(E)-4-(3-(2,5-dimethoxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid | 1352237-81-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-4-(3-(2,5-dimethoxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid
• 英文别名: 4-[(1e)-3-(2,5-Dimethoxyphenyl)-3-oxoprop-1-en-1-yl]benzoic acid；4-[(E)-3-(2,5-dimethoxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 1352237-81-0
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: BSAROFRSKAPDHU-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 、 对醛基苯甲酸 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以64 %的产率得到(E)-4-(3-(2,5-dimethoxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid
  参考文献：
  名称：

  作为黄嘌呤氧化酶抑制剂的羧化查尔酮和相关黄酮类化合物

  摘要：

  合成了羧基查尔酮和其他相关黄酮类化合物，并作为黄嘌呤氧化酶抑制剂进行了评估，黄嘌呤氧化酶是用于治疗高尿酸血症、痛风和其他疾病的合成药物和草药的已知靶点。A 环上带有羟基、甲氧基和乙氧基的 4-羧化查耳酮被发现具有体外抑制活性，IC 50值在 0.057 至 0.26 μM 范围内，比别嘌呤醇强 10-60 倍。具有 Δ 3,9-同型异黄酮和黄酮支架的结构相关的羧酸也显示出针对黄嘌呤氧化酶的微摩尔活性。同时，二氢查尔酮和Δ2,3-高异黄酮羧酸及其氧杂-类似物的抑制剂效果低两个数量级以上。动力学和分子对接研究表明，羧基查尔酮和Δ3,9-同异黄酮类化合物是混合型抑制剂，它们大多与占据黄嘌呤氧化酶活性位点的游离酶结合。 图形概要

  DOI：

  10.1007/s00044-023-03109-8

文献信息

• SYNTHESIS AND BIOLOGICAL EVALUATION OF 2',5'-DIMETHOXYCHALCONE DERIVATIVES AS MICROTUBULE-TARGETED ANTICANCER AGENTS
  申请人：Lin Chun-Nan

  公开号：US20110306775A1

  公开（公告）日：2011-12-15

  Disclosed are a serious of 2′,5′-dimethoxychalcone derivatives for treating cancer, wherein 2,5-dimethoxyacetophenone and methyl 4-formylbenzoate are condensed to form 4-carboxyl-2′,5′-dimethoxychalcone (compound 1), which is further reacted with alkyl halides or amines to synthesize the chalcone derivatives of compounds 2-17. In addition, 2,5-dimethoxyacetophenone is reacted with 5-formyl-2-thiophenecarboxylic acid to form compound 18 (3-(3-thiophene)carboxyl-1-(2,5-dimethoxyphenyl)prop-2-en-1-one). The synthesized 2′,5′-dimethoxychalcone derivatives can be acted as microtubule-targeted tubulin-polymerizing agents.

  揭示了一系列治疗癌症的2′,5′-二甲氧基茴香酮衍生物，其中2,5-二甲氧基苯乙酮和甲基4-甲醛苯甲酸酯缩合形成4-羧基-2′,5′-二甲氧基茴香酮（化合物1），进一步与烷基卤化物或胺反应以合成化合物2-17的茴香酮衍生物。此外，2,5-二甲氧基苯乙酮与5-甲醛-2-噻吩羧酸反应形成化合物18（3-（3-噻吩）羧基-1-（2,5-二甲氧基苯基）丙-2-烯-1-酮）。合成的2′,5′-二甲氧基茴香酮衍生物可作为微管靶向的微管蛋白聚合剂。
• A chalcone derivative binds a putative allosteric site of YopH: Inhibition of a virulence factor of Yersinia
  作者：Ana C.A. de Souza、Mattia Mori、Larissa Sens、Ruth F. Rocha、Tiago Tizziani、Luiz F.S. de Souza、Louise Domeneghini Chiaradia-Delatorre、Maurizio Botta、Ricardo J. Nunes、Hernán Terenzi、Angela C.O. Menegatti

  DOI：10.1016/j.bmcl.2020.127350

  日期：2020.8

  Identification of allosteric inhibitors of PTPs has attracted great interest as a new strategy to overcome the challenge of discover potent and selective molecules for therapeutic intervention. YopH is a virulence factor of the genus Yersinia , validated as an antimicrobial target. The finding of a second substrate binding site in YopH has revealed a putative allosteric site that could be further exploited. Novel chalcone compounds that inhibit PTPs activity were designed and synthesized. Compound 3j was the most potent inhibitor, interestingly, with different mechanisms of inhibition for the panel of enzymes evaluated. Further, our results showed that com- pound 3j is an irreversible non-competitive inhibitor of YopH that binds to a site different than the catalytic site, but close to the well-known second binding site of YopH.
• Carboxylated chalcones and related flavonoids as inhibitors of xanthine oxidase
  作者：Oleksandr L. Kobzar、Alona V. Tatarchuk、Galyna P. Mrug、Svitlana P. Bondarenko、Bohdan A. Demydchuk、Mykhaylo S. Frasinyuk、Andriy I. Vovk

  DOI：10.1007/s00044-023-03109-8

  日期：2023.8

  9-homoisoflavonoid and flavone scaffolds also showed micromolar activity towards xanthine oxidase. At the same time, dihydrochalcone and Δ2,3-homoisoflavonoid carboxylic acids as well as their oxa-analogues were more than two orders of magnitude less effective inhibitors. Kinetic and molecular docking studies indicated that the carboxylated chalcones and Δ3,9-homoisoflavonoids are mixed-type inhibitors

  合成了羧基查尔酮和其他相关黄酮类化合物，并作为黄嘌呤氧化酶抑制剂进行了评估，黄嘌呤氧化酶是用于治疗高尿酸血症、痛风和其他疾病的合成药物和草药的已知靶点。A 环上带有羟基、甲氧基和乙氧基的 4-羧化查耳酮被发现具有体外抑制活性，IC 50值在 0.057 至 0.26 μM 范围内，比别嘌呤醇强 10-60 倍。具有 Δ 3,9-同型异黄酮和黄酮支架的结构相关的羧酸也显示出针对黄嘌呤氧化酶的微摩尔活性。同时，二氢查尔酮和Δ2,3-高异黄酮羧酸及其氧杂-类似物的抑制剂效果低两个数量级以上。动力学和分子对接研究表明，羧基查尔酮和Δ3,9-同异黄酮类化合物是混合型抑制剂，它们大多与占据黄嘌呤氧化酶活性位点的游离酶结合。 图形概要