2-(4-chloro-phenyl)-3-hydroxy-propionic acid tropan-3-yl ester | 63978-23-4

• 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: 2-(4-chloro-phenyl)-3-hydroxy-propionic acid tropan-3-yl ester
• 英文别名: (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) 2-(4-chlorophenyl)-3-hydroxypropanoate
• CAS: 63978-23-4
• 化学式: C₁₇H₂₂ClNO₃
• 分子量: 323.82
• InChiKey: OLUBFGKMXSPBNJ-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

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-phenyl)-3-hydroxy-propionic acid tropan-3-yl ester 、 碘甲烷 以 乙醚 为溶剂， 生成 (8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl) 2-(4-chlorophenyl)-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-chlorophenyl)-3-hydroxypropanoic acid 在 盐酸 、 氯化亚砜 作用下， 反应 30.5h， 生成 2-(4-chloro-phenyl)-3-hydroxy-propionic acid tropan-3-yl ester
  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

文献信息

• Compounds, Compositions and Methods for Treatment of Myopia
  申请人：Aerie Pharmaceuticals, Inc.

  公开号：US20200247760A1

  公开（公告）日：2020-08-06

  Provided herein are 8-methyl-8-azabicyclo[3.2.1]octan-3-yl and pyridin-4-ylmethanyl ester and amide compounds and compositions. Also provided herein are methods of preventing or delaying the onset of myopia in a subject in need thereof, comprising administering the compounds or compositions provided herein to the subject. Also provided herein are methods of reducing or preventing the progression of myopia in a subject in need thereof, comprising administering the compounds or compositions provided herein to the subject.

  本文提供了8-甲基-8-氮杂双环[3.2.1]辛烷-3-基和吡啶-4-甲基酯和酰胺化合物及其组合物。本文还提供了一种预防或延迟需要该治疗的患者近视发生的方法，包括向该患者施用本文提供的化合物或组合物。本文还提供了一种减缓或预防需要该治疗的患者近视进展的方法，包括向该患者施用本文提供的化合物或组合物。
• Compounds, compositions and methods for treatment of myopia
  申请人：Aerie Pharmaceuticals, Inc.

  公开号：US11117869B2

  公开（公告）日：2021-09-14

  Provided herein are 8-methyl-8-azabicyclo[3.2.1]octan-3-yl and pyridin-4-ylmethanyl ester and amide compounds and compositions. Also provided herein are methods of preventing or delaying the onset of myopia in a subject in need thereof, comprising administering the compounds or compositions provided herein to the subject. Also provided herein are methods of reducing or preventing the progression of myopia in a subject in need thereof, comprising administering the compounds or compositions provided herein to the subject.

  本文提供了8-甲基-8-氮杂双环[3.2.1]辛烷-3-基和吡啶-4-基甲烷酯和酰胺化合物及组合物。本文还提供了预防或延迟有需要的受试者近视发生的方法，包括向受试者施用本文提供的化合物或组合物。本文还提供了减少或预防有需要的受试者近视发展的方法，包括对受试者施用本文提供的化合物或组合物。
• Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity
  作者：S Dei、A Bartolini、C Bellucci、C Ghelardini、F Gualtieri、D Manetti、M.N. Romanelli、S Scapecchi、E Teodori

  DOI：10.1016/s0223-5234(97)83285-0

  日期：1997.7

  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.