N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]-cyclohexane-1,2-dicarboximide | 102995-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]-cyclohexane-1,2-dicarboximide
• 英文别名: 2-[4-(4-Pyrimidin-2-yl-piperazin-1-yl)-butyl]-hexahydro-isoindole-1,3-dione;C4H4O4；2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• CAS: 102995-93-7
• 化学式: C₂₀H₂₉N₅O₂
• 分子量: 371.483
• InChiKey: VRNLQFXRAPWSFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  六氢邻苯二甲酰亚胺 在 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]-cyclohexane-1,2-dicarboximide
  参考文献：
  名称：

  Polycyclic aryl- and heteroarylpiperazinyl imides as 5-HT1A receptor ligands and potential anxiolytic agents: synthesis and structure-activity relationship studies

  摘要：

  A series of polycyclic aryl- and heteroarylpiperazinyl imides were prepared and tested in various receptor-binding and behavioral tests. Parameters measured included in vitro inhibition of D2 and 5-HT1A receptor binding, inhibition of apomorphine (APO) induced stereotyped and climbing behavior, and activity in blocking conditioned avoidance responding (CAR). Several compounds demonstrated moderate to high affinity for the 5-HT1A receptor binding site; compounds 27 and 36 containing the serotonin mimetic (o-methoxyphenyl)piperazinyl moiety and compounds 42 and 50 containing the 2-pyrimidinylpiperazinyl moiety displayed the highest affinity, being equal to that of the 5-HT1A agonist 8-OH-DPAT (Ki = 1-1.3 nM). In addition to affinity at 5-HT1A binding sites, many compounds were active in blocking CAR. Compound 34, 2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]hexahydro-4,7-etheno-1H- cyclobut[f]isoindole-1,3(2H)-dione, demonstrated 3 times the activity of buspirone, blocking CAR in rats with an AB50 of 13 mg/kg. It also displayed high affinity for the 5-HT1A receptor (Ki = 16 nM), which is at least 20 times higher than its affinity for D2 (Ki = 345 nM) and 5-HT2 (Ki = 458 nM) receptors. Compound 34 was selected for further preclinical and pharmacokinetic evaluations for possible development as an anxiolytic agent. Structure-activity relationships within this series are discussed.

  DOI：

  10.1021/jm00402a023

文献信息

• Succinimide derivatives and their production
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0109562A1

  公开（公告）日：1984-05-30

  A succinimide derivative of the formula: wherein A is straight or branched C2-C6 alkylene or alkenylene, B is straight or branched C3-C5 alkylene, D is straight or branched C2-C3 alkylene, E is straight or branched C2-C3 alkylene, R1 and R2 are each hydrogen or C1-C4 alkyl, or they may form a single bond and R3 is a phenyl group optionally substituted with C1-C4 alkyl, C1-C4 alkoxy, halogen and or trifluoromethyl, a 2-pyridyl group optionally substituted with halogen, a 2-pyrimidyl group optionally substituted with halogen, a group of the formula: (in which R4 is hydrogen or phenyl), a group of the formula: CO-R5 (in which R5 is adamantyl or furyl) or hydroxy(C2-C4)alkyl, and an acid addition salt thereof, which are useful as anti-anxiety drugs and/or anti-allergic drugs.

  一种琥珀酰亚胺衍生物，其式如下 其中 A 为直链或支链 C2-C6 亚烷基或烯基，B 为直链或支链 C3-C5 亚烷基，D 为直链或支链 C2-C3 亚烷基，E 为直链或支链 C2-C3 亚烷基，R1 和 R2 各为氢或 C1-C4 烷基，或它们可形成单键，R3 为任选被 C1-C4 烷基、C1-C4 烷氧基、卤素和或三氟甲基取代的苯基，任选被卤素取代的 2-吡啶基，任选被卤素取代的 2-嘧啶基，式中的一个基团： (其中 R4 为氢或苯基）、式中的一个基团： CO-R5（其中 R5 为金刚烷基或呋喃基）或羟基（C2-C4）烷基，以及它们的酸加成盐，可用作抗焦虑药和/或抗过敏药。
• ——
  作者：ISHIZUMI KIKUO、 ANTOKU FUJIO、 ASAML YUKIO

  DOI：——

  日期：——
• 5 HT RECEPTOR MEDIATED NEUROGENESIS
  申请人：Barlow Carrolee

  公开号：US20100009983A1

  公开（公告）日：2010-01-14

  The instant disclosure describes methods for treating diseases and conditions of the central and peripheral nervous system by stimulating or increasing neurogenesis. The disclosure includes compositions and methods based on use of a 5HTR agent, in combination with one or more other neurogenic agents, or anti-astrogenic agent, to stimulate or activate the formation of new nerve cells.
• US4562255A
  申请人：——

  公开号：US4562255A

  公开（公告）日：1985-12-31
• US4598078A
  申请人：——

  公开号：US4598078A

  公开（公告）日：1986-07-01