methyl (7α,12α)-7,12-di(methoxymethyloxy)-3-oxo-5β-cholan-24-oate | 831171-65-4

• 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 (7α,12α)-7,12-di(methoxymethyloxy)-3-oxo-5β-cholan-24-oate
• 英文别名: methyl (4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-bis(methoxymethoxy)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 831171-65-4
• 化学式: C₂₉H₄₈O₇
• 分子量: 508.696
• InChiKey: IPVXAACAMPYFBA-ZPTOEARBSA-N

物化性质

• 沸点：
  551.7±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  7alpha,12alpha-二羟基-3-氧代-5beta-胆烷-24-酸甲酯	3-oxo cholic acid methyl ester	14772-99-7	C25H40O5	420.59
  胆酸甲酯	methyl cholate	1448-36-8	C25H42O5	422.605
  胆酸	cholate	81-25-4	C24H40O5	408.579

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl (7α,12α)-7,12-di(methoxymethyloxy)-3-oxo-5α-cholan-24-oate	1319714-59-4	C29H48O7	508.696
  ——	methyl (4R)-4-[(3R,4R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-4-(3-hydroxypropyl)-3,7,12-tris(methoxymethoxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate	831170-69-5	C34H60O9	612.845
  别胆酸	allocholic acid	2464-18-8	C24H40O5	408.579
  ——	methyl (4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-2-cyano-7,12-bis(methoxymethoxy)-10,13-dimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate	1198228-16-8	C30H45NO7	531.69
  ——	methyl (4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-2-cyano-3-hydroxy-7,12-bis(methoxymethoxy)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate	1198227-95-0	C30H47NO7	533.706
  ——	methyl (7α,12α)-7,12-di(methoxymethyloxy)-3-oxo-chol-4-en-24-oate	1319714-57-2	C29H46O7	506.68

反应信息

• 作为反应物：
  描述：

  methyl (7α,12α)-7,12-di(methoxymethyloxy)-3-oxo-5β-cholan-24-oate 在 盐酸 、 2-iodoxybenzoic acid 、 氨 、 lithium 、 potassium tri-sec-butyl-borohydride 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 84.08h， 生成 别胆酸
  参考文献：
  名称：

  A stereoselective synthesis of the allo-bile acids from the 5β-isomers

  摘要：

  The allo-bile acids are a subset of the family of steroidal detergents found in most vertebrates. Because there are no major biological feedstocks for isolation of the alto-bile acids, they must be synthesized from the abundant 5 beta-reduced isomers. Here we report a general set of methods for the synthesis of allo-bile acids from the corresponding 5-beta isomers demarcated by a selective C-3 oxidation, IBX unsaturation, and stereoselective saturation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.140
• 作为产物：
  描述：

  胆酸甲酯 在 N,N-二异丙基乙胺 、 silver carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 methyl (7α,12α)-7,12-di(methoxymethyloxy)-3-oxo-5β-cholan-24-oate
  参考文献：
  名称：

  [EN] COMPOUNDS INCLUDING AN ANTI-INFLAMMATORY PHARMACORE AND METHODS OF USE
  [FR] COMPOSÉS COMPRENANT UN PHARMACORE ANTI-INFLAMMATOIRE ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2009146218A8

文献信息

• Liver-Selective Glucocorticoid Antagonists:  A Novel Treatment for Type 2 Diabetes
  作者：Thomas W. von Geldern、Noah Tu、Philip R. Kym、James T. Link、Hwan-Soo Jae、Chunqiu Lai、Theresa Apelqvist、Patrik Rhonnstad、Lars Hagberg、Konrad Koehler、Marlena Grynfarb、Annika Goos-Nilsson、Johnny Sandberg、Marie Österlund、Tomas Barkhem、Marie Höglund、Jiahong Wang、Steven Fung、Denise Wilcox、Phong Nguyen、Clarissa Jakob、Charles Hutchins、Mathias Färnegårdh、Björn Kauppi、Lars Öhman、Peer B. Jacobson

  DOI：10.1021/jm0400045

  日期：2004.8.1

  Hepatic blockade of glucocorticoid receptors (GR) suppresses glucose production and thus decreases circulating glucose levels, but systemic glucocorticoid antagonism can produce adrenal insufficiency and other undesirable side effects. These hepatic and systemic responses might be dissected, leading to liver-selective pharmacology, when a GR antagonist is linked to a bile acid in an appropriate manner

  肝脏对糖皮质激素受体（GR）的阻滞抑制了葡萄糖的产生，从而降低了循环葡萄糖的水平，但是全身性糖皮质激素拮抗作用会产生肾上腺功能不全和其他不良副作用。当GR拮抗剂以适当的方式与胆汁酸相连时，这些肝和全身反应可能会被分解，从而导致肝脏选择性药理学。胆汁酸结合可以在对GR的结合亲和力损失最小的情况下完成。所得的缀合物在基于细胞的功能测定中仍然有效。已经开发出一种新颖的体内测定法，以同时评估肝和全身性GR阻滞。该测定法已用于优化接头功能的性质和位点，以及选择GR拮抗剂和胆汁酸。
• COMPOUNDS INCLUDING AN ANTI-INFLAMMATORY PHARMACORE AND METHODS OF USE
  申请人：Anderson Eric

  公开号：US20100048887A1

  公开（公告）日：2010-02-25

  This invention provides novel compounds comprising the following anti-inflammatory pharmacore: wherein X, R 1 and R 2 are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.
• NATURAL PRODUCT ANALOGS INCLUDING AN ANTI-INFLAMMATORY CYANOENONE PHARMACORE AND METHODS OF USE
  申请人：REATA PHARMACEUTICALS, INC.

  公开号：US20160145200A1

  公开（公告）日：2016-05-26

  This invention provides novel compounds comprising the following anti-inflammatory pharmacore: wherein X, R 1 and R 2 are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.
• US8258329B2
  申请人：——

  公开号：US8258329B2

  公开（公告）日：2012-09-04
• US9233998B2
  申请人：——

  公开号：US9233998B2

  公开（公告）日：2016-01-12