(R)-EMCA | 1198786-98-9

• 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: (R)-EMCA
• 英文别名: 6α-ethyl-23(S)-methyl-3α,7α,12α trihydroxy-5β-cholan-24-oic acid；6α-ethyl-23(S)-methyl-3α,7α,12α-trihydroxy-5β-cholan-24-oic acid；3α,7α,12α-trihydroxy-6α-ethyl-23-methyl-5β-cholan-24-oic acid；6α-ethyl-23(R)-methylcholic acid；INT-777；R-EMCA；INT-777 R-enantiomer；(2R,4R)-4-[(3R,5S,6R,7R,8R,9S,10S,12S,13R,14S,17R)-6-ethyl-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid
• CAS: 1198786-98-9
• 化学式: C₂₇H₄₆O₅
• 分子量: 450.659
• InChiKey: NPBCMXATLRCCLF-VPYPQICLSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  602.8±55.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥ 100 mg/mL（221.90 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (4R)-4-[(3R,5S,6R,7R,8R,9S,10S,12S,13R,14S,17R)-6-ethyl-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以53%的产率得到6ALPHA-乙基-23(S)-甲基胆酸
  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

文献信息

• TGR5 MODULATORS AND METHODS OF USE THEROF
  申请人：Pellicciari Roberto

  公开号：US20100152151A1

  公开（公告）日：2010-06-17

  The invention relates to compounds of Formula A: or a salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including metabolic disease, inflammatory disease, liver disease, autoimmune disease, cardiac disease, kidney disease, cancer, and gastrointestinal disease.

  该发明涉及Formula A的化合物：或其盐、溶剂合物、水合物或前药。Formula A的化合物是TGR5调节剂，可用于治疗各种疾病，包括代谢性疾病、炎症性疾病、肝脏疾病、自身免疫疾病、心脏疾病、肾脏疾病、癌症和消化系统疾病。
• TGR5 Modulators and Methods of Use Thereof
  申请人：Pellicciari Roberto

  公开号：US20120115832A1

  公开（公告）日：2012-05-10

  The invention relates to compounds of Formula A: or a salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including metabolic disease, inflammatory disease, liver disease, autoimmune disease, cardiac disease, kidney disease, cancer, and gastrointestinal disease.

  本发明涉及A式化合物：或其盐、溶剂合物、水合物或前药。A式化合物是TGR5调节剂，可用于治疗各种疾病，包括代谢性疾病、炎症性疾病、肝脏疾病、自身免疫性疾病、心脏疾病、肾脏疾病、癌症和胃肠疾病。
• TGR5 modulators and method of use thereof
  申请人：Intercept Pharmaceuticals, Inc.

  公开号：EP2698375A2

  公开（公告）日：2014-02-19

  The invention relates to compounds of Formula A: (A) or a salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including metabolic disease, inflammatory disease, liver disease, autoimmune disease, cardiac disease, kidney disease, cancer and gastrointestinal disease.

  本发明涉及式 A 的化合物：(A)或其盐、溶液剂、水合物或原药。式 A 的化合物是 TGR5 调节剂，可用于治疗各种疾病，包括代谢性疾病、炎症性疾病、肝病、自身免疫性疾病、心脏病、肾病、癌症和胃肠道疾病。
• TGR5 MODULATORS AND METHOD OF USE THEREOF
  申请人：Intercept Pharmaceuticals, Inc.

  公开号：EP2376519A1

  公开（公告）日：2011-10-19
• US8114862B2
  申请人：——

  公开号：US8114862B2

  公开（公告）日：2012-02-14