methyl (1S,2R,3S,5S,7R)-3-benzoyloxy-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | 948890-20-8

• 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: methyl (1S,2R,3S,5S,7R)-3-benzoyloxy-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 948890-20-8
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: HZGBHCXYIQFHSB-AIEDFZFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,3S,5S,7R)-3-benzoyloxy-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Positional linker effects in haptens for cocaine immunopharmacotherapy

  摘要：

  Cocaine use remains a serious problem, despite intensive efforts to curb abuse. Given the lack of effective pharmacotherapeutics for the treatment of cocaine addiction, research groups have targeted immunopharmacotherapy in which the drug user's immune system is trained to recognize and remove cocaine prior to entry into the central nervous system. Antibody cocaine esterases and simple binders have been procured, however, rates and/or affinities still need improvement before clinical trials are warranted. Herein, we report the synthesis and testing of two new haptens for the procurement of cocaine binding antibodies and cocaine esterase catalytic antibodies. Central in the design of these haptens was the placement of the linker functionality distal from the anticipated cocaine epitopes in an attempt to bury the hapten deep within an antibody combining site to gain possible entropic and enthalpic advantages. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.032
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 生成 methyl (1S,2R,3S,5S,7R)-3-benzoyloxy-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Positional linker effects in haptens for cocaine immunopharmacotherapy

  摘要：

  Cocaine use remains a serious problem, despite intensive efforts to curb abuse. Given the lack of effective pharmacotherapeutics for the treatment of cocaine addiction, research groups have targeted immunopharmacotherapy in which the drug user's immune system is trained to recognize and remove cocaine prior to entry into the central nervous system. Antibody cocaine esterases and simple binders have been procured, however, rates and/or affinities still need improvement before clinical trials are warranted. Herein, we report the synthesis and testing of two new haptens for the procurement of cocaine binding antibodies and cocaine esterase catalytic antibodies. Central in the design of these haptens was the placement of the linker functionality distal from the anticipated cocaine epitopes in an attempt to bury the hapten deep within an antibody combining site to gain possible entropic and enthalpic advantages. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.032

文献信息

• Synthesis of the 6- and 7-hydroxylated cocaines and pseudococaines
  作者：A.P. Kozikowski、D. Simoni、S. Manfredini、M. Roberti、J. Stoelwinder

  DOI：10.1016/0040-4039(96)01123-9

  日期：1996.7

  In efforts aimed at further exploration of our finding that functionalization of the two-carbon bridge of cocaine can lead to a weak antagonist of cocaine, we report a route to the 6- and 7-hydroxylated analogues by use of the Willstätter synthesis. The hydroxylated derivatives can in principle be used to gain access to a diverse library of 6- and 7-functionalized cocaine analogues.

  为了进一步探索我们的发现，即可卡因的二碳桥可能导致弱的可卡因拮抗剂，我们报告了使用Willstätter合成法合成6-和7-羟基化类似物的途径。羟基化的衍生物原则上可用于获得6-和7-官能化的可卡因类似物的多样化文库。