methyl (3α-azidomethyl)-3β,7α,12α-trihydroxy-5β-cholan-24-oate | 1191418-23-1

• 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-azidomethyl)-3β,7α,12α-trihydroxy-5β-cholan-24-oate
• 英文别名: methyl (4R)-4-[(3S,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-(azidomethyl)-3,7,12-trihydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1191418-23-1
• 化学式: C₂₆H₄₃N₃O₅
• 分子量: 477.645
• InChiKey: YDCQCXVOMCCOJU-SRJCIEHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3α-azidomethyl)-3β,7α,12α-trihydroxy-5β-cholan-24-oate 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 30.0 ℃ 、310.27 kPa 条件下， 反应 3.0h， 以97%的产率得到methyl (3α-aminomethyl)-3β,7α,12α-trihydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Design and synthesis of bile acid-based amino sterols as antimicrobial agents

  摘要：

  New bile acid-based amino sterols were synthesized in good yields from C-3 beta-oxiranes as key intermediates. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. These compounds showed better antibacterial activity as compared to antifungal activity. Compounds 21 and 22 showed comparable antibacterial activity to gentamicin against Staphylococcus aureus with IC50 values of 5.14 and 4.46 mu g/mL. This is the first report for the synthesis of C-3 beta-oxiranes on the steroids having A/B cis ring junction and these oxiranes have been used for the synthesis of amino sterols 17, 18, 21, and 22. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.117
• 作为产物：
  描述：

  methyl (3β-oxirane)-7α,12α-dihydroxy-5β-cholan-24-oate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以90%的产率得到methyl (3α-azidomethyl)-3β,7α,12α-trihydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Design and synthesis of bile acid-based amino sterols as antimicrobial agents

  摘要：

  New bile acid-based amino sterols were synthesized in good yields from C-3 beta-oxiranes as key intermediates. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. These compounds showed better antibacterial activity as compared to antifungal activity. Compounds 21 and 22 showed comparable antibacterial activity to gentamicin against Staphylococcus aureus with IC50 values of 5.14 and 4.46 mu g/mL. This is the first report for the synthesis of C-3 beta-oxiranes on the steroids having A/B cis ring junction and these oxiranes have been used for the synthesis of amino sterols 17, 18, 21, and 22. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.117

文献信息

• Design and synthesis of bile acid-based amino sterols as antimicrobial agents
  作者：Nilkanth G. Aher、Vandana S. Pore、Nripendra N. Mishra、Praveen K. Shukla、Rajesh G. Gonnade

  DOI：10.1016/j.bmcl.2009.07.117

  日期：2009.9

  New bile acid-based amino sterols were synthesized in good yields from C-3 beta-oxiranes as key intermediates. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. These compounds showed better antibacterial activity as compared to antifungal activity. Compounds 21 and 22 showed comparable antibacterial activity to gentamicin against Staphylococcus aureus with IC50 values of 5.14 and 4.46 mu g/mL. This is the first report for the synthesis of C-3 beta-oxiranes on the steroids having A/B cis ring junction and these oxiranes have been used for the synthesis of amino sterols 17, 18, 21, and 22. (C) 2009 Elsevier Ltd. All rights reserved.