Synthesis of 4β-amido and 4β-sulphonamido analogues of podophyllotoxin as potential antitumour agents

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 23, 2003, Pages 5135-5142

  Kamal, Ahmed ^a   Kumar, B Ashwini ^a   Arifuddin, M ^a   Dastidar, Sunanda G ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b RANBAXY RESEARCH LABORATORIES   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4BETA (2'' CHLOROPYRIDINE 3'' FORMYL)AMINO 4' O NOREPIPODOPHYLLOTOXIN; 4BETA (2'' CHLOROPYRIDINE 3'' FORMYL)AMINOPODOPHYLLOTOXIN; 4BETA (3'' CHLORO 4'' METHYLBENZOPHENONE 2'' FORMYL)AMINO 4' O NOREPIPODOPHYLLOTOXIN; 4BETA (3'' CHLORO 4'' METHYLBENZOPHENONE 2'' FORMYL)AMINOPODOPHYLLOTOXIN; 4BETA (4 TOLUENESULFONYL)AMINO 4' O NOREPIPODOPHYLLOTOXIN; 4BETA (4 TOULENESULFONYL)AMINOPODOPHYLLOTOXIN; 4BETA (4'' CHLOROBENZOPHENONE 2'' FORMYL)AMINO O NOREPIPODOPHYLLOTOXIN; 4BETA (4'' CHLOROBENZOPHENONE 2'' FORMYL)AMINOPODOPHYLLOTOXIN; 4BETA (4'' METHYLBENZOPHENONE 2'' FORMYL)AMINO 4' O NOREPIPODOPHYLLOTOXIN; 4BETA (4'' METHYLBENZOPHENONE 2'' FORMYL)AMINOPODOPHYLLOTOXIN; 4BETA (6' CHLOROPYRIDINE 3'' FORMYL)AMINOPODOPHYLLOTOXIN; 4BETA (6'' CHLOROPYRIDINE 3'' FORMYL)AMINO 4' O NOREPIPODOPHYLLOTOXIN; 4BETA (BENZENESULFONYL)AMINO 4' O NOREPIPODOPHYLLOTOXIN; 4BETA (BENZENESULFONYL)AMINOPODOPHYLLOTOXIN; ANTINEOPLASTIC AGENT; CHLORIDE; DICHLOROMETHANE; DICYCLOHEXYLCARBODIIMIDE; PODOPHYLLOTOXIN DERIVATIVE; UNCLASSIFIED DRUG; AMIDE; PODOPHYLLOTOXIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAIN CANCER; BREAST CANCER; CANCER CELL CULTURE; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LUNG CANCER; PROSTATE CARCINOMA; STRUCTURE ANALYSIS; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

AMIDES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PODOPHYLLOTOXIN; SPECTROPHOTOMETRY, INFRARED;

EID: 0242266511     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.08.019     Document Type: Article

References (41)

