methyl 3α-acetoxy-6α-ethyl-7α-(3'-iodobenozyl)oxy-17α-chloro-5β-cholan-24-oate | 1227612-53-4

• 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 3α-acetoxy-6α-ethyl-7α-(3'-iodobenozyl)oxy-17α-chloro-5β-cholan-24-oate
• 英文别名: methyl 3α-acetoxy-6α-ethyl-7α-(3'-iodobenzoyl)oxy-17α-chloro-5β-cholan-24-oate；Methyl 3alpha-acetoxy-6alpha-ethyl-7alpha-(3'-iodobenzoyl)oxy-17a-chloro-5beta-cholan-24-oate；[(3R,5S,6R,7R,8R,9S,10S,13S,14S,17S)-3-acetyloxy-17-chloro-6-ethyl-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-7-yl] 3-iodobenzoate
• CAS: 1227612-53-4
• 化学式: C₃₆H₅₀ClIO₆
• 分子量: 741.147
• InChiKey: KDTADQHQYBEGGC-YUXJWHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3α-acetoxy-6α-ethyl-7α-(3'-iodobenozyl)oxy-17α-chloro-5β-cholan-24-oate 在 吡啶 、 Jones reagent 、 硼烷四氢呋喃络合物 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 11.0h， 生成 methyl 6α-ethyl-7α-(3'-iodobenozyl)oxy-3,16-dihydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Avicholic Acid: A Lead Compound from Birds on the Route to Potent TGR5 Modulators

  摘要：

  Grounding on our former 3D QSAR studies, a knowledge-based screen of natural bile acids from diverse animal species has led to the identification of avicholic acid as a selective but weak TGRS agonist. Chemical modifications of this compound resulted in the disclosure of 6 alpha-ethyl-16-epi-avicholic acid that shows enhanced potency at TGRS and FXR receptors. The synthesis, biological appraisals, and structure-activity relationships of this series of compounds are herein described. Moreover, a thorough physicochemical characterization of 6 alpha-ethyl-16-epi-avicholic acid as compared to naturally occurring bile acids is reported and discussed.

  DOI：

  10.1021/ml200256d
• 作为产物：
  描述：

  奥贝胆酸 在 calcium hydride 、 (二氯碘)-苯 、 苄基三乙基氯化铵 、 碳酸氢钠 、 对甲苯磺酸 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 51.0h， 生成 methyl 3α-acetoxy-6α-ethyl-7α-(3'-iodobenozyl)oxy-17α-chloro-5β-cholan-24-oate
  参考文献：
  名称：

  Avicholic Acid: A Lead Compound from Birds on the Route to Potent TGR5 Modulators

  摘要：

  Grounding on our former 3D QSAR studies, a knowledge-based screen of natural bile acids from diverse animal species has led to the identification of avicholic acid as a selective but weak TGRS agonist. Chemical modifications of this compound resulted in the disclosure of 6 alpha-ethyl-16-epi-avicholic acid that shows enhanced potency at TGRS and FXR receptors. The synthesis, biological appraisals, and structure-activity relationships of this series of compounds are herein described. Moreover, a thorough physicochemical characterization of 6 alpha-ethyl-16-epi-avicholic acid as compared to naturally occurring bile acids is reported and discussed.

  DOI：

  10.1021/ml200256d

文献信息

• [EN] TGR5 MODULATORS AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS DE TGR5 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：INTERCEPT PHARMACEUTICALS INC

  公开号：WO2010059859A1

  公开（公告）日：2010-05-27

  The invention relates to compounds of Formula (A): (A) or a salt, solvate, hydrate, or amino acid conjugate thereof. The compounds of formula A are TGR5 modulators useful for the prevention and treatment of disease.

  该发明涉及Formula (A)的化合物：(A)或其盐、溶剂合物、水合物或氨基酸共轭物。 Formula A的化合物是TGR5调节剂，可用于预防和治疗疾病。
• TGR5 Modulators and Methods of Use Thereof
  申请人：Pellicciari Roberto

  公开号：US20110263555A1

  公开（公告）日：2011-10-27

  The invention relates to compounds of Formula (A): (A) or a salt, solvate, hydrate, or amino acid conjugate thereof. The compounds of formula A are TGR5 modulators useful for the prevention and treatment of disease.

  该发明涉及公式（A）的化合物：（A）或其盐，溶剂化物，水合物或氨基酸结合物。公式A的化合物是TGR5调节剂，可用于预防和治疗疾病。
• TGR5 modulators and methods of use thereof
  申请人：Pellicciari Roberto

  公开号：US08999964B2

  公开（公告）日：2015-04-07

  The invention relates to compounds of Formula (A): (A) or a salt, solvate, hydrate, or amino acid conjugate thereof. The compounds of formula A are TGR5 modulators useful for the prevention and treatment of disease.

  该发明涉及公式（A）的化合物：（A）或其盐，溶剂化合物，水合物或氨基酸共轭物。公式A的化合物是TGR5调节剂，可用于预防和治疗疾病。
• TGR5 MODULATORS AND METHODS OF USE THEREOF
  申请人：Intercept Pharmaceuticals, Inc.

  公开号：EP2373673A1

  公开（公告）日：2011-10-12
• US8999964B2
  申请人：——

  公开号：US8999964B2

  公开（公告）日：2015-04-07