2-<3-<4-(1,1-dioxo-1,2-benzisothiazol-3-yl)-1-piperazinyl>propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide | 134133-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<3-<4-(1,1-dioxo-1,2-benzisothiazol-3-yl)-1-piperazinyl>propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide
• 英文别名: 2-{3-[4-(1,1-dioxo-1,2-benzisothiazol-3-yl)-1-piperazinyl]propyl}-2H-naphth(1,8-cd)isothiazole 1,1-dioxide；3-[3-[4-(1,1-Dioxo-1,2-benzothiazol-3-yl)piperazin-1-yl]propyl]-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene 2,2-dioxide；3-[3-[4-(1,1-dioxo-1,2-benzothiazol-3-yl)piperazin-1-yl]propyl]-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene 2,2-dioxide
• CAS: 134133-59-8
• 化学式: C₂₄H₂₄N₄O₄S₂
• 分子量: 496.611
• InChiKey: UVCMETSMBWPLJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,8-萘磺内酰胺 在 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 2-<3-<4-(1,1-dioxo-1,2-benzisothiazol-3-yl)-1-piperazinyl>propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide
  参考文献：
  名称：

  Naphthosultam derivatives: a new class of potent and selective 5-HT2 antagonists

  摘要：

  A series of 2-(aminoalkyl)naphth[1,8-cd]isothiazole 1,1-dioxides was synthesized and examined in various receptor binding tests. Most compounds demonstrated high affinity for the 5-HT2 receptor with moderate to high selectivity. A member of this series, compound 24 (RP 62203), displays high 5-HT2 receptor affinity (K(i) = 0.26 nM), which is respectively more than 100 and 1000 times higher than its affinity for alpha-1 (K(i) = 38 nM) and D2 (K(i) > 1000 nM) receptors. This compound is a potent orally effective and long lasting 5-HT2 antagonist in the mescaline-induced head-twitches test in mice and rats.

  DOI：

  10.1021/jm00112a025

文献信息

• Naphthosultam derivatives: a new class of potent and selective 5-HT2 antagonists
  作者：Jean Luc Malleron、Marie Therese Comte、Claude Gueremy、Jean Francis Peyronel、Alain Truchon、Jean Charles Blanchard、Adam Doble、Odile Piot、Jean Luc Zundel

  DOI：10.1021/jm00112a025

  日期：1991.8

  A series of 2-(aminoalkyl)naphth[1,8-cd]isothiazole 1,1-dioxides was synthesized and examined in various receptor binding tests. Most compounds demonstrated high affinity for the 5-HT2 receptor with moderate to high selectivity. A member of this series, compound 24 (RP 62203), displays high 5-HT2 receptor affinity (K(i) = 0.26 nM), which is respectively more than 100 and 1000 times higher than its affinity for alpha-1 (K(i) = 38 nM) and D2 (K(i) > 1000 nM) receptors. This compound is a potent orally effective and long lasting 5-HT2 antagonist in the mescaline-induced head-twitches test in mice and rats.