(S)-methyl 2-(benzyloxycarbonylamino)-6-(N-(tert-butoxycarbonyl) sulfamoylamino)hexanoate | 960129-63-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-methyl 2-(benzyloxycarbonylamino)-6-(N-(tert-butoxycarbonyl) sulfamoylamino)hexanoate
• 英文别名: methyl (2S)-6-[(2-methylpropan-2-yl)oxycarbonylsulfamoylamino]-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 960129-63-9
• 化学式: C₂₀H₃₁N₃O₈S
• 分子量: 473.547
• InChiKey: NCPKPXZCASHGMG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(benzyloxycarbonylamino)-6-(N-(tert-butoxycarbonyl) sulfamoylamino)hexanoate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-methyl 2-amino-6-(N-(tert-butoxycarbonyl)sulfamoylamino)hexanoate
  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：

  氯磺酰异氰酸酯 、 N-(benzyloxycarbonyl)lysine methyl ester hydrochloride 、 叔丁醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以74%的产率得到(S)-methyl 2-(benzyloxycarbonylamino)-6-(N-(tert-butoxycarbonyl) sulfamoylamino)hexanoate
  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

• Sulfamides as novel histone deacetylase inhibitors
  作者：Amal Wahhab、David Smil、Alain Ajamian、Martin Allan、Yves Chantigny、Eric Therrien、Natalie Nguyen、Sukhdev Manku、Silvana Leit、Jubrail Rahil、Andrea J. Petschner、Ai-Hua Lu、Alina Nicolescu、Sylvain Lefebvre、Samuel Montcalm、Marielle Fournel、Theresa P. Yan、Zuomei Li、Jeffrey M. Besterman、Robert Déziel

  DOI：10.1016/j.bmcl.2008.11.081

  日期：2009.1

  The sulfamide moiety has been utilized to design novel HDAC inhibitors. The potency and selectivity of these inhibitors were influenced both by the nature of the scaffold, and the capping group. Linear long-chain-based analogs were primarily HDAC6-selective, while analogs based on the lysine scaffold resulted in potent HDAC1 and HDAC6 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.