4-(5-methyl-1,3-dioxoisoindolin-2-yl)benzoic acid | 494764-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(5-methyl-1,3-dioxoisoindolin-2-yl)benzoic acid
• 英文别名: 4-(5-Methyl-1,3-dioxoisoindol-2-yl)benzoic acid
• CAS: 494764-55-5
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: HENFOGMTHOCWFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基苯酐 、 对氨基苯甲酸 在 溶剂黄146 作用下， 反应 24.0h， 以91%的产率得到4-(5-methyl-1,3-dioxoisoindolin-2-yl)benzoic acid
  参考文献：
  名称：

  Molecular design, synthesis and biological evaluation of cyclic imides bearing benzenesulfonamide fragment as potential COX-2 inhibitors. Part 2

  摘要：

  A group of cyclic imides (1-10) was designed for evaluation as a selective COX-2 inhibitors and investigated in vivo for their anti-inflammatory activity. Compounds 6a, 6b, 8a, 8b, 9a, 9b, 10a and 10b were proved to be potent COX-2 inhibitors with IC50 range of 0.1-4.0 mu M. In vitro COX-1/COX-2 inhibition structure-activity studies identified compound 8a as a highly potent (IC50 = 0.1 mu M), and an extremely selective [COX-2 (SI) > 1000] comparable to celecoxib [COX-2 (SI) > 384], COX-2 inhibitor that showed superior anti-inflammatory activity (ED50 = 72.4 mg/kg) relative to diclofenac (ED50 = 114 mg/kg). Molecular modeling was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. The study showed that the homosulfonamide fragment of 8a inserted deep inside the 2 degrees-pocket of the COX-2 active site, where the SO2NH2 group underwent H-bonding interaction with Gln(192)(2.95 angstrom), Phe(518)(2.82 angstrom) and Arg(513)(2.63 and 2.73 angstrom). Docking study of the synthesized compound 8a into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.107

文献信息

• COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS
  申请人：THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH

  公开号：US20160045514A1

  公开（公告）日：2016-02-18

  Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.

  本文描述了一种化合物和组合物，通过将间充质干细胞诱导为软骨细胞，用于改善关节炎或关节损伤的方法。
• Compounds and methods for inducing chondrogenesis
  申请人：The Scripps Research Institute

  公开号：US11045476B2

  公开（公告）日：2021-06-29

  Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.

  本文描述了通过诱导间充质干细胞转化为软骨细胞来改善关节炎或关节损伤的化合物和组合物。
• US20140271955A1
  申请人：——

  公开号：US20140271955A1

  公开（公告）日：2014-09-18
• US9452170B2
  申请人：——

  公开号：US9452170B2

  公开（公告）日：2016-09-27
• [EN] COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR L'INDUCTION DE LA CHONDROGENÈSE
  申请人：CALIFORNIA INST BIOMEDICAL RES

  公开号：WO2014151953A1

  公开（公告）日：2014-09-25

  Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.