4004-68-6Relevant articles and documents
Spectroscopic evaluation of synthesized 5β-dihydrocortisol and 5β-dihydrocortisol acetate binding mechanism with human serum albumin and their role in anticancer activity
Kallubai, Monika,Reddy, Srinivasa P.,Dubey, Shreya,Ramachary, Dhevalapally B.,Subramanyam, Rajagopal
, p. 1 - 18 (2018/02/22)
Our study focus on the biological importance of synthesized 5β-dihydrocortisol (Dhc) and 5β-dihydrocortisol acetate (DhcA) molecules, the cytotoxic study was performed on breast cancer cell line (MCF-7) normal human embryonic kidney cell line (HEK293), th
Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids
Ramachary, Dhevalapally B.,Sakthidevi, Rajasekar,Reddy, P. Srinivasa
, p. 13497 - 13506 (2013/09/02)
Kinetically controlled and organocatalytic syn-selective transfer hydrogenation has been successfully demonstrated for the reduction of the enone functional group of various steroids. Herein, diastereoselective synthesis of many 5β-steroids have been reported through organocatalysis, which have broad medicinal and pharmaceutical applications. The mechanistic studies and the selectivity of the products clearly indicated that the catalyst 1b·d-CSA is mild enough to activate the various chiral cyclic enones through iminium ion formation during the organocatalytic transfer hydrogenations with Hantzsch ester 2a as a hydrogen source. Further, clear evidence for the selective formation of intermediate iminium species [I]+ have been characterized through on-line monitoring of controlled experiments by NMR and ESI-HRMS analyses.
Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5 α- and 5 β-series
Okihara, Rika,Mitamura, Kuniko,Hasegawa, Maki,Mori, Megumi,Muto, Akina,Kakiyama, Genta,Ogawa, Shoujiro,Iida, Takashi,Shimada, Miki,Mano, Nariyasu,Ikegawa, Shigeo
experimental part, p. 344 - 353 (2011/02/22)
Here, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5 α- and 5 β-series. The principal reactions involved are: (1) selective protection of a specific hydroxy group in substrates; (2) catalytic hydrogenation at C-5 of Δ4-3-ketosteroids with 10% Pd(OH) 2/C to yield 3-oxo-5 β-steroids and reductive allomerization with 10% Pd/C to yield 3-oxo-5 α-isomers; (3) reduction of the resulting 3-oxo-5 β- and 3-oxo-5 α-steroids to the corresponding 3 α-hydroxy-compounds with Zn(BH4)2 and K-Selectride, respectively; and (4) sulfation of hydroxy groups at C-3 and/or C-21 in the tetrahydrocorticosteroid derivatives with sulfur trioxide-triethylamine complex.
