(3R,5R,8R,9S,10S,13R,14S,17R)-3-[2-(1H-imidazol-5-yl)ethylamino]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-7-one | 1447447-43-9

• 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: (3R,5R,8R,9S,10S,13R,14S,17R)-3-[2-(1H-imidazol-5-yl)ethylamino]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-7-one
• CAS: 1447447-43-9
• 化学式: C₃₂H₅₃N₃O
• 分子量: 495.792
• InChiKey: ZTRCRXQDSZIGDN-AUMTZHPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  histamine dichloride 、 (3R,5R,8R,9S,10S,13R,14S,17R)-3-[2-(1H-imidazol-5-yl)ethylamino]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-7-one 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以62%的产率得到3alpha,7alpha-Bis[2-(5-imidazolyl)ethyl]amino-5alpha-cholestane
  参考文献：
  名称：

  Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates

  摘要：

  A series of 3 alpha-amino-5 alpha-cholestane and 3 alpha,7 alpha-diamino-5 alpha-cholestane derivatives containing imidazole and pyridine rings were synthesized by simple and effective reductive amination, and their in vitro activities against a range of Gram-positive and Gram-negative strains were evaluated. Most of the compound exhibited enhanced activity against MRSA pathogen. 3 alpha,7 alpha-Di(pyridylmethyl)amino-5 alpha-cholestane 10 showed the highest potency in these series toward the Gram-positive bacteria, Staphylococcus epidermidis 887E, with the lowest MIC value of 1 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.098
• 作为产物：
  描述：

  5α-cholestane-3,7-dione 、 histamine dichloride 在 sodium triethoxyborohydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以62%的产率得到(3R,5R,8R,9S,10S,13R,14S,17R)-3-[2-(1H-imidazol-5-yl)ethylamino]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-7-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates

  摘要：

  A series of 3 alpha-amino-5 alpha-cholestane and 3 alpha,7 alpha-diamino-5 alpha-cholestane derivatives containing imidazole and pyridine rings were synthesized by simple and effective reductive amination, and their in vitro activities against a range of Gram-positive and Gram-negative strains were evaluated. Most of the compound exhibited enhanced activity against MRSA pathogen. 3 alpha,7 alpha-Di(pyridylmethyl)amino-5 alpha-cholestane 10 showed the highest potency in these series toward the Gram-positive bacteria, Staphylococcus epidermidis 887E, with the lowest MIC value of 1 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.098

文献信息

• Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates
  作者：Hong-Seok Kim、Jyoti R. Jadhav、Sung-Ji Jung、Jin-Hwan Kwak

  DOI：10.1016/j.bmcl.2013.05.098

  日期：2013.8

  A series of 3 alpha-amino-5 alpha-cholestane and 3 alpha,7 alpha-diamino-5 alpha-cholestane derivatives containing imidazole and pyridine rings were synthesized by simple and effective reductive amination, and their in vitro activities against a range of Gram-positive and Gram-negative strains were evaluated. Most of the compound exhibited enhanced activity against MRSA pathogen. 3 alpha,7 alpha-Di(pyridylmethyl)amino-5 alpha-cholestane 10 showed the highest potency in these series toward the Gram-positive bacteria, Staphylococcus epidermidis 887E, with the lowest MIC value of 1 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.