benzhydryl (1R,2R)-2-(1-hydroxy-2-methylprop-2-enyl)cyclohexane-1-carboxylate | 71550-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzhydryl (1R,2R)-2-(1-hydroxy-2-methylprop-2-enyl)cyclohexane-1-carboxylate
• CAS: 71550-82-8
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: OVWDNDYMUUGTNS-JAZPPYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzhydryl (1R,2R)-2-(1-hydroxy-2-methylprop-2-enyl)cyclohexane-1-carboxylate 在 ammonium hydroxide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 trans-2-(3-mercapto-2-methyl-1-oxopropyl)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011
• 作为产物：
  描述：

  methyl trans-2-formylcyclohexanecarboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 benzhydryl (1R,2R)-2-(1-hydroxy-2-methylprop-2-enyl)cyclohexane-1-carboxylate
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011

文献信息

• Thioalkanoylalkanoic acid compounds
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04206137A1

  公开（公告）日：1980-06-03

  Thioalkanoylalkanoic acid compounds and salts thereof having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkanoyl, benzoyl or ##STR2## A and B each is hydrogen or join together as a polymethylene chain --(CH.sub.2).sub.n -- to complete a 4-, 5- or 6- membered cycloalkyl group, and m is 0 or 1, are angiotensin converting enzyme inhibitors and are useful as hypotensive agents.

  Thioalkanoylalkanoic酸化合物及其盐具有以下公式##STR1##其中R.sub.1、R.sub.2、R.sub.3和R.sub.4分别是氢或较低的烷基；R.sub.5是氢、较低的烷酰基、苯甲酰基或##STR2##A和B分别是氢或结合在一起作为聚亚甲基链--(CH.sub.2).sub.n --以形成4、5或6-环脂肪族基团，m为0或1，是抑制血管紧张素转化酶的抑制剂，并且可用作降压剂。