2-(1H-吡咯-1-基)噻吩-3-甲腈 | 63647-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(1H-吡咯-1-基)噻吩-3-甲腈
• 英文名称: (pyrrolyl-1)-2 thiophene carbonitrile-3
• 英文别名: 2-(pyrrol-1-yl)thiophene-3-carbonitrile；2-(1-pyrrolyl)thienyl-3-carbonitrile；2-pyrrol-1-yl-thiophene-3-carbonitrile；2-(1H-Pyrrol-1-yl)thiophene-3-carbonitrile；2-pyrrol-1-ylthiophene-3-carbonitrile
• CAS: 63647-03-0
• 化学式: C₉H₆N₂S
• mdl: MFCD04125723
• 分子量: 174.226
• InChiKey: YBDDDGXQRINYPU-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 4 Torr)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(1H-吡咯-1-基)噻吩-3-甲腈 在 sodium hydroxide 、 sodium azide 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 5.33h， 生成 azoture de (formyl-2 pyrrolyl-1)-2 theonyle-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-氨基噻吩-3-甲腈 生成 2-(1H-吡咯-1-基)噻吩-3-甲腈
  参考文献：
  名称：

  RAULT S.; CUGNON DE SEVRICOURT M.; ROBBA M., C. R. ACAD. SCI., 1977, C 284, NO 14, 533-535

  摘要：

  DOI：

文献信息

• Reactivity of 3-(pyrrol-1-yl)thiophenes in Pd-catalysed direct arylations
  作者：Imen Smari、Chiraz Youssef、Hamed Ben Ammar、Bechir Ben Hassine、Jean-François Soulé、Henri Doucet

  DOI：10.1016/j.tet.2015.03.022

  日期：2015.9

  in moderate to good yields with a wide variety of aryl halides; whereas the use of 1-(4-methylthiophen-3-yl)-pyrrole affords the C2-arylated thiophenes. The sequential palladium catalysed 2,5-diheteroarylation of such 3-(pyrrol-1-yl)thiophene is also reported allowing the access to thiophenes bearing two different aryl units at C2 and C5. A pyrazole bearing an ester substituent at C4 and a pyrrole

  研究了Pd催化3-（吡咯-1-基）噻吩衍生物直接芳基化的区域选择性。报道了允许噻吩环在C 2或C 5处区域选择性芳基化的条件。由以KOAc为碱，DMA为溶剂和仅1 mol％Pd（OAc）2的3-（吡咯-1-基）噻吩-2-羧酸甲酯作为催化剂，目标5-芳基噻吩以中等至良好的收率得到了多种芳基卤化物。而1-（4-甲基噻吩-3-基）-吡咯的使用提供了C2-芳基噻吩。还报道了这种3-（吡咯-1-基）噻吩的顺序钯催化的2，5-二杂芳基化，允许接近在C2和C5带有两个不同芳基单元的噻吩。仅在吡咯环上的C2处芳基化在C4处带有酯取代基的吡唑和在C5处具有吡咯取代基的吡唑。
• 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.