3-{(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(3-azido-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentylamino}-propan-1-ol | 400710-96-5

• 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: 3-{(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(3-azido-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentylamino}-propan-1-ol
• 英文别名: 3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris(3-azidopropoxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl]amino]propan-1-ol
• CAS: 400710-96-5
• 化学式: C₃₆H₆₄N₁₀O₄
• 分子量: 700.969
• InChiKey: CMWMACHWXGCLNH-RKDRXVRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  50
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-{(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(3-azido-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentylamino}-propan-1-ol 在 sodium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 [3-(3-Benzyloxycarbonylamino-propylamino)-propyl]-{(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(3-azido-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Correlation of the Antibacterial Activities of Cationic Peptide Antibiotics and Cationic Steroid Antibiotics

  摘要：

  The antibacterial activities of cationic steroid antibiotics and cationic peptide antibiotics have been compared. Depolarization of bacterial membranes, activation of bacterial stress-related gene promoters, and changes in bacterial morphologies caused by these antibiotics suggest that cationic steroid and peptide antibiotics share mechanistic aspects. Modified cationic steroid antibiotics display improved selectivity for prokaryotic cells over eukaryotic cells presumably due to increased charge recognition.

  DOI：

  10.1021/jm0105070
• 作为产物：
  描述：

  3α,7α,12α-tris(3-azidopropoxy)-5β-cholan-24-ol 在 sodium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-{(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(3-azido-propoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentylamino}-propan-1-ol
  参考文献：
  名称：

  Correlation of the Antibacterial Activities of Cationic Peptide Antibiotics and Cationic Steroid Antibiotics

  摘要：

  The antibacterial activities of cationic steroid antibiotics and cationic peptide antibiotics have been compared. Depolarization of bacterial membranes, activation of bacterial stress-related gene promoters, and changes in bacterial morphologies caused by these antibiotics suggest that cationic steroid and peptide antibiotics share mechanistic aspects. Modified cationic steroid antibiotics display improved selectivity for prokaryotic cells over eukaryotic cells presumably due to increased charge recognition.

  DOI：

  10.1021/jm0105070

文献信息

• Cationic Steroid Antimicrobial Compositions and Methods of Use
  申请人：Savage B. Paul

  公开号：US20070190067A1

  公开（公告）日：2007-08-16

  The invention provides methods for decreasing or inhibiting human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) in vitro, ex vivo or in vivo, or an adverse side effect of human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).

  这项发明提供了用于在体外、体外或体内减少或抑制人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）、在体外、体外或体内与人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）相关的症状或病理、或在体外、体外或体内人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）的不良副作用的方法。在一种实施方式中，该发明的方法包括使用一种发明化合物（例如，阳离子类固体抗菌剂或CSA）治疗受试者。
• Cationic Steroid Microbial Compositions and Methods of Use
  申请人：Savage B. Paul

  公开号：US20070191322A1

  公开（公告）日：2007-08-16

  The invention relates to methods for decreasing or inhibiting influenza virus infection or pathogenesis of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with influenza infection or pathogenesis in vitro, ex vivo or in vivo, or an adverse side effect of influenza infection or pathogenesis in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).

  该发明涉及减少或抑制体外、体内或体外细胞的流感病毒感染或发病机制，体外、体内或体外与流感感染或发病机制相关的症状或病理学，或体外、体内或体外流感感染或发病机制的不良副作用的方法。在一种实施方式中，该发明的方法包括使用一种发明化合物（例如，阳离子类固醇抗微生物药物或CSA）治疗受试者。
• Correlation of the Antibacterial Activities of Cationic Peptide Antibiotics and Cationic Steroid Antibiotics
  作者：Bangwei Ding、Qunying Guan、Joshua P. Walsh、J. Scott Boswell、Tim W. Winter、Erica S. Winter、Stephanie S. Boyd、Chunhong Li、Paul B. Savage

  DOI：10.1021/jm0105070

  日期：2002.1.1

  The antibacterial activities of cationic steroid antibiotics and cationic peptide antibiotics have been compared. Depolarization of bacterial membranes, activation of bacterial stress-related gene promoters, and changes in bacterial morphologies caused by these antibiotics suggest that cationic steroid and peptide antibiotics share mechanistic aspects. Modified cationic steroid antibiotics display improved selectivity for prokaryotic cells over eukaryotic cells presumably due to increased charge recognition.