methyl 3-(4-aminobenzamido)propanoate | 342626-46-4

• 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: methyl 3-(4-aminobenzamido)propanoate
• 英文别名: N-(4-amino-benzoyl)-β-alanine methyl ester；methyl N-(4-aminobenzoyl)-beta-alaninate；Methyl 3-[(4-aminobenzoyl)amino]propanoate
• CAS: 342626-46-4
• 化学式: C₁₁H₁₄N₂O₃
• mdl: MFCD11505360
• 分子量: 222.244
• InChiKey: AGYOUYKNKGJRHR-UHFFFAOYSA-N

物化性质

• 沸点：
  448.5±30.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-aminobenzamido)propanoate 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 3-(4-(1H-indole-2-carboxamido)benzamido)propanoic acid
  参考文献：
  名称：

  N-Phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATP Competitive DNA Gyrase B Inhibitors: Design, Synthesis, and Evaluation

  摘要：

  Bacterial DNA gyrase is a well-known and validated target in the design of antibacterial drugs. However, inhibitors of its ATP binding subunit, DNA gyrase B (GyrB), have so far not reached clinical use. In the present study, three different series of N-phenyl-4,5-dibromop-yrrolamides and N-phenylindolamides were designed and prepared as potential DNA gyrase B inhibitors. The IC50 values of compounds on DNA gyrase from Escherichia coli were in the low micromolar range, with the best compound, (4-(4,5-dibromo-1H-pyrrole-2-carboxamido)benzoyl)glycine (18a), displaying an IC50 of 450 nM. For this compound, a high-resolution crystal structure in complex with E. coli DNA gyrase B was obtained, revealing details of its binding mode within the active site. The binding affinities. of three compounds with GyrB were additionally evaluated by surface plasmon resonance, and the results were in good agreement with the determined enzymatic activities. For the most promising compounds, the inhibitory activities against DNA gyrase from Staphylococcus aureus and topoisomerases IV from E. coli and S. aureus were determined. Antibacterial activities of the most potent compounds of each series were evaluated against two Gram-positive and two Gram-negative bacterial strains. The results obtained in this study provide valuable information on the binding mode and structure activity relationship of N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides as promising classes of ATP competitive GyrB inhibitors. IC50 =450 nM

  DOI：

  10.1021/acs.jmedchem.5b00775
• 作为产物：
  描述：

  methyl 3-(4-nitrobenzamido)propanoate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以99%的产率得到methyl 3-(4-aminobenzamido)propanoate
  参考文献：
  名称：

  N-Phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATP Competitive DNA Gyrase B Inhibitors: Design, Synthesis, and Evaluation

  摘要：

  Bacterial DNA gyrase is a well-known and validated target in the design of antibacterial drugs. However, inhibitors of its ATP binding subunit, DNA gyrase B (GyrB), have so far not reached clinical use. In the present study, three different series of N-phenyl-4,5-dibromop-yrrolamides and N-phenylindolamides were designed and prepared as potential DNA gyrase B inhibitors. The IC50 values of compounds on DNA gyrase from Escherichia coli were in the low micromolar range, with the best compound, (4-(4,5-dibromo-1H-pyrrole-2-carboxamido)benzoyl)glycine (18a), displaying an IC50 of 450 nM. For this compound, a high-resolution crystal structure in complex with E. coli DNA gyrase B was obtained, revealing details of its binding mode within the active site. The binding affinities. of three compounds with GyrB were additionally evaluated by surface plasmon resonance, and the results were in good agreement with the determined enzymatic activities. For the most promising compounds, the inhibitory activities against DNA gyrase from Staphylococcus aureus and topoisomerases IV from E. coli and S. aureus were determined. Antibacterial activities of the most potent compounds of each series were evaluated against two Gram-positive and two Gram-negative bacterial strains. The results obtained in this study provide valuable information on the binding mode and structure activity relationship of N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides as promising classes of ATP competitive GyrB inhibitors. IC50 =450 nM

  DOI：

  10.1021/acs.jmedchem.5b00775

文献信息

• Thiazole Derivatives and Use Thereof
  申请人：Quattropani Anna

  公开号：US20090029998A1

  公开（公告）日：2009-01-29

  The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及公式（I）的噻唑衍生物，特别是用于治疗和/或预防自身免疫性疾病和/或炎症性疾病，心血管疾病，神经退行性疾病，细菌或病毒感染，肾脏疾病，血小板聚集，癌症，移植，移植排斥或肺损伤。
• THIAZOLE DERIVATIVES AND USE THEREOF
  申请人：QUATTROPANI Anna

  公开号：US20140228365A1

  公开（公告）日：2014-08-14

  The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neturodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及式(I)的噻唑衍生物，特别是用于治疗和/或预防自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植、移植排斥或肺损伤。
• [EN] THIAZOLE DERIVATIVES AND USE THEREOF<br/>[FR] DERIVES THIAZOLE ET UTILISATION DE CES DERIVES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005068444A3

  公开（公告）日：2005-09-09
• Varma,R.S.; Kapoor,A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 325 - 326
  作者：Varma,R.S.、Kapoor,A.

  DOI：——

  日期：——
• VARMA R. S.; KAPOOR A., INDIAN J. CHEM., 1978, B 16, NO 4, 325-326
  作者：VARMA R. S.、 KAPOOR A.

  DOI：——

  日期：——