Antitumor agents. 234. Design, synthesis, and biological evaluation of novel 4β-[(4″-benzamido)-amino]-4′-O-demethyl- epipodophyllotoxin derivatives

Journal of Medicinal Chemistry

Volumn 47, Issue 21, 2004, Pages 5140-5148

  Xiao, Zhiyan ^a,d   Bastow, Kenneth F ^a   Vance, John R ^b   Sidwell, Robert S ^c   Wang, Hui Kang ^b   Chen, Ming S ^b   Shi, Qian ^b   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b Plantaceutica Inc   (United States)

^c UTAH STATE UNIVERSITY   (United States)

^d PEKING UNION MEDICAL COLLEGE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2'' DEOXY 2'' (DIMETHYLAMINO)ETOPOSIDE; 4' O DEMETHYL 4BETA [4'' (BENZYL DEXTRO ALANYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (BENZYLALANYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (BENZYLGLYCYL N CABONYL)ANILINO] 4 DESOXYPODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (METHYL 1,3,4 DIHYDROXYPHENYLALANYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (METHYL DEXTRO TRYPTOPHANYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (METHYLHISTIDYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (METHYLPHENYLALANYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (PHENYLETHYLAMIDO)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (TRYPTOPHANYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4'' (TYRAMIDO)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; 4' O DEMETHYL 4BETA [4''(METHYLMETHIONYL N CARBONYL)ANILINO] 4 DESOXY PODOPHYLLOTOXIN; CAMPTOTHECIN; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); ETOPOFOS; ETOPOSIDE; GYRASE INHIBITOR; PACLITAXEL; PODOPHYLLOTOXIN; TENIPOSIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST TUMOR; CANCER INHIBITION; CONTROLLED STUDY; DNA PROTEIN COMPLEX; DRUG DESIGN; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GLIOBLASTOMA; HUMAN; HUMAN CELL; INTESTINE TUMOR; KIDNEY TUMOR; LUNG TUMOR; MULTIDRUG RESISTANCE; NASOPHARYNX TUMOR; NONHUMAN; OVARY TUMOR; PROSTATE TUMOR; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZAMIDES; CELL DIVISION; CELL LINE, TUMOR; DNA TOPOISOMERASES, TYPE II; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; DRUG STABILITY; MICROSOMES, LIVER; PODOPHYLLOTOXIN; RATS; SERUM; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4744341416     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030609l     Document Type: Article

References (21)

