tert-butyl [2-({4-[5-(hydroxymethyl)-1,3-thiazol-2-yl]benzoyl}amino)phenyl]carbamate | 891863-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl [2-({4-[5-(hydroxymethyl)-1,3-thiazol-2-yl]benzoyl}amino)phenyl]carbamate
• 英文别名: tert-butyl N-[2-[[4-[5-(hydroxymethyl)-1,3-thiazol-2-yl]benzoyl]amino]phenyl]carbamate
• CAS: 891863-13-1
• 化学式: C₂₂H₂₃N₃O₄S
• 分子量: 425.508
• InChiKey: JRWCJHMYRVCDDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl [2-({4-[5-(hydroxymethyl)-1,3-thiazol-2-yl]benzoyl}amino)phenyl]carbamate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 C₂₃H₂₅N₃O₆S₂
  参考文献：
  名称：

  Design and campaign synthesis of piperidine- and thiazole-based histone deacetylase inhibitors

  摘要：

  A lead benzamide, 3, was identified as a potent and low molecular weight histone deacetylase ( HDAC) inhibitor. Optimization led to 16d, demonstrating an excellent balance of efficacy and non-efficacy properties, along with very desirable in vivo DMPK. The final compounds presented are > 1000-fold more potent than the initial screen hit, an improvement in potency which was achieved with a concomitant significant improvement in all the main non-efficacy properties. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.041
• 作为产物：
  描述：

  tert-butyl (2-{[4-(5-formyl-1,3-thiazol-2-yl)benzoyl]amino}phenyl)carbamate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以97%的产率得到tert-butyl [2-({4-[5-(hydroxymethyl)-1,3-thiazol-2-yl]benzoyl}amino)phenyl]carbamate
  参考文献：
  名称：

  Design and campaign synthesis of piperidine- and thiazole-based histone deacetylase inhibitors

  摘要：

  A lead benzamide, 3, was identified as a potent and low molecular weight histone deacetylase ( HDAC) inhibitor. Optimization led to 16d, demonstrating an excellent balance of efficacy and non-efficacy properties, along with very desirable in vivo DMPK. The final compounds presented are > 1000-fold more potent than the initial screen hit, an improvement in potency which was achieved with a concomitant significant improvement in all the main non-efficacy properties. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.041

文献信息

• N-(2-AMINIPHENYL)-4-(5-((ETHYLAMINO)METHYL)-1,2-THIAZOL-2-YL) BENZAMIDE AND N-(2-AMINOPHENYL)-4-(5-((ISOPROPYLAMINO)METHYL)-1,2-THIAZOL-2-YL) BENZAMIDE AS HDAC INHIBITORS
  申请人：Stokes Elaine Sophie, Elizabeth

  公开号：US20090312556A1

  公开（公告）日：2009-12-17

  The invention concerns novel benzamide compounds of Formula (I): wherein R wherein is ethyl or isopropyl; or a pharmaceutically acceptable salt or pro-drug form thereof. The invention also concerns processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions, which are sensitive to the inhibition of histone deacetylase (HDAC).

  该发明涉及公式（I）的新型苯甲酰胺化合物，其中R为乙基或异丙基；或其药学上可接受的盐或前药形式。该发明还涉及制备这种化合物的方法，含有它们的制药组合物以及它们在制造用作抗增殖剂的药物中的使用，用于预防或治疗对组蛋白去乙酰化酶（HDAC）抑制敏感的肿瘤或其他增殖性疾病。
• WO2006/64246
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] N- (2-AMINOPHENYL) -4- (5- ((ETHYLAMINO) METHYL) 1,3-THIAZOL-2-YL) BENZAMIDE AND N- (2-AMINOPHEYNL) -4- (5- ((ISOPROPYLAMINO) METHYL) -1,3-THIAZOL-2-YL) BENZAMIDE AS HDAC INHIBITORS<br/>[FR] N- (2-AMINOPHENYL) -4- (5- ((ETHYLAMINO) METHYL) 1,3-THIAZOL-2-YL) BENZAMIDE ET N- (2-AMINOPHENYL) -4- (5- ((ISOPROPYLAMINO) METHYL) -1,3-THIAZOL-2-YL) BENZAMIDE EN TANT QU'INHIBITEURS D'HDAC
  申请人：ASTRAZENECA AB

  公开号：WO2006064246A1

  公开（公告）日：2006-06-22

  [EN] The invention concerns novel benzamide compounds of Formula ( I ): wherein R wherein is ethyl or isopropyl; or a pharmaceutically acceptable salt or pro-drug form thereof. The invention also concerns processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions, which are sensitive to the inhibition of histone deacetylase (HDAC).
  [FR] La présente invention concerne de nouveaux composés de benzamide de formule ( I ) : dans laquelle R est éthyle ou isopropyle; ou un sel ou promédicament pharmaceutiquement acceptable de ceux-ci. Cette invention concerne également des procédés de préparation de ces composés, des compositions pharmaceutiques les contenant ainsi que leur utilisation pour la fabrication d'un médicament destiné à être utilisé en tant qu'agent antiprolifératif dans la prévention ou le traitement de tumeurs ou autres maladies prolifératives sensibles à l'inhibition de l'histone déacétylase (HDAC).
• Design and campaign synthesis of piperidine- and thiazole-based histone deacetylase inhibitors
  作者：David M. Andrews、Elaine S.E. Stokes、Greg R. Carr、Zbigniew S. Matusiak、Craig A. Roberts、Michael J. Waring、Madeleine C. Brady、Christine M. Chresta、Simon J. East

  DOI：10.1016/j.bmcl.2008.03.041

  日期：2008.4

  A lead benzamide, 3, was identified as a potent and low molecular weight histone deacetylase ( HDAC) inhibitor. Optimization led to 16d, demonstrating an excellent balance of efficacy and non-efficacy properties, along with very desirable in vivo DMPK. The final compounds presented are > 1000-fold more potent than the initial screen hit, an improvement in potency which was achieved with a concomitant significant improvement in all the main non-efficacy properties. (c) 2008 Elsevier Ltd. All rights reserved.