5-(carboxymethyl)thiophene-2-carboxylic acid | 23222-34-6

• 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-(carboxymethyl)thiophene-2-carboxylic acid
• 英文别名: 5-Carboxy-2-thiopheneacetic acid
• CAS: 23222-34-6
• 化学式: C₇H₆O₄S
• 分子量: 186.188
• InChiKey: YJOMETCVEOKZKG-UHFFFAOYSA-N

物化性质

• 沸点：
  431.3±35.0 °C(Predicted)
• 密度：
  1.566±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(carboxymethyl)thiophene-2-carboxylic acid 在 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 5-甲氧羰基噻吩-2-乙酸
  参考文献：
  名称：

  [EN] SELECTIVE HDAC6 INHIBITORS
  [FR] INHIBITEURS SÉLECTIFS DE HDAC6

  摘要：

  本发明提供了本文中描述的具有对抑制组蛋白去乙酰化酶活性的羟肟酸，特别是HDAC6的羟肟酸。还考虑了含有有效量所述羟肟酸化合物的药物组合物和使用方法，用于治疗受试者的疾病。在某些实施例中，受试者患有癌症、神经退行性疾病或HIV感染。

  公开号：

  WO2015100363A1
• 作为产物：
  描述：

  5-甲基噻吩-2-羧酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydroxide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 5-(carboxymethyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  [EN] SELECTIVE HDAC6 INHIBITORS
  [FR] INHIBITEURS SÉLECTIFS DE HDAC6

  摘要：

  本发明提供了本文中描述的具有对抑制组蛋白去乙酰化酶活性的羟肟酸，特别是HDAC6的羟肟酸。还考虑了含有有效量所述羟肟酸化合物的药物组合物和使用方法，用于治疗受试者的疾病。在某些实施例中，受试者患有癌症、神经退行性疾病或HIV感染。

  公开号：

  WO2015100363A1

文献信息

• Cobalt-catalysed carbonylation of aryl halides
  作者：M. Foà、F. Francalanci、E. Bencini、A. Gardano

  DOI：10.1016/0022-328x(85)87375-7

  日期：1985.4

  method for carbonylation of aromatic and heteroatomatic halides is described. The catalytic system consists of a combination of alkylcobalt carbonyl complexes, either preformed or made “in situ”, and bases such as alkoxides, NaOH and K2CO3 in aliphatic alcohols. Under these conditions new anionic cobalt complexes are formed which are characterized by a very high reactivity towards aromatic halides. The latter

  描述了一种新的芳族和杂原子卤化物羰基化的方法。催化系统由预先形成或“原位”制备的烷基钴羰基配合物和脂肪族醇中的碱（如醇盐，NaOH和K 2 CO 3）组成。在这些条件下，形成了新的阴离子钴配合物，其特征是对芳族卤化物的反应性非常高。后者在非常温和的条件下以高收率进行羰基化反应。
• Selective HDAC6 inhibitors
  申请人：The Trustees of Columbia University in the City of New York