1. Hayashi, K.; Chang, F. R.; Nakanishi, Y.; Bastow, K. F.; Cragg, G.; McPhail, A. T.; Nozaki, N.; Lee K. H. Antitumor Agents. 233. Lantalucratins A-F, New Cytotoxic Isoprenyl Naphthoquinones from Lantana involcrata. J. Nat. Prod., submitted for publication.
2. Osheroff, N.; Zechiedrich, E. L.; Gale, K. C. Catalytic Function of DNA Topoisomerase II. BioEssays 1991, 13, 269-275.
3. Alton, P. A.; Harris, A. L. The Role of DNA Topoisomerases II in Drug Resistance. Br. J. Haematol. 1993, 85, 241-245.
4. Jardine, I. In Anticancer Agents Based on Natural Products Models; Academic Press: New York, 1980; pp 319-351.
5. Issell, B. F. The Podophyllotoxin Derivatives VP16-213 and VM26. Cancer Chemother. Pharmacol. 1982, 7, 73-80.
6. Budman, D. R. Early Studies of Etoposide Phosphate, a Water-Soluble Prodrug. Semin. Oncol. 1996, 23 (Suppl), 8-14.
7. Greco, F. A.; Hainsworth, J. D. Clinical Studies with Etoposide Phosphate. Semin. Oncol. 1996, 23 (Suppl), 45-50.
8. Saito, H.; Yoshikawa, H.; Nishimura, Y.; Kondo, S.; Takeuchi, T.; Umezawa, H. Studies on Lignan Lactone Antitumor Agents. II. Synthesis of JV-Alkylamino- and 2,6-Dideoxy-2-aminoglycosidic Lignan Variants Related to Podophyllotoxin. Chem. Pharm. Bull. 1986, 34, 3741-3746.
9. Pagani, O.; Zucchetti, M.; Sessa, C.; De Jong, J.; D'Incalci, M.; De Fusco, M.; Kaeser-Froehlich, A.; Hanauske, A.; Cavalli, F. Clinical and Pharmacokinetic Study of Oral NK611, a New Podophyllotoxin Derivatives. Cancer Chemother. Pharmacol. 1996, 38, 541-547.
10. Lee, K. H. Novel Antitumor Agents from Higher Plants. Med. Res. Rev. 1999, 19, 569-596.
11. Byl, J. A. W.; Cline, S. D.; Utsugi, T.; Kobunai, T.; Yamada, Y.; Osheroff, N. DNA Topoisomerase II as the Target for the Anticancer Drug TOP-53: Mechanistic Basis for Drug Action. Biochemistry 2001, 40, 712-718.
12. Moraes, R. M.; Dayan, F. E.; Canel, C. The Lignans of Podophyllum. Stud. Nat. Prod. Chem. 2002, 26, 149-182.
13. MacDonald, T. L.; Lehnert, E. K.; Loper, J. T.; Chow, K. C.; Ross, W. E. On the Mechanisn of Interaction of DNA Topoisomerase II with Chemotherapeutic Agents. DNA Topoisomerase in Cancer; Oxford University Press: New York, 1991; pp 119-214.
14. 2-GRS Approach. J. Med. Chem. 1996, 39, 1383-1395.
15. Xiao, Z.; Xiao, Y. D.; Feng, J.; Golbraikh, A.; Tropsha, A.; Lee, K. H. Antitumor Agents. 213. Modeling of Epipodophyllotoxin Derivatives using Variable Selection k Nearest Neighbor QSAR Method. J. Med. Chem. 2002, 45, 2294-2309.
16. Xiao, Z.; Bastow, K. F.; Vance, J.; Lee, K. H. Antitumor Agents. 227. Studies on Novel 4′-O-Demethyl-Epipodophyllotoxins as Antitumor Agents Targeting Topoisomerase II. Bioorg. Med. Chem., submitted for publication.
17. Kamal, A.; Laxman, N.; Ramesh, G. Facile and Efficient One-Pot Synthesis of 4β-Arylaminopodophyllotoxins: Synthesis of DNA Topoisomerase II Inhibitors (NPF and W-68). Bioorg. Med. Chem. Lett. 2000, 10, 2059-2062.
18. Lee, K. H.; Imakura, Y.; Haruna, M.; Beers, S. A.; Thurston, L. S.; Dai, H. J.; Chen, C. H. Antitumor Agents 107. New Cytotoxic 4-Alkylamino Analogues of 4′-Demethylepipodophyllotoxin as Inhibitors of Human DNA Topoisomerase II. J. Nat. Prod. 1989, 52, 606-613.
19. Lee, K. H.; Beers, S. A.; Mori, M.; Wang, Z. Q.; Kuo, Y. H.; Li, L.; Liu, S. Y.; Chang, J. Y.; Han, F. S.; Cheng, Y. C. Antitumor Agents 111. New 4-Hydoxylated and 4-Halogenated Anilino Derivatives of 4′- Demethylepipodophyllotoxin as Potent Inhibitors of Human DNA Topoisomerase II. J. Med. Chem. 1990, 33, 1364-1368.
20. Rubinstein, L. V.; Shoemaker, R. H.; Paull, K. D.; Simon, R. M.; Tosini, S.; Skehan, P.; Scudiero, D. A.; Monks, M. R. Comparison of in vitro Anticancer-Drug-Screening Data Generated with a Tetrazolium Assay versus a Protein Assay against a Diverse Panel of Human Tumor Cell Lines. J. Natl. Cancer Inst. 1990, 82, 1113-1118.
21. Rowe, T. D.; Chen, G. L.; Hsiang, Y. H.; Liu, L. F. DNA Damage by Antitumor Acridines Mediated by Mammalian DNA Topoisomerase II. Cancer Res. 1986, 46, 2021-2026.