- Discovery of novel 3-hydroxyandrosta-5,7-Diene-17-Carboxylic acid derivatives as anti-inflammatory bowel diseases (IBD) agents
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A series of steroidal compounds based on 3-hydroxyandrosta-5,7-diene-17-carboxylic acid core structure were designed, synthesized and bio-evaluated for their anti-inflammatory potency. Among them, compound 5c, 6f, and 6q effectively inhibited the producti
- Chen, Jingxuan,Li, Ling,Liu, Jin,Yuan, Sijie,Liao, Wenzhen,Slominski, Andrzej T.,Li, Wei,?mijewski, Micha? A.,Chen, Jianjun
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- AZASTEROIDS FOR TREATMENT OF TUBERCULOSIS
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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.
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- 3-hydroxy-5-androstene -17 β method for the preparation of carboxylic acid methyl ester
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The invention discloses a 3-hydroxy-5-androstene-17 beta carboxylate (I) preparation method comprising the steps of: 3-hydroxy-5-androstene-17 beta carboxylic acid (II) is dissolved in alkali water, and added with dimethyl carbonate, and heated for reflux for esterification reaction, an alkali solution is added in the esterification reaction process every 20-40min to adjust the PH value to 8-10, after points are dispensed on a plate for reaction, circulating water is cooled to 65 to 75 DEG C, an acid is used to adjust the PH value to 6-8, vacuum concentration of excess dimethyl carbonate is performed, circulating water is cooled to below 40 DEG C, and 3-hydroxy-5-androstene-17 beta carboxylate (I) is obtained by direct spin-filtering, water washing to neutral, and spin-drying. The method avoids the use of highly corrosive strong acids and highly toxic methanol for esterification and use of hypertoxic dimethyl sulfate for esterification, and has the advantages of good quality, high yield, low cost, economy, environmental protection, simple after treatment.
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Paragraph 0033-0035
(2017/01/17)
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- An efficient approach to novel 17-5′-(1′,2′,4′)- oxadiazolyl androstenes via the cyclodehydration of cytotoxic O-steroidacylamidoximes, and an evaluation of their inhibitory action on 17α-hydroxylase/C17,20-lyase
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Novel 17-exo-oxadiazoles in the androst-5-ene series were efficiently synthesized in a two-step sequence via the corresponding O-acylamidoxime intermediates (obtained from steroidal 17-carboxylic acids and amidoximes in the presence of coupling reagent), which then underwent tetrabutylammonium fluoride-induced cyclocondensation under mild reaction conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their inhibitory effect on rat testicular C17,20-lyase and their antiproliferative action on four malignant human adherent cell lines (HeLa, MCF7, A2780 and A431). One of the oxadiazolyl derivatives proved to exert significant enzyme-inhibitory action (IC50 = 0.60 μM), while some of the isolated O-acylated amidoxime intermediates displayed high cytotoxic activities on all examined cell lines, with IC50 values in the range 0.22-3.94 μM.
- Kovács, Dóra,W?lfling, János,Szabó, Nikoletta,Szécsi, Mihály,Kovács, Ida,Zupkó, István,Frank, éva
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p. 649 - 660
(2013/12/04)
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- Design and diastereoselective synthesis of C-2,C-20-diaryl steroidal derivatives
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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.
- Rey, Jullien,O'Riordan, Timothy J. C.,Hu, Haipeng,Snyder, James P.,White, Andrew J. P.,Barrett, Anthony G. M.
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supporting information; experimental part
p. 3781 - 3794
(2012/10/08)
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- The first synthesis of Krempene B
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The synthesis of Krempene B, which can be isolated from the marine soft coral Cladiella krempfi, is achieved in 23.9% overall yield from commercially available 3β-acetoxy-5-pregnen-20-one by 11 steps. Key transformations include the dienone-phenol rearrangement of steroids and Wittig reaction.
- Shen, Li-Qun,Huang, Su-Yu,Tang, Yong,Lei, Fu-Hou
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p. 1398 - 1402
(2013/01/15)
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- Dimethylaluminum methyltellurate, a new reagent for the cleavage of hindered methyl esters under exceptionally mild conditions by a novel mechanism
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An efficient and effective new reagent (Me2AlTeMe)2 has been developed for the conversion of methyl esters to the corresponding carboxylic acids in toluene solution at 23°C.
