N-<3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl>-N-phenylbenzenesulfonamide | 134133-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-<3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl>-N-phenylbenzenesulfonamide
• 英文别名: N-[3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl]-N-phenylbenzenesulphonamide；N-phenyl-N-[3-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)propyl]benzenesulfonamide
• CAS: 134133-53-2
• 化学式: C₂₆H₂₈N₂O₂S
• 分子量: 432.587
• InChiKey: QWVPSLXKIGGBPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苯基-1,2,3,6-四氢吡啶 在 sodium hydride 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 22.5h， 生成 N-<3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl>-N-phenylbenzenesulfonamide
  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

• Serotonin antagonists, their preparation and medications containing them
  申请人：Rhone-Poulenc Sante

  公开号：US05130313A1

  公开（公告）日：1992-07-14

  This invention relates to compounds of formula: ##STR1## in which R.sub.1 denotes a 1,2,3,6-tetrahydro-1-pyridyl radical substituted in the 4-position by an optionally substituted phenyl, optionally substituted 3-indolyl or 3-(5-hydroxyindolyl) radical, a 1-piperazinyl radical substituted in the 4-position by an optionally substituted phenyl, 1,2-benzisothiazol-3-yl, 1,2-benzisoxazol-3-yl or 2-pyridyl radical, a piperidino radical substituted in the 4-position by an optionally substituted phenyl, bis(4-fluorophenyl)methylene, 4-fluorobenzoyl, optionally substituted 2-oxo-1-benzimidazolinyl, optionally substituted 3-indolyl or 3-(5-hydroxyindolyl) radical, by two phenyl radicals or a hydroxyl radical and an optionally substituted phenyl radical R.sub.2 denotes a radical SO.sub.2 R.sub.4 in which R.sub.4 denotes an alkyl or phenyl radical, R.sub.3 denotes a phenyl or naphthyl radical, or else R.sub.2 and R.sub.3 together with the nitrogen atom to which they are attached form a ring, n is equal to 2, 3 or 4, processes for their preparation and medications containing them. The invention relates to treating a disease ameliorated by serotonin.

  本发明涉及以下式的化合物：##STR1## 其中，R1表示在4位上由可选取代苯基，可选取代3-吲哚基或3-(5-羟基吲哚基)基团取代的1,2,3,6-四氢-1-吡啶基基团，由可选取代苯基取代的1-哌嗪基团，1,2-苯并异噻唑-3-基团，1,2-苯并噁唑-3-基团或2-吡啶基基团，由可选取代苯基取代的4-位取代的哌啶基基团，双(4-氟苯基)亚甲基基团，4-氟苯甲酰基，可选取代的2-氧代-1-苯并咪唑啉基团，可选取代的3-吲哚基或3-(5-羟基吲哚基)基团，由两个苯基基团或一个羟基基团和一个可选取代苯基基团取代的基团。R2表示SO2R4基团，其中R4表示烷基或苯基基团，R3表示苯基或萘基团，或者R2和R3与它们所连接的氮原子一起形成环，n等于2、3或4。本发明还涉及制备这些化合物的方法和含有它们的药物。本发明涉及治疗一种通过血清素改善的疾病。
• US5130313A
  申请人：——

  公开号：US5130313A

  公开（公告）日：1992-07-14
• 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.