(R)-N-hydrocinnamoylpiperidine-3-carboxylic acid | 474902-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-N-hydrocinnamoylpiperidine-3-carboxylic acid
• 英文别名: (3R)-1-(3-phenylpropanoyl)piperidine-3-carboxylic acid
• CAS: 474902-31-3
• 化学式: C₁₅H₁₉NO₃
• mdl: MFCD23058687
• 分子量: 261.321
• InChiKey: QKGZMEQFGUIDCI-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-hydrocinnamoylpiperidine-3-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到(R)-3-hydroxymethyl-N-(3-phenyl)propylpiperidine
  参考文献：
  名称：

  Structure–activity studies with ring E analogues of methyllycaconitine. Synthesis and evaluation of enantiopure isomers of selective antagonist at the α3 nicotinic receptor

  摘要：

  The four diastereomers 4a-d of methyllycaconitine (MLA) analogue 3 (R = (CH2)(3)Ph, R' = CH3) have been synthesized in enantiomerically pure form by coupling both (S)- and (R)-2-(methylsuccinimido)benzoic acid (5a and 5b) with both (S)- and (R)-3-hydroxymethyl-N-(3-phenyl) propylpiperidine (6a and 6b) using TBTU. These compounds were assayed for potency as nicotinic acetylcholine receptor (nAChRs) antagonist. All the four diastereomers showed the same potency at both the alpha3 and alpha7 receptors as racemic compound 3. This indicates that the binding at nicotine acetylcholine receptors (nAchRs) is probably non-stereospecific. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01353-3
• 作为产物：
  描述：

  3-苯丙酰氯 、 (R)-nipecotic acid (1R)-(+)-10-camphorsulfonic acid salt 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(R)-N-hydrocinnamoylpiperidine-3-carboxylic acid
  参考文献：
  名称：

  Structure–activity studies with ring E analogues of methyllycaconitine. Synthesis and evaluation of enantiopure isomers of selective antagonist at the α3 nicotinic receptor

  摘要：

  The four diastereomers 4a-d of methyllycaconitine (MLA) analogue 3 (R = (CH2)(3)Ph, R' = CH3) have been synthesized in enantiomerically pure form by coupling both (S)- and (R)-2-(methylsuccinimido)benzoic acid (5a and 5b) with both (S)- and (R)-3-hydroxymethyl-N-(3-phenyl) propylpiperidine (6a and 6b) using TBTU. These compounds were assayed for potency as nicotinic acetylcholine receptor (nAChRs) antagonist. All the four diastereomers showed the same potency at both the alpha3 and alpha7 receptors as racemic compound 3. This indicates that the binding at nicotine acetylcholine receptors (nAchRs) is probably non-stereospecific. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01353-3

文献信息

• [EN] AMINOPYRIDINE COMPOUNDS AND METHODS FOR THE PREPARATION AND USE THEREOF<br/>[FR] COMPOSÉS AMINOPYRIDINE ET PROCÉDÉS POUR LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：CORTEXYME INC

  公开号：WO2018209132A1

  公开（公告）日：2018-11-15

  The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its proteases arginine gingipain A/B (Rgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I and Formula III, as described herein, and pharmaceutically acceptable salts thereof.

  本发明一般涉及治疗靶向细菌Porphyromonas gingivalis的治疗药物，包括其蛋白酶精氨酸龈蛋白酶A/B（Rgp），以及它们用于治疗与P. gingivalis感染相关的疾病，包括脑部疾病如阿尔茨海默病。在某些实施例中，本发明提供根据本文所述的Formula I和Formula III的化合物，以及其药用可接受的盐。
• [EN] ARGININE GINGIPAIN INHIBITORS<br/>[FR] INHIBITEURS DE L'ARGININE-GINGIPAÏNE
  申请人：CORTEXYME INC

  公开号：WO2020191348A1

  公开（公告）日：2020-09-24

  Therapeutics targeting the bacterium Porphyromonas gingivalis, including its proteases arginine gingipain A and arginine gingipain B, are disclosed, as well as the use thereof for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I, Formula Ia, and Formula Ib, as described herein, and pharmaceutically acceptable salts thereof.

  揭示了针对细菌Porphyromonas gingivalis及其蛋白酶精氨酸龈蛋白A和精氨酸龈蛋白B的治疗方法，以及其用于治疗与P. gingivalis感染相关的疾病，包括脑部疾病如阿尔茨海默病。在某些实施例中，本发明提供了根据本文所述的Formula I、Formula Ia和Formula Ib的化合物，以及其药用可接受的盐。
• [EN] INHIBITORS OF ARGININE GINGIPAIN<br/>[FR] INHIBITEURS D'ARGININE GINGIPAÏNE
  申请人：CORTEXYME INC

  公开号：WO2017083433A1

  公开（公告）日：2017-05-18

  The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its proteases arginine gingipain A/B (Rgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I, as described herein, and pharmaceutically acceptable salts thereof.

  本发明通常涉及治疗靶向细菌 Porphyromonas gingivalis 的治疗药物，包括其蛋白酶精氨酸龈蛋白酶 A/B（Rgp），以及它们用于治疗与 P. gingivalis 感染相关的疾病，包括脑部疾病如阿尔茨海默病。在某些实施例中，本发明提供根据本文所述的 Formula I 的化合物及其药用盐。
• INHIBITORS OF LYSINE GINGIPAIN
  申请人：Cortexyme, Inc.

  公开号：US20160096830A1

  公开（公告）日：2016-04-07

  The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis , including its protease Lysine gingipain (Kgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I, as described herein, and pharmaceutically acceptable salts thereof.

  本发明通常涉及针对细菌牙龈脓红素Porphyromonas gingivalis及其蛋白酶赖氨酸龈蛋白酶（Kgp）的治疗方法，以及它们用于治疗与P. gingivalis感染相关的疾病，包括脑部疾病如阿尔茨海默病。在某些实施例中，本发明提供根据本文所述的I式化合物及其药用可接受的盐。
• Inhibitors of lysine gingipain
  申请人：Cortexyme, Inc.

  公开号：US10301301B2

  公开（公告）日：2019-05-28

  The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its protease Lysine gingipain (Kgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I, as described herein, and pharmaceutically acceptable salts thereof.

  本发明一般涉及针对牙龈卟啉单胞菌（包括其蛋白酶赖氨酸龈肽酶（Kgp））的治疗药物，及其用于治疗与牙龈卟啉单胞菌感染相关的疾病，包括脑部疾病，如阿尔茨海默氏症。在某些实施方案中，本发明提供了本文所述的根据式 I 的化合物及其药学上可接受的盐。