2-(1-吡咯基)-3-噻吩基羧酸叠氮化物 | 74772-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-(1-吡咯基)-3-噻吩基羧酸叠氮化物
• 英文名称: 2-(1-pyrrolyl)-3-thienylcarboxylic acid azide
• 英文别名: 2-(1-pyrrolyl)-3-thenoyl azide；2-(pyrrol-1-yl)thiophen-3-ylcarbonyl azide；2-pyrrol-1-ylthiophene-3-carbonyl azide
• CAS: 74772-14-8
• 化学式: C₉H₆N₄OS
• 分子量: 218.239
• InChiKey: GHZGUQPTBSKPOO-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：

  2-(1-吡咯基)-3-噻吩基羧酸叠氮化物 在 sodium hydroxide 作用下， 反应 6.0h， 生成 (Pyrrolyl-1)-2 thienylamine-3
  参考文献：
  名称：

  Rault, Sylvain; Effi, Yamien; Sevricourt, Michel Cugnon de, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 17 - 21

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1H-吡咯-1-基)噻吩-3-羧酸 在 sodium azide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 1.5h， 生成 2-(1-吡咯基)-3-噻吩基羧酸叠氮化物
  参考文献：
  名称：

  血清素4受体的新型拮抗剂：吡咯烷噻吩并吡嗪类化合物的合成和生物学评估

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2008.11.045

文献信息

• Tricyclic oxime ethers
  申请人：Adir et Compagnie

  公开号：US05627203A1

  公开（公告）日：1997-05-06

  The present invention relates to compounds of formula (I): ##STR1## wherein A, x, y, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description. The compounds are useful for treating diseases requiring a selective serotonin reuptake site and 5-HT.sub.2c or 5-HT.sub.3 ligand.

  本发明涉及以下化合物的结构（I）：##STR1## 其中A、x、y、R.sub.1、R.sub.2和R.sub.3如描述中所定义。这些化合物可用于治疗需要选择性5-羟色胺再摄取位点和5-HT.sub.2c或5-HT.sub.3配体的疾病。
• Methods of Inhibiting Metastasis from Cancer
  申请人：Salvino Joseph M.

  公开号：US20120141471A1

  公开（公告）日：2012-06-07

  The present invention includes compositions that are useful in preventing or treating metastasis in a subject diagnosed with cancer. The present invention also includes methods of preventing or treating metastasis in a subject diagnosed with cancer, wherein the method comprises administering to the subject in need thereof an effective amount of a pharmaceutical formulation comprising at least one pharmaceutically acceptable carrier and at least one CX 3 CR1 or fractalkine antagonist.

  本发明涉及一种用于预防或治疗被诊断为癌症的患者中的转移的组合物。本发明还包括一种用于预防或治疗被诊断为癌症的患者中的转移的方法，其中该方法包括向需要该药物的患者投与至少一种药用制剂，该制剂包括至少一种药用载体和至少一种CX3CR1或fractalkine拮抗剂的有效量。
• Compounds Useful for Inhibiting Metastasis from Cancer and Methods Using Same
  申请人：Drexel University College of Medicine Philadelphia Health & Education Corporation d/b/a

  公开号：US20130156761A1

  公开（公告）日：2013-06-20

  The present invention includes compositions that are useful in preventing or treating metastasis in a subject diagnosed with cancer. The present invention also includes methods of preventing or treating metastasis in a subject diagnosed with cancer, wherein the method comprises administering to the subject in need thereof an effective amount of a pharmaceutical formulation comprising at least one pharmaceutically acceptable carrier and at least one CX 3 CR1 or fractalkine antagonist.

  本发明涉及一种对已被诊断患有癌症的受试者预防或治疗转移的有用组合物。本发明还涉及一种预防或治疗已被诊断患有癌症的受试者的转移的方法，其中该方法包括向需要该药物的受试者施用至少一种药物制剂，该药物制剂包括至少一种药用载体和至少一种CX3CR1或fractalkine拮抗剂的有效量。
• Compounds useful for inhibiting metastasis from cancer and methods using same
  申请人：Drexel University

  公开号：US10414771B2

  公开（公告）日：2019-09-17

  The present invention includes compositions that are useful in preventing or treating metastasis in a subject diagnosed with cancer. The present invention also includes methods of preventing or treating metastasis in a subject diagnosed with cancer, wherein the method comprises administering to the subject in need thereof an effective amount of a pharmaceutical formulation comprising at least one pharmaceutically acceptable carrier and at least one CX3CR1 or fractalkine antagonist.

  本发明包括可用于预防或治疗确诊癌症患者转移的组合物。本发明还包括预防或治疗被诊断患有癌症的受试者的转移的方法，其中该方法包括向需要该方法的受试者施用有效量的药物制剂，该药物制剂包含至少一种药学上可接受的载体和至少一种CX3CR1或fractalkine拮抗剂。
• Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines
  作者：Sylvain Rault、Jean-Charles Lancelot、Hervé Prunier、Max Robba、Pierre Renard、Philippe Delagrange、Bruno Pfeiffer、Daniel-Henri Caignard、Béatrice Guardiola-Lemaitre、Michel Hamon

  DOI：10.1021/jm950543x

  日期：1996.1.1

  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.