azoture de (pyrrolyl-1)-3 thenoyle-2 | 74772-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: azoture de (pyrrolyl-1)-3 thenoyle-2
• 英文别名: 2-(1-pyrrolyl)-3-thenoyl azide；3-(1H-Pyrrol-1-yl)thiophene-2-carbonyl azide；3-pyrrol-1-ylthiophene-2-carbonyl azide
• CAS: 74772-18-2
• 化学式: C₉H₆N₄OS
• 分子量: 218.239
• InChiKey: RWSVHUMXTCBTBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  azoture de (pyrrolyl-1)-3 thenoyle-2 在 三氯氧磷 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 5-[4-[3-(Trifluoromethyl)phenyl]piperazine-1-yl]-3-thia-4,8a-diaza-as-indacene
  参考文献：
  名称：

  Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines

  摘要：

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.

  DOI：

  10.1021/jm950543x
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 sodium hydroxide 、 sodium azide 、 TEA 、 氯甲酸乙酯 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 5.0h， 生成 azoture de (pyrrolyl-1)-3 thenoyle-2
  参考文献：
  名称：

  Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines

  摘要：

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.

  DOI：

  10.1021/jm950543x

文献信息

• Novel antagonists of serotonin-4 receptors: Synthesis and biological evaluation of pyrrolothienopyrazines
  作者：Stéphane Lemaître、Alban Lepailleur、Ronan Bureau、Sabrina Butt-Gueulle、Véronique Lelong-Boulouard、Pascal Duchatelle、Michel Boulouard、Aline Dumuis、Cyril Daveu、Frank Lezoualc’h、Bruno Pfeiffer、François Dauphin、Sylvain Rault

  DOI：10.1016/j.bmc.2008.11.045

  日期：2009.3

  of a 5-HT4 receptor antagonist pharmacophore, a series of pyrrolo[1,2-a]thieno[3,2-e] and pyrrolo[1,2-a]thieno[2,3-e] pyrazine derivatives were designed, prepared, and evaluated to determine the properties necessary for high-affinity binding to 5-HT4 receptors. The compounds were synthesized by substituting the chlorine atom of the pyrazine ring with various N-alkyl-4-piperidinylmethanolates. They

  根据5-HT 4受体拮抗剂药效团的定义，一系列吡咯并[1,2- a ]噻吩并[3,2- e ]和吡咯并[1,2- a ]噻吩并[2,3- e ]设计，制备和评估吡嗪衍生物，以确定与5-HT 4受体高亲和力结合所需的性质。通过用各种N-烷基-4-哌啶基甲醇盐取代吡嗪环的氯原子来合成化合物。在结合测定中以[ 3 H] GR113808（1）作为5-HT 4受体放射性配体对它们进行了评估。亲和力值（K i（或抑制百分比）受到芳环上的取代基和侧哌啶链上的取代基的影响。三环上的甲基会显着增加亲和力，而N-丙基或N-丁基会产生具有纳摩尔亲和力的化合物。在最有效的配体中，选择34d用于进一步的药理研究并在体内进行评估。该化合物在稳定表达5-HT 4（a）受体的COS-7细胞中充当拮抗剂/弱部分激动剂，并作为一种外周镇痛药而引起了人们的极大兴趣。
• Rault, Sylvain; Effi, Yamien; Sevricourt, Michel Cugnon de, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 17 - 21
  作者：Rault, Sylvain、Effi, Yamien、Sevricourt, Michel Cugnon de、Lancelot, Jean-Charles、Robba, Max

  DOI：——

  日期：——
• Effi, Yamien; Rault, Sylvian; Lancelot, Jean-Charles, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 431 - 435
  作者：Effi, Yamien、Rault, Sylvian、Lancelot, Jean-Charles、Robba, Max

  DOI：——

  日期：——
• Rault, Sylvain; Sevricourt Michel Cugnon de; Robba, Max, Heterocycles, 1980, vol. 14, # 5, p. 651 - 652
  作者：Rault, Sylvain、Sevricourt Michel Cugnon de、Robba, Max

  DOI：——

  日期：——
• RAULT S.; SEVRICOURT M. C. DE; ROBBA M., HETEROCYCLES, 1980, 14, NO 5, 651-652
  作者：RAULT S.、 SEVRICOURT M. C. DE、 ROBBA M.

  DOI：——

  日期：——