Synthesis, characterization and biological evaluation of some 16E-arylidene androstane derivatives as potential anticancer agents

Steroids

Volumn 76, Issue 7, 2011, Pages 709-723

  Guo, Hao ^a   Wu, Haotian ^a   Yang, Jin ^a   Xiao, Yuling ^a   Altenbach, Hans Josef ^b   Qiu, Guofu ^a   Hu, Hao ^a   Wu, Zhongyuan ^a   He, Xianran ^a   Zhou, Dingshan ^a   Hu, Xianming ^a  

^a WUHAN UNIVERSITY   (China)

^b UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

16E arylidene androstane; Anticancer activity; Heterocycles; Synthesis

Indexed keywords

16 (3,4,5 TRIMETHOXYBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (3,4,5 TRIMETHOXYBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (4 BROMOBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (4 BROMOBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (4 CHLOROBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (4 CHLOROBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (4 FLUOROBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (4 FLUOROBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (4 METHOXYBENZYLIDENE) 3BETA MORPHOLINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 METHOXYBENZYLIDENE) 3BETA PIPERIDINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 METHOXYBENZYLIDENE) 3BETA PYRROLIDINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 METHOXYBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (4 METHOXYBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (4 METHYLBENZYLIDENE) 3BETA (4 METHYLPIPERAZINYL) 5ALPHA ANDROSTAN 17 ONE; 16 (4 METHYLBENZYLIDENE) 3BETA MORPHOLINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 METHYLBENZYLIDENE) 3BETA PIPERIDINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 METHYLBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (4 METHYLBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (4 NITROBENZYLIDENE) 3BETA (4 METHYLPIPERAZINYL) 5ALPHA ANDROSTAN 17 ONE; 16 (4 NITROBENZYLIDENE) 3BETA MORPHOLINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 NITROBENZYLIDENE) 3BETA PYRROLIDINO 5ALPHA ANDROSTAN 17 ONE; 16 (4 NITROBENZYLIDENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (4 NITROBENZYLIDENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16 (FURAN 2 YLMETHYLENE) 5ALPHA ANDROSTAN 3,17 DIONE; 16 (FURAN 2 YLMETHYLENE) 5ALPHA ANDROSTAN 3BETA OL 17 ONE; 16E ARYLIDENE ANDROSTANE DERIVATIVE; 6 (4 NITROBENZYLIDENE) 3BETA PIPERIDINO 5ALPHA ANDROSTAN 17 ONE; ANDROSTANE DERIVATIVE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HEPG2; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

ANDROSTANES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; HUMANS; INHIBITORY CONCENTRATION 50; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79956203988     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.03.015     Document Type: Article

References (35)

