73672-02-3Relevant academic research and scientific papers
AZASTEROIDS FOR TREATMENT OF TUBERCULOSIS
-
Page/Page column 68-69, (2017/12/15)
The present invention provides a compound having the structure: formula (I), for use in combinatoin with an anti-tuberculosis drug for treating a subject infected with M. tuberculosis.
Design and diastereoselective synthesis of C-2,C-20-diaryl steroidal derivatives
Rey, Jullien,O'Riordan, Timothy J. C.,Hu, Haipeng,Snyder, James P.,White, Andrew J. P.,Barrett, Anthony G. M.
supporting information; experimental part, p. 3781 - 3794 (2012/10/08)
A novel and efficient synthetic strategy to access unique C-2 substituted steroid analogues 3 and 4 is described. The unusual C-2 aryl ether analogues 3 were shown to act as virtual antagonists of LRH-1 and were prepared as single diastereoisomers, employing a fifteen-step sequence from pregnenolone (9). The key steps include the stereoconvergent nucleophilic displacement of an epimeric mixture of 3-keto 2-bromo steroids, chemoselective carbonylation of an enol triflate and conversion of a thiopyridyl ester into an aryl ketone. The related C-2 benzyl analogues 4 were prepared in a similar manner. Starting from pregnenolone, a diastereoselective fifteen-step synthesis was developed to access novel C-2-substituted steroid analogues. A range of C-2 benzyl and aryl ether analogues were prepared to probe their efficacy as antagonists of the nuclear receptor LRH-1. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents
Xia, Peng,Yang, Zheng-Yu,Xia, Yi,Zheng, Yun-Qing,Cosentino, L.Mark,Lee, Kuo-Hsiung
, p. 1907 - 1911 (2007/10/03)
In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 μM and 300, respectively.
Glycolipids as host resistance stimulators
Ponpipom,Hagmann,O'Grady,Jackson,Wood,Zweerink
, p. 861 - 867 (2007/10/02)
6-(5-Cholesten-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside (L-644,257) enhances natural host resistance in cyclophosphamide-treated mice against Pseudomonas aeruginosa in a dose-dependent manner. It is active sc, im, and ip but not orally. L-644,257 is substantially more protective against P. aeruginosa than its α anomer. The β-L-fucose glycolipid is more effective when given im and ip than sc. The lactose and β-D-glucose glycolipids were only marginally effective to nonprotective. The 17β-steroidal side chain of L-644,257 can be modified without substantial loss of protective activity.
Azasteroids as Inhibitors of Rat Prostatic 5α-Reductase
Rasmusson, Gary H.,Reynolds, Glenn F.,Utne, Torleif,Jobson, Ronald B.,Primka, Raymond L.,et al.
, p. 1690 - 1701 (2007/10/02)
A series of A-ring heterocyclic steroids has been prepared and tested for inhibition of rat prostatic steroid 5α-reductase in vitro.Strinkingly high inhibitory activity was found with a group of 17β-substituted 4-methyl-4-aza-5α-androstan-3-ones.These compounds were prepared from 3-keto-Δ4-precursors by oxidative (O3 or NaIO4-KMnO4) A-ring cleavage followed, in turn, by ring closure with an amine and hydrogenation over platinum catalyst.Other A-ring azasteroids were made by Beckmann rearrangement of oximes of 2-oxo-A-nor-, 3-oxo- and 4-oxo-5α-androstanes.An A-nor-2-oxo-3-azasteroid was prepared by oxidative decarbonylation of a precursor 2,3-dioxo-4-azasteroid with m-chloroperbenzoic acid.A-ring modifications of the 4-azasteroids included Δ1-unsaturation, 2- and 4-substituents, and 3-carbonyl replacements.Side chains at the 17-position were varied with an emphasis on carboxylate derivatives (salts, esters, and amides).
