methyl 3α,16β-dihydroxy-7α-(3'-iodobenozyl)oxy-5β-cholan-24-oate | 1359731-65-9

• 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: methyl 3α,16β-dihydroxy-7α-(3'-iodobenozyl)oxy-5β-cholan-24-oate
• CAS: 1359731-65-9
• 化学式: C₃₂H₄₅IO₆
• 分子量: 652.61
• InChiKey: BBICWWPMARLOQP-DIKHALRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3α,16β-dihydroxy-7α-(3'-iodobenozyl)oxy-5β-cholan-24-oate 在 甲醇 、 sodium hydroxide 作用下， 以51%的产率得到3α,7α,16β-trihydroxy-5β-cholan-24-oic acid sodium salt
  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：

  鹅去氧胆酸 在 吡啶 、 Jones reagent 、 calcium hydride 、 硼烷四氢呋喃络合物 、 (二氯碘)-苯 、 硼烷-叔丁基胺 、 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 、 丙酮 、 甲苯 为溶剂， 反应 62.5h， 生成 methyl 3α,16β-dihydroxy-7α-(3'-iodobenozyl)oxy-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