2-<3-<4-(4-methylphenyl)-1-piperazinyl>propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide | 127625-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<3-<4-(4-methylphenyl)-1-piperazinyl>propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide
• 英文别名: 2-{3-[4-(4-Methylphenyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide；3-[3-[4-(4-methylphenyl)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: 127625-58-5
• 化学式: C₂₄H₂₇N₃O₂S
• 分子量: 421.563
• InChiKey: OFDXTWFEOOKPAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,8-萘磺内酰胺 在 sodium hydride 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 39.0h， 生成 2-<3-<4-(4-methylphenyl)-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

• Derivatives of (AZA) naphthalensultam, their preparation and
  申请人：Rhone-Poulenc Sante

  公开号：US05036075A1

  公开（公告）日：1991-07-30

  This invention relates to a compound of the formula: ##STR1## in which R.sub.1 represents a 1,2,3,6-tetrahydro-1-pyridyl radical substituted in the 4-position. a 1-piperazinyl radical substituted in the 4-position. a piperidino radical substituted in the 4-position either: R.sub.2 and R.sub.3, which are identical, represent a hydrogen or halogen atom and R.sub.4 represents a hydrogen atom or R.sub.2 and R.sub.4 represent a hydrogen atom and R.sub.3 represents a halogen atom or an acetylamino radical or R.sub.2 and R.sub.3 represent a hydrogen atom and R.sub.4 represents a halogen atom and R.sub.5 represents a --CH.dbd. group. or R.sub.2, R.sub.3 and R.sub.4 represent a hydrogen atom and R.sub.5 represents a nitrogen atom. R.sub.6 represents an alkylene chain containing 2 to 4 carbon atoms or a propylene chain substituted in the 1- or 3-position by an alkyl radical or in the 2-position by an alkyl, alkoxy, hydroxy, dialkylamino, piperidino, morpholino or thiomorpholino radical, and their salts, are useful in therapy for their ability to block serotonin receptors.

  本发明涉及一种式为：##STR1##其中R.sub.1代表在4位取代的1,2,3,6-四氢-1-吡啶基基团，4位取代的1-哌嗪基基团或4位取代的哌啶基基团，其中：R.sub.2和R.sub.3相同，代表氢或卤素原子，R.sub.4代表氢原子，或R.sub.2和R.sub.4代表氢原子，R.sub.3代表卤素原子或乙酰氨基基团，或R.sub.2和R.sub.3代表氢原子，R.sub.4代表卤素原子，R.sub.5代表--CH.dbd.基团，或R.sub.2、R.sub.3和R.sub.4代表氢原子，R.sub.5代表氮原子。R.sub.6代表含有2至4个碳原子的烷基链或在1-或3-位被烷基基团取代的丙烯基链，或在2-位被烷基、烷氧基、羟基、二烷基氨基基团、哌啶基、吗啉基或硫代吗啉基取代的丙烯基链，以及它们的盐，用于治疗因其阻断5-羟色胺受体的能力而具有的功效。
• US5036075A
  申请人：——

  公开号：US5036075A

  公开（公告）日：1991-07-30
• 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.