4-(thiophen-2-yl)-2-hydroxy-4-oxobut-2-enoic acid | 488111-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(thiophen-2-yl)-2-hydroxy-4-oxobut-2-enoic acid
• 英文别名: 2-hydroxy-4-(thiophen-2-yl)-4-oxobut-2-enoic acid；2-Hydroxy-4-oxo-4-(thien-2-yl)but-2-enoic acid；2-hydroxy-4-oxo-4-thiophen-2-ylbut-2-enoic acid
• CAS: 488111-17-7
• 化学式: C₈H₆O₄S
• 分子量: 198.199
• InChiKey: HTBXLUKKKPUQOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-(thiophen-2-yl)-2-hydroxy-4-oxobut-2-enoic acid 在 丙酸酐 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 4-nitro-N′-[2-oxo-5-(thiophen-2-yl)furan-3(2H)-ylidene]benzohydrazide
  参考文献：
  名称：

  Synthesis, anti-inflammatory activity, and acute toxicity of the substituted 2-[2-(4-nitrobenzoyl)hydrazono]-4-oxobutanoates

  摘要：

  DOI：

  10.1007/s11172-023-3973-0
• 作为产物：
  描述：

  ethyl-2-hydroxy-4-(3-thienyl)-4-oxo-2-butenoate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.75h， 以76%的产率得到4-(thiophen-2-yl)-2-hydroxy-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Synthesis and SAR optimization of diketo acid pharmacophore for HCV NS5B polymerase inhibition

  摘要：

  Hepatitis C virus (HCV) NS5B polymerase is a key target for anti-HCV therapeutics development. Here we report the synthesis and biological evaluation of a new series of alpha,gamma-diketo acids (DKAs) as NS5B polymerase inhibitors. We initiated structure-activity relationship (SAR) optimization around the furan moiety of compound 1a [IC50 = 21.8 mu M] to achieve more active NS5B inhibitors. This yielded compound 3a [IC50 = 8.2 mu M] bearing the 5-bromobenzofuran-2-yl moiety, the first promising lead compound of the series. Varying the furan moiety with thiophene, thiazole and indazole moieties resulted in compound 11a [IC50 = 7.5 mu M] bearing 3-methylthiophen-2-yl moiety. Finally replacement of the thiophene ring with a bioisosteric phenyl ring further improved the inhibitory activity as seen in compounds 21a [IC50 = 5.2 mu M] and 24a [IC50 = 2.4 mu M]. Binding mode of compound 24a using glide docking within the active site of NS5B polymerase will form the basis for future SAR optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.028

文献信息

• Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and <i>o</i>-aminothiophenol
  作者：Ekaterina E Stepanova、Maksim V Dmitriev、Andrey N Maslivets

  DOI：10.3762/bjoc.16.193

  日期：——

  Two synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out.

  通过呋喃-2,3-二酮或酰基丙酮酸在碳化二亚胺存在下与邻氨基苯硫酚的反应，我们开发了两种合成融合了 1,4-苯并噻嗪-2-酮分子的烯酰胺酮的方法，这些烯酰胺酮在生物活性、化学传感器和荧光研究方面具有重要意义。目标烯酮与具有药学意义的 2-羟基-2H-1,4-苯并噻嗪-3(4H)-酮一起形成。通过呋喃-2,3-二酮与邻氨基苯硫酚的溶剂切换反应，开发了一种 2-羟基-2H-1,4-苯并噻嗪-3(4H)-酮的选择性合成方法。对新化合物进行了初步的生物检测（抗菌、急性毒性）。
• Synthesis and search for compounds with hemostatic activity in the series of 4-(het)aryl-4-oxobut-2-enoic acid derivatives
  作者：N. A. Pulina、V. Yu. Kozhukhar、A. S. Kuznetsov、A. E. Rubtsov、A. V. Starkova

  DOI：10.1007/s11172-017-1914-5

  日期：2017.8

  ut-2-ene-1,4-diones and 2-[2-(3-R-adamantan-1-yl)-2-oxoethylidene]hydrazinyl}-4-(het)aryl-4-oxobut-2-enoic acids were synthesized and used to obtain water-soluble compounds. Their influence on the blood coagulation system was studied, which revealed compounds with a high hemostatic activity and a low acute toxicity. A relationship between structure and pharmacological effect of the synthesized compounds

  新的4-芳基-2-(4-芳基氨基)-1-(哌嗪-1-基)丁-2-烯-1,4-二酮和2-[2-(3-R-金刚烷-1-基) )-2-oxoethylidene]hydrazinyl}-4-(het)aryl-4-oxobut-2-enoic 酸被合成并用于获得水溶性化合物。研究了它们对凝血系统的影响，揭示了具有高止血活性和低急性毒性的化合物。建立了合成化合物的结构和药理作用之间的关系。
• Synthesis, intramolecular cyclization, and antinociceptive activity of 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids
  作者：I. A. Gorbunova、I. P. Nikonov、R. R. Makhmudov、D. A. Shipilovskikh、P. S. Silaichev、S. A. Shipilovskikh

  DOI：10.1007/s11172-023-4023-7

  日期：2023.9

  Synthesis and intramolecular cyclization of the substituted 4-(het)aryl-2-[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids were studied. It was found that the synthesized compounds underwent the intramolecular cyclization to give the substituted ethyl 4-(4-chlorophenyl)-2-[2-oxofuran-3(2H)-ylidene]-amino}thiophene-3-carboxylates. Evaluation of the biological activity

  研究了取代的4-(杂)芳基-2-[4-(4-氯苯基)-3-(乙氧基羰基)噻吩-2-基]氨基}-4-氧代丁-2-烯酸的合成和分子内环化。结果发现，合成的化合物经过分子内环化，得到取代的4-(4-氯苯基)-2-[2-氧代呋喃-3(2H)-亚基]-氨基}噻吩-3-甲酸乙酯。合成化合物的生物活性评估表明它们具有显着的抗伤害活性和低毒性。
• Synthesis and anti-inflammatory activity of N-arylamides of 4-aryl- and 4-(thiophen-2-yl)-2-[2-(furan-2-carbonyl)hydrazono]-4-oxobutanoic acids
  作者：S. N. Igidov、A. Yu. Turyshev、S. V. Chashchina、D. A. Shipilovskikh、I. N. Chernov、O. V. Zvereva、P. S. Silaichev、N. M. Igidov、S. A. Shipilovskikh

  DOI：10.1007/s11172-023-4021-9

  日期：2023.9