3-(aminomethyl)thiophene hydrochloride

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(aminomethyl)thiophene hydrochloride
• 英文别名: Thiophen-3-ylmethyl-ammonium, chloride；thiophen-3-ylmethylazanium;chloride
• 化学式: C₅H₇NS*ClH
• mdl: MFCD03306024
• 分子量: 149.644
• InChiKey: CUWJIHMNGIOCCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(甲氧基羰基)苯基异氰酸酯 、 3-(aminomethyl)thiophene hydrochloride 在 sodium hydride 作用下， 生成 2-[(Thiophen-3-ylmethyl)-amino]-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  2-Amino-4H-3,1-benzoxazin-4-ones as Inhibitors of C1r Serine Protease

  摘要：

  A series of 2-amino-4H-3,1-benzoxazin-4-ones have been synthesized and evaluated as inhibitors of the complement enzyme C1r. C1r is a serine protease at the beginning of the complement cascade, and complement activation by beta-amyloid may represent a major contributing pathway to the neuropathology of Alzheimer's disease. Compounds such as 7-chloro-2-[(2-iodophenyl)amino]benz[d][1,3]oxazin-4-one (32) and 7-methyl-2-[(2-iodophenyl)amino]benz[d] 4-one (37) show improved potency compared to the reference compound FUT-175. Many of these active compounds also possess increased selectivity for C1r compared to trypsin and enhanced hydrolytic stability relative to 2-(2-iodophenyl)-4H-3,1-benzoxazin-4-one (1).

  DOI：

  10.1021/jm970394d

文献信息

• Discovery of Biased Mu‐Opioid Receptor Agonists for the Treatment of Pain
  作者：Mengjun Ma、Xiang Li、Kun Tong、Jingchao Cheng、Zixing Yu、Fengxia Ren、Bohua Zhong、Weiguo Shi

  DOI：10.1002/cmdc.201900575

  日期：2020.1.7

  agonists have been developed as promising new potent analgesic drugs with fewer adverse side effects than standard MOR agonists. PZM21 represents a unique chemotype unrelated to known opioids, which makes it a desirable lead for modification to find analgesics with new chemical entities. In the present study, we synthesized and tested novel PZM21 derivatives as potent biased MOR agonists by introducing a benzodioxolane

  G蛋白偏向型阿片受体（MOR）激动剂已被开发为有前景的新型有效止痛药，与标准MOR激动剂相比，副作用更少。PZM21代表与已知阿片类药物无关的独特化学型，这使其成为进行修饰以寻找具有新化学实体的止痛药的理想先导。在本研究中，我们通过引入苯并二氧戊环基团取代PZM21的羟基苯，合成并测试了新型PZM21衍生物作为强效的MOR激动剂。与PZM21相比，新化合物在体内显示出更强的镇痛活性，并在体外对G蛋白信号传导产生更大的偏见。这些结果表明，苯并二氧戊环基团对于维持偏倚是必不可少的。化合物7 i（（S）-1-（3-（苯并[d] [1，
• Polymerizable thiophene monomers
  申请人：Cookson Group plc

  公开号：US04992559A1

  公开（公告）日：1991-02-12

  Thiophene derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are certain specified substituent groups can be homopolymerized or copolymerized to form polymers which are electroconductive. These polymers find many uses, for example, as EMI/RF shielding materials, in electrochromic display systems, as antistatics, as ion and pH sensors, as battery electrode materials etc.

