benzyl (3-(4,5-dimethoxy-2-nitrophenyl)-2-oxopropamido)acetate | 912849-97-9

• 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: benzyl (3-(4,5-dimethoxy-2-nitrophenyl)-2-oxopropamido)acetate
• 英文别名: [3-(4,5-Dimethoxy-2-nitro-phenyl)-2-oxo-propionylamino]-acetic acid benzyl ester；Benzyl 2-[[3-(4,5-dimethoxy-2-nitrophenyl)-2-oxopropanoyl]amino]acetate；benzyl 2-[[3-(4,5-dimethoxy-2-nitrophenyl)-2-oxopropanoyl]amino]acetate
• CAS: 912849-97-9
• 化学式: C₂₀H₂₀N₂O₈
• 分子量: 416.387
• InChiKey: ZSNYKKSLSVCFNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (3-(4,5-dimethoxy-2-nitrophenyl)-2-oxopropamido)acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以94%的产率得到N-[(5,6-dimethoxy-1H-indol-2-yl)carbonyl]glycine
  参考文献：
  名称：

  From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

  摘要：

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.095
• 作为产物：
  描述：

  6-硝基藜芦醛 在 盐酸 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.5h， 生成 benzyl (3-(4,5-dimethoxy-2-nitrophenyl)-2-oxopropamido)acetate
  参考文献：
  名称：

  From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

  摘要：

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.095

文献信息

• Dual Antitubercular and Antileishmanial Profiles of Quinoxaline Di-N-Oxides Containing an Amino Acidic Side Chain
  作者：Juan F. González、María-Auxiliadora Dea-Ayuela、Lena Huck、José María Orduña、Francisco Bolás-Fernández、Elena de la Cuesta、Nazia Haseen、Ashraf Ali Mohammed、J. Carlos Menéndez

  DOI：10.3390/ph17040487

  日期：——

  We present a new category of quinoxaline di-N-oxides (QdNOs) containing amino acid side chains with dual antituberculosis and antileishmanial activity. These compounds were synthesized by combining a regioselective 2,5-piperazinedione opening and a Beirut reaction and were screened for their activity against Mycobacterium tuberculosis and the promastigote and amastigote forms of representative species

  我们提出了一类新的喹喔啉二氮氧化物 (QdNOs)，其含有氨基酸侧链，具有双重抗结核和抗利什曼胺活性。这些化合物是通过结合区域选择性 2,5-哌嗪二酮开环和贝鲁特反应来合成的，并筛选了它们对结核分枝杆菌以及利什曼原虫属代表性物种的前鞭毛体和无鞭毛体形式的活性。大多数 QdNO 表现出有希望的抗结核活性，IC50 值范围为 4.28 至 49.95 μM，与临床开发的药物相当。构效关系分析强调了芳环和侧链上取代基的重要性。抗利什曼原虫测试表明，一些选定的化合物表现出与阳性对照米替福辛相当的抗亚马逊利什曼原虫和杜氏利什曼原虫前鞭毛体的活性。值得注意的是，在针对亚马逊利什曼原虫的细胞内无鞭毛体测定中，发现一些化合物比米替福辛更有效且毒性更低。该化合物表现出最佳的双重抗结核和杀利什曼病特性以及良好的选择性指数4h，可以被视为一种热门化合物，为开发针对合并感染的综合疗法开辟了新的机会。
• From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics
  作者：Juan Francisco González、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/j.tetlet.2006.07.095

  日期：2006.9

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.