Review on the synthesis of 8-azasteroids

Current Organic Chemistry

Volumn 8, Issue 15, 2004, Pages 1521-1528

  Surya Prakash Rao, H ^a   Senthilkumar, S P ^a  

^a PONDICHERRY UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AZASTEROIDS;

10BETA HYDROXY 13BETA METHYLCYCLOHEXA[A]QUINOZILIDINE; 12 PHENYL DEXTRO HOMO 8 AZASTEROID; 16 PHENYL DEXTRO HOMO 8 AZASTEROID DERIVATIVE; 3B,4,5,6,7,8,10,11 OCTAHYDROCYCLOPENTA[F]THIENO[3,2 A]QUINOLIZIN 5 ONE; 8 AZA 16 THIOGONANE DERIVATIVE; 8 AZA 3 THI A NORESTRA1,5(10),13 TRIEN 12 ONE; 8 AZAESTRONE; 8 AZASTEROID; 8 METHOXY 1,2,3,3A,5,6,10B,11,12,12A DECAHYDROCYCLOPENTA[5,6]PYRIDO[2,1 A]ISOQUINOLIN 12 ONE DERIVATIVE; 8,13 DIAZA 2,3 DIMETHOXYGONA 1,3,5(10),9(11) TETRAEN 12 ONE; 8,13 DIAZASTEROID; ANDROSTERONE DERIVATIVE; ANTIANDROGEN; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; AZATHIASTEROID DERIVATIVE; CONTRACEPTIVE AGENT; ESTROGEN DERIVATIVE; ESTRONE DERIVATIVE; GONANE DERIVATIVE; HYPOCHOLESTEROLEMIC AGENT; IMMUNOMODULATING AGENT; ISOQUINOLINE DERIVATIVE; NEUROMUSCULAR BLOCKING AGENT; NORETHISTERONE DERIVATIVE; PROGESTERONE DERIVATIVE; STEROID; STEROID 5ALPHA REDUCTASE INHIBITOR; TESTOSTERONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

CYCLIZATION; DEHYDROGENATION; DRUG STRUCTURE; DRUG SYNTHESIS; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 4544303152     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043369881     Document Type: Review

References (40)

