 7, 29.
80. Posner, G.H.; McGarvey, D.J.; Oh, C.H.; Kuman, N.; Meshnick, S.R.; Asawamahasadka, W. J. Med. Chem. 1995, 38, 607.
81. Adovelande, J.; Boulard, Y.; Berry, J.P.; Galle, P.; Slodzian, G. Chem. Engg. News 1995, Feb 27, 39.
82. Adovelande, J.; Boulard, Y.; Berry, J.P.; Galle, P.; Slodzian, G. Biol. Cell. 1994, 81, 185.
83. Ming Pu,Y.; Torok, P.S.; Ziffer, H. J. Med. Chem. 1995, 38, 4120.
84. Hu, Y.; Ziffer, H.; Li, G.; Yeh, H.J.C. Bioorg. Chem. 992, 20, 148.
85. Nga, T.T.T.; Menage, C.; Begue, J.-P.; Bonnel-Deepon, D.; Gantier, J.-C.; Pradines, B.; Doury, J.-C.; Thac, T.D. J. Med. Chem. 1998, 41, 4101.
86. Ma, J.; Katz, E.; Ziffer, H. Tetrahedron Lett., 1994, 35, 8543.
87. O'Neill, P.M.; Searle, N.L.; Kan. K.-W.; Storr, R.L.; Maggs, J.L.; Ward, S.A.; Raynes, K.; Park, B.K. J. Med. Chem., 1999, 42, 5487.
88. Ma, J.; Katz, E.; Kayle, D.E. and Herman Ziffer. J. Med. Chem. 2000, 43, 4228.
89. Prakash,; G.K.S.; Krishnamurti, R.; Olah, G.A. J. Am. Chem. Soc. 1989, 111, 393
90. Dondoni, A.; Schermann, M. C. J. Org. Chem. 1994, 59, 6404.
91. Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275.
92. O'Dowd, H., Ploypradith, P.; Suji, X.; Shapiro, T.A.; Posner, G.H. Tetrahedron. 1999, 55, 3625.
93. Ley, V.S.; Norman, J.; Griffith, W.P.; Marsden, S. P. Synthesis, 1994, 639.
94. Wang, D.-Y.; Wu, Y.; Wu, Y.-L.; Li Y.; Shan, F. J. Chem. Soc. Perkin Trans. I, 1999, 1827.
95. Wu, W.-M.; Yao, Z.-J.; Wu, Y.-L., Jiang, P. K.; Wang, Y.-F.; Chen, H.-B.; Shan, F.; Li, Y. J. Chem. Soc. Chem. Commun., 1996, 2213.
96. Grellepois, F.; Bonnett-Delpon, D.; Begue, J.-P. Tetrahedron Lett., 2001, 42, 2125.
97. Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Lal, B.; Chatterjee, D.K.; Iyer, S.N.; Blumbach, J. Eur. Pat. Ep 456,149,1991;
98. Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Lal, B. Chatterjee, D.K.; Iyer, S.N.; Blumbach, Chem. Abstr. 1992, 116, 83708z.
99. Venugopalan, B.; Bapat, C.P.; Karnik, P. J. Bioorg. Med. Chem. Lett., 1994, 4, 751.
100. Lin, A.J.; Lee, M.; Klayman, D.L. J. Med. Chem., 1989, 32, 1249.
101. Venugopalan, B.; Bapat, C.P.; Karnik, P.J.; Lal, B.; Chatterjee, D.K.; Iyer, S.N.; Lepcha, D.J. J. Med. Chem., 1995, 38, 1922.
102. Lin, A.J.; Li, L.-Q.; Klaymann, D.L.; George, C.F.; Fippan-Anderson, J.L. J. Med. Chem., 1990, 33, 2610.
103. Miljkovic, D.; Djurendic, E.; Vukojevic, N.; Gasi, K.; Casanadi, J. Carbohydrate Res., 1992, 233, 251.
104. Torok, D.S.; Ziffer, H. Tetrahedron Lett., 1995, 36, 829.
105. Haynes, R.K.; Pai, H.-O.H.; Voerste, A. Tetrahedron Lett., 1999, 40, 4715
106. Hufford, C.D.; Kheufa, S.I.; Orabi, K.Y.; Wigges, F.T.; Kumar, R.; Rogers, R.D.; Campana, C.F. J. Nat. Prof., 1995, 58, 751.