1. J.L. Everett, J.J. Roberts, and W.C.J. Ross Aryl-2-halogenoalkylamines. Part XII. Some carboxylic derivatives of NN-di-2-chloroethylaniline J Chem Soc 1953 2386 2392
2. L.A. Shervington, N. Smith, E. Norman, T. Ward, R. Phillips, and A. Shervington To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines Eur J Med Chem 44 2009 2944 2951
3. A. McLean, D. Newell, G. Baker, and T. Connors The metabolism of chlorambucil Biochem Pharmacol 29 1980 2039 2047 (Pubitemid 10077082)
4. K. Loven, L. Stein, K. Furst, and S. Levy Evaluation of the efficacy and tolerability of 0.5% fluorouracil cream and 5% fluorouracil cream applied to each side of the face in patients with actinic keratosis Clin Ther 24 2002 990 1000 (Pubitemid 34734743)
5. A. Skladanowski, and J. Konopa Adriamycin and daunomycin induce programmed cell death (apoptosis) in tumour cells Biochem Pharmacol 46 1993 375 382 (Pubitemid 23239986)
6. M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, and A.T. McPhail Plant antitumor agents VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia J Am Chem Soc 93 1971 2325 2327
7. A. Chugun, K. Temma, T. Oyamada, N. Suzuki, Y. Kamiya, and Y. Hara Doxorubicin-induced late the sarcoplasmic reticulum in the rat Can J Physiol Pharmacol 78 2000 329 338
8. T. Ohga, T. Uchiumi, Y. Makino, K. Koike, M. Wada, and M. Kuwano Direct involvement of the Y-box binding protein YB-1 in genotoxic stress-induced activation of the human multidrug resistance 1 gene J Biol Chem 273 1998 5997 6000 (Pubitemid 28144673)
9. Y. Wang, and M. Tamara A novel cancer therapy: combined liposomal hypoxia inducible factor 1 alpha antisense oligonucleotides and an anticancer drug Biochem Pharmacol 68 2004 2031 2042 (Pubitemid 39346193)
10. V. Kaklamani, and R.M. O'Regan Aromatase inhibitors as adjuvant therapy in breast cancer Oncology 17 2003 335 342
11. H.J. Mitchell, W.P. Dankulich, G.D. Hartman, T. Prueksaritanont, A. Schmidt, and R.L. Vogel Design synthesis, and biological evaluation of 16-substituted 4-azasteroids as tissue-selective androgen receptor modulators (SARMs) J Med Chem 52 2009 4578 4581
12. Q. He, and D. Jiang A novel aminosteroid is active for proliferation inhibition and differentiation induction of human acute myeloid leukemia HL-60 cells Leukemia Res 23 1999 369 372 (Pubitemid 29166771)
13. J. Roy, P. DeRoy, and D. Poirier 2β-(N-Substituted Piperazino)-5α-androstane-3α,17β-diols: parallel solid-phase synthesis and antiproliferative activity on human leukemia HL-60 cells J Combin Chem 9 2007 347 358
14. K.A. Latham, A. Zamora, H. Drought, S. Subramanian, A. Matejuk, and H. Offner Estradiol treatment redirects the isotype of the autoantibody response and prevents the development of autoimmune arthritis J Immunol 171 2003 5820 5827 (Pubitemid 37467198)
15. D. Hosking, C.E. Chilvers, C. Christiansen, P. Ravn, R. Wasnich, and P. Ross Prevention of bone loss with alendronate in postmenopausal women under 60 years of age N Engl J Med 338 1998 485 492 (Pubitemid 28103131)
16. D.S. Savage A novel class of antitumour agents I. Chemistry and animal experiments Cancer Lett 2 1977 267 272 (Pubitemid 8070193)
17. R. Chattopadhaya, D.P. Jindal, M. Minu, and R. Gupta Synthesis and cytotoxic studies of hydroximino derivatives of some 16E-arylidenosteroids Arzneimittel Forschung 54 2004 551 556 (Pubitemid 39274017)
18. R. Bansal, and S. Guleria Synthesis of 16E-[3-methoxy-4-(2-aminoethoxy)- benzylidene]androstene derivatives as potent cytotoxic agents Steroids 73 2008 1391 1399
19. S. Dubey, P. Piplani, and D.P. Jindal Synthesis and in vitro antineoplastic evaluation of certain 16-(4-Substituted Benzylidene) derivatives of androst-5-ene Chem Biodiver 1 2004 1529 1536
20. S. Dubey, P. Kaur, D.P. Jindal, Y.D. Satyanarayan, and P. Piplani Synthesis and evaluation QSAR studies of 16-(4 & 3,4-substituted) benzylidene androstene derivatives as anticancer agents Med Chem 4 2008 229 236 (Pubitemid 351827297)
21. F.A. Luzzio, and F.S. Guziec Jr. Recent applications of oxochromiumamine complexes as oxidants in organic synthesis. A review Org Prep Proced Int 20 1988 533 584
22. K.E. Harding, L.M. May, and K.F. Dick Selective oxidation of allylic alcohols with chromic acid J Org Chem 40 1975 1664 1665
23. B.H. Walker Effect of manganese on the chromic acid oxidation of secondary-tertiaryvicinal glycols J Org Chem 32 1967 1098 1103
24. R.F. Borch, M.D. Bernstein, and H.D. Durst Cyanohydridoborate anion as a selective reducing agent J Am Chem Soc 93 1971 2897 2904
25. M.R. Reithofer, S.M. Valiahdi, M.A. Jakupec, V.B. Arion, A. Egger, and M. Galanski Novel di- and tetracarboxylatoplatinum(iv) complexes. Synthesis, characterization cytotoxic activity, and DNA platination J Med Chem 50 2007 6692 6699 (Pubitemid 350309106)
26. Y. Yang, P. Shang, C. Cheng, D. Wang, P. Yang, and F. Zhang Novel N-phenyl dichloroacetamide derivatives as anticancer reagents: design, synthesis and biological evaluation Eur J Med Chem 45 2010 4300 4306
27. C. Tseng, Y. Chen, K. Chung, C. Cheng, C. Wang, and C. Tzeng Synthesis and antiproliferative evaluation of 6- arylindeno [1,2-c] quinoline derivatives Bioorg Med Chem 17 2009 7465 7476
28. B. Kongkathip, A. Hasakunpaisarn, S. Boonananwong, and N. Kongkathip Synthesis of cytotoxic novel 9, 11-secosterol analogs: structure/activity studies Steroids 75 2010 834 847
29. F. Li, S. Awale, Y. Tezuka, and S. Kadota Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship Bioorg Med Chem 16 2008 5434 5440 (Pubitemid 351694485)
30. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J Immunol Methods 65 1983 55 63 (Pubitemid 14203433)
31. M. El-Far, G.A. Elmegeed, E.F. Eskander, H.M. Rady, and M.A. Tantawy Novel modified steroid derivatives of androstanolone as chemotherapeutic anti-cancer agents Eur J Med Chem 44 2009 3936 3946
32. H.J. Woerdenbag, T.A. Moskal, N. Pras, T.M. Malingre, F.S. El-Feraly, and H.H. Kampinga Cytotoxicity of artemisinin-related endoperoxides to ehrlich ascites tumor cells J Nat Prod 56 1993 849 856 (Pubitemid 23195612)
33. H.O. Saxena, U. Faridi, J.K. Kumar, S. Luqman, M.P. Darokar, and K. Shanker Synthesis of chalcone derivatives on steroidal framework and their anticancer activities Steroids 72 2007 892 900 (Pubitemid 47422269)
34. S. Thamotharan, V. Parthasarathi, R. Gupta, S. Guleria, D.P. Jindal, and A. Linden 16-[3-Methoxy-4-(2-piperidin-1-yl-ethoxy)benzylidene]-17-oxoandrost-5- en-3β-yl acetate monohydrate Acta Cryst C 58 2002 o727 o729
35. S. Thamotharan, V. Parthasarathi, R. Gupta, S. Guleria, D.P. Jindal, and A. Linden Two androst-5-ene derivatives: 16-[4-(3-chloropropoxy)-3- methoxybenzylidene]-17-oxoandrost-5-en-3β-ol and 16-[3-methoxy-4-(2- pyrrolidin-1-ylethoxy)benzylidene]-3β-pyrrolidinoandrost-5-en-17β-ol monohydrate Acta Cryst C 60 2004 o75 o78