methyl 3α,6α-dihydroxy-7-keto-5β-cholan-24-oate | 28071-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 3α,6α-dihydroxy-7-keto-5β-cholan-24-oate
• 英文别名: methyl 3α, 6α-dihydroxy-7-keto-5β-cholanoate；Methyl 3,6-dihydroxy-7-oxo-cholan-24-oic Acid Ester；methyl (4R)-4-[(3R,5R,6R,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 28071-17-2
• 化学式: C₂₅H₄₀O₅
• 分子量: 420.59
• InChiKey: RYTXBFUFNOVAOB-WKGRRQNDSA-N

物化性质

• 沸点：
  540.0±45.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3α,6α-dihydroxy-7-keto-5β-cholan-24-oate 以96%的产率得到
  参考文献：
  名称：

  IIDA, TAKASHI;MOMOSE, TOSHIAKI;TAMURA, TOSHITAKE;MATSUMOTO, TARO;GHANG, F+, J. LIPID RES., 30,(1989) N, C. 1267-1279

  摘要：

  DOI：
• 作为产物：
  描述：

  鹅去氧胆酸 在 甲醇 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 氢溴酸 、 溴 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 63.33h， 生成 methyl 3α,6α-dihydroxy-7-keto-5β-cholan-24-oate
  参考文献：
  名称：

  [EN] SYNTHETIC DERIVATIVES OF CHOLIC ACID 7-SULFATE AND USES THEREOF
  [FR] DÉRIVÉS SYNTHÉTIQUES DU 7-SULFATE D'ACIDE CHOLIQUE ET UTILISATIONS DE CEUX-CI

  摘要：

  公开号：

  WO2020117945A8

文献信息

• Fluorinated bile acid derivatives, processes for the preparation thereof
  申请人：Giuliani S.p.A.

  公开号：US05175320A1

  公开（公告）日：1992-12-29

  Compounds of general formula I ##STR1## wherein R.sub.1 is hydrogen or hydroxy, and the hydroxy group at the 7-position can be either in .alpha. or .beta. configuration, are valuable in human therapy. Compounds I can be prepared by fluorination of the suitably protected 6.alpha.-hydroxy-7-keto-derivatives.

  通式I的化合物其中R.sub.1是氢或羟基，而7位的羟基可以是α或β构型，在人类治疗中具有价值。化合物I可通过适当保护的6-α-羟基-7-酮衍生物的氟化制备。
• Bile Acid Derivatives as Ligands of the Farnesoid X Receptor. Synthesis, Evaluation, and Structure−Activity Relationship of a Series of Body and Side Chain Modified Analogues of Chenodeoxycholic Acid
  作者：Roberto Pellicciari、Gabriele Costantino、Emidio Camaioni、Bahman M. Sadeghpour、Antonio Entrena、Timothy M. Willson、Stefano Fiorucci、Carlo Clerici、Antimo Gioiello

  DOI：10.1021/jm049904b

  日期：2004.8.1

  The farnesoid X receptor (FXR) is activated by endogenous bile acids (BAs) and plays a variety of physiological roles related to modulation of gene transcription. In particular, FXR positively regulates the cholesterol catabolism while feedback inhibits the BA synthesis by repressing the expression of the CYP7A and CYP8B genes. We have previously shown that 6alpha-ethyl-CDCA (6ECDCA) is a potent and selective FXR agonist. In this paper we report an extensive structure-activity relationship for a series of synthetic bile acids. Our results indicate that the 6alpha position plays a fundamental role in determining affinity and that the side chain of BA is amenable to a variety of chemical modification. Although none of the new derivatives is more potent than 6ECDCA, we show here that a wide variability in efficacy, from full agonists to partial antagonists, can be obtained.
• SYNTHETIC DERIVATIVES OF CHOLIC ACID 7-SULFATE AND USES THEREOF
  申请人：President and Fellows of Flarvard College

  公开号：US20220016138A1

  公开（公告）日：2022-01-20

  The compositions and methods provided herein are related, in part, to the discovery of cholic acid 7-sulfate as a treatment for diabetes. Provided herein is a method for treating a metabolic disorder (e.g., diabetes, obesity), or an inflammatory disease (e.g., Crohn's disease, inflammatory bowel disease, ulcerative colitis, pancreatitis, hepatitis, appendicitis, gastritis, diverticulitis, celiac disease, food intolerance, enteritis, ulcer, gastroesophageal reflux disease (GERD), psoriatic arthritis, psoriasis, and rheumatoid arthritis) in a subject in need thereof comprising administering to a subject a compound of Formulae (I)-(XVII).