3α-(3'-pyridinecarbonyloxy)-tropane | 108875-48-5

• 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: 3α-(3'-pyridinecarbonyloxy)-tropane
• 英文别名: 3α-(3-pyridinecarbonyloxy)-tropane；3α-nicotinoyloxytropane；nicotinic acid tropane-3endo-yl ester；Nicotinsaeure-tropan-3endo-ylester
• CAS: 108875-48-5
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: NHFDVEVAKLYKKT-ITGUQSILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  18.0
• 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：
  42.43
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3α-(3'-pyridinecarbonyloxy)-tropane 、 氯甲酸-2,2,2-三氯乙酯 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 2.33h， 生成
  参考文献：
  名称：

  Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding

  摘要：

  (Hetero) aromatic mono- and diesters of tropine and nortropine were prepared. Modulation of [H-3] strychnine binding to glycine receptors of rat spinal cord was examined with a ternary allosteric model. The esters displaced [H-3] strychnine binding with nano- or micromolar potencies and strong negative cooperativity. Coplanarity and distance of the ester moieties of diesters affected the binding affinity being nanomolar for isophthaloyl-bistropane and nortropeines. Nortropisetron had the highest affinity (K-A similar to 10 nM). Two esters displayed negative cooperativity with glycine in displacement, while three esters of low-affinity and nor-tropisetron exerted positive cooperativity with glycine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.097
• 作为产物：
  描述：

  烟酸乙酯 、 3-tropanol 在 sodium 作用下， 120.0 ℃ 、2.0 kPa 条件下， 反应 24.0h， 以69%的产率得到3α-(3'-pyridinecarbonyloxy)-tropane
  参考文献：
  名称：

  Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding

  摘要：

  (Hetero) aromatic mono- and diesters of tropine and nortropine were prepared. Modulation of [H-3] strychnine binding to glycine receptors of rat spinal cord was examined with a ternary allosteric model. The esters displaced [H-3] strychnine binding with nano- or micromolar potencies and strong negative cooperativity. Coplanarity and distance of the ester moieties of diesters affected the binding affinity being nanomolar for isophthaloyl-bistropane and nortropeines. Nortropisetron had the highest affinity (K-A similar to 10 nM). Two esters displayed negative cooperativity with glycine in displacement, while three esters of low-affinity and nor-tropisetron exerted positive cooperativity with glycine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.097

文献信息

• US2824106
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding
  作者：Gábor Maksay、Péter Nemes、Zoltán Vincze、Timea Bíró

  DOI：10.1016/j.bmc.2007.10.097

  日期：2008.2.15

  (Hetero) aromatic mono- and diesters of tropine and nortropine were prepared. Modulation of [H-3] strychnine binding to glycine receptors of rat spinal cord was examined with a ternary allosteric model. The esters displaced [H-3] strychnine binding with nano- or micromolar potencies and strong negative cooperativity. Coplanarity and distance of the ester moieties of diesters affected the binding affinity being nanomolar for isophthaloyl-bistropane and nortropeines. Nortropisetron had the highest affinity (K-A similar to 10 nM). Two esters displayed negative cooperativity with glycine in displacement, while three esters of low-affinity and nor-tropisetron exerted positive cooperativity with glycine. (c) 2007 Elsevier Ltd. All rights reserved.