3,3-dimethyl-5-oxo-5-(4-mercaptophenyl)pentanoic acid | 135312-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dimethyl-5-oxo-5-(4-mercaptophenyl)pentanoic acid
• 英文别名: 3,3-dimethyl-5-oxo-5-(4-sulfanylphenyl)pentanoic acid
• CAS: 135312-46-8
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: KVJKSIKKHIJNNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.37
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-<4-(chloromethyl)-2-hydroxy-3-propylphenyl>ethanone 、 3,3-dimethyl-5-oxo-5-(4-mercaptophenyl)pentanoic acid 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以27%的产率得到5-<4-<<(4-acetyl-3-hydroxy-2-propylphenyl)methyl>thio>phenyl>-3,3-dimethyl-5-oxopentanoic acid
  参考文献：
  名称：

  (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists

  摘要：

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.

  DOI：

  10.1021/jm00113a014
• 作为产物：
  描述：

  4-p-Anisoyl-3.3-dimethylbuttersaeure 在 sodium hydroxide 、 甲烷磺酸 、 吡啶盐酸盐 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3,3-dimethyl-5-oxo-5-(4-mercaptophenyl)pentanoic acid
  参考文献：
  名称：

  (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists

  摘要：

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.

  DOI：

  10.1021/jm00113a014