107. Hufford, C.D.; Lee, I.-S.; Elsholy, H.N.; Chi, H.T.; Baker, J. K. Pharm. Res., 1990, 7, 923.
108. Hu, Y; Ziffer, H.; Li, G.; Yeh, H.J.C. Bioorganic Chem., 1992, 20, 148.
109. Abourashed, E.A.; Hufford, C.D. J. Nat. Prod., 1996, 59, 251.
110. Hu, Y.; Highet, R.J.; Marion, D.; Ziffer, H. J. Chem. Soc. Chem. Commun., 1991, 1176.
111. Acton, N. J. Nat. Prod., 1999, 62, 790.
112. (a) Roth, R.J.; Acton, N. J. Nat. Prod., 1989, 53, 1183.
113. (b) Roth, R.J.; Acton, N. J. Chem. Edu., 1991, 68, 612.
114. (c) Acton, N.; Roth, R.J. J. Org. Chem. 1992, 57, 3610.
115. Haynes, R.K.; Vonwiller, S.C. Int. Applic. PCT/AU90/00456 (27/9/90) WO (Chem. Abstr., 1992, 116, 59094a);
116. Haynes, R.K.; Vonwiller, S.C. Synlett, 1992, 481;
117. Haynes, R.K.; Vonwiller, S.C. PCT Int. Applc. WO 920195 (29/4/93) (Chem. Abstr., 1993, 119, 181047q);
118. Haynes, R.K.; Vonwiller, S.C.; Wang, H.-J. Tetrahedron Lett., 1995, 36, 4641.
119. Jung, M.; Li, X.; Bustos, D.A.; Elsohly, H.N.; McChesney, J.D. Tetrahedron Lett., 1989, 30, 5973.
120. Bustoso, D. A.; Jung, M.; Elsohly, H.N.; McChesney, J.D. Heterocycles, 1989, 29, 2773;
121. Jung, M.; Bustos, D.A.; Elsohly, H.N.; McChesney, J.D. Synlett, 1990, 743;
122. Jung, M.; Yu, D.; Bustos, D.A.; Elsohly, H.N.; McChesney, J.D. Bioorganic Med. Chem. Lett., 1991, 1, 741,
123. Jung, M.; Bustos, D.A.; Elsohly, H.N.; McChesney, J.D. Synlett, 1993, 43.
124. Haynes, R.K.; King, G.R.; Vonwiller, S.C. J. Org. Chem., 1994, 59, 4743.
125. Posner, G.H.; Parker, M.H.; Northorp, J.; Elias, J.S.; Ploypradith, P.; Xie, S.;Shapiro, A. J. Med. Chem., 1999, 43, 300.
126. Kalita, B.; Barua, A.; Bez, G.; Barua, N. C. Ind. J. Chem. Sec. B, 2001, 40, 1125.
127. Pyne, G. B.; Smith, C. W. J. Org. Chem., 1957, 22, 1682.
128. Adam, W.; Rios, A. J. Chem. Soc. Chem. Commun., 1971, 822.
129. Miura, M.; Ikegami, M.; Nojima, M.; Kusabayasaki, S. J. Chem. Soc. Chem. Commun., 1980, 1279.
130. Miura, M.; Nojima, M.; Kusabayasaki, S. J. Chem. Soc. Chem. Commun., 1981, 581.
131. Akutagowa, M.; Aoyama, H.; Omote, Y.; Yamamoto, H. J. Chem. Soc. Chem. Commun., 1976, 180.
132. Akutagowa, M.; Aoyama, H.; Omote, Y.; Yamamoto, H. J. Chem. Soc. Chem. Commun., 1976, 180.
133. Jefford, C. W.; Joggi, D.; Bonkovalas, J.; Shigeo, K. J. Am. Chem. Soc., 1983, 105, 6497.
134. a) Adam, W.; Enearnocion, L. A. A. Chem. Ber., 1982, 115, 2592.
135. b) Bartlet, P. D.; Schap, A. P. J. Am. Chem. Soc., 1970, 92, 3223.
136. Hardling, L. B.; Goddard, W. A. III Tetrahedron Lett., 1978, 747;
137. Hardling, L. B.; Goddard, W. A. III J. Am. Chem. Soc., 1980, 102, 439.
138. Kearns, D. R. J. Am. Chem. Soc., 1969, 91, 6554.
139. Gormann, A. A.; Gould, I. R.; Hamblett, I. J. Am. Chem. Soc., 1982, 104, 7098.
140. Foote, C. S.; Dzakpasu, A. A.; Lin, J. W. P. Tetrahedron Lett., 1978, 1247.
141. Jefford, C. W.; Kohmoto, S.; Boukouvalax, J.; Burger, U. J. Am. Chem. Soc. 1983, 105, 6498.
142. Avery, M.A.; Chong, W. K. M.; Detre, G. Tetrahedron Lett., 1990, 31, 1799.
143. Avery, M. A.; Chong, W. K. M.; Bapp, J. E. J. Chem. Soc., 1990, 1487.
144. Imakura, Y.; Hachiya, K.; Ikemoto, T.; Kobayashi, S.; Yamashita, S. Heterocycles, 1990, 31, 2125.
145. Ikamura, Y.; Yokoi, T.; Yamaguchi, T.; Koyama, J.; Hu, H.; McPhail, D. R.; McPhail, A. T.; Lee, K. H. J. Chem. Soc. Chem Commun., 1988, 372.
