5-(3,4-di-methylphenyl)-1H-pyrazole-3-carboxylic acid | 1197631-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3,4-di-methylphenyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 3-(3,4-dimethylphenyl)-1H-pyrazole-5-carboxylic acid
• CAS: 1197631-29-0
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD03420243
• 分子量: 216.239
• InChiKey: KLZBOPQBGJBTRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  邻二甲苯 在 aluminum (III) chloride 、 sodium methylate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 5-(3,4-di-methylphenyl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII

  摘要：

  Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.052

文献信息

• INTESTINAL ALKALINE PHOSPHATASE MODULATORS AND USES THEREOF
  申请人：Burnham Institute for Medical Research

  公开号：EP2291372A2

  公开（公告）日：2011-03-09
• [EN] INTESTINAL ALKALINE PHOSPHATASE MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE LA PHOSPHATASE ALCALINE INTESTINALE ET LEURS UTILISATIONS
  申请人：BURNHAM INST MEDICAL RESEARCH

  公开号：WO2009143150A2

  公开（公告）日：2009-11-26

  Disclosed are modulators, i.e., activators and inhibitors, of Intestinal Alkaline Phosphatase (IAP). Also disclosed are methods for treating bacterial infections of the intestinal tract and methods for maintaining the health of the intestinal tract using IAP activators. Further disclosed are methods to assist in weight gain of emaciated patients and those having reduced or negligible fat absorption using IAP inhibitors.