5-phenyl-3-thiopheneamine | 75782-81-9

• 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: 5-phenyl-3-thiopheneamine
• 英文别名: 4-Amino-2-phenylthiophene；5-phenyl-3-thienylamine；3-amino-5-phenylthiophene；5-phenyl-thien-3-ylamine；5-phenylthiophen-3-amine
• CAS: 75782-81-9
• 化学式: C₁₀H₉NS
• 分子量: 175.254
• InChiKey: GQNDKVSFMBAOLF-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  375.9±30.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenyl-3-thiopheneamine 在 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 20.0h， 生成 N-(4-methoxyphenyl)-N'-(5-phenyl-3-thienyl)thiourea
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-heteroarylimino-1,3-thiazolidin-4-ones as potential anti-tumor agents

  摘要：

  A series of 35 heteroarylimino-1,3-thiazolidinones with three sites of functionalization were synthesized and their antiproliferative properties were studied. The in vitro screening by MTT assay was performed against five cancer cell lines (human colon cancer cell lines HT29, HCT116 and SW620 and breast cancer cell lines MCF7 and MDA-MB-231). It was observed that N3-substituted thiazolidinones had moderate activities whereas 5-benzylidene thiazolidinones showed promising activities. To investigate the mechanism of action, detailed biological studies of six selected compounds (those presenting the lower mitotic index) were carried out on the human colon cancer HT29 cell line. Cell cycle assay revealed that those compounds induced cell accumulation in G2/M and in subG0/G1 phases of cell cycle. Moreover, dissipation of mitochondria membrane potential was observed as well as redox changes in treated cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.053
• 作为产物：
  描述：

  3-氯-3-苯基丙烯腈 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 7.5h， 生成 5-phenyl-3-thiopheneamine
  参考文献：
  名称：

  通过原位生成的3-氨基噻吩从3-氨基噻吩-2-羧酸酯一锅合成2-取代的噻吩并[3,2- b ]吲哚

  摘要：

  一种方便的协议，可使用易于获得的5-取代的3-氨基噻吩-2-羧酸酯一锅合成噻吩并[3,2- b ]吲哚，在C-2位带有芳香，噻吩-2-基或苯乙烯基片段Fischer吲哚化反应是在这项研究期间开发的。该方法的两个主要步骤是用氢氧化钠对起始的3-氨基酯进行皂化，然后在冰醋酸溶液中用芳基肼对粗制的3-氨基酸钠盐进行下一步处理。后面的步骤包括将游离的3-氨基噻吩-2-羧酸原位脱羧为3-氨基噻吩，并使其与芳基肼的酸促进反应，最初形成5-取代噻吩-3（2 H的芳基hydr））-平滑地导致吲哚化以提供所需的噻吩并[3,2- b ]吲哚。

  DOI：

  10.1016/j.tetlet.2019.151185

文献信息

• Phenoxypiperidines and analogs thereof useful as histamine H3 antagonists
  申请人：Mutahi W. Mwangi

  公开号：US20070167435A1

  公开（公告）日：2007-07-19

  Disclosed are compounds of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein: M is CH or N; U and W are each CH, or one of U and W is CH and the other is N; X is a bond, alkylene, —C(O)—, —C(N—OR 5 )—, —C(N—OR 5 )—CH(R 6 )—, —CH(R 6 )—C(N—OR 5 )—, —O—, —OCH 2 —, —CH 2 O— or —S(O) 0-2 —; Y is —O—, —(CH 2 ) 2 —, —C(═O)—, —C(═NOR 7 )— or —SO 0-2 —; Z is a bond, optionally substituted alkylene or alkylene interrupted by a heteroatom or heterocyclic group; R 1 is optionally substituted alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heterocycloalkyl, or benzimidazolyl or a derivative thereof; R 2 is optionally substituted alkyl, alkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl; and the remaining variables are as defined in the specification; compositions and methods for treating an allergy-induced airway response, congestion, diabetes, obesity, an obesity-related disorder, metabolic syndrome and a cognition deficit disorder using said compounds, alone or in combination with other agents.

