2-isopropyl-5-(1-piperazinyl)-2-(2-methylphenyl)valeronitrile | 350854-86-3

• 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: 2-isopropyl-5-(1-piperazinyl)-2-(2-methylphenyl)valeronitrile
• 英文别名: 1-[4-Cyano-5-methyl-4-(2-tolyl)hexyl]piperazine；2-(2-Methylphenyl)-5-piperazin-1-yl-2-propan-2-ylpentanenitrile
• CAS: 350854-86-3
• 化学式: C₁₉H₂₉N₃
• 分子量: 299.459
• InChiKey: FHQBVRVZHVUZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-3-氨磺酰基苯甲酰氯 、 2-isopropyl-5-(1-piperazinyl)-2-(2-methylphenyl)valeronitrile 在 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 5-<4-(4-chloro-3-sulfamoylbenzoyl)-1-piperazinyl>-2-isopropyl-2-(2-methylphenyl)valeronitrile
  参考文献：
  名称：

  Some New Analogues of Verapamil and Mepamil. Synthesis and Basic Pharmacological Properties

  摘要：

  一些新的维拉帕米（Ia）和美帕米（Ib）的类似物，属于芳基烷胺型钙拮抗剂，已经合成并进行心血管活性筛选。基本结构进行了修改：a）在苯环上，连接到季铵碳上，b）在烷基团上，连接到季铵碳上，c）在烷基氨基团上，连接到n-丙基片段的位置3。除了2-(2-氯苯基)-2-异丙基-5-(N-甲基同位素香豆酰胺)戊腈（VIa）外，所有合成的化合物表现出较低的降压活性，低于母化合物维拉帕米。

  DOI：

  10.1135/cccc19921967

文献信息

• Nitrogen-containing cyclic compound and pharmaceutical composition containing the compound
  申请人：Eisai Co., Ltd.

  公开号：US20040220193A1

  公开（公告）日：2004-11-04

  The present invention provides a novel compound having a superior calcium antagonism, in particular, a neuron-selective calcium antagonism. Namely, it provides a compound represented by the following formula, a salt thereof or a hydrate of them. 1 In the formula, Ar indicates an optionally substituted 5- to 14-membered aromatic ring etc.; the ring A indicates any one ring selected from a piperazine, a homopiperazine, a piperidine and the like; the ring B indicates an optionally substituted C 3-14 hydrocarbon ring etc.; E indicates a single bond, a group represented by the formula —CO—, etc.; X indicates a single bond, an oxygen atom etc.; R 1 indicates a hydrogen atom, a halogen atom, a hydroxyl group etc.; and D 1 , D 2 , W 1 and W 2 are the same as or different from each other and each represents a single bond or an optionally substituted C 1-6 alkylene chain.

  本发明提供了一种具有卓越的钙拮抗作用，特别是神经元选择性钙拮抗作用的新化合物。即，提供了下式所示的化合物、其盐或水合物。其中，Ar表示可选取的5-至14-成员芳香环等；环A表示选自哌嗪、同哌嗪、吡啶等任意一环；环B表示可选取的C3-14碳氢环等；E表示单键、由公式—CO—表示的基团等；X表示单键、氧原子等；R1表示氢原子、卤原子、羟基等；D1、D2、W1和W2相同或不同，每个代表单键或可选取的C1-6烷基链。
• Nitrogen-containing heterocyclic compounds and pharmaceutical composition containing the compounds
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1818326A1

  公开（公告）日：2007-08-15

  The present invention provides a novel compound having a superior calcium antagonism, in particular, a neuron-selective calcium antagonism. Namely, it provides a compound represented by the following formula (I), a salt thereof or a hydrate of them: wherein Ar is a thiophene or benzene ring which may be substituted,the ring A is a piperazine ring, homopiperazine ring or piperidine ring which may be substituted, the ring B is a C6-14 aromatic hydrocarbon ring or 5- to 14-membered aromatic heterocyclic ring which may be substituted, the partial structure -D1-E-D2- is a C1-4 alkylene group, W1 and W2 are the same as or different from each other and each represents (1) a single bond or (2) a C1-6 alkylene chain which may be substituted, X is (1) an oxygen atom, a group represented by (2) the formula -NR2- (wherein R2 indicates a hydrogen atom, or a C1-6 alkyl group, a C3-8 cycloalkyl group, a lower acyl group or a C1-6 alkylsulfonyl group which may be substituted) or (3) -NH-SO2-, R1 is a methyl group, an ethyl group, a n-propyl group or an isopropyl group.

  本发明提供了一种新型化合物，它具有优异的钙拮抗作用，尤其是神经元选择性钙拮抗作用。也就是说，本发明提供了由下式（I）代表的化合物、其盐或它们的水合物： 其中 Ar 是可被取代的噻吩环或苯环，环 A 是可被取代的哌嗪环、均哌嗪环或哌啶环，环 B 是可被取代的 C6-14 芳烃环或 5-14 元芳香杂环，部分结构 -D1-E-D2- 是 C1-4 烯基、W1和W2彼此相同或不同，各自代表(1)单键或(2)可被取代的C1-6亚烷基链，X是(1)氧原子、由(2)式-NR2-（其中R2表示氢原子）代表的基团或C1-6烷基、或 C1-6 烷基、C3-8 环烷基、低级酰基或可能被取代的 C1-6 烷基磺酰基）或 (3) -NH-SO2- 所代表的基团，R1 是甲基、乙基、正丙基或异丙基。
• NITROGENOUS CYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1254895B1

  公开（公告）日：2007-05-23
• US6906072B1
  申请人：——

  公开号：US6906072B1

  公开（公告）日：2005-06-14
• Some New Analogues of Verapamil and Mepamil. Synthesis and Basic Pharmacological Properties
  作者：Gabriel Butora、Ludvík Bláha、Miroslav Rajšner、Ivan Helfert

  DOI：10.1135/cccc19921967

  日期：——

  Some new analogues of verapamil (Ia) and mepamil (Ib), calcium antagonists of arylalkylamine type, were synthesized and screened for cardiovascular activities. The basic structure was modified a) on the phenyl ring, attached to the quaternary carbon, b) on the alkyl group, attached to the quaternary carbon and c) on the alkylamino group, attached in position 3 to the n-propyl fragment. Except of 2-(2-chlorophenyl)-2-isopropyl-5-(N-methylhomoveratrylamino)valeronitrile (VIa), all the synthesized compounds exhibited lower hypotensive activity, than the mother compound, verapamil.

  一些新的维拉帕米（Ia）和美帕米（Ib）的类似物，属于芳基烷胺型钙拮抗剂，已经合成并进行心血管活性筛选。基本结构进行了修改：a）在苯环上，连接到季铵碳上，b）在烷基团上，连接到季铵碳上，c）在烷基氨基团上，连接到n-丙基片段的位置3。除了2-(2-氯苯基)-2-异丙基-5-(N-甲基同位素香豆酰胺)戊腈（VIa）外，所有合成的化合物表现出较低的降压活性，低于母化合物维拉帕米。