3-(5-chlorotetrazol-2-yl)-1-azabicyclo[2.2.2]octane | 142482-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 3-(5-chlorotetrazol-2-yl)-1-azabicyclo[2.2.2]octane
• CAS: 142482-77-7
• 化学式: C₈H₁₂ClN₅
• 分子量: 213.67
• InChiKey: HUMBNACZQNGUSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(tetrazol-2-yl)-1-azabicyclo<2.2.2>octane 在 叔丁基锂 、 氯 作用下， 生成 3-(5-chlorotetrazol-2-yl)-1-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

  摘要：

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm00091a007

文献信息

• Azabicyclic compounds, process and intermediates for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0427390A2

  公开（公告）日：1991-05-15

  A compound of formula (I) or a pharmaceutically acceptable salt thereof: in which one of X and Y represents hydrogen and the other represents Z, where Z is a group in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises zero, one or two nitrogen atoms, Q being optionally C-substituted by a group R1 selected from halogen, CN, OR2, SR2, N(R2)2, NHCOR2, NHCOOCH3, NHCOOC2H5, NHOR2, N3, NHNH2, N02, COR2, COR3, C2-4 alkenyl, C2-4 alkynyl, cyclopropyl or C1-2 alkyl optionally substituted with OR2, N(R2)2, SR2, C02R2, CON(R2)2 or one, two or three halogen atoms, in which each R2 is independently hydrogen or C1-2 alkyl and R3 is OR2, NH2 or NHR2; r represents an integer of 2 or 3, s represents an integer of 1 or 2 and t represents 0 or 1; Ra and Rb each represent hydrogen or, when X is hydrogen, optionally together represent a bond; with the proviso that when Y is hydrogen s is 1.

  式 (I) 的化合物或其药学上可接受的盐： 其中 X 和 Y 的一个代表氢，另一个代表 Z，其中 Z 是一个基团 其中 Q 代表完成 5 元芳香环的 3 元二价残基，包含 0、1 或 2 个氮原子，Q 任选被选自卤素、CN、OR2、SR2、N(R2)2、NHCOR2、NHCOOCH3、NHCOOC2H5、NHOR2、N3、NHNH2、N02、COR2、COR3、C2-4 烯基、C2-4 炔基、环丙基或任选被 OR2、N(R2)2、SR2、C02R2、CON(R2)2 或一个、两个或三个卤素原子取代的 C1-2 烷基，其中每个 R2 独立为氢或 C1-2 烷基，R3 为 OR2、NH2 或 NHR2；r 代表 2 或 3 的整数，s 代表 1 或 2 的整数，t 代表 0 或 1；Ra 和 Rb 各自代表氢，或当 X 为氢时，可选择共同代表一个键；但当 Y 为氢时，s 为 1。
• US5981545A
  申请人：——

  公开号：US5981545A

  公开（公告）日：1999-11-09
• Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands
  作者：Sarah M. Jenkins、Harry J. Wadsworth、Steven Bromidge、Barry S. Orlek、Paul A. Wyman、Graham J. Riley、Julie Hawkins

  DOI：10.1021/jm00091a007

  日期：1992.6

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.