6-Isopropyl-3-[4-(toluene-4-sulfonylamino)-butyl]-azulene-1-sulfonic acid butyl ester | 178870-98-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 6-Isopropyl-3-[4-(toluene-4-sulfonylamino)-butyl]-azulene-1-sulfonic acid butyl ester
• CAS: 178870-98-9
• 化学式: C₂₈H₃₇NO₅S₂
• 分子量: 531.737
• InChiKey: XYPBSLAKQVRBIK-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  6-Isopropyl-3-[4-(toluene-4-sulfonylamino)-butyl]-azulene-1-sulfonic acid butyl ester 在 四丁基氢氧化铵 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 6-(1-Hydroxy-1-methyl-ethyl)-3-[4-(toluene-4-sulfonylamino)-butyl]-azulene-1-sulfonic acid butyl 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
• 作为产物：
  描述：

  1-碘丁烷 、 Sodium; 6-isopropyl-3-[4-(toluene-4-sulfonylamino)-butyl]-azulene-1-sulfonate 以 六甲基磷酰三胺 为溶剂， 反应 48.0h， 生成 6-Isopropyl-3-[4-(toluene-4-sulfonylamino)-butyl]-azulene-1-sulfonic acid butyl 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