methyl 11β-azido-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate | 851086-20-9

• 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 11β-azido-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate
• 英文别名: methyl (4R)-4-[(3R,5S,7R,8S,9S,10S,11R,13R,14S,17R)-3,7-diacetyloxy-11-azido-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 851086-20-9
• 化学式: C₂₉H₄₃N₃O₇
• 分子量: 545.676
• InChiKey: HDYPAVVYAXYFBB-ILEZZNOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 11β-azido-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以100%的产率得到methyl 11α-azido-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate
  参考文献：
  名称：

  An efficient method for the synthesis of methyl 11α-amino-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate

  摘要：

  The synthesis of methyl 11 alpha-azido-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate, methyl 11 beta-azido-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate and methyl 11 alpha-amino-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate have been achieved. Mechanistic aspects for the decomposition of steroidal azidoketones to its enamines are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.073
• 作为产物：
  描述：

  胆酸甲酯 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium azide 、 硫酸 、 三氟化硼乙醚 、 水 、 溴 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 101.08h， 生成 methyl 11β-azido-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate
  参考文献：
  名称：

  Amino Functionalized Novel Cholic Acid Derivatives Induce HIV-1 Replication and Syncytia Formation in T Cells

  摘要：

  Synthesis of C-11 azido/amino functionalized cholic acid derivatives has been achieved in excellent yields. Contrary to the previous prediction of analogous compounds to be HIV-1 protease inhibitors, in the present study these novel cholic acid derivatives induced host cell fusion during the progress of HIV-1 infection and produced multinucleated giant cells. This is the first report of syncytia induction and enhancement of viral replication in HIV-1 infected T cells by cholic acid derivatives.

  DOI：

  10.1021/jm051114u

文献信息

• 11-substituted bile acid derivatives, process for the preparation thereof and use of these compounds as medicaments
  申请人：Council of Scientific and Industrial Research

  公开号：US10000527B2

  公开（公告）日：2018-06-19

  The present invention discloses a novel bile acid derivatives having substituted nitrogen functionality at C-11 and process for synthesis thereof. These C-11 substituted bile acid derivatives shows anticancer and antimycobacterial activity.

  本发明公开了一种 C-11 位具有取代氮官能团的新型胆汁酸衍生物及其合成工艺。这些 C-11 取代的胆汁酸衍生物具有抗癌和抗霉菌活性。
• 11-SUBSTITUTED BILE ACID DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND USE OF THESE COMPOUNDS AS MEDICAMENTS
  申请人：Council of Scientific and Industrial Research

  公开号：US20160311848A1

  公开（公告）日：2016-10-27

  The present invention discloses a novel bile acid derivatives having substituted nitrogen functionality at C-11 and process for synthesis thereof. These C-11 substituted bile acid derivatives shows anticancer and antimycobacterial activity.
• Amino Functionalized Novel Cholic Acid Derivatives Induce HIV-1 Replication and Syncytia Formation in T Cells
  作者：Deepak B. Salunke、Dyavar S. Ravi、Vandana S. Pore、Debashis Mitra、Braja G. Hazra

  DOI：10.1021/jm051114u

  日期：2006.4.1

  Synthesis of C-11 azido/amino functionalized cholic acid derivatives has been achieved in excellent yields. Contrary to the previous prediction of analogous compounds to be HIV-1 protease inhibitors, in the present study these novel cholic acid derivatives induced host cell fusion during the progress of HIV-1 infection and produced multinucleated giant cells. This is the first report of syncytia induction and enhancement of viral replication in HIV-1 infected T cells by cholic acid derivatives.
• An efficient method for the synthesis of methyl 11α-amino-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate
  作者：Deepak B. Salunke、Braja G. Hazra、Rajesh G. Gonnade、Mohan M. Bhadbhade、Vandana S. Pore

  DOI：10.1016/j.tet.2005.01.073

  日期：2005.4

  The synthesis of methyl 11 alpha-azido-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate, methyl 11 beta-azido-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate and methyl 11 alpha-amino-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate have been achieved. Mechanistic aspects for the decomposition of steroidal azidoketones to its enamines are discussed. (c) 2005 Elsevier Ltd. All rights reserved.