Synthesis and biological evaluation of 4β-[(4-substituted)-1,2,3-triazol-1-yl]podophyllotoxins as potential anticancer agents

Chemistry and Biodiversity

Volumn 5, Issue 9, 2008, Pages 1792-1802

  Reddy, Pitta Bhaskar ^a   Agrawal, Satyam Kumar ^a   Singh, Swaran ^a   Bhat, Bilal A ^a   Saxena, Ajit K ^a   Kumar, Halmuthur M Sampath ^a   Qazi, Gulam N ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 (PHENOXYMETHYL)[1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7] NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 [(2 METHYLPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7] NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 [(3 METHYLPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7] NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 [(4 METHYLPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7] NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 [(4 NITROPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 [(PHENYLSULFANYL)METHYL][1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL) 9 [4 [[(4 METHYLPHENYL)SULFANYL]METHYL][1,2,3]TRIAZOL 1 YL] FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 (PHENOXYMETHYL)[1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 [(2 METHYLPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 [(3 METHYLPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 [(4 METHYLPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 [(4 NITROPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 [(PHENYLSULFANYL)METHYL][1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 5,8,8A,9 TETRAHYDRO 9 [4 [[(4 METHYLPHENYL)SULFANYL]METHYL][1,2,3]TRIAZOL 1 YL] 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7] NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 9 [4 [(2 CHLOROPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5,8,8A,9 TETRAHYDRO 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 9 [4 [(2 CHLOROPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 9 [4 [(4 CHLOROPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5,8,8A,9 TETRAHYDRO 5 (3,4,5 TRIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 9 [4 [(4 CHLOROPHENOXY)METHYL][1,2,3]TRIAZOL 1 YL] 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 9 [4 [[(2 CHLOROPHENYL)SULFANYL]METHYL][1,2,3]TRIAZOL 1 YL] 5,8,8A,9 TETRAHYDRO 5 (3,4,5 TRIMETHOXYPHENYL) FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; 9 [4 [[(4 CHLOROPHENYL)SULFANYL]METHYL][1,2,3]TRIAZOL 1 YL] 5,8,8A,9 TETRAHYDRO 5 (4 HYDROXY 3,5 DIMETHOXYPHENYL)FURO[3',4':6,7]NAPTHO[2,3 D][1,3]DIOXOL 6(5AH) ONE; ANTINEOPLASTIC AGENT; ETOPOSIDE; PODOPHYLLOTOXIN DERIVATIVE; UNCLASSIFIED DRUG; PODOPHYLLOTOXIN; TRIAZOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HT29; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PODOPHYLLOTOXIN; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 56149123935     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200890168     Document Type: Article

References (31)

1. K. H. Lee, in 'Human Medicinal Agents from Plants', Eds. A. D. Kinghorn, M. F. Balandrin, American Chemical Society, Symposium Series, Washington, 1993, p. 170-190.
2. W. D. MacRae, J. B. Hudson, G. H. N. Towers, Planta Med. 1989, 55, 531.
3. I. Jardine, in 'Anticancer Based on Natural Product Models' Eds. J. M. Cassady, J. D. Douros, Academic Press, New York 1980, pp. 319-351 and refs. cit. therein.
4. a) K. H. Lee, S. A. Beers, M. Mori, Z. Q. Wang, Y. H. Kuo, L. Li, S. Y. Liu, J. Y. Chang, F. S. Han, Y. C. Cheng, J. Med. Chem. 1990, 33, 1364;
5. b) Z. Q. Wang, Y. H. Kuo, D. Schnur, J. P. Bowen, S. Y. Liu, F. S. Han, J. Y. Chang, Y. C. Cheng, K. H. Lee, J. Med. Chem. 1990, 33, 2660;
6. c) H. Stahelin, A. Von Wartburg, Prog. Drug Res. 1989, 33, 169.
7. B. F. Issell, Cancer Chemother. Pharmacol. 1982, 7, 73.
8. J. M. S. Van Maanen, J. Retèl, J. De Vries, H. M. Pinedo, J. Natl. Cancer Inst. 1988, 80, 1526;
9. J. D. Hainsworth, S. D. Williams, L. H. Einhorn, R. Birch, F. A. Greco, J. Clin. Oncol. 1985, 3, 666;
10. J. C. Shah, J. R. Chen, D. Chow, Pharm. Res. 1989, 6, 408.
11. R. M. Moraes, F. E. Dayan, C. Canel, Stud. Nat. Prod. Chem. 2002, 26, 149.
12. T. Terada, K. Fujimoto, M. Nomura, J.-i. Yamashita, K. Wierzba, R. Yamazaki, J. Shibata, Y. Sugimoto, Y. Yamada, T. Kobunai, S. Takeda, Y. Minami, K.-i. Yoshida, H. Yamaguchi, J. Med. Chem. 1993, 36, 1689.
13. W. Choy, Genelabs Technologies, personal communication.
14. K. H. Lee, Med. Res. Rev. 1999, 19, 569.
15. J.-Y. Chang, F.-S. Han, S.-Y. Liu, Z.-Q. Wang, K.-H. Lee, Y.-C. Cheng, Cancer Res. 1991, 51, 1755.
16. T. Utsugi, J. Shibata, Y. Sugimoto, K. Aoyagi, K. Wierzba, T. Kobunai, T. Terada, T. Oh-hara, T. Tsuruo, Y. Yamada, Cancer Res. 1996, 56, 2809.
17. J. A. Wilson Byl, S. D. Cline, T. Utsugi, T. Kobunai, Y. Yamada, N. Osheroff, Biochemistry 2001, 40, 712.
18. T. L. Macdonald, E. K. Lehnert, J. T. Loper, K. C. Chow, W. E. Ross, in 'DNA Topoisomerase in Cancer', Ed. M. Potmesil, K. W. Kohn, Oxford University New York, 1991, p. 119.
19. Z. Xiao, S. Hang, K. F. Bastow, K.-H. Lee, Bioorg. Med. Chem. 2004, 14, 1581.
20. Z. Xiao, Y.-D. Xiao, J. Feng, A. Golbraikh, A. Tropsha, K.-H. Lee, J. Med. Chem. 2002, 45, 2294;
21. D. S. VanVliet, Y. Tachibana, K. F. Bastow, E.-S. Huang, K.-H. Lee, J. Med. Chem. 2001, 44, 1422.
22. S.-Y. Liu, B.-D. Hwang, M. Haruna, Y. Imakura. K.-H. Lee, Y.-C. Cheng, Mol. Pharmacol. 1989, 36, 78.
23. X. M. Zhou, Z. Q. Wang, J. Y. Chang, H. X. Chen, Y. C. Cheng, K. H. Lee, J. Med. Chem. 1991, 34, 3346.
24. W. P. Purcell, J. A. Singer, J. Phys. Chem. 1967, 71, 4316.
25. a) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596;
26. b) C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057;
27. c) J.-F. Shi, Y.-G. Wang, Youji Huaxue 2003, 23, 1244.
28. A. Kamal, N. Laxman, G. Ramesh, Bioorg. Med. Chem. Lett. 2000, 10, 2059.
29. C. N. Cao, Y. Y. Chen, Y. G. Wang, Y. Z. Chen, Chin. Chem. Lett. 1999, 10, 1003;
30. L. Tao, Y.-G. Wang, C. Ma, B. Zheng, Y.-Z. Chen, Synth. Commun. 1999, 29, 2053.
31. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1107.