N-cyclohexyl-gamma-aminobutyric acid ethyl ester | 129095-36-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-cyclohexyl-gamma-aminobutyric acid ethyl ester
• 英文别名: ethyl 4-(cyclohexylamino)butanoate
• CAS: 129095-36-9
• 化学式: C₁₂H₂₃NO₂
• mdl: MFCD20356179
• 分子量: 213.32
• InChiKey: RPDZLVIGJFJNAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.916
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-gamma-aminobutyric acid ethyl ester 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-[3-(3-tert-Butyl-2-hydroxy-5-methoxy-phenyl)-1-cyclohexyl-ureido]-butyric acid ethyl ester
  参考文献：
  名称：

  新型的针对酰基辅酶A的羟苯基脲双重抑制剂：胆固醇酰基转移酶（ACAT）和低密度脂蛋白（LDL）氧化作为抗动脉粥样硬化剂。

  摘要：

  合成了新型羟基苯基脲衍生物，并评估了其对酰基辅酶A：胆固醇酰基转移酶（ACAT）的抑制能力。定量结构活性关系分析表明，它们的ACAT抑制活性受整个分子的疏水性控制。尿素部分的取代方式，以及羧酸的存在。具有强活性的衍生物抑制了泡沫孔的形成。此外，这些化合物由于其特征性的3-叔丁基-2-羟基-5-甲氧基苯基亚结构而对低密度脂蛋白（LDL）表现出抗氧化作用。基于动脉粥样硬化的发生机理，这种针对ACAT和LDL氧化的羟苯基脲类双重抑制剂有望成为一种有前途的动脉粥样硬化药物。

  DOI：

  10.1016/s0968-0896(00)00303-5
• 作为产物：
  描述：

  N-benzyloxycarbonyl-γ-aminobutyric acid ethyl ester 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、354.64 kPa 条件下， 反应 7.5h， 生成 N-cyclohexyl-gamma-aminobutyric acid ethyl ester
  参考文献：
  名称：

  新型的针对酰基辅酶A的羟苯基脲双重抑制剂：胆固醇酰基转移酶（ACAT）和低密度脂蛋白（LDL）氧化作为抗动脉粥样硬化剂。

  摘要：

  合成了新型羟基苯基脲衍生物，并评估了其对酰基辅酶A：胆固醇酰基转移酶（ACAT）的抑制能力。定量结构活性关系分析表明，它们的ACAT抑制活性受整个分子的疏水性控制。尿素部分的取代方式，以及羧酸的存在。具有强活性的衍生物抑制了泡沫孔的形成。此外，这些化合物由于其特征性的3-叔丁基-2-羟基-5-甲氧基苯基亚结构而对低密度脂蛋白（LDL）表现出抗氧化作用。基于动脉粥样硬化的发生机理，这种针对ACAT和LDL氧化的羟苯基脲类双重抑制剂有望成为一种有前途的动脉粥样硬化药物。

  DOI：

  10.1016/s0968-0896(00)00303-5

文献信息

• Agent for Preventing and Alleviating Wrinkles
  申请人：TSUNENAGA Makoto

  公开号：US20100113450A1

  公开（公告）日：2010-05-06

  The present invention provides an agent for preventing and alleviating wrinkles which has excellent effects of preventing and alleviating wrinkles formed by decreased barrier function of the skin owing to aging or photo aging, that is graphic wrinkles or linear wrinkles. The agent for preventing and alleviating wrinkles consisting of one or more compounds selected from the group consisting of gamma-aminobutyric acid derivatives represented by the following formula (1) or N,N,N-trimethyl gamma-aminobutyric acid represented by the following formula (3) and salts thereof: wherein R 1 and R 2 independently represent any of a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a benzyloxycarbonyl group, a cyclohexyl group, a cyclohexanemethyl group, a cyclohexanecarbonyl group, a guanidino group formed with nitrogen atom in the formula (1), an ureido group formed with nitrogen atom in the formula (1), and a group represented by following formula (2). Additionally, R 1 and R 2 may jointly form a piperidine ring, morpholine ring, or pyrrolidine ring. Both of R 1 and R 2 are not simultaneously a hydrogen atom.

  本发明提供了一种用于预防和缓解皮肤屏障功能下降引起的老化或光老化形成的皱纹（即图形皱纹或线性皱纹）的药剂。该药剂由以下式（1）所表示的γ-氨基丁酸衍生物或以下式（3）所表示的N，N，N-三甲基γ-氨基丁酸及其盐中的一种或多种化合物组成：其中R1和R2独立地表示氢原子，具有1至3个碳原子的烷基，苄氧羰基基团，环己基基团，环己基甲基基团，环己基羧基基团，在式（1）中的氮原子形成的鸟氨酸基团，在式（1）中的氮原子形成的尿素基团，以及以下式（2）所表示的基团。此外，R1和R2可以共同形成哌啶环，吗啉环或吡咯烷环。R1和R2都不同时为氢原子。
• Agent for alleviating wrinkles
  申请人：Shiseido Company Ltd.

