(S)-N-hydrocinnamoylpiperidine-3-carboxylic acid | 474902-29-9

• 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: (S)-N-hydrocinnamoylpiperidine-3-carboxylic acid
• 英文别名: (3S)-1-(3-phenylpropanoyl)piperidine-3-carboxylic acid
• CAS: 474902-29-9
• 化学式: C₁₅H₁₉NO₃
• mdl: MFCD25072009
• 分子量: 261.321
• InChiKey: QKGZMEQFGUIDCI-ZDUSSCGKSA-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：

  (S)-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(S)-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 、 (S)-nipecotic acid (S)-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69.4%的产率得到(S)-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

• Structure–activity studies with ring E analogues of methyllycaconitine. Synthesis and evaluation of enantiopure isomers of selective antagonist at the α3 nicotinic receptor
  作者：K.A Ismail、S.C Bergmeier

  DOI：10.1016/s0223-5234(02)01353-3

  日期：2002.6

  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.