3-(4-Azatricyclo[2.2.1.02,6]heptan-1-yl)-4-[3-(3-chlorophenyl)prop-2-ynoxy]-1,2,5-thiadiazole | 198143-40-7

• 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: 3-(4-Azatricyclo[2.2.1.02,6]heptan-1-yl)-4-[3-(3-chlorophenyl)prop-2-ynoxy]-1,2,5-thiadiazole
• CAS: 198143-40-7
• 化学式: C₁₇H₁₄ClN₃OS
• 分子量: 343.837
• InChiKey: HPTGNTPIZBKTDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Azatricyclo[2.2.1.02,6]heptan-1-yl)-4-[3-(3-chlorophenyl)prop-2-ynoxy]-1,2,5-thiadiazole 在 Oxone 、 sodium hydroxide 作用下， 生成 1-<3-<3-(3-chlorophenyl)-2-propyn-1-yloxy>-1,2,5-thiadiazol-4-yl>-4-azatricyclo<2,2,1,0^2,6>heptane 4-oxide
  参考文献：
  名称：

  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0^2,6]heptanes as New Potent Muscarinic M₁ Agonists:  Structure−Activity Relationship for 3-Aryl-2-propyn-1-yloxy and 3-Aryl-2-propyn-1-ylthio Derivatives

  摘要：

  Two new series of 1-(1,2,5-thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes were synthesized and evaluated for their in vitro activity in cell lines transfected with either the human M-1 or M-2 receptor. 3-Phenyl-2-propyn-1-yloxy and -1-ylthio analogues substituted with halogen in the meta position showed high functional potency, efficacy, and selectivity toward the M-1 receptor subtype. A quite unique functional M-1 receptor selectivity was observed for compounds 8b, 8d, 8f, 9b, 9d, and 9f. Bioavailability studies in rats indicated an oral bioavailability of about 20-30%, with the N-oxide as the only detected metabolite.

  DOI：

  10.1021/jm9910019
• 作为产物：
  描述：

  4-氮杂三环[2.2.1.02,6]庚烷-1-甲醛 在 盐酸 、 Oxone 、 ammonium hydroxide 、 sodium hydrogensulfide 、 sulfur monochloride 、 ammonium chloride 、 水 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 3-(4-Azatricyclo[2.2.1.02,6]heptan-1-yl)-4-[3-(3-chlorophenyl)prop-2-ynoxy]-1,2,5-thiadiazole
  参考文献：
  名称：

  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0^2,6]heptanes as New Potent Muscarinic M₁ Agonists:  Structure−Activity Relationship for 3-Aryl-2-propyn-1-yloxy and 3-Aryl-2-propyn-1-ylthio Derivatives

  摘要：

  Two new series of 1-(1,2,5-thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes were synthesized and evaluated for their in vitro activity in cell lines transfected with either the human M-1 or M-2 receptor. 3-Phenyl-2-propyn-1-yloxy and -1-ylthio analogues substituted with halogen in the meta position showed high functional potency, efficacy, and selectivity toward the M-1 receptor subtype. A quite unique functional M-1 receptor selectivity was observed for compounds 8b, 8d, 8f, 9b, 9d, and 9f. Bioavailability studies in rats indicated an oral bioavailability of about 20-30%, with the N-oxide as the only detected metabolite.

  DOI：

  10.1021/jm9910019