Synthesis, in vitro structure-activity relationship, and in vivo studies of 2-arylthiazolidine-4-carboxylic acid amides as anticancer agents

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 2, 2010, Pages 477-495

  Lu, Yan ^a   Wang, Zhao ^a   Li, Chien Ming ^b   Chen, Jianjun ^a   Dalton, James T ^b   Li, Wei ^a   Miller, Duane D ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

Antiproliferative activity; Colony formation; In vivo evaluation; Melanoma; Prostate cancer; Structure activity relationship; Thiazolidine

Indexed keywords

2 (3,4 DIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID OCTADEC 8 ENYLAMIDE; 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID HEXADECYLAMIDE; 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID OCTADEC 8 ENYLAMIDE; 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID OCTADEC 8 TRANSENYLAMIDE; 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID OCTADECYLAMIDE; 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID TETRADECYLAMIDE; 2 (4 ACETYLAMINOPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID (FLUOREN 2 YL)AMIDE; 2 (4 ACETYLAMINOPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID HEXADECYLAMIDE; 2 (4 UREIDOPHENYL)THIAZOLIDINE 4 CARBOXYLIACID HEXADECYLAMIDE; 2 [4 (2 CHLOROACETYLAMINO)PHENYL]THIAZOLIDINE 4 CARBOXYLIC ACID HEXADECYLAMIDE; 2 ARYLTHIAZOLIDINE 4 CARBOXYLIC ACID AMIDE; 2 PHENYLTHIAZOLIDINE 4 CARBOXYLIC ACID OCTADEC 8 ENYLAMIDE; 2 PHENYLTHIAZOLIDINE 4 CARBOXYLIC ACID OCTADECYLAMIDE; ANTINEOPLASTIC AGENT; CISPLATIN; DACARBAZINE; PHENYL GROUP; SORAFENIB; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE; CELL STRAIN LNCAP; COLONY FORMATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; EVALUATION; FIBROBLAST; HUMAN; HUMAN CELL; IN VIVO STUDY; MELANOMA; NONHUMAN; NUDE MOUSE; PROSTATE CANCER; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; ANTINEOPLASTIC AGENTS; CARBOXYLIC ACIDS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINES; TUMOR CELLS, CULTURED;

MUS MUSCULUS;

EID: 76449093092     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.12.020     Document Type: Article

References (33)

1. Cancer Facts & Figures; American Cancer Society: Atlanta, 2007.
2. Carlson J.A., Ross Jeffery S., Slominski A., Linette G., Mysliborski J., Hill J., and Mihm Jr. M. J. Am. Acad. Dermatol. 52 (2005) 743
3. Gogas H.J., Kirkwood J.M., and Sondak V.K. Cancer (Hoboken, NJ, U.S.A.) 109 (2007) 455
4. Jemal A., Tiwari Ram C., Murray T., Ghafoor A., Samuels A., Ward E., and Feuer Eric J. CA Cancer J. Clin. 54 (2004) 8
5. Bosland M.C., McCormick D.L., Melamed J., Walden P.D., Zeleniuch-Jacquotte A., and Lumey L.H. Eur. J. Cancer Prev. 11 (2002) S18
6. Karan D., Holzbeierlein J., and Thrasher J.B. Cancer Res. 69 (2009) 2
7. Gududuru V., Hurh E., Dalton J.T., and Miller D.D. J. Med. Chem. 48 (2005) 2584
8. Li W., Lu Y., Wang Z., Dalton J.T., and Miller D.D. Bioorg. Med. Chem. Lett. 17 (2007) 4113
9. Chen J., Wang Z., Lu Y., Dalton J.T., Miller D.D., and Li W. Bioorg. Med. Chem. Lett. 18 (2008) 3183
10. Li W., Wang Z., Gududuru V., Zbytek B., Slominski A.T., Dalton J.T., and Miller D.D. Anticancer Res. 27 (2007) 883
11. Gududuru V., Zeng K., Tsukahara R., Makarova N., Fujiwara Y., Pigg K.R., Baker D.L., Tigyi G., and Miller D.D. Bioorg. Med. Chem. Lett. 16 (2006) 451
12. Gududuru V., Hurh E., Sullivan J., Dalton J.T., and Miller D.D. Bioorg. Med. Chem. Lett. 15 (2005) 4010
13. Schubert M.P. J. Biol. Chem. 114 (1936) 341
14. Zhao L., Huang W., Liu H., Wang L., Zhong W., Xiao J., Hu Y., and Li S. J. Med. Chem. 49 (2006) 4059
15. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815
16. Burns C.J., Guitton J.-D., Baudoin B., Lelievre Y., Duchesne M., Parker F., Fromage N., and Commercon A. J. Med. Chem. 40 (1997) 1763
17. Kurzer F. Org. Synth. 31 (1951) 8
18. Wilhelm S., Carter C., Lynch M., Lowinger T., Dumas J., Smith R.A., Schwartz B., Simantov R., and Kelley S. Nat. Rev. Drug Disc. 5 (2006) 835
19. McFadyen M.C.E., Melvin W.T., and Murray G.I. Mol. Cancer Ther. 3 (2004) 363
20. Rooseboom M., Commandeur J.N.M., and Vermeulen N.P.E. Pharmacol. Rev. 56 (2004) 53
21. Lu Y., Li C.M., Wang Z., Ross II C.R., Chen J., Dalton J.T., Li W., and Miller D.D. J. Med. Chem. 52 (2009) 1701
22. Brugarolas A., and Gosalvez M. Lancet 1 (1980) 68
23. Liu J., Qu S., Li B., and Li D. Yiyao Gongye 19 (1988) 203
24. Ohta H., Sato K., Murata N., Damirin A., Malchinkhuu E., Kon J., Kimura T., Tobo M., Yamazaki Y., Watanabe T., Yagi M., Sato M., Suzuki R., Murooka H., Sakai T., Nishitoba T., Im D.S., Nochi H., Tamoto K., Tomura H., and Okajima F. Mol. Pharmacol. 64 (2003) 994
25. Meyskens Jr. F.L., Moon T.E., Dana B., Gilmartin E., Casey W.J., Chen H.S., Franks D.H., Young L., and Salmon S.E. Br. J. Cancer 44 (1981) 787
26. Von Hoff D.D., Casper J., Bradley E., Sandbach J., Jones D., and Makuch R. Am. J. Med. 70 (1981) 1027
27. Zmijewski M.A., Li W., Zjawiony J.K., Sweatman T.W., Chen J., Miller D.D., and Slominski A.T. Steroids 74 (2009) 218
28. Zmijewski M.A., Li W., Zjawiony J.K., Sweatman T.W., Chen J., Miller D.D., and Slominski A.T. Photochem. Photobiol. Sci. 7 (2008) 1570
29. Zbytek B., Janjetovic Z., Tuckey R.C., Zmijewski M.A., Sweatman T.W., Jones E., Nguyen M.N., and Slominski A. J. Invest. Dermatol. 128 (2008) 2271
30. Panayiotis P., and Constantinides C.M.L. J. Controlled Release 34 (1995) 109
31. Povlsen C.O., and Jacobsen G.K. Cancer Res. 35 (1975) 2790
32. Guo W., Wu S., Liu J., and Fang B. Cancer Res. 68 (2008) 7403
33. Chen J., Smith M., Kolinsky K., Adames V., Mehta N., Fritzky L., Rashed M., Wheeldon E., Linn M., and Higgins B. Cancer Chemother. Pharmacol. 59 (2007) 651