4-(methoxycarbonyl)thiophene-3-carboxylic acid | 4282-30-8

• 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: 4-(methoxycarbonyl)thiophene-3-carboxylic acid
• 英文别名: 4-methoxycarbonylthiophene-3-carboxylic acid
• CAS: 4282-30-8
• 化学式: C₇H₆O₄S
• mdl: MFCD20639325
• 分子量: 186.188
• InChiKey: CLHYGZGCRAMYSW-UHFFFAOYSA-N

物化性质

• 熔点：
  115.5-116.5 °C
• 沸点：
  344.8±27.0 °C(Predicted)
• 密度：
  1.439±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：
  0.142
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(methoxycarbonyl)thiophene-3-carboxylic acid 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 3,4-噻吩二羧酸
  参考文献：
  名称：

  Benko, Jan; Vollarova, Olga, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 6, p. 1268 - 1273

  摘要：

  DOI：
• 作为产物：
  描述：

  噻吩-3,4-二羧酸二甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以87%的产率得到4-(methoxycarbonyl)thiophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase

  摘要：

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.009

文献信息

• Synthesis of 2-oxoglutarate derivatives and their evaluation as cosubstrates and inhibitors of human aspartate/asparagine-β-hydroxylase
  作者：Lennart Brewitz、Yu Nakashima、Christopher J. Schofield

  DOI：10.1039/d0sc04301j

  日期：——

  natural product present in human nutrition, was the most efficient alternative cosubstrate identified; crystallographic analyses reveal the binding mode of (R)-3-methyl-2OG and other 2OG derivatives to AspH and inform on the balance between turnover and inhibition. The results will enable the use of 2OG derivatives as mechanistic probes for other 2OG utilizing enzymes and suggest 2-oxoacids other than

  2-氧戊二酸 (2OG) 参与生物过程，包括 2OG 加氧酶催化的氧化反应，它是 2OG 加氧酶的共底物。真核生物 2OG 加氧酶在胶原蛋白生物合成、脂质代谢、DNA/RNA 修饰、转录调节和缺氧反应中发挥作用。天冬氨酸/天冬酰胺-β-羟化酶 (AspH) 是一种人 2OG 加氧酶，催化内质网表皮生长因子样结构域 (EGFD) 中 Asp/Asn 残基的翻译后羟基化。 AspH 具有化学意义，因为它的 Fe( II ) 辅因子由两个而不是典型的三个残基络合。 AspH 在缺氧情况下上调，是癌细胞表面的预后标志物。我们描述了关于其天然 2OG 共底物的衍生物如何调节 AspH 活性的研究。据报道，通过氰基硫内鎓中间体进行 C3-和/或 C4-取代的 2OG 衍生物的有效合成。对 >30 2OG 衍生物进行的基于质谱的 AspH 测定表明，某些衍生物通过与 2OG 竞争来有效抑制 AspH，这
• [EN] ALDOSE REDUCTASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'ALDOSE RÉDUCTASE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：UNIV COLUMBIA

  公开号：WO2017223179A1

  公开（公告）日：2017-12-28

  The present disclosure relates to novel compounds and pharmaceutical compositions thereof, and methods for promoting healthy aging of skin, the treatment of skin disorders, the treatment of cardiovascular disorders, the treatment of renal disorders, the treatment of angiogenesis disorders, such as cancer, treatment of tissue damage, such as non-cardiac tissue damage, the treatment of evolving myocardial infarction, the treatment of ischemic injury, and the treatment of various other disorders, such as complications arising from diabetes with the compounds and compositions of the invention. Other disorders can include, but are not limited to, atherosclerosis, coronary artery disease, diabetic nephropathy, diabetic neuropathy, diabetic retinopathy, diabetic cardiomyopathy, infections of the skin, peripheral vascular disease, stroke, asthma, and the like.

  本公开涉及新颖化合物及其制药组合物，以及促进皮肤健康老化、治疗皮肤疾病、心血管疾病、肾脏疾病、血管生成障碍（如癌症）、组织损伤（如非心脏组织损伤）、急性心肌梗死、缺血性损伤以及其他各种疾病（例如由糖尿病引起的并发症）的治疗方法，所述的化合物和组合物。其他疾病可以包括但不限于动脉粥样硬化、冠状动脉疾病、糖尿病肾病、糖尿病神经病、糖尿病视网膜病变、糖尿病心肌病、皮肤感染、周围血管疾病、中风、哮喘等。
• Aldose reductase inhibitors and methods of use thereof
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US10150779B2

  公开（公告）日：2018-12-11

  The present disclosure relates to novel compounds and pharmaceutical compositions thereof, and methods for promoting healthy aging of skin, the treatment of skin disorders, the treatment of cardiovascular disorders, the treatment of renal disorders, the treatment of angiogenesis disorders, such as cancer, treatment of tissue damage, such as non-cardiac tissue damage, the treatment of evolving myocardial infarction, the treatment of ischemic injury, and the treatment of various other disorders, such as complications arising from diabetes with the compounds and compositions of the invention. Other disorders can include, but are not limited to, atherosclerosis, coronary artery disease, diabetic nephropathy, diabetic neuropathy, diabetic retinopathy, diabetic cardiomyopathy, infections of the skin, peripheral vascular disease, stroke, asthma, and the like.

  本公开涉及新型化合物及其药物组合物，以及促进皮肤健康老化、治疗皮肤疾病、治疗心血管疾病、治疗肾脏疾病、治疗血管生成疾病（如癌症）、治疗组织损伤（如非心脏组织损伤）、治疗演变性心肌梗塞、治疗缺血性损伤，以及用本发明化合物和组合物治疗各种其他疾病（如糖尿病引起的并发症）的方法。其他疾病包括但不限于动脉粥样硬化、冠状动脉疾病、糖尿病肾病、糖尿病神经病变、糖尿病视网膜病变、糖尿病心肌病、皮肤感染、外周血管疾病、中风、哮喘等。
• Kaluz, Stefan; Toma, Stefan, Gazzetta Chimica Italiana, 1987, vol. 117, # 9, p. 529 - 532
  作者：Kaluz, Stefan、Toma, Stefan

  DOI：——

  日期：——
• KALUZ, STEFAN;TOMA, STEFAN, GAZZ. CHIM. ITAL., 117,(1987) N 9, 529-531
  作者：KALUZ, STEFAN、TOMA, STEFAN

  DOI：——

  日期：——