3-(4-chlorobutyl)-1,2,3-benzotriazin-4(3H)-one | 158659-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: 3-(4-chlorobutyl)-1,2,3-benzotriazin-4(3H)-one
• 英文别名: 3-(4-Chlorobutyl)-1,2,3-benzotriazin-4-one
• CAS: 158659-66-6
• 化学式: C₁₁H₁₂ClN₃O
• 分子量: 237.689
• InChiKey: JAQUXXLWQCCDTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.7±44.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobutyl)-1,2,3-benzotriazin-4(3H)-one 、 1-胡椒基哌嗪 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis by microwave irradiation and binding properties of novel 5-HT1A receptor ligands

  摘要：

  This work reports the synthesis by microwave irradiation and the binding tests on the 5-HT1A, 5-HT2A and 5-HT2C receptors of new substituted piperazines in order to identify selective ligands for 5-HT1A subtype receptor. Conventional heating and microwave irradiation of the reactions was compared. Synthesis by microwave irradiation gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. Some resulting active compounds (29 and 39) were characterised by a good selectivity profile for the 5-HT1A subtype receptor. The more active compounds were selected and further evaluated for their binding affinities on D-1, D-2 dopaminergic and alpha(1), alpha(2) adrenergic receptors. The compound with higher affinity and selectivity for the 5-HT1A over all the considered receptors was the 3-{4-[4-(1,2,3,4-tetrahydronaplithyl)-1-piperazinyl]butan}-benzotriazinone (-)29 (5-HT1A K-i = 36 nM, other receptors not active). (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01287-9
• 作为产物：
  描述：

  1-溴-4-氯丁烷 、 1,2,3-苯并三嗪-4-酮 在 sodium hydride 作用下， 生成 3-(4-chlorobutyl)-1,2,3-benzotriazin-4(3H)-one
  参考文献：
  名称：

  环状苯甲酰胺作为多巴胺D2 / 5-羟色胺5-HT2受体拮抗剂的混合物：潜在的非典型抗精神病药。

  摘要：

  制备了一系列新颖的4-（4-（1,2-苯并噻唑-3-基）-1-哌嗪基）丁基）环酰胺，并将其评估为潜在的抗精神病药。在体外检查靶标化合物与多巴胺D2、5-羟色胺5-HT2和5-羟色胺5-HT1a受体的结合亲和力，并在体内拮抗阿朴吗啡诱导的小鼠爬升反应的能力。选择在体外表现出良好的D2 / 5-HT2选择性和在体内具有良好效能的衍生物，以在旨在评估其潜在锥体外系副作用的测试中进行进一步评估。本文讨论的结构修饰着眼于双环酰胺亚基，导致制备各种杂环系统（即邻苯二甲酰亚胺，异吲哚啉酮，异喹啉酮，苯并ze庚酮，吲唑酮，酞嗪酮，4-甲基酞嗪酮，1,1-二甲基苯并异噻唑酮，苯并三嗪酮，高邻苯二甲酰亚胺，苯并异噻唑酮，邻苯二嗪二酮，喹唑啉和饱和邻苯二氮酮。发现该系列中的效力和选择性取决于环的大小，共价连接单元的性质，官能团的相对位置，不饱和度和相对立体化学。通常，在这项研究中检查的环状苯甲酰胺表现出受体结合

  DOI：

  10.1021/jm00042a008

文献信息

• Cyclic Benzamides as Mixed Dopamine D2/Serotonin 5-HT2 Receptor Antagonists: Potential Atypical Antipsychotic Agents
  作者：Mark H. Norman、Greg C. Rigdon、Frank Navas、Barrett R. Cooper

  DOI：10.1021/jm00042a008

  日期：1994.8

  A series of novel 4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl) cyclic amides was prepared and evaluated as potential antipsychotic agents. The target compounds were examined in vitro for their binding affinities to the dopamine D2, serotonin 5-HT2, and serotonin 5-HT1a receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice. Derivatives that exhibited

  制备了一系列新颖的4-（4-（1,2-苯并噻唑-3-基）-1-哌嗪基）丁基）环酰胺，并将其评估为潜在的抗精神病药。在体外检查靶标化合物与多巴胺D2、5-羟色胺5-HT2和5-羟色胺5-HT1a受体的结合亲和力，并在体内拮抗阿朴吗啡诱导的小鼠爬升反应的能力。选择在体外表现出良好的D2 / 5-HT2选择性和在体内具有良好效能的衍生物，以在旨在评估其潜在锥体外系副作用的测试中进行进一步评估。本文讨论的结构修饰着眼于双环酰胺亚基，导致制备各种杂环系统（即邻苯二甲酰亚胺，异吲哚啉酮，异喹啉酮，苯并ze庚酮，吲唑酮，酞嗪酮，4-甲基酞嗪酮，1,1-二甲基苯并异噻唑酮，苯并三嗪酮，高邻苯二甲酰亚胺，苯并异噻唑酮，邻苯二嗪二酮，喹唑啉和饱和邻苯二氮酮。发现该系列中的效力和选择性取决于环的大小，共价连接单元的性质，官能团的相对位置，不饱和度和相对立体化学。通常，在这项研究中检查的环状苯甲酰胺表现出受体结合
• FERRAND, GERARD;DUMAS, HERVE;DEPIN, JEAN-CLAUDE;CHAVERNAC, GILLES, EUR. J. MED. CHEM., 22,(1987) N 4, 337-345
  作者：FERRAND, GERARD、DUMAS, HERVE、DEPIN, JEAN-CLAUDE、CHAVERNAC, GILLES

  DOI：——

  日期：——
• Synthesis by microwave irradiation and binding properties of novel 5-HT1A receptor ligands
  作者：G Caliendo

  DOI：10.1016/s0223-5234(01)01287-9

  日期：2001.12.1

  This work reports the synthesis by microwave irradiation and the binding tests on the 5-HT1A, 5-HT2A and 5-HT2C receptors of new substituted piperazines in order to identify selective ligands for 5-HT1A subtype receptor. Conventional heating and microwave irradiation of the reactions was compared. Synthesis by microwave irradiation gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. Some resulting active compounds (29 and 39) were characterised by a good selectivity profile for the 5-HT1A subtype receptor. The more active compounds were selected and further evaluated for their binding affinities on D-1, D-2 dopaminergic and alpha(1), alpha(2) adrenergic receptors. The compound with higher affinity and selectivity for the 5-HT1A over all the considered receptors was the 3-4-[4-(1,2,3,4-tetrahydronaplithyl)-1-piperazinyl]butan}-benzotriazinone (-)29 (5-HT1A K-i = 36 nM, other receptors not active). (C) 2001 Editions scientifiques et medicales Elsevier SAS.