3-bromobenzoylpyruvic acid | 105356-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromobenzoylpyruvic acid
• 英文别名: 4-(3-bromophenyl)-2,4-dioxobutanoic acid
• CAS: 105356-64-7
• 化学式: C₁₀H₇BrO₄
• 分子量: 271.067
• InChiKey: DLBFPLZJXXVHIG-UHFFFAOYSA-N

物化性质

• 沸点：
  422.3±30.0 °C(Predicted)
• 密度：
  1.674±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromobenzoylpyruvic acid 以 异丙醇 、 苯 为溶剂， 反应 3.33h， 生成 3-(3-bromobenzoyl)-8-chloro-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: XCVIII. [4 + 2]-cycloaddition of alkyl vinyl ethers to 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones. A new synthetic approach to heteroanalogs of 13(14→8)-abeo steroids

  摘要：

  3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with alkyl vinyl ethers according to the [4 + 2]-cycloaddition pattern with formation of substituted (1S*,16R*)- and (1R*,16R*)-16-alkoxy-14-aryl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-triones. The structure of (1S*,16R*)-7-chloro-16-ethoxy-14-phenyl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-trione was determined by X-ray analysis. A new synthetic approach was developed to heteroanalogs of 13(14 -> 8)-abeo steroids, substituted 3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadecanes.

  DOI：

  10.1134/s1070428013120105
• 作为产物：
  描述：

  溴苯 在 aluminum (III) chloride 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-bromobenzoylpyruvic 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