(20R)-20,25-epoxy-2α,12β-dihydroxy-6-oxo-A-nordammaran-2-carboxylic acid methyl ester | 1160164-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (20R)-20,25-epoxy-2α,12β-dihydroxy-6-oxo-A-nordammaran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3aR,3bR,5R,5aR,6S,8aR,8bR,10aR)-2,5-dihydroxy-1,1,3a,8a,8b-pentamethyl-10-oxo-6-[(2R)-2,6,6-trimethyloxan-2-yl]-3,3b,4,5,5a,6,7,8,9,10a-decahydroindeno[5,4-e]indene-2-carboxylate
• CAS: 1160164-69-1
• 化学式: C₃₁H₅₀O₆
• 分子量: 518.734
• InChiKey: BNIYAACSNPWWCA-RZNROCIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (20R)-20,25-epoxy-2α,12β-dihydroxy-6-oxo-A-nordammaran-2-carboxylic acid 、 三甲基硅烷化重氮甲烷 在 甲醇 作用下， 反应 30.0h， 以48.2%的产率得到(20R)-20,25-epoxy-2α,12β-dihydroxy-6-oxo-A-nordammaran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases

  摘要：

  We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure-activity relationships. All of the mono- and di-succinyl derivatives (5a-5f) were powerful inhibitors of HIV-1 protease (IC50 < 10 mu M). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 < 10 mu M). A-nor dammarane- type triterpenes (4a and 4b, IC50 10.0 and 29.9 mu M, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 > 1000 mu M). These findings indicated that the mono-succinyl dammarane type derivatives (5a-5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.019

文献信息

• Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases
  作者：Ying Wei、Chao-Mei Ma、Masao Hattori

  DOI：10.1016/j.bmc.2009.03.019

  日期：2009.4

  We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure-activity relationships. All of the mono- and di-succinyl derivatives (5a-5f) were powerful inhibitors of HIV-1 protease (IC50 < 10 mu M). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 < 10 mu M). A-nor dammarane- type triterpenes (4a and 4b, IC50 10.0 and 29.9 mu M, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 > 1000 mu M). These findings indicated that the mono-succinyl dammarane type derivatives (5a-5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. (C) 2009 Elsevier Ltd. All rights reserved.