methyl 3α,7,12α-trimethylsiloxy-5β-cholan-6-en-24-oate | 1198787-00-6

• 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,7,12α-trimethylsiloxy-5β-cholan-6-en-24-oate
• 英文别名: methyl (4R)-4-[(3R,5S,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-tris(trimethylsilyloxy)-2,3,4,5,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1198787-00-6
• 化学式: C₃₄H₆₄O₅Si₃
• 分子量: 637.136
• InChiKey: QFHIIAKBYMFQNB-DVVVTZDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.24
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3α,7,12α-trimethylsiloxy-5β-cholan-6-en-24-oate 、 乙醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Discovery of 6α-Ethyl-23(S)-methylcholic Acid (S-EMCA, INT-777) as a Potent and Selective Agonist for the TGR5 Receptor, a Novel Target for Diabesity

  摘要：

  In the framework of the design and development of TGR5 agonists, we reported that the introduction of a C-23(S)methyl group in the side chain of bile acids such as chenodeoxycholic acid (CDCA) and 6-ethylchenodeoxycholic acid (6-ECDCA, INT-747) affords selectivity for TGR5. Herein we report further lead optimization efforts that have led to the discovery of 6 alpha-ethyl-23(S)-methylcholic acid (S-EMCA. INT-777)as a novel Potent and selective TGR5 agonist with remarkable in vivo activity.

  DOI：

  10.1021/jm901390p
• 作为产物：
  描述：

  三甲基氯硅烷 、 (3alpha,5beta,12alpha)-3,12-二羟基-7-酮基胆烷-24-酸甲酯 在 正丁基锂 、 二异丙胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.75h， 生成 methyl 3α,7,12α-trimethylsiloxy-5β-cholan-6-en-24-oate
  参考文献：
  名称：

  Discovery of 6α-Ethyl-23(S)-methylcholic Acid (S-EMCA, INT-777) as a Potent and Selective Agonist for the TGR5 Receptor, a Novel Target for Diabesity

  摘要：

  In the framework of the design and development of TGR5 agonists, we reported that the introduction of a C-23(S)methyl group in the side chain of bile acids such as chenodeoxycholic acid (CDCA) and 6-ethylchenodeoxycholic acid (6-ECDCA, INT-747) affords selectivity for TGR5. Herein we report further lead optimization efforts that have led to the discovery of 6 alpha-ethyl-23(S)-methylcholic acid (S-EMCA. INT-777)as a novel Potent and selective TGR5 agonist with remarkable in vivo activity.

  DOI：

  10.1021/jm901390p