(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol | 222165-77-7

• 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: (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol
• 英文别名: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triamino-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentan-1-ol
• CAS: 222165-77-7
• 化学式: C₂₄H₄₅N₃O
• 分子量: 391.641
• InChiKey: CRWPLUHYTCFPNV-YHEMGIGTSA-N

物化性质

• 沸点：
  512.0±50.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  98.3
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol 在 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 2-Amino-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-bis-(2-amino-acetylamino)-17-((R)-4-hydroxy-1-methyl-butyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-12-yl]-acetamide
  参考文献：
  名称：

  制备氨基酸附加的胆酸衍生物作为革兰氏阴性细菌的敏化剂

  摘要：

  氨基酸与胆酸衍生物的连接产生了使革兰氏阴性细菌对疏水性抗生素敏感的化合物。仅通过非α-支链氨基酸，可实现通过酯键将三个氨基酸结合到胆酸衍生物上。通过酰胺键将三个非α-支链或三个α-支链氨基酸偶联至类固醇主链。

  DOI：

  10.1016/s0040-4039(99)00075-1
• 作为产物：
  描述：

  methyl 3,7,12-trioxo-5β-cholan-24-oate 在 sodium tetrahydroborate 、 盐酸羟胺 、 sodium acetate 、 四氯化钛 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol
  参考文献：
  名称：

  胆酸三胺衍生物的短合成

  摘要：

  去氢胆酸甲基酯用NaBH的trioxime衍生物的还原4 TiCl 4胆酸产生三胺衍生物。还原的主要产物是3α，7α，12α非对映异构体。还原产物的立体化学通过NMR光谱和X射线晶体学测定。

  DOI：

  10.1016/s0040-4039(99)00076-3

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。
• Steroid derived antibiotics
  申请人：Brigham Young University

  公开号：US06350738B1

  公开（公告）日：2002-02-26

  A series of novel steroid derivatives are described. The steroid derivatives are antibacterial agents. The steroid derivatives also act to sensitize bacteria to other antibiotics including erythromycin and novobiocin.

  一系列新型类固醇衍生物被描述。这些类固醇衍生物是抗菌剂。这些类固醇衍生物还能增加细菌对其他抗生素的敏感性，包括红霉素和新霉素。
• CATIONIC STEROID ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE
  申请人：SAVAGE PAUL B.

  公开号：US20100330086A1

  公开（公告）日：2010-12-30

  The invention provides methods for decreasing or inhibiting herpesviridae (HV) infection or pathogenesis of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with a herpesviridae (HV) infection or pathogenesis in vitro, ex vivo or in vivo, or an adverse side effect of herpesviridae (HV) 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).

  该发明提供了用于在体外、体外或体内减少或抑制细胞感染或发病的疱疹病毒科（HV）的方法，症状或病理与体外、体外或体内疱疹病毒科（HV）感染或发病相关，或在体外、体外或体内疱疹病毒科（HV）感染或发病的不良副作用。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，阳离子类固醇抗菌药物或CSA）治疗受试者。
• Synthesis and Characterization of Peptide−Cationic Steroid Antibiotic Conjugates
  作者：Bangwei Ding、Uale Taotofa、Thomas Orsak、Matthew Chadwell、Paul B. Savage

  DOI：10.1021/ol048845t

  日期：2004.9.1

  New cationic steroid antibiotics have been prepared by conjugating tripeptides to a triamino analogue of cholic acid. These compounds were synthesized on a solid phase in an indexed library that was screened for antibacterial activity against Gram-negative and Gram-positive bacteria. Selected compounds were synthesized on a larger scale, and minimum inhibition concentrations were measured. These results correlated very well with the screening of the indexed library of antibiotics. The most active antibiotics demonstrate a marked improvement over a related and well characterized cationic steroid antibiotic.