(S)-tert-butyl 5-(benzyloxycarbonylamino)-5-(5-phenyl-1H-1,2,4-triazol-3-yl)pentylcarbamate | 960130-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-tert-butyl 5-(benzyloxycarbonylamino)-5-(5-phenyl-1H-1,2,4-triazol-3-yl)pentylcarbamate
• 英文别名: (S)-benzyl 5-t-butoxycarbonylamino-1-(5-phenyl-1H-1,2,4-triazol-3-yl)pentylcarbamate；benzyl N-[(1S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-1-(3-phenyl-1H-1,2,4-triazol-5-yl)pentyl]carbamate
• CAS: 960130-56-7
• 化学式: C₂₆H₃₃N₅O₄
• 分子量: 479.579
• InChiKey: GCLZWCZSMCEQRN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 5-(benzyloxycarbonylamino)-5-(5-phenyl-1H-1,2,4-triazol-3-yl)pentylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-benzyl 5-amino-1-(5-phenyl-1H-1,2,4-triazol-3-yl)pentylcarbamate
  参考文献：
  名称：

  Synthesis and evaluation of lysine derived sulfamides as histone deacetylase inhibitors

  摘要：

  We have recently reported on a novel class of histone deacetylase (HDAC) inhibitors bearing a sulfamide group as the zinc-binding unit. Herein, we report on the synthesis of sulfamide based inhibitors designed around a lysine scaffold and their structure-activity relationships against HDAC1 and HDAC6 isotypes as well as 293T cells. Our efforts led us to an improvement of the originally disclosed lysine-based sulfamide, 2a to compound 12h which has equal potency in enzyme and cell-based assays as well as enhanced metabolic stability and PK profile. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.075
• 作为产物：
  描述：

  苯甲亚胺酸甲酯盐酸盐 、 Z-Lys-(BOC)-hydrazid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以100%的产率得到(S)-tert-butyl 5-(benzyloxycarbonylamino)-5-(5-phenyl-1H-1,2,4-triazol-3-yl)pentylcarbamate
  参考文献：
  名称：

  SULFAMIDE AND SULFAMATE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS

  摘要：

  这项发明涉及用于抑制组蛋白去乙酰化酶的化合物。更具体地，该发明提供了符合式(I)的化合物，以及它们的外消旋和内消旋混合物、非对映体和对映体： 或其N-氧化物、水合物、溶剂合物、药学上可接受的盐、前药或其复合物，其中Y、L、Z、W、M、R a 、R b 和R c 如规范中所定义。

  公开号：

  US20070293530A1

文献信息

• SULFAMIDE AND SULFAMATE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS
  申请人：Smil David

  公开号：US20070293530A1

  公开（公告）日：2007-12-20

  This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I), and racemic and scalemic mixtures, diastereomers and enantiomers thereof: or an N-oxide, hydrate, solvate, pharmaceutically acceptable salt, prodrug or complex thereof, wherein Y, L, Z, W, M, R a , R b and R c are as defined in the specification.

  这项发明涉及用于抑制组蛋白去乙酰化酶的化合物。更具体地，该发明提供了符合式(I)的化合物，以及它们的外消旋和内消旋混合物、非对映体和对映体： 或其N-氧化物、水合物、溶剂合物、药学上可接受的盐、前药或其复合物，其中Y、L、Z、W、M、R a 、R b 和R c 如规范中所定义。
• [EN] SIRTUIN INHIBITORS<br/>[FR] INHIBITEURS DE SIRTUINE
  申请人：METHYLGENE INC

  公开号：WO2009026701A1

  公开（公告）日：2009-03-05

  This invention relates to compounds and methods for the inhibition of sirtuin enzymatic activity. More particularly, the invention provides for compounds of formula (I), Y__L__Z__D, and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein Y, L, Z and D are as defined in the specification.

  这项发明涉及化合物和用于抑制sirtuin酶活性的方法。更具体地，该发明提供了式(I)的化合物，Y__L__Z__D，以及其N-氧化物、水合物、溶剂合物、药用可接受盐、前药和复合物，以及它们的外消旋和内消旋混合物、非对映体和对映体，其中Y、L、Z和D如规范中所定义。
• [EN] SULFAMIDE AND SULFAMATE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] SULFAMIDE ET DÉRIVÉS DE SULFAMATE COMME INHIBITEURS DE DÉSACÉTYLASE D'HISTONE
  申请人：METHYLGENE INC

  公开号：WO2007143822A1

  公开（公告）日：2007-12-21

  [EN] This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I), and racemic and scalemic mixtures, diastereomers and enantiomers thereof: (I) or an N-oxide, hydrate, solvate, pharmaceutically acceptable salt, prodrug or complex thereof, wherein Y, L, Z, W, M, R^a, R^b and R^c are as defined in the specification.
  [FR] La présente invention concerne des composés pour l'inhibition de la désacétylase d'histone. Plus particulièrement, l'invention propose des composés de formule (I), et des mélanges racémiques et scalémiques, des diastéréomères et énantiomères de ceux-ci : (I) ou un N-oxyde, un hydrate, un solvate, un sel pharmaceutiquement acceptable, un médicament précurseur ou un complexe de ceux-ci, dans lesquels Y, L, Z, W, M, R^a, R^b et R^csont comme défini dans le mémoire.
• Synthesis and evaluation of lysine derived sulfamides as histone deacetylase inhibitors
  作者：Sukhdev Manku、Martin Allan、Natalie Nguyen、Alain Ajamian、Jacques Rodrigue、Eric Therrien、James Wang、Tim Guo、Jubrail Rahil、Andrea J. Petschner、Alina Nicolescu、Sylvain Lefebvre、Zuomei Li、Marielle Fournel、Jeffrey M. Besterman、Robert Déziel、Amal Wahhab

  DOI：10.1016/j.bmcl.2009.02.075

  日期：2009.4

  We have recently reported on a novel class of histone deacetylase (HDAC) inhibitors bearing a sulfamide group as the zinc-binding unit. Herein, we report on the synthesis of sulfamide based inhibitors designed around a lysine scaffold and their structure-activity relationships against HDAC1 and HDAC6 isotypes as well as 293T cells. Our efforts led us to an improvement of the originally disclosed lysine-based sulfamide, 2a to compound 12h which has equal potency in enzyme and cell-based assays as well as enhanced metabolic stability and PK profile. (C) 2009 Elsevier Ltd. All rights reserved.