2-<3-(4-phenyl-1-piperazinyl)propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide | 127625-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<3-(4-phenyl-1-piperazinyl)propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide
• 英文别名: 2-[3-(4-Phenyl-1-piperazinyl)propyl]naphtho[1,8-cd]isothiazole 1,1-dioxide；3-[3-(4-phenylpiperazin-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: 127625-35-8
• 化学式: C₂₃H₂₅N₃O₂S
• 分子量: 407.536
• InChiKey: AWSBXOYZYNLCBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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-phenyl-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)naphthalenesultam, their preparation and
  申请人：Rhone-Poulenc Sante

  公开号：US05021420A1

  公开（公告）日：1991-06-04

  This invention relates to a compound ##STR1## in which R.sub.1 represents a 1,2,3,6-tetrahydro-1-pyridyl radical substituted in the 4-position by (a) a phenyl radical, (b) a phenyl radical substituted by a halogen atom or an alkyl, hydroxy or alkoxy radical, (c) a 3-indolyl radical, (d) a 3-indolyl radical substituted on the nitrogen atom by an alkyl or alkylcarbonyl radical and/or in the 5-position by a halogen atom or (e) a 3-(5-hydroxyindolyl) radical. a 1-piperazinyl radical substituted in the 4-position by (a) a phenyl radical, (b) a phenyl radical substituted by an alkoxy, alkyl, hydroxy, nitro or amino radical or a halogen atom, (c) a 1,2-benzisothiazol-3-yl radical, (d) a 1,2-benzisoxazol-3-yl radical or (e) a 2-pyridyl radical. a piperidino radical substituted in the 4-position by (a) a phenyl radical, (b) a phenyl radical substituted by a halogen atom or a hydroxy, alkyl or alkoxy radical, (c) two phenyl radicals, (d) a bis(4-fluorophenyl)methylene radical, (e) a 4-fluorobenzoyl radical, (f) a 2-oxo-1-benzimidazolinyl radical, (g) a 2-oxo-1-benzimidazolinyl radical substituted in the 3-position by an alkylcarbonyl or benzoyl radical, (b) a hydroxy radical and a phenyl radical optionally substituted with an alkyl, alkoxy or hydroxy radical or a halogen atom, (i) a 3-indolyl radical, (j) a 3-indolyl radical substituted on the nitrogen atom by an alkyl or alkylcarbonyl radical and/or in the 5-position by a halogen atom or (k) a 3-(5-hydroxyindolyl) radical. 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, with the reservation that when R.sub.6 represents a propylene radical substituted in the 2-position by a dialkylamino, piperidino, morpholino or thiomorpholino radical, R.sub.1 cannot be a radical containing a hydroxy radical, and their salts, are useful in therapy for their ability to block serotonin receptors.

  本发明涉及化合物##STR1## 其中R.sub.1代表1,2,3,6-四氢-1-吡啶基取代在4位上的基团，所述基团可以是(a)苯基基团，(b)被卤素原子或烷基、羟基或烷氧基取代的苯基基团，(c)3-吲哚基基团，(d)在氮原子上取代烷基或烷基羰基基团和/或在5位上取代卤素原子的3-吲哚基基团，或(e)3-(5-羟基吲哚基)基团；1-哌嗪基取代在4位上的基团，所述基团可以是(a)苯基基团，(b)被烷氧基、烷基、羟基、硝基或氨基基团或卤素原子取代的苯基基团，(c)1,2-苯并异噻唑-3-基基团，(d)1,2-苯并异恶唑-3-基基团或(e)2-吡啶基基团；取代在4位的哌啶基基团，所述基团可以是(a)苯基基团，(b)被卤素原子或羟基、烷基或烷氧基取代的苯基基团，(c)两个苯基基团，(d)双(4-氟苯基)亚甲基基团，(e)4-氟苯甲酰基基团，(f)2-氧代-1-苯并咪唑啉基团，(g)在3位上取代烷基羰基或苯甲酰基基团的2-氧代-1-苯并咪唑啉基团，(h)羟基基团和一个苯基基团，所述苯基基团可以选择取代烷基、烷氧基或羟基基团或卤素原子，(i)3-吲哚基基团，(j)在氮原子上取代烷基或烷基羰基基团和/或在5位上取代卤素原子的3-吲哚基基团，或(k)3-(5-羟基吲哚基)基团。R.sub.2和R.sub.3相同，分别代表氢原子或卤素原子，R.sub.4代表氢原子，或者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，或者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，或者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到4个碳原子的烷基链或在1位或3位上取代烷基基团或在2位上取代烷基、烷氧基、羟基、二烷基氨基、哌啶基、吗啉基或硫代吗啉基的丙烯基链，但当R.sub.6代表在2位上取代二烷基氨基、哌啶基、吗啉基或硫代吗啉基的丙烯基链时，R.sub.1不能是含有羟基基团的基团。这些化合物及其盐在治疗中具有阻断血清素受体的能力。
• 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。
• COMTE, MARIE-THERESE;MALLERON, JEAN-LUC;PEYRONEL, JEAN-FRANCOIS;TRUCHON, +
  作者：COMTE, MARIE-THERESE、MALLERON, JEAN-LUC、PEYRONEL, JEAN-FRANCOIS、TRUCHON, +

  DOI：——

  日期：——
• US5021420A
  申请人：——

  公开号：US5021420A

  公开（公告）日：1991-06-04
• US5036075A
  申请人：——

  公开号：US5036075A

  公开（公告）日：1991-07-30