1-(1-methylindol-3-yl)cyclopentanecarbonitrile | 145132-23-6

• 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)cyclopentanecarbonitrile
• 英文别名: 1-(1-methyl-3-indolyl)-cyclopentanecarbonitrile；1-(1-Methyl-3-indolyl)cyclopentanecarbonitrile；1-(1-methylindol-3-yl)cyclopentane-1-carbonitrile
• CAS: 145132-23-6
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: GSKFIHSXGUNXNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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)cyclopentanecarbonitrile 在 2,4,6-三异丙基苯磺酰基肼 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 7.5h， 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
• 作为产物：
  描述：

  吲哚-3-乙腈 在 sodium hydroxide 、 苄基三甲基氢氧化铵 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 1-(1-methylindol-3-yl)cyclopentanecarbonitrile
  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

• A New Ring-Forming Methodology for the Synthesis of Conformationally Constrained Bioactive Molecules
  作者：Demetris P. Papahatjis、Spyros Nikas、Andrew Tsotinis、Margarita Vlachou、Alexandros Makriyannis

  DOI：10.1246/cl.2001.192

  日期：2001.3

  A new, general, one pot method for introducing carbocyclic rings alpha to a nitrile moiety is described. Treatment of readily available arylacetonitriles with potassium bis(trimethylsilyl)amide and subsequent alkylation with α, ω-dibromo or dichloroalkanes in tetrahydrofuran under anhydrous conditions at 0 °C produces cycloalkyl adducts in good yields and short reaction times.

  描述了一种新的通用一锅法，用于在腈基前引入碳环。将 readily available 的芳基乙腈与氨基钾双(trimethylsilyl)处理，随后在无水条件下于0 °C的四氢呋喃中与α,ω-二溴或二氯烷烃进行烷基化，可以在短反应时间内以良好的产率生成环烷基附加物。
• 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。
• Beta 3 adrenergic agonists
  申请人：Sall Jon Daniel

  公开号：US20050080110A1

  公开（公告）日：2005-04-14

  The present invention relates to a β3 adrenergic receptor agonist of formula (I); or a pharmaceutical salt thereof; which is capable of increasing lipolysis and energy expenditure in cells and, therefore, is useful, e.g., for treating Type 2 diabetes and/or obesity.

  本发明涉及一种β3肾上腺素能受体激动剂，其化学式为（I）；或其药用盐；该激动剂能够增加细胞中的脂解和能量消耗，因此，它可以用于治疗2型糖尿病和/或肥胖等疾病。
• 3-substituted oxindole beta-3 agonists
  申请人：——

  公开号：US20040242668A1

  公开（公告）日：2004-12-02

  The present invention relates to a &bgr;3 adrenergic receptor agonist of formula (I); or a pharmaceutical salt thereof; which is capable of increasing lipolysis and energy expenditure in cells and, therefore, is useful for treating Type 2 diabetes and/or obesity.

  本发明涉及一种&bgr;3肾上腺素受体激动剂，其化学式为(I)；或其药用盐；该激动剂能够增加细胞内的脂肪分解和能量消耗，因此对于治疗2型糖尿病和/或肥胖症具有有用性。
• 3-Substituted oxindole beta3 agonists
  申请人：Sall Jon Daniel

  公开号：US20050159473A1

  公开（公告）日：2005-07-21

  The present invention relates to a β3 adrenergic receptor agonist of formula I: or a pharmaceutical salt thereof; which is capable of increasing lipolysis and energy expenditure in cells and, therefore, is useful for treating Type 2 diabetes and/or obesity.

  本发明涉及一种式子为I的β3肾上腺素能受体激动剂或其药用盐; 该激动剂能够增加细胞内的脂肪分解和能量消耗，因此可用于治疗2型糖尿病和/或肥胖症。