1. Fieser, L. F.; Fieser, M. Steroids; Asia Publishing House: New York, 1962; pp. 1.
2. Turkes, A.; Dyas, J.; Read, G. F.; Riad Fahmy, D. Steroids, 1980, 35, 445.
3. Oelkers, Wolfgang K. H. Steroids, 1996, 61, 4166.
4. Trappen, Y. Van.; Duvivier, P.; Thiery, M.; Kets, H. Van.; Defoort, P. Arzneim. Forsch., 1989, 39, 717.
5. Morray, J.; Toeroet, J.; Sas, M. Pharmazie, 1981, 36, 18.
6. Sedee, A. G. J.; Henegouven, Gerardus M. J.; Beijers, V.; Monique, E. de; Erkelens, C. Steroids, 1985, 45, 101.
7. Akhrem, A. A.; Kuzmickiy, B. B.; Lakhvich, F. A.; Khripach, V. A.; Zhuravkov, Yu. L. Zhuravkov, in: Khimya i Biologiya Immunoregulyatorov Riga, 1985, 265.
8. Kuzmickiy, B. B.; Dad'kov, I. G.; Zhuravkov, Yu. L.; Konoplya, N. A.; Lyubin, G. S.; Mashkovich, A. E.; Nasek, V. M.; Gulyakevich,O. V.; Pshenichny, V. N.; Khripach, V. A. Vesti. Acad. Nauk. BSSR, Ser. Khim. Nauk., 1989, 1, 64.
9. Singh, H.; Bharadwaj, T. R.; Ahuja, N. A.; Paul, D. J. Chem. Soc. Perkin Trans 1, 1979, 305.
10. Gandiha, A.; Marshall, I. G.; Paul, D.; Singh, H. J. Pharm. Pharmacol., 1974, 26, 871.
11. Chesnut, R. W.; Durham, N. N.; Brown, R. A.; Mawdsley, E. A.; Berlin, K. D. Steroids, 1976, 27, 525.
12. Solomons, W. E.; Doorenbos, N. J. J. Pharm. Sci., 1973, 63, 19.
13. Doorenbos, N. J.; Solomons, W. E. J. Pharm. Sci., 1973, 62, 638.
14. Counsell, R. E.; Klimstra, P. D.; Ranney, R. E.; Cook, D. L. J. Med. Pharm. Chem., 1962, 5, 720.
15. Counsell, R. E.; Klimstra, P. D.; Nysted, L. N.; Ranney, R. E. J. Med. Chem., 1965, 8, 45.
16. Dolle, R. E.; Allaudeen, H. S.; Kruse, L. I. J. Med. Chem., 1990, 33, 877.
17. Barton, D. H. R.; Lusinchi, X.; Menendez, A. M.; Milliet, P. Tetrahedron, 1983, 39, 2201.
18. Rasmusson, G. H.; Reynolds, G. F.; Steinberg, N. G.; Walton, E,; Patel, G. F.; Liang, T.; Cascieri, M. A.; Cheung, A. H.; Brooks, J. R.; Berman, C. J. Med. Chem., 1986, 29, 2298.
19. Rasmusson, G. H.; Reynolds, G. F.; Utne, T.; Jobson, R. B.; Primka, R. L.; Berman, C.; Brooks, J. R. J. Med. Chem., 1984, 27, 1690.
20. Bowler, J.; Clarkson, R. J. Chem. Soc., 1968, 2111.
21. Konoplya, N. A.; Gulyakevich, O. V.; Mikhalchuk, A. L.; Kuzmickiy, B. B. Vesti. Acad. Nauk. Belarusi, Ser. Khim. Nauk, 1994, 3, 91.
22. Akhrem, A. A.; Borisvich, N. A.; Gulyakevich, O. V.; Mikhalchuk, A. L.; Raichenok, T. F.; Tolstorozhev, G. B. J. Appl. Spectrosc., 1998, 65, 323.
23. Lakhavich, F. A.; Akhrem, A. A. Uspekhi Khimii, 1984, 53, 1014. CAN: 101:72990.
24. Akhrem, A. A.; Lakhvich, F. A.; Lis, L. G.; Kuz'mitskii, B. B. Ser. Khim. Navuk., 1982, 6, 81. CAN: 98:161007.
25. Pshenichnyl, V. N.; Golub, N. I.; Litvinovskaya, R. P.; Akhrem, A. A. Ser. Khim. Navuk., 1984, 4, 96. CAN: 102:6914.
26. Akhrem, A. A.; Kurbako, V. Z.; Gulyakevich, O. V.; Pshenichnyi, V. N.; Khripach, V. A.; Garbuz, N. I. Khim. Geterotsikli. Soedin., 1985, 8, 1135.
27. Tailor, S. H.; Kamat, A. K.; Bhide, G. V. Ind. J. Chem., 1988, 27B, 330.
28. Gertsev, V. V.; Romanov, Yu. A. Khim. Geterotsikli. Soedin., 1989, 11, 1483. CAN: 113:40385.
29. Meyers, A. I.; Elworthy, T. R. J. Org. Chem., 1992, 57, 4732.
30. Mikhalchuk, A. L.; Gulyakevich, O. V.; Rubinov, D. B. Akhrem, A. A. Khim. Geterosikli. Soedin., 1993, 3, 374. CAN: 120:107444.
31. Barluenga, J.; Thomas, M.; Suarez-Sobrino, A.; Rubio, E. J. Org. Chem., 1993, 58, 700,
32. Mikhalchuk, A. L.; Gulyakevich, O. V.; Zenyuk, A. A.; Shklyaev, Yu. V.; Shklyaev, V. S.; Akhrem, A. A. Zhur. Obsh. Khim., 1993, 63, 1891. CAN: 121:35963.
33. Gulyakevich, O. V.; Mikhalchuk, A. L.; Akhrem, A. A. Khim. Geterosikli. Soedin., 1995, 2, 187. CAN: 123:112489.
34. Gulyakevich, O. V.; Mikhalchuk, A. L.; Akhrem, A. A. Khim. Geterosikli. Soedin., 1995, 2, 266. CAN: 123:112490.
35. Gondos, G.; Gera, L.; Toth, G.; Kalman, A.; Bridson, J. Stroids, 1998, 63, 375.
36. Mikhalchuk, A. L.; Gulyakevich, O. V.; Rubinov, D. B.; Rubinova, I. L. Zhur. Obsh. Khim., 1998, 34, 906. CAN: 130:178228.
37. Budnikova, M. V.; Lis, L. G.; Mikhalchuk, A. L. Zhur. Obsh. Khim., 1999, 69, 1012. CAN: 132:64441.
38. Celanire, S.; Salliot-Maire, I.; Ribereau, P.; Godard, A.; Queguiner, G. Tetrahedron, 1999, 55, 9269.
39. Budnikova, M. V.; Zheldakova, T. A.; Rubinov, D. B.; Mikhalchuk, A. L. Zhur. Organic. Khim., 2001, 37, 293. CAN: 135:242389.
40. Rao, H. S. P.; Senthilkumar, S. P. (unpublished results).