Tert-butyl 3-[(3-nitrophenyl)carbamoyl]piperidine-1-carboxylate | 667454-34-4

• 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: Tert-butyl 3-[(3-nitrophenyl)carbamoyl]piperidine-1-carboxylate
• CAS: 667454-34-4
• 化学式: C₁₇H₂₃N₃O₅
• 分子量: 349.387
• InChiKey: OHFPIEBFSCSJGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-[(3-nitrophenyl)carbamoyl]piperidine-1-carboxylate 在 盐酸 作用下， 以 氯仿 为溶剂， 生成 N-(3-nitrophenyl)piperidine-3-carboxamide hydrochloride
  参考文献：
  名称：

  Investigation of platelet aggregation inhibitory activity by phenyl amides and esters of piperidinecarboxylic acids

  摘要：

  A series of anilides and phenyl esters of piperidine-3-carboxylic acid (nipecotic acid) were synthesized and tested for the ability to inhibit aggregation of human platelet rich-plasma triggered by adenosine 5'-diphosphate (ADP) and adrenaline. As a rule, amides were about two times more active than the corresponding esters, and derivatives bearing substituents at the para position of the phenyl ring were significantly more active than the meta-substituted ones. Among the tested compounds, 4-hexyloxyanilide of nipecotic acid (18a) was found to be the most active one, its IC50 value being close to that of the most active bis-3-carbamoyl-piperidines reported in literature (ca. 40 muM) and aspirin (ca. 60 muM) in ADP- and adrenaline-induced aggregation, respectively. Compared with the isomeric 4-hexyloxyanilides of piperidine-2-carboxylic (pipecolinic) and piperidine-4-carboxylic (isonipecotic) acids, compound 18a showed higher activity, and a Hansch-type quantitative structure-activity relationship (QSAR) study highlighted lipophilicity and increase in electron density of the phenyl ring as the properties which mainly increase the antiplatelet activity (r(2) = 0.74, q(2) = 0.64). The interaction of nipecotoyl anilides with phosphatidylinositol, a major component of the inner layer of the platelet membranes, was investigated by means of flexible docking calculation methods to give an account of a key event underlying their biological action. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00599-0
• 作为产物：
  描述：

  1-BOC-哌啶-3-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Tert-butyl 3-[(3-nitrophenyl)carbamoyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Investigation of platelet aggregation inhibitory activity by phenyl amides and esters of piperidinecarboxylic acids

  摘要：

  A series of anilides and phenyl esters of piperidine-3-carboxylic acid (nipecotic acid) were synthesized and tested for the ability to inhibit aggregation of human platelet rich-plasma triggered by adenosine 5'-diphosphate (ADP) and adrenaline. As a rule, amides were about two times more active than the corresponding esters, and derivatives bearing substituents at the para position of the phenyl ring were significantly more active than the meta-substituted ones. Among the tested compounds, 4-hexyloxyanilide of nipecotic acid (18a) was found to be the most active one, its IC50 value being close to that of the most active bis-3-carbamoyl-piperidines reported in literature (ca. 40 muM) and aspirin (ca. 60 muM) in ADP- and adrenaline-induced aggregation, respectively. Compared with the isomeric 4-hexyloxyanilides of piperidine-2-carboxylic (pipecolinic) and piperidine-4-carboxylic (isonipecotic) acids, compound 18a showed higher activity, and a Hansch-type quantitative structure-activity relationship (QSAR) study highlighted lipophilicity and increase in electron density of the phenyl ring as the properties which mainly increase the antiplatelet activity (r(2) = 0.74, q(2) = 0.64). The interaction of nipecotoyl anilides with phosphatidylinositol, a major component of the inner layer of the platelet membranes, was investigated by means of flexible docking calculation methods to give an account of a key event underlying their biological action. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00599-0

文献信息

• Investigation of platelet aggregation inhibitory activity by phenyl amides and esters of piperidinecarboxylic acids
  作者：Modesto de Candia、Luciana Summo、Antonio Carrieri、Cosimo Altomare、Adele Nardecchia、Saverio Cellamare、Angelo Carotti

  DOI：10.1016/s0968-0896(02)00599-0

  日期：2003.4

  A series of anilides and phenyl esters of piperidine-3-carboxylic acid (nipecotic acid) were synthesized and tested for the ability to inhibit aggregation of human platelet rich-plasma triggered by adenosine 5'-diphosphate (ADP) and adrenaline. As a rule, amides were about two times more active than the corresponding esters, and derivatives bearing substituents at the para position of the phenyl ring were significantly more active than the meta-substituted ones. Among the tested compounds, 4-hexyloxyanilide of nipecotic acid (18a) was found to be the most active one, its IC50 value being close to that of the most active bis-3-carbamoyl-piperidines reported in literature (ca. 40 muM) and aspirin (ca. 60 muM) in ADP- and adrenaline-induced aggregation, respectively. Compared with the isomeric 4-hexyloxyanilides of piperidine-2-carboxylic (pipecolinic) and piperidine-4-carboxylic (isonipecotic) acids, compound 18a showed higher activity, and a Hansch-type quantitative structure-activity relationship (QSAR) study highlighted lipophilicity and increase in electron density of the phenyl ring as the properties which mainly increase the antiplatelet activity (r(2) = 0.74, q(2) = 0.64). The interaction of nipecotoyl anilides with phosphatidylinositol, a major component of the inner layer of the platelet membranes, was investigated by means of flexible docking calculation methods to give an account of a key event underlying their biological action. (C) 2003 Elsevier Science Ltd. All rights reserved.