Stereoselective synthesis and antimicrobial activity of steroidal C-20 tertiary alcohols with thiazole/pyridine side chain

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 3681-3689

  Shingate, Bapurao B ^a,b   Hazra, Braja G ^a   Salunke, Deepak B ^a   Pore, Vandana S ^a   Shirazi, Fazal ^a   Deshpande, Mukund V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Antibacterial activity; Antifungal activity; Grignard reaction; Steroid side chain; Steroidal ketones

Indexed keywords

3BETA ACETOXY 16ALPHA (PYRIDIN 2 YL) PREGNA 5 EN 20 ONE; 3BETA ACETOXY 5ALPHA PREGNAN 20 (PYRIDIN 2 YL) 20 OL; 3BETA ACETOXY 5ALPHA PREGNAN 20 (THIAZOL 2 YL) 20 OL; 3BETA ACETOXY PREGNA 5 EN 20 (PYRIDIN 2 YL) 20 OL; 3BETA ACETOXY PREGNA 5 EN 20 (THIAZOL 2 YL) 20 OL; 3BETA HYDROXY 16ALPHA (PYRIDIN 2 YL)PREGNA 5 EN 20 ONE; 3BETA TERT BUTYL DIMETHYLSILYLOXY PREGNA 5,16 DIEN 20 ONE; 3BETA TERT BUTYLDIMETHYLSILYLOXY 16ALPHA (PYRIDIN 2 YL)PREGNA 5 EN 20 ONE; 3BETA TERT BUTYLDIMETHYLSILYLOXY 5ALPHA PREGNAN 20 (PYRIDIN 2 YL) 20 OL; 3BETA TERT BUTYLDIMETHYLSILYLOXY 5ALPHA PREGNAN 20 (THIAZOL 2 YL) 20 OL; 3BETA TERT BUTYLDIMETHYLSILYLOXY PREGNA 5 EN 20 (PYRIDIN 2 YL) 20 OL; 3BETA TERT BUTYLDIMETHYLSILYLOXY PREGNA 5 EN 20 (THIAZOL 2 YL) 20 OL; 5ALPHA PREGNAN 20 (PYRIDIN 2 YL) 3,20 DIOL; 5ALPHA PREGNAN 20 (THIAZOL 2 YL) 3,20 DIOL; AMPHOTERICIN B; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ERYTHROMYCIN; FLUCONAZOLE; PREGNA 5 EN 20 (PYRIDIN 2 YL) 3BETA,20 DIOL; PREGNA 5 EN 20 (THIAZOL 2 YL) 3BETA,20 DIOL; STEROID; TETRACYCLINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; GRIGNARD REACTION; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STEREOCHEMISTRY;

ALCOHOLS; ANTI-INFECTIVE AGENTS; BACTERIA; CHROMATOGRAPHY, LIQUID; FUNGI; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; PYRIDINES; STEREOISOMERISM; THIAZOLES;

EID: 80052952663     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.05.032     Document Type: Article

References (62)