  Thiophene衍生物的化学式为##STR1##其中R.sup.1和R.sup.2是特定的指定取代基团，可以进行均聚或共聚反应形成具有电导性的聚合物。这些聚合物有许多用途，例如作为EMI/RF屏蔽材料，在电致色变显示系统中，作为防静电材料，作为离子和pH传感器，作为电池电极材料等。
• Benzisoxazolyl-,pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists
  申请人：Shutske M. Gregory

  公开号：US20050107377A1

  公开（公告）日：2005-05-19

  The compounds are of the class of benzisoxazolyl-, pyridoisoxazolyl- and benzthienyl-phenoxy derivatives, useful as D 4 antagonists. Said compounds are useful for the treatment of medical conditions mediated by inhibition of D 4 receptor. These conditions comprise, for example, Attention Deficit Hyperactivity Disorder, Obsessive-Compulsive Disorder, Psychoses, Substance Abuse, Substance Dependence, Parkinson's Disease, Parkinsonism, Tardive Diskinesia, Gilles de la Tourette Syndrome, Conduct Disorder, and Oppositional Defiant Disorder. A further aspect of the invention is to provide a pharmaceutical composition, intermediates, and a method of making said class of compounds.

  这些化合物属于苯并异噁唑基、吡啶异噁唑基和苯并噻吩基苯氧基衍生物类，可用作D4拮抗剂。这些化合物可用于治疗由D4受体抑制引起的医疗状况，例如注意力缺陷多动障碍、强迫症、精神病、物质滥用、物质依赖、帕金森病、帕金森综合症、迟发性运动障碍、图雷特综合症、行为障碍和反抗性障碍等。本发明的另一个方面是提供一种制药组合物、中间体和制备该类化合物的方法。
• THIENOISOXAZOLYL-AND THIENYLPYRRAZOLYL PHENOXY SUBSTITUTED PROPYL DERIVATIVES USEFUL AS D4 ANTAGONISTS
  申请人：Fink M. David

  公开号：US20070004695A1

  公开（公告）日：2007-01-04

  The compounds are of the class thienoisoxazolyl- and thienylpyrrazolyl-phenoxy substituted propyl derivatives, useful as D 4 antagonists. Said compounds are useful for the treatment of medical conditions mediated by inhibition of D 4 receptor. These conditions comprise, for example, Attention Deficit Hyperactivity Disorder, Obsessive-Compulsive Disorder, Psychoses, Substance Abuse, Substance Dependence, Parkinson's Disease, Parkinsonism, Tardive Diskinesia, Gilles de la Tourette Syndrome, Conduct Disorder, and Oppositional Defiant Disorder. A further aspect of the invention is to provide a pharmaceutical composition, intermediates, and a method of making said class of compounds.

  这些化合物属于类别为噻唑异噁唑基和噻吩吡唑基苯氧基取代的丙基衍生物，可用作D4受体拮抗剂。这些化合物可用于治疗通过抑制D4受体介导的医疗状况。这些状况包括例如注意力缺陷多动障碍、强迫症、精神病、物质滥用、物质依赖、帕金森病、帕金森综合症、迟发性运动障碍、吉尔·德·拉·图雷特综合症、行为障碍和反抗行为障碍。发明的另一个方面是提供一种制药组合物、中间体和制备该类化合物的方法。
• Discovery and Structural Explorations of G‐Protein Biased μ‐Opioid Receptor Agonists
  作者：Xiang Li、Yanhao Guo、Jing Li、Zixing Yu、Jingchao Cheng、Fengxia Ren、Hongxin Jia、Yatong Zhang、Shiqiang Cui、Tao Zhang、Weiguo Shi

  DOI：10.1002/cmdc.202200416

  日期：2022.12.16

  We report two classes of PZM21 derivatives containing benzothiophene or biphenyl groups as biased μ-opioid receptor (μOR) agonists. The new compound SWG-LX-33 showed potent μOR agonist activity and produced μOR-dependent analgesia. SWG-LX-33 does not activate the β-arrestin-2 signalling pathway in vitro even at high concentrations.

  我们报告了两类含有苯并噻吩或联苯基团的 PZM21 衍生物作为偏向 μ-阿片受体 (μOR) 激动剂。新化合物 SWG-LX-33 显示出有效的 μOR 激动剂活性并产生 μOR 依赖性镇痛。即使在高浓度下，SWG-LX-33 也不会在体外激活 β-arrestin-2 信号通路。