endo-8-methyl-8-azabicyclo<3.2.1>octan-3-yl pyridine-2-carboxylate | 744953-68-2

• 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: endo-8-methyl-8-azabicyclo<3.2.1>octan-3-yl pyridine-2-carboxylate
• 英文别名: isonicotinic acid tropane-3endo-yl ester；Isonicotinsaeure-tropan-3endo-ylester
• CAS: 744953-68-2
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: QRZNETZWEVNJFK-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

• 作为产物：
  描述：

  异烟酸乙酯 、 3-tropanol 在 sodium tropane-3endo-olate 作用下， 120.0~125.0 ℃ 、1.6 kPa 条件下， 生成 endo-8-methyl-8-azabicyclo<3.2.1>octan-3-yl pyridine-2-carboxylate
  参考文献：
  名称：

  US2824106

  摘要：

  公开号：

文献信息

• Tropinol esters and related compounds to promote normal processing of APP
  申请人：John Varghese

  公开号：US11325904B2

  公开（公告）日：2022-05-10

  In various embodiments, compositions and methods are provided for treatment and/or prevention of amyloidogenic diseases. In certain embodiments, the methods entail administering an effective amount of a tropinol ester to a subject in need thereof for prophylactic or therapeutic effect. The methods are particularly useful for prophylactic and therapeutic treatment of Alzheimer's disease. In certain embodiments, methods of reducing the risk, lessening the severity, or delaying the progression or onset of a disease characterized by beta-amyloid deposits in the brain of a mammal are also provided. In certain embodiments, methods of directly or indirectly inhibiting the C-terminal cleavage of APP resulting in the formation of APP-C31 peptide and APPneo (AP-P664) in a mammal are provided.

  在各种实施方式中，提供了用于治疗和/或预防淀粉样病变疾病的组合物和方法。在某些实施方式中，该方法包括向需要预防或治疗作用的受试者施用有效量的tropinol酯，以达到预防或治疗效果。该方法特别适用于预防和治疗阿尔茨海默病。在某些实施方式中，还提供了减少哺乳动物大脑中β-淀粉样沉积所致疾病的风险、减轻其严重程度或延缓其进展或发作的方法。在某些实施方式中，还提供了直接或间接抑制APP的C-末端裂解，从而形成APP-C31肽和APPneo（AP-P664）的方法。
• Structural analysis of 5-HT3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters or amides derived from tropane and 1,2,6-trisubstituted piperidine
  作者：M Langlois、JL Soulier、D Yang、B Bremont、C Florac、V Rampillon、A Giudice

  DOI：10.1016/0223-5234(93)90039-h

  日期：1993.1

  Preliminary results of a structure-activity relationship in the field of 5-HT3 receptor antagonists on the influence of the aromatic ring and steric hindrance around the basic nitrogen atom are reported. The favorable role of the naphthalene moiety substituted by a carbonyl function in position 1 was demonstrated by measuring the biological activity using the inhibition of the specific binding of [H-3]BRL 43694 and the inhibition of the Bezold-Jarisch reflex. Several esters and amides of 1,2,6-trisubstituted piperidine derivatives with a suitable fit with the antagonist reference compounds were synthesized. The lack of biological activity of these compounds emphasizes the importance of steric hindrance for binding with the anionic receptor site. These data confirm the major role of the tropane and quinuclidine frameworks in the potency of a number of 5-HT3 antagonists.
• TROPINOL ESTERS AND RELATED COMPOUNDS TO PROMOTE NORMAL PROCESSING OF APP
  申请人：John Varghese

  公开号：US20140364451A1

  公开（公告）日：2014-12-11

  In various embodiments, compositions and methods are provided for treatment and/or prevention of amyloidogenic diseases. In certain embodiments, the methods entail administering an effective amount of a tropinol ester to a subject in need thereof for prophylactic or therapeutic effect. The methods are particularly useful for prophylactic and therapeutic treatment of Alzheimer's disease. In certain embodiments, methods of reducing the risk, lessening the severity, or delaying the progression or onset of a disease characterized by beta-amyloid deposits in the brain of a mammal are also provided. In certain embodiments, methods of directly or indirectly inhibiting the C-terminal cleavage of APP resulting in the formation of APP-C31 peptide and APPneo (AP-P664) in a mammal are provided.