146. (a) Zaman, S. S.; Debnath, J.; Sarmah, P.; Barua, N. C.; Sharma, R. P. 17th IUPAC International Symposium on the Chemistry of Natural Products, New Delhi, 1990, 138.
147. (b) Zaman, S. S.; Debnath, J.; Sarmah, P.; Barua, N. C.; Sharma, R. P. J. Chem. Soc. Chem. Commun., 1992, 329.
148. Jefford, C. W.; Velarde, J.; Barnardinelli, G.; Bray, D. H.; Warhaurst, D. C.; Milhous, W. K. Helv. Chem. Acta., 1993, 76, 2775.
149. Jefford, C. W.; Velarde, J.; Barnardinelli, G. Tetrahedron Lett., 1989, 30, 4485.
150. Posner, G. H.; Oh, C. H.; Milhous, W. Tetrahedron Lett., 1991, 32, 4535.
151. Singh, C. Tetrahedron Lett., 1990, 31, 6901.
152. Singh, C.; Mishra, D.; Saxena, G.; Chandra, S. Bioorg. & Med. Chem. Lett., 1995, 17, 1913.
153. Bloodworth, A. J.; Karen, A. J. Tetrahedron Lett., 1994, 35, 8057.
154. Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; Le Nair, I.; Moussy, C. Tetrahedron Lett., 1997, 38, 635.
155. Cai, W.; Devis, A. G. J. Chem. Soc. Perkin Trans. I, 1992, 3383.
156. Ushigoe, Y.; Kand, Y.; Nojima, M. J. Chem. Soc. Perkin Trans. I, 1997, 5.
157. (a) Zhang, F.; Gosser, D. K. Jr.; Mashnick, S. R. Biochem. Pharma., 1992, 42, 238-42.
158. (b) Vanerstrom, S. R.; Eaton, J. W. J. Med. Chem., 1988, 31, 1269.
159. Scott, M. D.; Mashnick, S. R.; Williams, R. H.; Chiu, D. T.-Y.; Pan, H. C.; Lubin, B. H.; Kuypers, F. A. J. Lab. Chem. Med., 1989, 114, 401.
160. Hong, Y. L.; Yang, Y. -Z.; Meshnick, S. R. Mol. Biochem. Parasitol., 1994, 63, 121.
161. Posner, G. H.; Oh, C. H. J. Am. Chem. Soc., 1992, 114, 8328.
162. Posner, G. H.; Oh, C. H.; Wong, D.; Germa, L.; Milhous, W. J. Med. Chem., 1994, 37, 1256.
163. Posner, G. H.; Oh, C. H.; Gerena, L.; Milhous, W. K. Heteroatom Chem., 1995, 6, 105.
164. Bloodworth, A. J.; Shah, A. Tetrahedron Lett., 1995, 36, 7551.
165. Posner, G. H.; Wong, D.; Gonzalez, L.; Tao, X.; Cunnings, J. N.; Kleindienst, D.; Shapiro, T. A. Tetrahedron Lett., 1996, 37, 815.
166. Jefford, C. W.; Kohmoto, S.; Jaggi, D.; Timeri, G.; Rossier, J. -C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, H.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C.J.; Fleck, S. L.; Robinson, B. L.; Peters, W. Helv. Chem. Acta., 1995, 78, 647.
167. Avery, M. A.; Fan, P.; Karle, J. M.; Miller, R.; Goins, K. Tetrahedron Lett., 1995, 36, 3965.
168. Provot, O.; Hamzauoi, M.; Naguyen, Huy, D.; Mayarangne, J.; Moskowitz, H. Heterocyclic Commun., 1996, 3, 267.
169. Hamazaui, M.; Provot, O.; Gregoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrangne, J. Tetrahedron Asymmetry, 1997, 8, 2085.
170. Bez, G.; Barua, N. C. 2001, unpublished result.
171. Cumming, J. N.; Wang, D.; Park, S. B.; Shapiro, T. A.; Posner, G. H. J. Med. Chem., 1998, 41, 952.
172. O'Neill, P. M.; Miller, A.; Bickley, J. F.; Scheinmann, F.; Oh, C. H.; Posner, G. H. Tetrahedron Lett., 1999, 40, 9133.