t-butyl N-{7-[5-(hydroxycarbamoyl)pent-1-yn-1-yl]-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl}carbamate | 1449305-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: t-butyl N-{7-[5-(hydroxycarbamoyl)pent-1-yn-1-yl]-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl}carbamate
• 英文别名: tert-butyl N-[7-[6-(hydroxyamino)-6-oxohex-1-ynyl]-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl]carbamate
• CAS: 1449305-71-8
• 化学式: C₂₇H₃₀N₄O₅
• 分子量: 490.559
• InChiKey: DVVGHYFWVHMODH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  t-butyl N-{7-[5-(hydroxycarbamoyl)pent-1-yn-1-yl]-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl}carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 6-(3-amino-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-7-yl)-N-hydroxyhex-5-ynamide hydrochloride
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of a series of histone deacetylase inhibitors carrying a benzodiazepine ring

  摘要：

  A series of new histone deacetylase inhibitors were designed and synthesized based on hybridization between SAHA or oxamflatin and 5-phenyl-1,4-benzodiazepines. The compounds were tested for their enzyme inhibitory activity on HeLa nuclear extracts, and on human recombinant HDAC1 and HDAC6. Antiproliferative activity was tested on different cancer cells types, while proapoptotic activity was primarily tested on NB4 cells. The compounds showed IC50 values similar to those of SAHA. Compound (S)-8 displayed interesting activity against hematological and solid malignancies. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.017
• 作为产物：
  描述：

  2-氨基-5-碘苯甲酮 在 copper(l) iodide 、 四(三苯基膦)钯 、 草酰氯 、 氢溴酸 、 氯甲酸乙酯 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 40.0h， 生成 t-butyl N-{7-[5-(hydroxycarbamoyl)pent-1-yn-1-yl]-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl}carbamate
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of a series of histone deacetylase inhibitors carrying a benzodiazepine ring

  摘要：

  A series of new histone deacetylase inhibitors were designed and synthesized based on hybridization between SAHA or oxamflatin and 5-phenyl-1,4-benzodiazepines. The compounds were tested for their enzyme inhibitory activity on HeLa nuclear extracts, and on human recombinant HDAC1 and HDAC6. Antiproliferative activity was tested on different cancer cells types, while proapoptotic activity was primarily tested on NB4 cells. The compounds showed IC50 values similar to those of SAHA. Compound (S)-8 displayed interesting activity against hematological and solid malignancies. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.017