  公开号：US08173705B2

  公开（公告）日：2012-05-08

  The present invention provides an agent for preventing and alleviating wrinkles which has excellent effects of preventing and alleviating wrinkles formed by decreased barrier function of the skin owing to aging or photo aging, that is graphic wrinkles or linear wrinkles. The agent for preventing and alleviating wrinkles consisting of one or more compounds selected from the group consisting of gamma-aminobutyric acid derivatives represented by the following formula (1) or N,N,N-trimethyl gamma-aminobutyric acid represented by the following formula (3) and salts thereof: wherein R1 and R2 independently represent any of a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a benzyloxycarbonyl group, a cyclohexyl group, a cyclohexanemethyl group, a cyclohexanecarbonyl group, a guanidino group formed with nitrogen atom in the formula (1), an ureido group formed with nitrogen atom in the formula (1), and a group represented by following formula (2). Additionally, R1 and R2 may jointly form a piperidine ring, morpholine ring, or pyrrolidine ring. Both of R1 and R2 are not simultaneously a hydrogen atom.

  本发明提供了一种防止和缓解皱纹的剂，具有优异的防止和缓解因皮肤屏障功能降低而形成的皱纹的效果，即图形皱纹或线性皱纹。该防止和缓解皱纹的剂由以下式（1）表示的γ-氨基丁酸衍生物或以下式（3）表示的N,N,N-三甲基γ-氨基丁酸及其盐中的一种或多种化合物组成：其中，R1和R2独立地表示氢原子、具有1到3个碳原子的烷基、苄氧羰基基团、环己基基团、环己甲基基团、环己基羰基基团、在公式（1）中与氮原子形成的鸟氨酸基团、在公式（1）中与氮原子形成的尿素基团以及以下式（2）所表示的基团中的任意一种。此外，R1和R2可以共同形成哌啶环、吗啉环或吡咯烷环。R1和R2中的任意一个都不是氢原子。
• WRINKLING-PREVENTING AND -MODIFYING AGENT
  申请人：Shiseido Company, Ltd.

  公开号：EP2123253A1

  公开（公告）日：2009-11-25

  The present invention provides an agent for preventing and alleviating wrinkles which has excellent effects of preventing and alleviating wrinkles formed by decreased barrier function of the skin owing to aging or photo aging, that is graphic wrinkles or linear wrinkles. The agent for preventing and alleviating wrinkles consisting of one or more compounds selected from the group consisting of gamma-aminobutyric acid derivatives represented by the following formula (1) or N,N,N-trimethyl gamma-aminobutyric acid represented by the following formula (3) and salts thereof: wherein R1 and R2 independently represent any of a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a benzyloxycarbonyl group, a cyclohexyl group, a cyclohexanemethyl group, a cyclohexanecarbonyl group, a guanidino group formed with nitrogen atom in the formula (1), an ureido group formed with nitrogen atom in the formula (1), and a group represented by following formula (2). Additionally, R1 and R2 may jointly form a piperidine ring, morpholine ring, or pyrrolidine ring. Both of R1 and R2 are not simultaneously a hydrogen atom.

  本发明提供了一种用于预防和减轻皱纹的药剂，该药剂对预防和减轻由于老化或光老化导致皮肤屏障功能降低而形成的皱纹（即图形皱纹或线性皱纹）具有极佳的效果。 这种预防和缓解皱纹的制剂由一种或多种化合物组成，这些化合物选自由下式（1）代表的γ-氨基丁酸衍生物或下式（3）代表的N,N,N-三甲基γ-氨基丁酸及其盐组成的组： 其中，R1 和 R2 独立地代表氢原子、具有 1 至 3 个碳原子的烷基、苄氧羰基、环己基、环己基甲基、环己基羰基、与式（1）中氮原子形成的胍基、与式（1）中氮原子形成的脲基以及下式（2）所代表的基团中的任意一种。此外，R1 和 R2 可共同形成哌啶环、吗啉环或吡咯烷环。R1 和 R2 不能同时为氢原子。
• ANTIDEPRESSANT COMPOUND AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP3564253A1

  公开（公告）日：2019-11-06

  An antidepressant steroid compound and a preparation method and an application thereof; the structure of said compound is shown in formula (I), and the definition of each substituent is as described in the description and claims. Compound of the present invention may be used in the prevention, treatment, therapy or alleviation of a plurality of diseases and conditions such as depression.

  一种抗抑郁类固醇化合物及其制备方法和应用；所述化合物的结构如式（I）所示，各取代基的定义如说明书和权利要求书所述。本发明的化合物可用于预防、治疗、治疗或缓解多种疾病和病症，如抑郁症。
• Antidepressant compound and preparation method and application thereof
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：US11142543B2

  公开（公告）日：2021-10-12

  An antidepressant steroid compound and a preparation method and an application thereof; the structure of said compound is shown in formula (I), and the definition of each substituent is as described in the description and claims. Compound of the present invention may be used in the prevention, treatment, therapy or alleviation of a plurality of diseases and conditions such as depression.

  一种抗抑郁类固醇化合物及其制备方法和应用；所述化合物的结构如式（I）所示，各取代基的定义如说明书和权利要求书所述。本发明的化合物可用于预防、治疗、治疗或缓解多种疾病和病症，如抑郁症。