benzyl cholate | 105730-97-0

• 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: benzyl cholate
• 英文别名: benzyl 3α,7α,12α-trihydroxy-5β-cholan-24-oate；benzyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 105730-97-0
• 化学式: C₃₁H₄₆O₅
• 分子量: 498.703
• InChiKey: FPYOLKTYFHLRKO-WTZIRUNOSA-N

物化性质

• 沸点：
  621.7±55.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl cholate 在 4-二甲氨基吡啶 氢氧化钾 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.24h， 生成 N-(3Alpha,7Alpha,12Alpha)三羟基-5β-胆甾烷-24-酰基牛黄酸
  参考文献：
  名称：

  Chemical modifications of bile acids under high-intensity ultrasound or microwave irradiation

  摘要：

  High-intensity ultrasound (HIU) and microwave (MW) irradiation, having emerged as effective promoters of organic reactions, were exploited for the synthesis of bile acids derivatives. Esterification, amidation, hydrolysis, oxidation, and reduction were investigated. Compared to conventional methods, both techniques proved much more efficient, increasing product yields and dramatically cutting down reaction times. Scaled-up studies are now under way. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.09.007
• 作为产物：
  描述：

  胆酸 以 甲醇 、 二氯甲烷 、 苯甲醇 为溶剂， 以81%的产率得到benzyl cholate
  参考文献：
  名称：

  CATIONIC STEROID ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE

  摘要：

  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。

  公开号：

  US20100330086A1

文献信息

• Bile acid derivatives and production thereof
  申请人：Wakunaga Seiyaku Kabushiki Kaisha

  公开号：US04793948A1

  公开（公告）日：1988-12-27

  A bile acid derivative having carcinostatic activity represented by the following formula (1): ##STR1## wherein each of R.sub.1 and R.sub.2 is a hydrogen atom or a hydroxyl group, R.sub.3 is a hydroxyl group, benzyloxyl group or --NH--CH.sub.2n R.sub.5 (wherein R.sub.5 is a carboxyl group or sulfonyl group, and n represents the integer of 1 or 2), X is a halogen atom, R.sub.4 is a hydrogen atom or XCH.sub.2 CH.sub.2 --,.chi. is an .alpha.-bond, and .chi. is an .alpha.- or .beta.-bond is produced by the steps (a) and (b), the steps (a), (b) and (c), or the steps (a), (b), (c) and (d) described below: (a) causing an active carbonation reagent to react with a bile acid derivative wherein the carboxyl group is esterified; (b) causing an aminoalkylhalide to react with the active carbonated product obtained; (c) subjecting the bile acid derivative obtained in the above steps (a) and (b) to hydrolysis; and (d) causing the above hydrolyzate to react with an aminoalkyl derivative in the presence of a condensing agent.

  具有抗癌活性的胆酸衍生物的化学式如下（1）：##STR1## 其中R.sub.1和R.sub.2各自是氢原子或羟基，R.sub.3是羟基、苄氧基或--NH--CH.sub.2n R.sub.5（其中R.sub.5是羧基或磺酰基，n表示1或2的整数），X是卤素原子，R.sub.4是氢原子或XCH.sub.2 CH.sub.2 --，.chi.是α-键，.chi.是α-或β-键，通过以下步骤（a）和（b），步骤（a），（b）和（c），或步骤（a），（b），（c）和（d）产生：（a）使活性碳酸化试剂与酯化的胆酸衍生物发生反应；（b）使氨基烷基卤化物与所得的活性碳酸化产物发生反应；（c）将上述步骤（a）和（b）中获得的胆酸衍生物进行水解；和（d）使上述水解物在存在缩合剂的情况下与氨基烷基衍生物发生反应。
• Novel Macrocyclic Bile Acid Derivatives; Selective and Easy Binding of Two Cholic Acid Moieties at the 3- and 3′-Positions
  作者：Nikolay Lukashev、Alexey Kazantsev、Alexey Averin、Pavel Donez、Mikhail Baranov、Elina Sievänen、Erkki Kolehmainen

  DOI：10.1055/s-0029-1217057

  日期：——

  The synthesis of macrocyclic derivatives of bile acids (cholaphanes) is elaborated using the formation of ester or amide linkages at the 3α,3′α- and 24,24′-positions of lithocholic, deoxycholic or cholic acids. The conditions were found under which the selective diacylation at the 3α,3′α- and 24,24′-positions of two molecules of cholic acid by dichloroanhydrides of arene(hetarene)dicarboxylic acid proceeds in good yields without prior protection of the 7α- and 12α-hydroxy groups.

  胆酸（cholaphanes）大环衍生物的合成通过在3α,3′α-和24,24′-位形成酯或酰胺键来进行，涉及了石胆酸、去氧胆酸或胆酸。研究发现，在不事先保护7α-和12α-羟基的情况下，通过芳香（杂芳香）二羧酸的二氯酐对两个胆酸分子的3α,3′α-和24,24′-位进行选择性的二酰化反应，能够以良好的产率进行。
• 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。
• [EN] CATIONIC STEROID ANTIMICROBIAL DIAGNOSTIC, DETECTION, SCREENING AND IMAGING METHODS<br/>[FR] PROCÉDÉS DE DIAGNOSTIC, DE DÉTECTION, DE TRI ET D'IMAGERIE DE STÉROÏDES CATIONIQUES ANTIMICROBIENS
  申请人：UNIV BRIGHAM YOUNG

  公开号：WO2010036427A1

  公开（公告）日：2010-04-01

  The invention relates to diagnostic, detection, screening and imaging methods. In various embodiments, methods of diagnosis, detection, screening and imaging include administering a cationic steroid antimicrobial or CSA to a subject having or at risk of having an infection or a hyperproliferative disorder (e.g., a tumor, cancer or neoplasia) in an amount effective to diagnose or detect the infection or the hyperproliferative disorder (e.g., a tumor, cancer or neoplasia) in the subject. In a particular aspect, a detectable CSA, namely CSA- 13 labeled with 99mTc is used to detect the presence of an infection.

  该发明涉及诊断、检测、筛查和成像方法。在各种实施方式中，诊断、检测、筛查和成像的方法包括向患有感染或有感染风险的受试者施用阳离子类固醇抗菌药物或CSA，以有效诊断或检测受试者体内的感染或过度增殖疾病（例如肿瘤、癌症或新生物）。在一个特定方面，一种可检测的CSA，即用99mTc标记的CSA-13，被用于检测感染的存在。