Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans

Steroids

Volumn 78, Issue 5, 2013, Pages 494-499

  Yu, Bin ^a   Zhang, En ^a   Sun, Xiao Nan ^a   Ren, Jing Li ^a   Fang, Yuan ^a   Zhang, Bao Le ^a   Yu, De Quan ^b   Liu, Hong Min ^a  

^a ZHENGZHOU UNIVERSITY   (China)

^b INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

2H pyrans; Dehydroepiandrosterone; Dienamides

Indexed keywords

3 BETA ACETOXYL 5 EN 16 (2 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (2 CYANOBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (2,4 DICHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (2,4 DIFLUOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (3 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (3 METHOXYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (4 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 (4 ISOPROPYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 BENZYLIDENE ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 FURYLMETHYLENE ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3 BETA ACETOXYL 5 EN 16 THIENYLMETHYLENE ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); ALCOHOL; ALDEHYDE; PYRAN DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ALDEHYDES; ALKENES; CHEMISTRY TECHNIQUES, SYNTHETIC; PYRANS; STEROIDS;

EID: 84875191834     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2013.02.004     Document Type: Article

References (29)

1. J.E. Cabaj, D. Kairys, and T.R. Benson Development of a commercial process to produce oxandrolone Org Process Res Dev 11 2007 378 388
2. O.O. Clement, C.M. Freeman, R.W. Hartmann, V.D. Handratta, T.S. Vasaitis, and A.M.H. Brodie Three dimensional pharmacophore modeling of human CYP17 inhibitors. Potential agents for prostate cancer therapy J Med Chem 46 2003 2345 2351
3. Y. Matsuya, Y. Yamakawa, C. Tohda, K. Teshigawara, M. Yamada, and H. Nemoto Synthesis of sominone and its derivatives based on an RCM strategy: discovery of a novel anti-alzheimer's disease medicine candidate "Denosomin" Org Lett 11 2009 3970 3973
4. S. Boonananwong, B. Kongkathip, and N. Kongkathip First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa Steroids 73 2008 1123 1127
5. I.S. Levina, E.V. Pokrovskaya, L.E. Kulikova, A.V. Kamernitzky, V.V. Kachala, and A.N. Smirnov 3- and 19-Oximes of 16α,17α- cyclohexanoprogesterone derivatives: synthesis and interactions with progesterone receptor and other proteins Steroids 73 2008 815 827
6. D. Romano, V. Ferrario, D. Mora, R. Lenna, and F. Molinari Enantioselective production of 3-hydroxy metabolites of tibolone by yeast reduction Steroids 73 2008 112 115
7. S. Mennerick, Y. He, X. Jiang, B.D. Manion, M. Wang, and A. Shute Selective antagonism of 5α-reduced neurosteroid effects at GABAA receptors Mol Pharmacol 65 2004 1191 1197
8. F. Babudri, V. Fiandanese, F. Naso, and A. Punzi A new straightforward and general approach to dienamide natural products Tetrahedron Lett 35 1994 2067 2070
9. K. Fukuhara, and H. Urabe Iron-catalyzed 1,6-addition of aryl Grignard reagents to 2,4-dienoates and -dienamides Tetrahedron Lett 46 2005 603 606
10. Y. Maekawa, T. Sakaguchi, H. Tsuchikawa, and S. Katsumura New type of azacyclization: thermal preparation of 4,6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect Tetrahedron Lett 53 2012 837 841
11. H. McAlonan, J.P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P.K.S. Sarma, and P.J. Stevenson 4-Phenyloxazolidin-2-ones and isoindolin-1-ones: chiral auxiliaries for Diels-Alder reactions of N-substituted 1, 3-dienes J Chem Soc Perk Trans 1 2002 69 79
12. Y. Huang, T. Iwama, and V.H. Rawal Highly enantioselective Diels-Alder reactions of 1-amino-3-siloxy-dienes catalyzed by Cr(III)-salen complexes J Am Chem Soc 122 2000 7843 7844
13. A. Bhattacharjee, O.R. Seguil, and J.K. De Brabander Total synthesis and biological evaluation of apicularen A and synthetic analogs Tetrahedron Lett 42 2001 1217 1220
14. 17,18Z isomer Angew Chem Int Ed 41 2002 3701 3704
15. K.L. Erickson, J.A. Beutler, J.H. Cardellina II, and M.R. Boyd Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge haliclona sp J Org Chem 62 1997 8188 8192
16. L.C. Dias, and L.G. de Oliveira Total synthesis of (+)-crocacin C Org Lett 3 2001 3951 3954
17. J. Tanaka, and T. Higa Zampanolide, a new cytotoxic marcrolide from a marine sponge Tetrahedron Lett 37 1996 5535 5538
18. L.H. Huang, J. Li, G. Xu, X.H. Zhang, Y.G. Wang, and Y.L. Yin Biotransformation of dehydroepiandrosterone (DHEA) with Penicillium griseopurpureum Smith and Penicillium glabrum (Wehmer) Westling Steroids 75 2010 1039 1046
19. L.H. Huang, Y.G. Wang, G. Xu, X.H. Zhang, Y.F. Zheng, and H.L. He Novel 4-azasteroidal N-glycoside analogues bearing sugar-like D ring: synthesis and anticancer activities Bioorg Med Chem Lett 21 2011 6203 6205
20. L.H. Huang, Y.F. Zheng, Y.Z. Lu, C.J. Song, Y.G. Wang, and B. Yu Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines Steroids 77 2012 710 715
21. L.H. Huang, Y.F. Zheng, C.J. Song, Y.G. Wang, Z.Y. Xie, and Y.W. Lai Synthesis of novel D-ring fused 7′-aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines Steroids 77 2012 367 374
22. H.P. Li, H.M. Liu, W.Z. Ge, L.H. Huang, and L.H. Shan Synthesis of 7α-hydroxy-dehydroepiandrosterone and 7β-hydroxy- dehydroepiandrosterone Steroids 70 2005 970 973
23. H.M. Liu, W.Z. Ge, H.P. Li, and J. Wu Microbial transformation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one by Trichoderma viride Steroids 72 2007 509 513
24. H.M. Liu, H.P. Li, L.H. Shan, and J. Wu Synthesis of steroidal lactone by penicillium citreo-viride Steroids 71 2006 931 934
25. L.H. Shan, H.M. Liu, K.X. Huang, G.F. Dai, C. Cao, and R.J. Dong Synthesis of 3β, 7α,11α-trihydroxy-pregn-21-benzylidene-5-en- 20-one derivatives and their cytotoxic activities Bioorg Med Chem Lett 19 2009 6637 6639
26. S.M. Wang, Y.B. Zhang, H.M. Liu, G.B. Yu, and K.R. Wang Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide Steroids 72 2007 26 30
27. H.W. Xu, G.Z. Liu, S.L. Zhu, G.F. Hong, H.M. Liu, and Q. Wu Digoxin derivatives substituted by alkylidene at the butenolide part Steroids 75 2010 419 423
28. 3 substituted dienamides via rearrangement of 2H-pyran derivatives Tetrahedron 67 2011 7618 7621
29. T.H. Babu, S. Pawar, D. Muralidharan, and P.T. Perumal Rearrangement of pyran derivatives obtained from vinyl malononitriles and aldehydes via vinylogous aldol reaction: a novel facile method for the synthesis of dienamides Synlett 2010 2010 2125 2129