- Reddy, B.V. Subba,Reddy, Leleti Rajender,Corey
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p. 4589 - 4593
(2007/10/03)
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- Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents
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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.
- Xia, Peng,Yang, Zheng-Yu,Xia, Yi,Zheng, Yun-Qing,Cosentino, L.Mark,Lee, Kuo-Hsiung
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p. 1907 - 1911
(2007/10/03)
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- Steroidal Aphidicolin Analogues Derived from Pregnenolone
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The converision of pregnenolone into the 3β,5α-, 3α,5α-, 4β,5α-, 3β,4α, 3α,4β- and 3α,4α-dihydroxy derivatives of 17β-hydroxymethyl-5α-androstane as steroidal analogues of the diterpenoid DNA polymerase α inhibitor, aphidicolin, is described.
- Hanson, James R.,Yildirim, Kudret
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p. 2975 - 2991
(2007/10/03)
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- Synthesis of 4-trifluoromethylsteroids: A novel class of steroid 5α-reductase inhibitors
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A concise synthetic approach to 4-trifluoromethyl steroids, a novel class of steroid 5α-reductase inhibitors, is described. Direct trifluoromethylation of steroid olefinic bromide with methyl fluorosulfonyldifluoroacetate was used as a key step in the synthesis. The compound 4 exhibited highly inhibitory activity than Finasteride in in vitro assay.
- Fei, Xiang-Shu,Tian, Wei-Sheng,Chen, Qing-Yun
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p. 3113 - 3118
(2007/10/03)
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- Process for the preparation of 17β-substituted-4-aza-5α-androstan-3-one derivatives
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The preparation of a compound of formula (I) STR1 wherein X is oxygen or sulphur; R1 is hydrogen or C1 -C6 alkyl; each of R2 and R3 is, independently, hydrogen, C1 -C6 alkyl, C5 or C6 cycloalkyl or C6 -C9 cycloalkylalkyl; R4 is hydrogen, C1 -C6 alkyl, C3 - or C6 cycloalkyl, C6 -C9 cycloalkylalkyl or aryl; and the symbol represents a single or a double bond; by a multi-step process is disclosed.
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- Acetylenic Inhibitors of C-22 Hydroxylase of Ecdysone Biosynthesis
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Acetylenic derivatives of cholesterol designed to be inhibitors of ecdysteroid biosynthesis were prepared.The side chains of these compounds differ additionally from that of cholesterol by stereochemical modifications at C-17 and C-20.A bicyclic acetylenic compound containing the partial structure of the C and D rings of the cholesterol nucleus was also synthesized.These compounds were devised with the aim of inhibiting the C-22 hydroxylation of ecdysone biosynthesis by a suicide substrate mechanism.One of these molecules inhibits very efficiently the synthesis of ecdysone in prothoracic glands in vitro.
- Mauvais, Antony,Burger, Alain,Roussel, Jean Pierre,Hetru, Charles,Luu, Bang
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- Azasteroids as Inhibitors of Rat Prostatic 5α-Reductase
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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).
- Rasmusson, Gary H.,Reynolds, Glenn F.,Utne, Torleif,Jobson, Ronald B.,Primka, Raymond L.,et al.
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p. 1690 - 1701
(2007/10/02)
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- Process for preparing 17β-carboxy-5-androsten-3-ones
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A process for preparing 17β-carboxy-4-androsten-3-ones comprising the steps of (1) reacting a 17β-(1-ketoethyl)-5-androsten-3-ol, for example, pregnenolene, with pyridine and iodine to form a pyridinium iodide compound; (2) reacting the pyridinium iodide compound with alkali metal methoxide in methanol to form a methyl-5-androsten-3-ol-17β carboxylate; (3) oxidizing the product of Step (2) preferably with aluminum isopropoxide to form methyl-4-androsten-3-one-17β-carboxylate; and (4) hydrolyzing the product of Step (3) to the corresponding 17β-carboxylic acid, salt, or ester. The 17β-carboxy-4-androsten-3-ones are useful as intermediates for preparation of N-substituted-17β-carbamoylandrost-4-en-3-one and 4-aza-17β-substituted-5α-androstan-3-one 5α reductase inhibitors.
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