4-溴-alpha-(羟基甲基)苯乙酸 8-甲基-8-氮杂双环[3.2.1]辛烷-3-基酯 | 63978-22-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 中文名称: 4-溴-alpha-(羟基甲基)苯乙酸 8-甲基-8-氮杂双环[3.2.1]辛烷-3-基酯
• 中文别名: 4-溴-alpha-(羟基甲基)苯乙酸8-甲基-8-氮杂双环[3.2.1]辛烷-3-基酯
• 英文名称: 2-(4-bromo-phenyl)-3-hydroxy-propionic acid tropan-3-yl ester
• 英文别名: 3-Tropanyl 4'-bromotropate；(8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 2-(4-bromophenyl)-3-hydroxypropanoate
• CAS: 63978-22-3
• 化学式: C₁₇H₂₂BrNO₃
• 分子量: 368.271
• InChiKey: HMXQSWAWRXDIOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-溴-alpha-(羟基甲基)苯乙酸 8-甲基-8-氮杂双环[3.2.1]辛烷-3-基酯 、 碘甲烷 以 乙醚 为溶剂， 生成 (8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl) 2-(4-bromophenyl)-3-hydroxypropanoate;iodide
  参考文献：
  名称：

  Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity

  摘要：

  The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.

  DOI：

  10.1016/s0223-5234(97)83285-0
• 作为产物：
  描述：

  2-(4-bromophenyl)-3-hydroxypropanoic acid 在 盐酸 、 氯化亚砜 作用下， 反应 30.5h， 生成 4-溴-alpha-(羟基甲基)苯乙酸 8-甲基-8-氮杂双环[3.2.1]辛烷-3-基酯
  参考文献：
  名称：

  Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity

  摘要：

  The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.

  DOI：

  10.1016/s0223-5234(97)83285-0