2-(4-benzyl-piperazin-1-yl)-benzothiazole | 35463-75-3

• 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: 2-(4-benzyl-piperazin-1-yl)-benzothiazole
• 英文别名: 2-(4-Benzylpiperazin-1-yl)-1,3-benzothiazole
• CAS: 35463-75-3
• 化学式: C₁₈H₁₉N₃S
• mdl: MFCD01418003
• 分子量: 309.435
• InChiKey: SNRZSONRAFJJSB-UHFFFAOYSA-N

物化性质

• 沸点：
  451.3±55.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)
• 溶解度：
  1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.277
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基苯并噻唑 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 18.25h， 生成 2-(4-benzyl-piperazin-1-yl)-benzothiazole
  参考文献：
  名称：

  Synthesis of 2-Piperazinylbenzothiazole and 2-Piperazinylbenzoxazole Derivatives with 5-HT3 Antagonist and 5-HT4 Agonist Properties

  摘要：

  New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [H-3]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunics muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 6-methoxytryptamine Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.

  DOI：

  10.1021/jm00035a012

文献信息

• Non-imidazole histamine H3 ligands. Part I. Synthesis of 2-(1-piperazinyl)- and 2-(hexahydro-1H-1,4-diazepin-1-yl)benzothiazole derivatives as H3-antagonists with H1 blocking activities
  作者：Krzysztof Walczyński、Roman Guryn、Obbe P. Zuiderveld、Henk Timmerman

  DOI：10.1016/s0014-827x(99)00081-6

  日期：1999.10

  New 2-(1-Piperazinyl)- and 2-(hexahydro-1H-1,4-diazepin-1-yl)benzothiazoles were prepared and tested as H1- and H3-receptor antagonists. A number of compounds showed weak H1-antagonistic activity, with pA2 values ranging from 5.5 to 6.1. The simple alkyl substituted, 2-[1-(4-methyl and 4-ethyl)piperazinyl] analogues show increasing, moderate H3-antagonistic activity (pA2 = 6.0, and pA2 = 7.0). The

  制备了新的2-（1-哌嗪基）-和2-（六氢-1H-1,4-二氮杂-1-基）苯并噻唑并作为H1-和H3-受体拮抗剂进行了测试。许多化合物表现出较弱的H1拮抗活性，pA2值为5.5至6.1。简单的烷基取代的2- [1-（1-（4-甲基和4-乙基）哌嗪基]类似物显示出中等的H3拮抗活性（pA2 = 6.0，pA2 = 7.0）。对于哌嗪基和六氢-1H-1,4-二氮杂-1-基同系物序列，具有4-苯基烷基取代基的化合物，无论苯环上对位取代基的物理化学性质如何，均表现出弱的H3-拮抗性pA2值介于4.4至5.6之间的活性。
• 1,4-Disubstituted piperazines. 3. Piperazinylbenzothiazoles
  作者：Matthew Verderame

  DOI：10.1021/jm00276a039

  日期：1972.6
• 1-(BENZOTHIAZOL-2-YL)-4-(1-PHENYLMETHYL)PIPERAZINES: DOPAMINE RECEPTOR SUBTYPE SPECIFIC LIGANDS
  申请人：NEUROGEN CORPORATION

  公开号：EP1089990A1

  公开（公告）日：2001-04-11
• US6291463B1
  申请人：——

  公开号：US6291463B1

  公开（公告）日：2001-09-18
• [EN] 1-(BENZOTHIAZOL-2-YL)-4-(1-PHENYLMETHYL)PIPERAZINES: DOPAMINE RECEPTOR SUBTYPE SPECIFIC LIGANDS<br/>[FR] 1-(BENZOTHIAZOL-2-YL)-4-(1-PHENYLMETHYL)PIPERAZINES EN TANT QUE LIGANDS SPECIFIQUES DU SOUS-TYPE DU RECEPTEUR DE LA DOPAMINE
  申请人：NEUROGEN CORP

  公开号：WO2000000482A1

  公开（公告）日：2000-01-06

  Disclosed are compounds of formula (A) or pharmaceutically acceptable addition salts thereof wherein: R1 and R2 are the same or different and represent hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono- or di(C1-C6) alkylamino, cyano or trifluoromethyl; Ar represents aryl or heteroaryl, each of which is optionally substituted with R3, R4 and/or R6; R3, R4, and R6 independently represent hydrogen, halogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, perfluoro (C1-C6) alkyl, perfluoro (C1-C6) alkoxy, or SO2NH2; or R3 and R4 together with the atoms to which they are attached represent a ring having 5-7 atoms; and R5 represents hydrogen or C1-C6 alkyl, which compounds are useful for the treatment and/or prevention of neuropsychological disorders including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents.