1452-33-1Relevant academic research and scientific papers
STEROIDAL ANTIFEEDANTS FROM THE DORID NUDIBRANCH ALDISA SANGUINEA COOPERI
Ayer, Stephen W.,Andersen, Raymond J.
, p. 1039 - 1042 (1982)
Two steroids, 3-oxo-chol-4-ene-24-oic acid (2) and its unsaturated analog 4, have been isolated from the dorid nudibranch Aldisa sanguinea cooperi, and the acid 2 has been shown to have antifeedant properties.
A convenient synthesis of 3β,12α-, 3β,7α-, and 3β,7β-dihydroxy-5-cholen-24-oic acids: Unusual bile acids in human biological fluids
Tohma,Mahara,Takeshita,Kurosawa
, p. 331 - 338 (1986)
The unusual bile acids 3β,12α- (V), 3β,7α- (XIIIa), and 3β,7β- (XIIIb) dihydroxy-5-cholen-24-oic acids were synthesized conveniently from the 3-oxo derivatives of deoxycholic (I) and lithocholic (VI) acids, respectively, to provide authentic samples for the gas chromatography-mass spectrometric determination of these bile acids in the abnormal metabolism of bile acids.
A Highly Regio- and Stereoselective C5 Oxyfunctionalization of Coprostane Steroids by Dioxiranes: an Improved Access to Progestogen and Androgen Hormones.
Bovicelli, Paolo,Gambacorta, Augusto,Lupattelli, Paolo,Mincione, Enrico
, p. 7411 - 7412 (1992)
Coprostane steroids are selectively oxyfunctionalized at C5 by dimethyldioxirane and methyltrifluoromethyldioxirane to give useful intermediates for bioactive compounds.
Cholic acid derivative and preparation method and application thereof
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Paragraph 0027; 0262; 0272, (2019/12/25)
The invention discloses a cholic acid derivative represented by the formula (I) and a preparation method thereof. The target product cholic acid derivative is prepared by esterification, oxidation, bromination, debromination, 4,4-dimethylation, C-7 oxidation, reduction, TBSCl protection, iodation, cyano substitution, Wittig, Grignard, TBS-removing protection and other reactions. The invention alsoprovides an application of the cholic acid derivative in inhibiting cholesterol synthesis and reducing cholesterol and triglyceride levels in a body; the cholic acid derivative can be used for preparing drugs for preventing and treating hypercholesterolemia, hypertriglyceride, atherosclerosis and other diseases, and has good application prospects.
Cholesterol molecular probe as well as preparation method and application thereof
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Paragraph 0113; 0114, (2017/07/21)
The invention discloses a cholesterol molecular probe and a preparation method thereof. The cholesterol molecular probe shown as a formula (I) is prepared by taking lithocholic acid as a raw material through esterification reaction, oxidization reaction, dehydrogenation reaction, carbonyl protection reaction, reduction reaction, hydroxyl protection reaction, reduction reaction, iodination reaction, substitution reaction and de-protection reaction. The invention further discloses application of the cholesterol molecular probe shown as the formula (I) to identification of cholesterol modified protein. The cholesterol molecular probe provided by the invention can be used for simulating normal cholesterol to promote cell growth, and prompting the shearing ripening of the cholesterol modified protein hedgehog, and can also be used for researching cholesterol modification of the protein.
Novel 3,4-seco bile acid diamides as selective anticancer proliferation and migration agents
Mao, Shi-Wei,Chen, Huang,Yu, Li-Fang,Lv, Fang,Xing, Ya-Jing,Liu, Ting,Xie, Jia,Tang, Jie,Yi, Zhengfang,Yang, Fan
, p. 574 - 583 (2016/07/22)
A series of new seco-A ring bile acid diamides were synthesized, and their antiproliferative activities against PC3M (prostate), HT29 (colon) and ES-2 (ovarian) cancer cell lines were investigated using SRB assays. Most synthesized compounds presented improved antiproliferative activities compared to the parent bile acids (IC50> 80 μM), especially the piperazine conjugated compound 27 with IC50values of 1.07, 4.58 and 3.86 μM against PC3M, HT29 and ES-2 cancer cell lines, respectively. In addition, all the tested compounds showed less cytotoxic activity on a noncancerous cell line (HAF), and the most active compound 27 exhibited the highest selectivity (Selectivity Index, SIPC3M= 26.3). Furthermore, 27 could also enhance G1 arrest in PC3M cell, revealed by cell cycle analysis, and increase anti-migration activity on PC3M cells, confirmed by transwell migration assay.
Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis
Iida, Takashi,Omura, Kaoru,Sakiyama, Ryou,Kodomari, Mitsuo
, p. 45 - 51 (2014/03/21)
Mild and regioselective conversion of 3-keto-5α- and 3-keto-5β-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Δ1- and Δ4-3- ketones) by treatment with o-iodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the α- and β-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Paragraph 00427, (2013/03/26)
Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, wherein Z is a group of the formula (i), (ii), (iii), (iv), or (v), and wherein L1, L2, L3, X1, X2, Y, Rz4, Rz5, Rz6, n, R1, R2, R3a, R3b, R4a, R4b, R6a, R6b, R7a, R7b, R11a, R11b, R14, R17, R19, R20, R23a, R23b, and R24 are as defined herein, and pharmaceutical compositions thereof. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of CNS-related conditions in mammals.
Synthesis and biological evaluation of 4,4-dimethyl lithocholic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B
He, Hai-Bing,Gao, Li-Xin,Deng, Qi-Feng,Ma, Wei-Ping,Tang, Chun-Lan,Qiu, Wen-Wei,Tang, Jie,Li, Jing-Ya,Li, Jia,Yang, Fan
, p. 7237 - 7242 (2013/01/15)
Protein tyrosine phosphatase 1B (PTP1B) is a major negative regulator of both insulin and leptin signals. For years, inhibiting of PTP1B has been considered to be a potential therapeutics for treating Type 2 diabetes and obesity. Recently, we recognized lithocholic acid (LCA) as a natural inhibitor against PTP1B (IC50 = 12.74 μM) by a vertical screen for the first time. Further SAR research was carried out by synthesizing and evaluating a series of compounds bearing two methyls at C-4 position and a fused heterocycle to ring A. Among them, compound 14b achieved a PTP1B inhibitory activity about eightfold than LCA and a 14-fold selectivity over the homogenous enzyme TCPTP.
Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450: Osmiumporphyrin complex/tert-butyl hydroperoxide system
Iida, Takashi,Ogawa, Shoujiro,Hosoi, Keiji,Makino, Mitsuko,Fujimoto, Yasuo,Goto, Takaaki,Mano, Nariyasu,Goto, Junichi,Hofmann, Alan F.
, p. 823 - 830 (2007/10/03)
(Chemical Equation Presented) tert-Butyl hydroperoxide catalyzed by (5,10,15,20-tetramesitylporphyrinate) osmium(II) carbonyl [Os(TMP)CO] complex was found to be a highly efficient versatile oxidant for C-H carbons in steroid substrates. When reacted with representative steroids with an estrane, pregnane, 5β-cholane, or 5α-cholestane structure, regioselective oxyfunctionalization and/or oxidative degradation occurred to give a variety of novel and uncommon derivatives in one step.