1. F.J. Zeelen Medicinal Chemistry of Steroids 1990 Elsevier Science B. V New York
2. F.J. Zeelen B. Testa, U.A. Meyer, Advances in Drug Research vol. 25 1994 Academic Press London 87 102
3. B.P. Morgan, and M.S. Moynihan J.I. Kroschwitz, M. Howe-Grant, Kirk-Othmer Encyclopedia of Chemical Technology vol. 22 1997 John Wiley & Sons New York 851 921
4. S.V. Drach, R.P. Litvinovskaya, and V.A. Khripach Chem. Nat. Comp. 36 2000 233 255
5. J.P. Burkhart, C.A. Gates, M.E. Laughlin, R.J. Resvick, and N.P. Peet Bioorg. Med. Chem. 4 1996 1411 1420
6. C. Camoutsis J. Heterocycl. Chem. 33 1996 539 558
7. E. Ramirez, M. Cabeza, I. Heuze, E. Gutierrez, E. Bratoeff, M. Membrillo, and A. Lira Chem. Pharm. Bull. 50 2002 15 20
8. H. Singh, D.P. Jindal, M.R. Yadav, M. Kumar, In: G.P. Ellis, B. West (Ed.), Progress in Medicinal Chemistry, vol. 28, Elsevier, Amsterdam, p. 233-300.
9. D.-H. Ko, M.F. Maponya, M.A. Khalil, Z. You, and H.J. Lee Med. Chem. Res. 7 1997 313 323
10. R. Gupta, I. Singh, and D.P. Jindal Ind. J. Chem. 35B 1996 1017 1020
11. K. Penov-gassi, M. Sakac, E. Djurendic, R. Kovacevic, and S. Andric J. Serb. Chem. Soc. 63 1998 189 192
12. R.K. Petit, G.D. Cage, G.R. Petit, and J.A. Liebman Antimicrob. Agents 15 2000 299 304
13. P.B. Savage Eur. J. Org. Chem. 5 2002 759 768
14. P.B. Savage, C. Li, U. Taotafa, B. Ding, and Q. Guan FEMS Microbiol. Lett. 217 2002 1 7
15. J. Wolfling, L. Hackler, E. Mernyak, G. Schneider, I. Toth, M. Szecsi, J. Julesz, P. Sohar, and A. Csampai Steroids 69 2004 451 460
16. M. Watanabe, S. Mataka, and T. Thiemann Steroids 70 2005 856 866
17. E. Frank, B. Kazi, K. Ludanyi, and G. Keglevichd Tetrahedron Lett. 47 2006 1105 1108
18. Y.-Z. Ling, J.-S. Li, Y. Liu, K. Kato, G.T. Klus, and A.Brodie J. Med. Chem. 40 1997 3297 3304
19. M. Jarman, S.E. Barrie, and J.M. Llera J. Med. Chem. 41 1998 5375 5381
20. A. Guarna, E.G. Occhiato, F. Machetti, and V. Giacomelli J. Org. Chem. 64 1999 4985 4989
21. R.W. Hartmann, M. Hector, B.G. Wachall, A. Palusczak, M. Palzer, V. Huch, and M. Veith J. Med. Chem. 43 2000 4437 4445
22. S. Haider, P.B. Ehmer, and R.W. Hartmann Arch. Pharma. Pharma. Med. Chem. 334 2001 373 374
23. V.D. Handratta, T.S. Vasaitis, V.C.O. Njar, L.K. Gediya, R. Kataria, P. Chopra, D. Newman Jr., R. Farquhar, Z. Guo, Y. Qiu, and A.M.H. Brodie J. Med. Chem. 48 2005 2972 2984
24. K.M.P. Gasi, M.D. Brensel, E.A. Djurendic, S. Andric, D.M. Sladic, T.T. Bozic, I.T. Novakovic, and Z.D. Juranic Steroids 72 2007 31 40
25. V.M.A. Moreira, T.S. Vasaitis, V.C.O. Njar, and J.A.R. Salvodor Steroids 72 2007 939 948
26. E. Djurendic, J. Daljev, M. Sakac, J. Canadi, S.J. Santa, S. Andric, O. Klisuric, V. Kojic, G. Bogdanovic, M. Djurendic-Brenesel, S. Novakovic, and K.P. Gasi Steroids 73 2008 129 138
27. Z. Jin Nat. Prod. Rep. 22 2005 196 229
28. R.A. Hughes, S.P. Thompson, L. Alcaraz, and C.J. Moody J. Am. Chem. Soc. 127 2005 15644 15651
29. M. de Souza J. Sulfur Chem. 26 2005 429 449
30. Z. Jin Nat. Prod. Rep. 23 2006 464 496
31. O. Delgado, G. Heckmann, H.M. Muller, and T. Bach J. Org. Chem. 71 2006 4599 4608
32. H.M. Muller, O. Delgado, and T. Bach Angew. Chem. Int. Ed. 46 2007 4771 4774
33. H. Takayama, K. Kato, M. Kimura, and H. Akita Heterocycles 71 2007 75 86
34. F. Magaraci, C.J. Jimenez, C. Rodrigues, J.C.F. Rodrigues, M.V. Braga, V. Yardley, K. de Luca-Fradley, S.L. Croft, W. de Souza, L.M. Ruiz-Perez, J. Urbina, D.G. Pacanowska, and I.H. Gilbert J. Med. Chem. 46 2003 4714 4727
35. D.M. Piatak, and J. Wicha Chem. Rev. 78 1978 199 241
36. B.G. Hazra, V.S. Pore, S.K. Dey, S. Datta, P.M. Darokar, D. Saikia, S.P.S. Khanuja, and A.P. Thakur Bioorg. Med. Chem. Lett. 14 2004 773 777
