6α-methyl-chenodeoxycholic acid

• 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: 6α-methyl-chenodeoxycholic acid
• 英文别名: 6αMeCDCA；6α-MeCDCA；3alpha,7alpha-Dihydroxy-6alpha-methyl-5beta-cholan-24-oic acid；(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-3,7-dihydroxy-6,10,13-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• 化学式: C₂₅H₄₂O₄
• 分子量: 406.606
• InChiKey: MXZOUETYQZMNJY-TWPJQBFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3Α-羟基-7-氧代-5Β-胆烷酸 在 sodium tetrahydroborate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 生成 6α-methyl-chenodeoxycholic acid
  参考文献：
  名称：

  6α-Ethyl-Chenodeoxycholic Acid (6-ECDCA), a Potent and Selective FXR Agonist Endowed with Anticholestatic Activity

  摘要：

  A series of 6alpha-alkyl-substituted analogues of chenodeoxycholic acid (CDCA) were synthesized and evaluated as potential farnesoid X receptor (FXR) ligands. Among them, 6alpha-ethyl-chenodeoxycholic acid (6-ECDCA) was shown to be a very potent and selective FXR agonist (EC50 = 99 nM) and to be endowed with anticholeretic activity in an in vivo rat model of cholestasis.

  DOI：

  10.1021/jm025529g

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。
• Steroids as Agonists for FXR
  申请人：Intercept Pharmaceuticals, Inc.

  公开号：US20160152657A1

  公开（公告）日：2016-06-02

  The invention relates to compounds of formula (I): wherein R is ethyl, propyl or allyl, and pharmaceutically acceptable salts, solvates or amino acid conjugates thereof. The compounds of formula (I) are useful as FXR agonists.

  该发明涉及以下结构的化合物（I）：其中R为乙基、丙基或烯丙基，并且其药用可接受的盐、溶剂合物或氨基酸结合物。该化合物（I）的化合物可用作FXR激动剂。
• TGR5 modulators and methods of use thereof
  申请人：Intercept Pharmaceuticals, Inc.

  公开号：EP1947108A1

  公开（公告）日：2008-07-23

  The invention relates to compounds of Formula I: or a pharmaceutically effective salt, solvate, hydrate, or prodrug thereof, wherein: R1 is hydrogen, hydroxy, or halogen; R2 is hydrogen or α-hydroxy; R3 is hydroxy, NH(CH2)mSO3H, or NH(CH2)nCO2H; R4 is hydrogen, alkyl, or halogen; R5 is unsubstituted or substituted alkyl, or aryl; R6 is hydrogen or R5 and R6 taken together with the carbons to which they are attached form a ring of size 3, 4, 5, or 6 atoms; m is an integer 0, 1, 2, 3, 4, or 5, and n is an integer 0, 1, 2, 3, 4, or 5. The compounds of Formula I are TGR5 modulators useful for the treatment of various diseases.

  本发明涉及式I的化合物：或其药学有效的盐、溶剂化合物、水合物或前药，其中：R1为氢、羟基或卤素；R2为氢或α-羟基；R3为羟基、NH(CH2)mSO3H或NH(CH2)nCO2H；R4为氢、烷基或卤素；R5为未取代或取代的烷基或芳基；R6为氢或R5和R6共同与它们所连接的碳形成大小为3、4、5或6原子的环；m为整数0、1、2、3、4或5，n为整数0、1、2、3、4或5。式I的化合物是TGR5调节剂，可用于治疗各种疾病。
• [EN] STEROIDS AS AGONISTS FOR FXR<br/>[FR] STEROIDES COMME AGONISTES DE FXR
  申请人：PELLICCIARI ROBERTO

  公开号：WO2002072598A1

  公开（公告）日：2002-09-19

  The invention relates to compounds of formula (I) wherein R is ethyl, propyl or allyl, and pharmaceutically acceptable salts, solvates or amino acid conjugates thereof. The compounds of formula (I) are useful as FXR agonists.

  本发明涉及式（I）化合物，其中R为乙基，丙基或烯丙基，以及药学上可接受的盐，溶剂合物或氨基酸结合物。式（I）化合物可用作FXR激动剂。
• STEROIDS AS AGONISTS FOR FXR
  申请人：Pellicciari Roberto

  公开号：US20100022498A1

  公开（公告）日：2010-01-28

  The invention relates to compounds of formula (I): wherein R is ethyl and pharmaceutically acceptable salts, solvates or amino acid conjugates thereof. The compounds of formula (I) are useful as FXR agonists.

  该发明涉及式(I)的化合物：其中R为乙基和其药学上可接受的盐，溶剂合物或氨基酸共轭物。式(I)的化合物可用作FXR激动剂。