2-phenylbenzofuran-3-carboxylic acid | 6774-47-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-phenylbenzofuran-3-carboxylic acid
• 英文别名: 2-Phenyl-benzofuran-3-carbonsaeure；2-phenyl-1-benzofuran-3-carboxylic acid
• CAS: 6774-47-6
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: GUUYLMTUBSOVGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylbenzofuran-3-carboxylic acid 在 吡啶 、 氯化亚砜 、 苯 作用下， 生成 2-diazo-1-(2-phenyl-benzofuran-3-yl)-ethanone
  参考文献：
  名称：

  Chatterjea, Journal of the Indian Chemical Society, 1956, vol. 33, p. 447,451

  摘要：

  DOI：
• 作为产物：
  描述：

  邻溴苯乙酸 在 1,10-菲罗啉 、 氧气 、 copper diacetate 、 乙酸酐 、 三乙胺 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 2-phenylbenzofuran-3-carboxylic acid
  参考文献：
  名称：

  Cu-Catalyzed Consecutive Hydroxylation and Aerobic Oxidative Cycloetherification under Microwave Conditions: Entry to 2-Arylbenzofuran-3-carboxylic Acids

  摘要：

  A convenient one-pot synthesis of 2-arylbenzofuran-3-carboxylic acids from (E)-2-(2-bromophenyl)-3-phenylacrylic acids via Cu-catalyzed consecutive hydroxylation and aerobic oxidative cycloetherification under microwave conditions has been developed. This protocol employed the reagent combination of Cu(OAc)(2), 1,10-phen, and KOH in DMSO/H2O (1:1), all of which are cost-effective, readily available, and easily removable from the reaction mixture. Utilizing this synthetic protocol, various 2-arylbenzofuran-3-carboxylic acids as well as the natural product moracin M have been synthesized in satisfactory yields under mild conditions.

  DOI：

  10.1021/jo502802k

文献信息

• Synthesis of aryl α-keto esters via the rearrangement of aryl cyanohydrin carbonate esters
  作者：Nopporn Thasana、Vilailak Prachyawarakorn、Sopchok Tontoolarug、Somsak Ruchirawat

  DOI：10.1016/s0040-4039(02)02725-9

  日期：2003.1

  A facile synthesis of aryl α-keto esters is reported involving the rearrangement of aryl cyanohydrin carbonate esters induced by the α-carbanion to the nitrile group generated by LDA. However, under similar conditions, an o-benzyloxycyanohydrin carbonate ester rearranged via a domino reaction leading to 2-phenylbenzofuran-3-carboxylic acid.

  据报道，一种简便的芳基α-酮酯合成方法涉及将由α-碳负离子诱导的芳基氰醇碳酸酯重排至LDA生成的腈基。然而，在相似的条件下，邻-苄氧基氰醇碳酸酯经多米诺反应重排，生成2-苯基苯并呋喃-3-羧酸。
• 一种2-芳基苯并呋喃-3-甲酸类化合物的制备方 法
  申请人：中科院广州化学有限公司

  公开号：CN104478837B

  公开（公告）日：2016-06-29

  本发明属于化学合成技术领域，公开了一种2-芳基苯并呋喃-3-甲酸类化合物的制备方法。该制备方法是将含邻溴苯乙酸结构的化合物、含苯甲醛结构的化合物、有机溶剂和碱A放入反应器中，搅拌混合均匀，在90～130℃的温度下反应5～7h反应完毕，将反应产物分离处理，得到2-(2-溴苯基)-3-苯基丙烯酸类化合物；然后将其溶于溶剂中，在催化剂、配体、碱B的存在下，搅拌，微波加热至100～130℃反应0.5h～1.5h反应完毕，将反应产物分离纯化处理，得到2-芳基苯并呋喃-3-甲酸类化合物。本发明方法新颖、简捷，对底物适应范围广，反应原料及所得产物取代基种类及取代位置具有多样性。
• Calpain modulators and therapeutic uses thereof
  申请人：Blade Therapeutics, Inc.

  公开号：US10934261B2

  公开（公告）日：2021-03-02

  Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

  本文公开了小分子钙蛋白酶调节剂组合物、药物组合物及其用途和制备方法。
• [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF<br/>[FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BLADE THERAPEUTICS INC

  公开号：WO2018064119A8

  公开（公告）日：2019-04-25
• Encoded Library Technology as a Source of Hits for the Discovery and Lead Optimization of a Potent and Selective Class of Bactericidal Direct Inhibitors of <i>Mycobacterium tuberculosis</i> InhA
  作者：Lourdes Encinas、Heather O’Keefe、Margarete Neu、Modesto J. Remuiñán、Amish M. Patel、Ana Guardia、Christopher P. Davie、Natalia Pérez-Macías、Hongfang Yang、Maire A. Convery、Jeff A. Messer、Esther Pérez-Herrán、Paolo A. Centrella、Daniel Álvarez-Gómez、Matthew A. Clark、Sophie Huss、Gary K. O’Donovan、Fátima Ortega-Muro、William McDowell、Pablo Castañeda、Christopher C. Arico-Muendel、Stane Pajk、Joaquín Rullás、Iñigo Angulo-Barturen、Emilio Álvarez-Ruíz、Alfonso Mendoza-Losana、Lluís Ballell Pages、Julia Castro-Pichel、Ghotas Evindar

  DOI：10.1021/jm401326j

  日期：2014.2.27

  Tuberculosis (TB) is one of the world's oldest and deadliest diseases, killing a person every 20 s. InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis, is the target of the frontline antitubercular drug isoniazid (INH). Compounds that directly target InhA and do not require activation by mycobacterial catalase peroxidase KatG are promising candidates for treating infections caused by INH resistant strains. The application of the encoded library technology (ELT) to the discovery of direct InhA inhibitors yielded compound 7 endowed with good enzymatic potency but with low antitubercular potency. This work reports the hit identification, the selected strategy for potency optimization, the structure-activity relationships of a hundred analogues synthesized, and the results of the in vivo efficacy studies performed with the lead compound 65.