Sodium;3-[4-[(4-methoxyphenyl)sulfonylamino]butyl]-6-propan-2-ylazulene-1-sulfonate | 129648-98-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: Sodium;3-[4-[(4-methoxyphenyl)sulfonylamino]butyl]-6-propan-2-ylazulene-1-sulfonate
• CAS: 129648-98-2
• 化学式: C₂₄H₂₈NO₆S₂*Na
• 分子量: 513.611
• InChiKey: JGQBBXKKRWHBAD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Sodium;3-[4-[(4-methoxyphenyl)sulfonylamino]butyl]-6-propan-2-ylazulene-1-sulfonate 在 sodium hydroxide 、 四丁基氢氧化铵 、 氧气 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 74.0h， 生成 Sodium; 6-(1-hydroxy-1-methyl-ethyl)-3-[4-(4-methoxy-benzenesulfonylamino)-butyl]-azulene-1-sulfonate
  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：

  Methyl 3-(4-phenylmethoxybutyl)-6-propan-2-ylazulene-1-carboxylate 在 吡啶 、 三氯化铝 、 磷酸 、 sodium methylate 、 三氧化硫吡啶 、 sodium hydride 、 苯甲醚 作用下， 生成 Sodium;3-[4-[(4-methoxyphenyl)sulfonylamino]butyl]-6-propan-2-ylazulene-1-sulfonate
  参考文献：
  名称：

  Azulene衍生物：新型非前列腺素血栓烷A2受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00171a004

文献信息

• TOMIYAMA, T.;WAKABAYASHI, SH.;KOSAKAI, K., J. MED. CHEM., 33,(1990) N, C. 2323-2326
  作者：TOMIYAMA, T.、WAKABAYASHI, SH.、KOSAKAI, K.

  DOI：——

  日期：——
• US5081152A
  申请人：——

  公开号：US5081152A

  公开（公告）日：1992-01-14
• Azulene derivatives as TXA2/PGH2 receptor antagonists—II. Synthesis and biological activity of 6-mono- and 6-dihydroxylated-isopropylazulenes
  作者：Masayuki Yokota、Satoko Uchibori、Hiromi Hayashi、Rei Koyama、Kazuhiro Kosakai、Shuichi Wakabayashi、Tsuyoshi Tomiyama

  DOI：10.1016/0968-0896(96)00038-7

  日期：1996.4

  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
• Azulene derivatives: new non-prostanoid thromboxane A2 receptor antagonists
  作者：Tsuyoshi Tomiyama、Shuichi Wakabayashi、Kazuhiro Kosakai、Masayuki Yokota

  DOI：10.1021/jm00171a004

  日期：1990.9