1-(1-methylindol-3-yl)cyclopentaneacetonitrile | 145132-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(1-methylindol-3-yl)cyclopentaneacetonitrile
• 英文别名: 1-(1-Methyl-3-indolyl)cyclopentaneacetonitrile；2-[1-(1-methylindol-3-yl)cyclopentyl]acetonitrile
• CAS: 145132-28-1
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: GPJDAHHAHFQLOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±18.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-methylindol-3-yl)cyclopentaneacetonitrile 在 lithium aluminium tetrahydride 作用下， 以74%的产率得到2-[1-(1-Methylindol-3-yl)cyclopentyl]ethanamine
  参考文献：
  名称：

  New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships

  摘要：

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.

  DOI：

  10.1016/0223-5234(96)80445-4
• 作为产物：
  描述：

  吲哚-3-乙腈 在 sodium hydroxide 、 2,4,6-三异丙基苯磺酰基肼 、 苄基三甲基氢氧化铵 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 、 甲苯 为溶剂， 反应 14.5h， 生成 1-(1-methylindol-3-yl)cyclopentaneacetonitrile
  参考文献：
  名称：

  New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships

  摘要：

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.

  DOI：

  10.1016/0223-5234(96)80445-4

文献信息

• Indole derivatives, preparation processes and medicinal products
  申请人：Lipha, Lyonnaise Industrielle Pharmaceutique

  公开号：US05219859A1

  公开（公告）日：1993-06-15

  The invention relates to indole derivatives of formula 1, ##STR1## in which: R.sub.1 and R.sub.2 represent H, alkyl, alkenyl, cycloalkyl, N-alkylamino- or N,N-dialkylaminoalkyl, benzyl, pyridylmethyl or phenyl, optionally substituted, R.sub.3 and R.sub.4 represent H, halogen, alkyl, alkoxy, alkylthio, CF.sub.3, NO.sub.2, N-alkylamino or N,N-dialkylamino, benzyl or phenyl, optionally substituted, R.sub.5 represents H, alkyl, cycloalkyl or optionally substituted benzyl, R.sub.6 denotes an alkyl, phenyl or heterocyclic radical, optionally substituted, Z denotes the bivalent radicals --(CH.sub.2).sub.n --C(R.sub.7 R.sub.8)--(CH.sub.2).sub.p --, --CH=CH--C(R.sub.7 R.sub.8)-- in which n=0--2, p=0--2 and n+p.ltoreq.2, R.sub.7 and R.sub.8 represent H, alkyl, alkenyl, cycloalkyl, N-alkylamino, N,N-dialkylamino, N-alkylamino- or N,N-dialkylaminoalkyl, benzyl or phenyl, where appropriate substituted, or together form polymethylene or oxa-, thia- or azapolymethylene chains, as well as their tautomeric forms, to processes for preparing them and to their application as hypolipidaemic, antiatheromatous and antidiabetic pharmaceutical products.

  该发明涉及公式1的吲哚衍生物，其中：R.sub.1和R.sub.2代表H，烷基，烯基，环烷基，N-烷基氨基或N，N-二烷基氨基烷基，苄基，吡啶基甲基或苯基，可选地取代，R.sub.3和R.sub.4代表H，卤素，烷基，烷氧基，烷硫基，CF.sub.3，NO.sub.2，N-烷基氨基或N，N-二烷基氨基，苄基或苯基，可选地取代，R.sub.5代表H，烷基，环烷基或可选地取代的苄基，R.sub.6表示烷基，苯基或杂环基，可选地取代，Z表示二价基团--(CH.sub.2).sub.n --C(R.sub.7 R.sub.8)--(CH.sub.2).sub.p --，--CH=CH--C(R.sub.7 R.sub.8)--其中n=0-2，p=0-2且n+p≤2，R.sub.7和R.sub.8代表H，烷基，烯基，环烷基，N-烷基氨基，N，N-二烷基氨基，N-烷基氨基或N，N-二烷基氨基烷基，苄基或苯基，必要时取代，或共同形成聚亚甲基或氧杂硫氮聚亚甲基链，以及它们的互变异构体形式，其制备过程以及它们作为降血脂，抗动脉粥样硬化和抗糖尿病药物的应用。
• US5219859A
  申请人：——

  公开号：US5219859A

  公开（公告）日：1993-06-15
• New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships
  作者：R Bellemin、J Decerprit、D Festal

  DOI：10.1016/0223-5234(96)80445-4

  日期：1996.1

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.