37. D.B. Salunke, B.G. Hazra, V.S. Pore, M.K. Bhat, P.B. Nahar, and M.V. Deshpande J. Med. Chem. 47 2004 1591 1594
38. D.B. Salunke, B.G. Hazra, and V.S. Pore Curr. Med. Chem. 13 2006 813 847
39. N.S. Vatmurge, B.G. Hazra, V.S. Pore, F. Shirazi, P.S. Chavan, and M.V. Deshpande Bioorg. Med. Chem. Lett. 18 2008 2043 2047
40. N.S. Vatmurge, B.G. Hazra, V.S. Pore, F. Shirazi, M.V. Deshpande, S. Kadreppa, S. Chattopadhyay, and R.G. Gonnade Org. Biomol. Chem. 6 2008 3823 3830
41. S.N. Bavikar, D.B. Salunke, B.G. Hazra, V.S. Pore, R.H. Dodd, J. Thierry, F. Shirazi, M.V. Deshpande, S. Kadreppa, and S. Chattopadhyay Bioorg. Med. Chem. Lett. 18 2008 5512 5517
42. The plant dioscoria, which is cultivated in many parts of India, is an abundant source of diosgenin. 16-Dehydropegnenolone acetate (1) is prepared from commercially available diosgenin following Marker's procedure R.E. Marker, R.B. Wagner, P.R. Ulshafer, E.L. Wittbecker, D.P.J. Goldsmith, and C.H. Rouf J. Am. Chem. Soc. 69 1947 2167 2230
43. B.G. Hazra, S. Basu, B.B. Bahule, V.S. Pore, B.N. Vyas, and V.M. Ramraj Tetrahedron 53 1997 4909 4920
44. B.B. Shingate, B.G. Hazra, V.S. Pore, R.G. Gonnade, and M.M. Bhadbhade Chem. Commun. 10 2004 2194 2195
45. B.B. Shingate, B.G. Hazra, V.S. Pore, R.G. Gonnade, and M.M. Bhadbhade Tetrahedron Lett. 47 2006 9343 9347
46. B.B. Shingate, B.G. Hazra, V.S. Pore, R.G. Gonnade, and M.M. Bhadbhade Tetrahedron 63 2007 5622 5635
47. A. Dondoni, and A. Nuzzi J. Org. Chem. 71 2006 7574 7582 and references cited therein
48. H. Hikino, T. Okuyama, S. Arihara, Y. Hikino, T. Takemoto, H. Mori, and K. Shibata Chem. Pharm. Bull. 23 1975 1458 1479
49. J. Drew, M. Letellier, P. Morand, and A.G. Szabo J. Org. Chem 52 1987 4047 4052
50. R.P. Litvinovskaya, S.V. Drach, E.N. Masalova, and V.A. Khripach Russ. J. Org. Chem. 40 2004 1456 1461
51. F. Trecourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, and G. Queguiner Tetrahedron Lett. 40 1999 4339 4342
52. F. Trecourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, and G. Queguiner Tetrahedron 56 2000 1349 1360
53. L. Ingrassia, P. Nshimyumukiza, J. Dewelle, F. Lefranc, L. Wlodarczak, S. Thomas, G. Dielie, C. Chiron, C. Zedde, P. Tisnes, R. van Soest, J.-C. Braekman, F. Darro, and R. Kiss J. Med. Chem. 49 2006 1800 1807
54. S.P. Modi, J.O. Gardner, A. Milowsky, M. Wierzba, L. Forgione, P. Mazur, A.J. Solo, W.L. Duax, Z. Galdecki, P. Grochulski, and Z. Wawrzak J. Org. Chem. 54 1989 2317 2321
55. A. Mauvais, A. Burger, J.P. Roussel, C. Hetru, and B. Luu Bioorg. Chem. 22 1994 36 50
56. J.C. Braekman, E. Van Quaquebeke, L. Ingrassia, J. Dewelle, R. Kiss, F. Darro, Patent WO2004/055039, 2004.
57. J.C. Braekman, L. Ingrassia, P. Nshimyumukiza, E. Van Quaquebeke, J. Dewelle, L. Van den Hove, R. Kiss, F. Darro, Patent WO2005/058934, 2005.
58. M.V. Deshpande Recent Trends Mycoses 1998 55 63
59. V. Ghormade, and M.V. Deshpande Naturwissenschaften 87 2000 236 240
60. National Committee for Clinical Laboratory Standard Reference Method for Broth Dilution Antifungal Susceptibility Testing of YeasS200t, Approved Standard Document M27-A 1997 National Committee for Clinical Laboratory Standards Wayne, PA, USA
61. National Committee for Clinical Laboratory Standard Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium Forming Filamentous Fungi: Proposed Standard Document M38-P 1998 National Committee for Clinical Laboratory Standard Wayne, PA, USA
62. National Committee for Clinical Laboratory Standards Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard fifth ed. 2000 NCCLS Villanova, PA M7-A5