4-(3-hydroxycarbamoyl-propyl)-piperidine-1-carboxylic acid benzylamide | 910537-86-9

• 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: 4-(3-hydroxycarbamoyl-propyl)-piperidine-1-carboxylic acid benzylamide
• 英文别名: N-benzyl-4-[4-(hydroxyamino)-4-oxobutyl]piperidine-1-carboxamide
• CAS: 910537-86-9
• 化学式: C₁₇H₂₅N₃O₃
• 分子量: 319.404
• InChiKey: YHGLEBNSCHQGHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxycarbamoyl-propyl)-piperidine-1-carboxylic acid benzylamide 、 2,2-二乙氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到[3-(5,5-Dimethyl-[1,4,2]dioxazol-3-yl)-propyl]-piperidine-1-carboxylic acid benzylamide
  参考文献：
  名称：

  WO2006/97460

  摘要：

  公开号：
• 作为产物：
  描述：

  4-(1-benzylcarbamoyl-piperidin-4-yl)-butyric acid methyl ester 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 4-(3-hydroxycarbamoyl-propyl)-piperidine-1-carboxylic acid benzylamide
  参考文献：
  名称：

  Alkyl piperidine and piperazine hydroxamic acids as HDAC inhibitors

  摘要：

  We report here the strategy used in our research group to find a new class of histone deacetylase (HDAC) inhibitors.A series of N-substituted 4-alkylpiperazine and 4-alkylpiperidine hydroxamic acids, corresponding to the basic structure of HDAC inhibitors (zinc binding moiety-linker-capping group) has been designed, prepared, and tested for HDAC inhibition.Linker length and aromatic capping group connection were systematically varied to find the optimal geometric parameters. A new series of submicromolar inhibitors was thus identified, which showed antiproliferative activity on HCT-116 colon carcinoma cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.085

文献信息

• Hydroxamates as Histone Deacetylase Inhibitors and Pharmaceutical Formulations Containing Them
  申请人：Rossi Cristina

  公开号：US20080207694A1

  公开（公告）日：2008-08-28

  Compounds of structure (I) having histone deacetylase (HDAC) inhibitor activity are described. The compounds are chemically characterised by the presence of hydroxamic acid, with zinc as chelator, and an aromatic nucleus connected by a linker in which either a bicyclic aromatic system or a piperidino ring are present.

  结构（I）的化合物具有组蛋白去乙酰化酶（HDAC）抑制剂活性。这些化合物在化学上特征为存在羟肟酸，锌作为螯合剂，并且通过连接剂连接的芳香核与一个双环芳香系统或哌啶环存在。
• HYDROXAMATES AS HISTONE DEACETYLASE INHIBITORS AND PHARMACEUTICAL FORMULATIONS CONTAINING THEM
  申请人：Menarini International Operations Luxembourg S.A.

  公开号：EP1868997A1

  公开（公告）日：2007-12-26
• [EN] HYDROXAMATES AS HISTONE DEACETYLASE INHIBITORS AND PHARMACEUTICAL FORMULATIONS CONTAINING THEM<br/>[FR] HYDROXAMATES UTILISES EN TANT QU'INHIBITEURS DE DESACETYLASE D'HISTONES ET FORMULATIONS PHARMACEUTIQUES LES CONTENANT
  申请人：MENARINI INT OPERATIONS LU SA

  公开号：WO2006097460A1

  公开（公告）日：2006-09-21

  [EN] Compounds of structure (I) having histone deacetylase (HDAC) inhibitor activity are described. The compounds are chemically characterised by the presence of hydroxamic acid, with zinc as chelator, and an aromatic nucleus connected by a linker in which either a bicyclic aromatic system or a piperidino ring are present.
  [FR] L'invention concerne des composés ayant la structure (I) ayant une activité d'inhibiteurs d'hystone désacétylase (HDAC). Les composés sont caractérisés chimiquement par la présence d'acide hydroxamique, le zinc étant utilisé comme chélateur, et par un noyau aromatique connecté par un lieur dans lequel est présent soit un système aromatique bicyclique soit un anneau pipéridino.
• Alkyl piperidine and piperazine hydroxamic acids as HDAC inhibitors
  作者：Cristina Rossi、Marina Porcelloni、Piero D’Andrea、Christopher I. Fincham、Alessandro Ettorre、Sandro Mauro、Antonella Squarcia、Mario Bigioni、Massimo Parlani、Federica Nardelli、Monica Binaschi、Carlo A. Maggi、Daniela Fattori

  DOI：10.1016/j.bmcl.2011.02.085

  日期：2011.4

  We report here the strategy used in our research group to find a new class of histone deacetylase (HDAC) inhibitors.A series of N-substituted 4-alkylpiperazine and 4-alkylpiperidine hydroxamic acids, corresponding to the basic structure of HDAC inhibitors (zinc binding moiety-linker-capping group) has been designed, prepared, and tested for HDAC inhibition.Linker length and aromatic capping group connection were systematically varied to find the optimal geometric parameters. A new series of submicromolar inhibitors was thus identified, which showed antiproliferative activity on HCT-116 colon carcinoma cells. (C) 2011 Elsevier Ltd. All rights reserved.
• WO2006/97460
  申请人：——

  公开号：——

  公开（公告）日：——