1. Lee, K. H. In Human Medicinal Agents from Plants; Kinghorn, A. D., Balandrin, M., Eds.; American Chemical Society, Symposium Series: American Chemical Society: Washington, DC, 1993; p 170.
2. MacRae W.D., Hudson J.B., Towers B.H.N. Planta Med. 55:1993;531.
3. Jardine, I. In Anti-Cancer Agents Based on Natural Products Models; Cassady, J. M., Doures, J., Eds.; Academic: New York, 1980; p 319.
4. (a) Lee K.H., Beers S.A., Mori M., Wang Z., Kuo Y., Li L., Liu S., Cheng Y., Han F., Cheng Y. J. Med. Chem. 33:1990;1364
5. (b) Stahelin H., Von Wartburg A. Prog. Drug. Res. 33:1989;169
6. (c) Doyle, T. W. Etoposide (VP-16) Current Status and New Developments; Academic: New York, 1984.
7. Wang Z., Kuo Y., Schnur D., Bowen J.P., Liu S., Hen F., Chang J., Cheng Y., Lee K.H. J. Med. Chem. 33:1990;2660.
8. Macdonald, T. L.; Lehnert, E. K.; Loper, J. T.; Chow, K. C.; Ross, W. E. In DNA Topoisomerases in Cancer; Potmesil, M., Kohn, K. W., Eds.; Oxford University: New York, 1991; p 199, and references cited therein.
9. (a) Leteurtre F., Madalengoitia J., Orr A., Cuzi T.J., Lenhert E., Macdonald T., Pommier Y. Cancer Res. 52:1992;4478
10. (b) Ward R.S. Synthesis. 1992;719, and references cited therein
11. (c) Sauliner M.G., LeBoullence K.L., McGee D.P.C., Long B.H., Crosswell A.R., Vyas D. M. Bioorg. Med. Chem. Lett. 3:1993;1619
12. (d) Terrada T., Fujimoto K., Nomura M., Yamazaki R., Shibata J., Sugimoto Y., Yamada Y. J. Med. Chem. 36:1993;1689
13. (e) Bush J.E., Jones D.W. J. Chem. Soc., Chem. Commun. 1993;1200
14. (f) Tomioka K., Kubota Y., Kogo K. Tetrahederon Lett. 49:1993;1891
15. (g) Watt P.M., Hickson I.D. J. BioChem. 303:1994;681, and references cited therein
16. (h) Hitosuyanagi Y., Naka Y., Yamagami K., Fiji A., Tahara T. J. Chem. Soc., Chem. Commun. 1995;49
17. (i) Hitosuyanagi Y., Kobayashi M., Takoya K., Itokawa H. J. Chem. Soc., Perkin Trans. 1. 1995;1387.
18. (a) Liu S.Y., Hwang B.D., Haruna M., Imakura Y., Lee K.H., Cheng Y.C. Mol. Pharmacol. 36:1989;78
19. (b) Chang J.Y., Han F.S., Liu S.Y., Wang Z.Q., Lee K.H., Cheng Y.C. Cancer Res. 51:1991;1755.
20. Lee K.H., Beers S.A., Mori M., Wang Z.Q., Kuo Y.H., Li L., Liu S.Y., Cheng J.Y., han F.S., Cheng Y.C. J. Med. Chem. 33:1990;1364.
21. Wang Z.Q., Kuo Y.H., Schnur D., Bower J.P., Liu S.Y., Han F.S., Chang J.Y. J. Med. Chem. 33:1990;2660.
22. (a) Zhou X.M., Wang Z.Q., Chang J.Y., Chen H.X., Cheng Y.C., Lee K.H. J. Med. Chem. 34:1991;3346
23. (b) Xiao Z., Xiao Y-D., Golbraikh A., Tropsha A., Lee K.H. J. Med. Chem. 45:2002;2294
24. (c) VanVilet D.S., Tachibana Y., Bastow K.F., Huang E.S., Lee K.H. J. Med. Chem. 44:2001;1422.
25. (a) Huang T.S., Shu C.H., Shih Y.L., Huang H.C., Su Y.C., Chao Y., Yang W.K., Peng J.W. Cancer Lett. 110:1996;77
26. (b) Kuo M.L., Shen S.C., Yang C.H., Chuang S.E., Cheng A.L., Huang T.S. Oncogene. 17:1998;2225
27. (c) VanVliet, D. S. PhD Dissertation, The University of North Carolina at Chapel Hill, 1999.
28. Pan J.L., Wang Y.G., Chen Y.Z. Curr. Sci. 72:1997;268.
29. Zhou X.M., Wang Z., Chen H.X., Cheng Y.C., Lee K.H. Pharm. Res. 10:1993;214.
30. (a) Kamal A., Gayatri N.L. Tetrahedron Lett. 37:1996;3359
31. (b) Kamal A., Laxminarayana B., Gayatri N.L. Tetrahedron Lett. 38:1997;6871
32. (c) Kamal A., Gayatri N.L., Rao N.V. Bioorg. Med. Chem. Lett. 8:1998;3097
33. (d) Kamal A., Damyanthi Y. Bioorg. Med. Chem. Lett. 7:1997;657
34. Gayatri, N. L. PhD Thesis, Osmania University, 1999.
35. (f) Laxman, E. L. PhD Thesis, Osmania University, 2000.
36. Kamal, A.; Gayatri, N. L. Indian Pat. Appl. No. 1712/DEL/ 1997.
37. (g) Kamal, A.; Laxman, E.; Arifuddin, M.; Khanna, G. B. R. US Pat. 6441198, 2002. (h) Kamal, A.; Gayatri, N. L. Indian Pat. Appl. No. 1712/DEL/ 1997.
38. Kamal, A.; Arifuddin, M.; Kumar, B. A.; Dastidar, S. G. Indian Pat. Appl. No. 136/DEL/ 2003.
39. Kamal A., Laxman N., Ramesh G. Bioorg. Med. Chem. Lett. 10:2000;2059.
40. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M. J. Natl. Cancer Inst. 83:1991;757.
41. Boyd M.R., Paull K.D. Drug. Dev. Res. 34:1995;91.