3-(3-chlorophenylsulfanyl)-8-methyl-8-azabicyclo[3.2.1]octane

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 3-(3-chlorophenylsulfanyl)-8-methyl-8-azabicyclo[3.2.1]octane
• 化学式: C₁₄H₁₈ClNS
• 分子量: 267.823
• InChiKey: FMSLBDQGHOAIMZ-DABQJJPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  Tropine-3-mesylate 、 3-氯苯硫酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(3-chlorophenylsulfanyl)-8-methyl-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and Analgesic Activity of Some Side-Chain Modified Anpirtoline Derivatives

  摘要：

  New derivatives of anpirtoline and deazaanpirtoline modified in the side chain have been synthesized. The series includes compounds 3 with side-chains containing piperidine or pyrrolidine rings, compounds 4 containing 8-azabicyclo[3.2.1]octane moiety, and compounds 5 having piperazine ring in their side-chains. Their receptor binding profiles (5-HT1A, 5-HT1B) and analgesic activity (hot plate, acetic acid induced writhing) have been studied. Optimized structures (PM3-MOPAC, Alchemy 2000, Tripos Inc.) of the synthesized compounds 3-5 were compared with that of anpirtoline.

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<107::aid-ardp107>3.0.co;2-y

文献信息

• Synthesis and Analgesic Activity of Some Side-Chain Modified Anpirtoline Derivatives
  作者：Stanislav Rádl、Petr Hezký、Jan Proška、Lucie Hejnová、Ivan Krejcí

  DOI：10.1002/(sici)1521-4184(20005)333:5<107::aid-ardp107>3.0.co;2-y

  日期：2000.5

  New derivatives of anpirtoline and deazaanpirtoline modified in the side chain have been synthesized. The series includes compounds 3 with side-chains containing piperidine or pyrrolidine rings, compounds 4 containing 8-azabicyclo[3.2.1]octane moiety, and compounds 5 having piperazine ring in their side-chains. Their receptor binding profiles (5-HT1A, 5-HT1B) and analgesic activity (hot plate, acetic acid induced writhing) have been studied. Optimized structures (PM3-MOPAC, Alchemy 2000, Tripos Inc.) of the synthesized compounds 3-5 were compared with that of anpirtoline.