5-乙基噻吩-3-羧酸 | 19156-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-乙基噻吩-3-羧酸
• 英文名称: 5-ethyl-thiophene-3-carboxylic acid
• 英文别名: 5-Aethyl-thiophen-3-carbonsaeure；5-Ethylthiophene-3-carboxylic acid
• CAS: 19156-51-5
• 化学式: C₇H₈O₂S
• mdl: MFCD03419849
• 分子量: 156.205
• InChiKey: WGPALAIKGVKNGT-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  286.1±28.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-乙基噻吩-3-羧酸 在 potassium permanganate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 氯化亚砜 、 水 、 碳酸氢钠 、 sodium carbonate 、 magnesium sulfate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 苯 为溶剂， 生成 2-Amino-5-(5-ethylthiophen-3-yl)-3-methyl-5-(3-pyrimidin-5-ylphenyl)imidazol-4-one
  参考文献：
  名称：

  New pyrazolyl and thienyl aminohydantoins as potent BACE1 inhibitors: Exploring the S2′ region

  摘要：

  The proteolytic enzyme beta-secretase (BACE1) plays a central role in the synthesis of the pathogenic beta-amyloid in Alzheimer's disease. SAR studies of the S2' region of the BACE1 ligand binding pocket with pyrazolyl and thienyl P2' side chains are reported. These analogs exhibit low nanomolar potency for BACE1, and demonstrate >50-to 100-fold selectivity for the structurally related aspartyl proteases BACE2 and cathepsin D. Small groups attached at the nitrogen of the P2' pyrazolyl moiety, together with the P3 pyrimidine nucleus projecting into the S3 region of the binding pocket, are critical components to ligand's potency and selectivity. P2' thiophene side chain analogs are highly potent BACE1 inhibitors with excellent selectivity against cathepsin D, but only modest selectivity against BACE2. The cell-based activity of these new analogs tracked well with their increased molecular binding with EC50 values of 0.07-0.2 mu M in the ELISA assay for the most potent analogs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.057
• 作为产物：
  描述：

  噻吩-3-甲酸乙酯 在 二硫化碳 、 sodium hydroxide 、 三氯化铝 、 乙二醇 作用下， 生成 5-乙基噻吩-3-羧酸
  参考文献：
  名称：

  Otsuji et al., Nippon Kagaku Zasshi, 1959, vol. 80, p. 1021,1023

  摘要：

  DOI：

文献信息

• Multicyclic bis-amide MMP inhibitors
  申请人：Powers Timothy

  公开号：US20060173183A1

  公开（公告）日：2006-08-03

  The present invention relates generally to bis-amide group containing pharmaceutical agents, and in particular, to multicyclic bis-amide MMP-13 inhibitor compounds. More particularly, the present invention provides a new class of MMP-13 inhibiting compounds, containing a pyrimidinyl bis-amide group in combination with a heterocyclic moiety, that exhibit an increased potency and solubility in relation to currently known bis-amide group containing MMP-13 inhibitors.

  本发明总体涉及含有双酰胺基团的药物制剂，特别是多环双酰胺MMP-13抑制剂化合物。更具体地，本发明提供了一类新型的MMP-13抑制化合物，它们含有与杂环部分结合的嘧啶基双酰胺基团，与目前已知含双酰胺基团的MMP-13抑制剂相比，显示出增加的活性和溶解度。
• [EN] AMIDO-THIOPHENE COMPOUNDS AND THEIR USE AS 11-BETA-HSD1 INHIBITORS<br/>[FR] COMPOSÉS AMIDO-THIOPHÈNE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE 11-BÊTA-HSD1
  申请人：UNIV EDINBURGH

  公开号：WO2009074789A1

  公开（公告）日：2009-06-18

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain amido-thiophene compounds that, inter alia, inhibit 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit 11β-hydroxysteroid dehydrogenase type 1; to treat disorders that are ameliorated by the inhibition of 11β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes disorders such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS disorders such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc. Formula (I).

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些酰胺噻吩化合物，其中包括抑制11β-羟基类固醇脱氢酶1（11β-HSD1）。本发明还涉及包含这些化合物的药物组合物，以及利用这些化合物和组合物在体外和体内抑制11β-羟基类固醇脱氢酶1；治疗通过抑制11β-羟基类固醇脱氢酶1而得到改善的疾病；治疗代谢综合征，其中包括2型糖尿病和肥胖等疾病，以及相关疾病，包括胰岛素抵抗、高血压、脂质紊乱和心血管疾病，如缺血性（冠状）心脏病；治疗中枢神经系统疾病，如轻度认知障碍和早期痴呆，包括阿尔茨海默病等。公式（I）。
• Substituted bis-amide metalloprotease inhibitors
  申请人：Sucholeiki Irving

  公开号：US20070155739A1

  公开（公告）日：2007-07-05

  This invention relates to substituted bis-amide pyrimidine compounds of Formula (I), which are useful for the treatment of metalloprotease mediated diseases, in particular MMP-13 related diseases.

  这项发明涉及Formula (I)的取代双酰胺嘧啶化合物，这些化合物对于治疗金属蛋白酶介导的疾病，特别是MMP-13相关疾病是有用的。
• ISOSERINE DERIVATIVES FOR USE AS COAGULATION FACTOR IXA INHIBITORS
  申请人：STEINHAGEN Henning

  公开号：US20090233949A1

  公开（公告）日：2009-09-17

  The invention relates to the compounds of formula (I) having antithrombotic activity which especially inhibit blood clotting factor IXa, to methods for producing the same and to the use thereof as drugs.

  本发明涉及具有抗血栓作用的化合物(I)的公式，特别是抑制血凝因子IXa的化合物，以及其制备方法和作为药物的用途。
• NOVEL INHIBITORS OF INSULIN-LIKE GROWTH FACTOR 2 MRNA BINDING PROTEINS
  申请人：Martin-Luther-Universität Halle-Wittenberg

  公开号：EP4008717A3

  公开（公告）日：2022-09-07

  The presented invention provides compounds of formula (I) and (VIII), or a pharmaceutically acceptable salt, solvate or polymorph thereof, including all tautomers and stereoisomers thereof, wherein R1, R2, W, X, Y, Z, m, n and o are as defined herein. Said compounds of formula (I) are inhibitors of insulin-like growth factor 2 mRNA binding proteins (IGF2BP). Provided are novel inhibitors of IGF2BPs and processes for manufacturing the same. Efficacy of the new compounds is shown in solid cancer models.

  所提供的发明提供了式（I）和（VIII）的化合物，或其药学上可接受的盐、溶剂或多晶形式，包括其所有互变异构体和立体异构体，其中R1，R2，W，X，Y，Z，m，n和o如本文所定义。式（I）的这些化合物是胰岛素样生长因子2 mRNA结合蛋白（IGF2BP）的抑制剂。提供了IGF2BP的新型抑制剂和其制造过程。新化合物的功效在实体癌模型中得到了证明。