  公开号：US10626100B2

  公开（公告）日：2020-04-21

  The present invention provides a compound having the structure: wherein R1 is halogen, —NR5R6, —NR5—C(═O)—R6, —NH—C(═O)—OR7, —OR7, —NO2, —CN, —SR7, —SO2R7, —CO2R7, CF3, —SOR7, —POR7, —C(═S)R7, —C(═O)—NR5R6, —CH2—C(═O)—NR5R6, —C(═NR5)R6, —P(═O)(OR5)(OR6), —P(OR5)(OR6), —C(═S)R7, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, aryl, heteroaryl, or heterocyclyl, wherein R5, R6, and R7 and are each, independently, H, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, hydroxyalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C1-5 alkyl-aryl, or C1-5 alkyl-NH-aryl; Ar1 is phenyl or thiophene; wherein when Ar1 is phenyl, then R1 is other than —C(═O)—NR5R6, where one of R5 or R6 is phenyl or quinoline and the other of R5 or R6 is hydroxyalkyl, or where one of R5 or R6 is quinoline and the other of R5 or R6 is H; and wherein when Ar1 is phenyl, then R1 is other than —NR5—C(═O)—R6, where one of R5 is H and R6 is quinoline, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有以下结构的化合物： 其中 R1 是卤素，-NR5R6，-NR5-C(═O)-R6，-NH-C(═O)-OR7，-OR7，-NO2，-CN，-SR7，-SO2R7，-CO2R7，-CF3，-SOR7，-POR7，-C(═S)R7，-C(═O)-NR5R6、-CH2-C(═O)-NR5R6、-C(═NR5)R6、-P(═O)(OR5)(OR6)、-P(OR5)(OR6)、-C(═S)R7、C1-5 烷基、C2-5 烯基、C2-5 烷炔基、芳基、杂芳基或杂环基、 其中 R5、R6 和 R7 各自独立地为 H、C1-5 烷基、C2-5 烯基、C2-5 炔基、杂烷基、羟烷基、环烷基、杂环烷基、芳基、杂芳基、C1-5 烷基芳基或 C1-5 烷基-NH-芳基； Ar1 是苯基或噻吩； 其中当 Ar1 是苯基时，R1 不是-C(═O)-NR5R6，其中 R5 或 R6 之一是苯基或喹啉，R5 或 R6 之二是羟烷基，或者 R5 或 R6 之一是喹啉，R5 或 R6 之二是 H；以及 其中当 Ar1 是苯基时，R1 不是-NR5-C(═O)-R6，其中 R5 之一是 H，R6 是喹啉、 或其药学上可接受的盐。
• Analogues of Methotrexate in Rheumatoid Arthritis. 1. Effects of 10-Deazaaminopterin Analogues on Type II Collagen-Induced Arthritis in Mice
  作者：Joseph I. DeGraw、William T. Colwell、Jac Crase、R. Lane Smith、James R. Piper、William R. Waud、Francis M. Sirotnak

  DOI：10.1021/jm9505526

  日期：1997.1.1

  Carbonation of the dianions (LDA) of 5-methylthiophene-2-carboxylic, 2-methylpyridine-5-carboxylic, and 3-methylpyridine-6-carboxylic acids provided the respective carboxy heteroarylacetic acids. The crude diacids were directly esterified in MeOH-HCl to afford the diesters. Alkylation of the sodio anions with ethyl iodide yielded the appropriate a-ethyl diesters. The anions of the various diester substrates were then alkylated by 2,4-diamino-6-(bromomethyl)-pteridine followed by ester saponification at room temperature to afford the respective 2,4-diamino-4-deoxy-10-carboxy-10-deazapteroic acids. The 10-carboxyl group was readily decarboxylated by heating in DMSO at temperatures of 110-135 degrees C to give the diamino 10-deaza heteropteroic acid intermediates. Coupling with diethyl L-glutamate followed by ester hydrolysis afforded the target aminopterins. The analogues were evaluated for antiinflammatory effect in the mouse type II collagen model. The thiophene analogue of 10-ethyl-10-deazaaminopterin was found to be an effective inhibitor in terms of reduced visual evidence of inflammation and swelling as determined by caliper measurement.
• SELECTIVE HDAC6 INHIBITORS
  申请人：Breslow Ronald

  公开号：US20160347732A1

  公开（公告）日：2016-12-01

  The present invention provides a compound having the structure: wherein R 1 is halogen, —NR 5 R 6 , —NR 5 —C(═O)—R 6 , —NH—C(═O)—OR 7 , —OR 7 , —NO 2 , —CN, —SR 7 , —SO 2 R 7 , —CO 2 R 7 , CF 3 , —SOR 7 , —POR 7 , —C(═S)R 7 , —C(═O)—NR 5 R 6 , —CH 2 —C(═O)—NR 5 R 6 , —C(═NR 5 ) R 6 , —P(═O)(OR 5 )(OR 6 ), —P(OR 5 )(OR 6 ), —C(═S)C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, aryl, heteroaryl, or heterocyclyl, wherein R 5 , R 6 , and R7 and are each, independently, H, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, heteroalkyl, hydroxyalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1-5 alkyl-aryl, or C 1-5 alkyl-NH-aryl; Ar 1 is phenyl or thiophene; wherein when Ar 1 is phenyl, then R 1 is other than —O(═O)—NR 5 R 6 , where one of R 5 or R 6 is phenyl or quinoline and the other of R 5 or R 6 is hydroxyalkyl, or where one of R 5 or R 6 is quinoline and the other of R 5 or R 6 is H; and wherein when Ar 1 is phenyl, then R 1 is other than —NR 5 —C(═O)—R 6 , where one of R 5 is H and R 6 is quinoline, or a pharmaceutically acceptable salt thereof.
• US5536724A
  申请人：——

  公开号：US5536724A

  公开（公告）日：1996-07-16