6-(1-Benzoyloxymethyl-vinyl)-3-[4-(4-chloro-benzenesulfonylamino)-butyl]-azulene-1-carboxylic acid methyl ester | 178871-17-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 6-(1-Benzoyloxymethyl-vinyl)-3-[4-(4-chloro-benzenesulfonylamino)-butyl]-azulene-1-carboxylic acid methyl ester
• CAS: 178871-17-5
• 化学式: C₃₂H₃₀ClNO₆S
• 分子量: 592.112
• InChiKey: UKDGPJABAJDNEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  98.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-(1-Benzoyloxymethyl-vinyl)-3-[4-(4-chloro-benzenesulfonylamino)-butyl]-azulene-1-carboxylic acid methyl ester 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 磷酸 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.17h， 生成 1-[4-(4-chlorobenzenesulfonylamino)butyl]-6-(2-hydroxy-1-hydroxymethyl)ethylazulene
  参考文献：
  名称：

  Azulene derivatives as TXA2/PGH2 receptor antagonists—II. Synthesis and biological activity of 6-mono- and 6-dihydroxylated-isopropylazulenes

  摘要：

  In order to examine the correlation between activity and hydrophilicity of the side chain of sodium 3-[4-(4-chlorobenzenesulfonylamino)butyl]-6-isopropylazulene-1-sulfonate (KT2-962), a non-prostanoid TXA(2)/PGH(2) receptor antagonist, one or two hydroxyl groups were introduced into the isopropyl moiety. A series of 6-hydroxylated-isopropylazulenes were synthesized by regioselective oxidation of 6-isopropylazulenes and their in vitro and in vivo antagonistic activities were studied. Both the primary and tertiary alcohols, monohydroxylated derivatives, exhibited potent biological activities comparable to unmodified 6-isopropylazulenes both in vitro and in vivo. In contrast, the activities of 1,2- and 1,3-diols of 6-substituted derivatives, markedly decreased, but recovered by O-isopropylidenation of the dihydroxyl moiety. These findings indicate that the moderate hydrophobicity of substituent at the 6-position of the azulene ring might be required for the activity and the size of the substituent at this position, not so rigid for keeping potent biological activity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00038-7
• 作为产物：
  描述：

  3-[4-(4-Chloro-benzenesulfonylamino)-butyl]-6-(1-hydroxy-1-methyl-ethyl)-azulene-1-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 叔丁醇 、 苯 为溶剂， 反应 20.66h， 生成 6-(1-Benzoyloxymethyl-vinyl)-3-[4-(4-chloro-benzenesulfonylamino)-butyl]-azulene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Azulene derivatives as TXA2/PGH2 receptor antagonists—II. Synthesis and biological activity of 6-mono- and 6-dihydroxylated-isopropylazulenes

  摘要：

  In order to examine the correlation between activity and hydrophilicity of the side chain of sodium 3-[4-(4-chlorobenzenesulfonylamino)butyl]-6-isopropylazulene-1-sulfonate (KT2-962), a non-prostanoid TXA(2)/PGH(2) receptor antagonist, one or two hydroxyl groups were introduced into the isopropyl moiety. A series of 6-hydroxylated-isopropylazulenes were synthesized by regioselective oxidation of 6-isopropylazulenes and their in vitro and in vivo antagonistic activities were studied. Both the primary and tertiary alcohols, monohydroxylated derivatives, exhibited potent biological activities comparable to unmodified 6-isopropylazulenes both in vitro and in vivo. In contrast, the activities of 1,2- and 1,3-diols of 6-substituted derivatives, markedly decreased, but recovered by O-isopropylidenation of the dihydroxyl moiety. These findings indicate that the moderate hydrophobicity of substituent at the 6-position of the azulene ring might be required for the activity and the size of the substituent at this position, not so rigid for keeping potent biological activity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00038-7