(S)-ethyl 8-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylamino)-8-oxooctanoate | 1229611-68-0

• 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)-ethyl 8-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylamino)-8-oxooctanoate
• 英文别名: ethyl 8-[[(3S)-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl]amino]-8-oxooctanoate
• CAS: 1229611-68-0
• 化学式: C₂₆H₃₁N₃O₄
• 分子量: 449.55
• InChiKey: MDHCFWBSSXPTPP-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 8-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylamino)-8-oxooctanoate 在 dimethyl-t-butylhydroxylamine 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 (S)-N¹-hydroxy-N⁸-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1Hbenzo[e][1,4]diazepin-3-yl)nonanediamide
  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：

  辛二酸氢乙酯 、 (S)-3-amino-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one 在 1-羟基苯并三唑 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以60%的产率得到(S)-ethyl 8-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylamino)-8-oxooctanoate
  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

文献信息

• Design, synthesis and preliminary evaluation of a series of histone deacetylase inhibitors carrying a benzodiazepine ring
  作者：L. Guandalini、M. Balliu、C. Cellai、M.V. Martino、A. Nebbioso、C. Mercurio、V. Carafa、G. Bartolucci、S. Dei、D. Manetti、E. Teodori、S. Scapecchi、L. Altucci、F. Paoletti、M.N. Romanelli

  DOI：10.1016/j.ejmech.2013.05.017

  日期：2013.8

  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.