  揭示了以下化合物的结构式或其药学上可接受的盐或溶剂，其中：M为CH或N；U和W分别为CH，或者U和W中的一个为CH，另一个为N；X为键，烷基，—C(O)—，—C(N—OR5)—，—C(N—OR5)—CH(R6)—，—CH(R6)—C(N—OR5)—，—O—，—OCH2—，—CH2O—或—S(O)0-2—；Y为—O—，—(CH2)2—，—C(═O)—，—C(═NOR7)—或—SO0-2—；Z为键，可选择地取代的烷基或被杂原子或杂环基中断的烷基；R1为可选择地取代的烷基，环烷基，芳基，芳基烷基，杂芳基，杂环烷基或苯并咪唑基或其衍生物；R2为可选择地取代的烷基，烯基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基或杂环烷基；其余变量如规范中所定义；使用这些化合物，单独或与其他药剂联合使用，治疗由过敏引起的气道反应、充血、糖尿病、肥胖症、与肥胖有关的疾病、代谢综合征和认知缺陷障碍的组合物和方法。
• Antihypertensive thienopyridines
  申请人：The Boots Company PLC

  公开号：US04710506A1

  公开（公告）日：1987-12-01

  Novel thienopyridones with antihypertensive activity have the formula I, ##STR1## wherein the ring A represents an optionally substituted thiophene ring; m is 0 or 1; n is 0, 1 or 2; R is lower alkyl and R.sub.1 is lower alkyl. The fused thieno-ring may carry one or two substituents. Formula I encompasses thieno[3,2-b]pyridones, thieno[3,4-b]pyridones and thieno[2,3-b]pyridones. Processes for preparing the novel thienopyridones and pharmaceutical compositions containing them are described. Pharmaceutically acceptable acid addition salts of the compounds of formula I are also described. The thienopyridones of formula I are antihypertensive agents and are also indicated for use in treating heart failure and ischaemic heart disease.

  新型具有降压活性的噻吩吡啶酮具有以下式I，其中环A代表可选择地取代的噻吩环；m为0或1；n为0、1或2；R为低碳基，R.sub.1为低碳基。融合的噻吩环可以携带一个或两个取代基。式I包括噻吩[3,2-b]吡啶酮，噻吩[3,4-b]吡啶酮和噻吩[2,3-b]吡啶酮。描述了制备新型噻吩吡啶酮和含有它们的药物组合物的方法。还描述了式I化合物的药用可接受的酸盐。式I的噻吩吡啶酮是降压剂，也适用于治疗心力衰竭和缺血性心脏病。
• PTP1B inhibitors
  申请人：Lee Jinbo

  公开号：US20080004325A1

  公开（公告）日：2008-01-03

  This invention relates to modulating (e.g., inhibiting) protein tyrosine phosphatase 1b (PTP1b).

  这项发明涉及调节（例如，抑制）蛋白酪氨酸磷酸酶1b（PTP1b）。
• Thieno[3,2-b]pyridine-6-carbonitriles and thieno[2,3-b]pyridine-5-carbonitriles as protein kinase inhibitors
  申请人：Wyeth

  公开号：US20040242883A1

  公开（公告）日：2004-12-02

  This invention provides compounds of Formula (1a)-(1f), II 1 wherein: X, m, n, q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Y, Q, Z, Z′, Z′″, Z″ and J are defined hereinbefore in the specification, which are useful in the treatment of cancer, stroke, myocardial infarction, neuropathic pain, osteoporosis, polycystic kidney disease, autoimmune disease, rheumatoid arthritis, and transplant rejection and process for producing said compounds.

  这项发明提供了式（1a）-（1f）的化合物，II1，其中：X、m、n、q、R1、R2、R3、R4、R5、R6、R7、R8、R9、Y、Q、Z、Z′、Z′″、Z″和J在本说明书中有定义，这些化合物在治疗癌症、中风、心肌梗死、神经病痛、骨质疏松症、多囊性肾脏病、自身免疫疾病、类风湿关节炎和移植排斥方面具有用途，并提供了生产这些化合物的方法。
• Synthesis of Novel N-Substituted 2-(Hetero)arylimino-1,3-thiazolidin-4-ones
  作者：Stéphanie Hesse、Germain Revelant、Gilbert Kirsch

  DOI：10.1055/s-0030-1257867

  日期：2010.10

  The preparation of new N-substituted 2-arylimino-1,3-thiazolidin-4-ones from 5-substituted-3-aminothiophenes using an easy three-step procedure is described. 5-substituted 3-aminothiophenes - isothiocyanates - thioureas - N-substituted 1,3-thiazolidin-4-ones

  描述了使用简单的三步程序从5个取代的3-氨基噻吩制备新的N-取代的2-limlinino-1,3-thiazolidin-4-ones。 5-取代的3-氨基噻吩-异硫氰酸酯-硫脲-N-取代的1,3-噻唑烷-4-酮