An Overview of Partial Synthesis and Transformations of Secosteroids

被引:18
作者
Gasi, Katarina Penov [1 ]
Sakac, Marija [1 ]
Jovanovic-Santa, Suzana [1 ]
Djurendic, Evgenija [1 ]
机构
[1] Univ Novi Sad, Fac Sci, Dept Chem Biochem & Environm Protect, Novi Sad 21000, Serbia
关键词
Secosteroids; partial synthesis; reactivity; modification; BECKMANN FRAGMENTATION REACTION; CONTAINING D-HOMOESTRONE; RAY CRYSTAL-STRUCTURE; BIOLOGICAL EVALUATION; AZA-STEROIDS; PHOTOINDUCED TRANSFORMATIONS; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE SYNTHESIS; OXIDATION-PRODUCTS; RADICAL OXIDATION;
D O I
10.2174/13852728113176660147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Secosteroids are an important group of modified steroids, which exhibits a variety of different biological activities. Studies on secosteroids have shown that modifications of the rigid tetracyclic steroidal carbon skeleton by cleavage of the internal C-C bonds provides more flexible compounds with new biological properties. The search for steroid compounds analogs with improved biological properties includes ring transformation into seco system. The recent development in the partial syntheses of secosteroids is described herein, as well as studies of methods for modifications of such molecules.
引用
收藏
页码:216 / 259
页数:44
相关论文
共 170 条
[71]   Synthesis and biological activity of new 16,17-secoestrone derivatives [J].
Jovanovic-Santa, S ;
Andric, S ;
Kovacevic, R ;
Pejanovic, V .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (01) :77-82
[72]  
Jovanovic-Santa SS, 1999, J SERB CHEM SOC, V64, P393
[73]   Evaluation of biological activity of new hemiesters of 17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile [J].
Jovanovic-Santa, Suzana S. ;
Andric, Silvana ;
Andric, Nebojsa ;
Bogdanovic, Gordana ;
Petrovic, Julijana A. .
MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (07) :1102-1110
[74]   Effect of solvent on stereoselectivity in Pd/C (type 39K)-Catalyzed hydrogenation of methyl 3-oxo-4-aza-5-androstene-17-carboxylateg, a key intermediate for Finasteride and Dutasteride [J].
Karrothu, Srihari Babu ;
Kolla, Naveenkumar ;
Lekkala, Amarnath Reddy ;
Golla, China Malakondaiah ;
Anand, Ramasamy Vijaya ;
Gandu, Venkateswarlu ;
Bhattacharya, Apurba ;
Padi, Pratap Reddy ;
Bandichhor, Rakeshwar .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (05) :889-891
[75]   Epalons: 6-substituted derivatives of 7-norepiallopregnanolone [J].
Kasal, A .
TETRAHEDRON, 2000, 56 (22) :3559-3565
[76]   Reaction of (13S)-13-iodo-6β-methoxy-3α-,5-cyclo-13,14-seco-5α-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids [J].
Khripach, VA ;
Zhabinskii, VN ;
Kuchto, AI ;
Fando, GP ;
Zhiburtovich, YY ;
Lyakhov, AS ;
Govorova, AA ;
Groen, MB ;
van der Louw, J ;
de Groot, A .
STEROIDS, 2004, 69 (07) :511-514
[77]   Synthesis of 13,14-secotestosterone derivatives [J].
Khripach, VA ;
Zhabinskii, VN ;
Kuchto, AI ;
Zhiburtovich, YY ;
Fando, GP ;
Lyakhov, AS ;
Govorova, AA ;
Groen, MB ;
van der Louw, J ;
de Groot, A .
STEROIDS, 2004, 69 (07) :501-509
[78]   The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation [J].
Khripach, VA ;
Zhabinskii, VN ;
Fando, GP ;
Kuchto, AI ;
Lyakhov, AS ;
Govorova, AA ;
Groen, MB ;
van der Louw, J ;
de Groot, A .
STEROIDS, 2004, 69 (07) :495-499
[79]   Radical oxidation of 17-functionalized 14α-hydroxy steroids [J].
Khripach, VA ;
Zhabinskii, VN ;
Kotyatkina, AI ;
Fando, GP ;
Zhiburtovich, YY ;
Lyakhov, AS ;
Govorova, AA ;
Groen, MB ;
van der Louw, J ;
de Groot, A .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2001, 66 (12) :1764-1776
[80]   Intramolecular cycloaddition/cycloreversion of (E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one [J].
Khripach, Vladimir A. ;
Zhabinskii, Vladimir N. ;
Kuchto, Anna I. ;
Zhiburtovich, Yuliya Y. ;
Gromak, Vladimir V. ;
Groen, Marinus B. ;
van der Louw, Jaap ;
de Groot, Aede .
TETRAHEDRON LETTERS, 2006, 47 (38) :6715-6718