ethyl N-benzoyl-N-(3-nitrophenyl)glycinate | 119656-67-6

• 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: ethyl N-benzoyl-N-(3-nitrophenyl)glycinate
• 英文别名: ethyl 2-(N-benzoyl-3-nitroanilino)acetate
• CAS: 119656-67-6
• 化学式: C₁₇H₁₆N₂O₅
• 分子量: 328.324
• InChiKey: LYUWILDNKFGZTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-benzoyl-N-(3-nitrophenyl)glycinate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 N-Benzoyl-N-(3-nitrophenyl)glycine
  参考文献：
  名称：

  Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety

  摘要：

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.

  DOI：

  10.1021/jm00125a017
• 作为产物：
  描述：

  N-(3-硝基苯基)苯甲酰胺 、 溴乙酸乙酯 在 sodium hydride 作用下， 生成 ethyl N-benzoyl-N-(3-nitrophenyl)glycinate
  参考文献：
  名称：

  Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety

  摘要：

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.

  DOI：

  10.1021/jm00125a017

文献信息

• PSEUDO- AND NON-PEPTIDE BRADYKININ RECEPTOR ANTAGONISTS
  申请人：SCIOS NOVA INC.

  公开号：EP0716661A1

  公开（公告）日：1996-06-19
• US5817756A
  申请人：——

  公开号：US5817756A

  公开（公告）日：1998-10-06
• [EN] PSEUDO- AND NON-PEPTIDE BRADYKININ RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR DE LA PSEUDO-BRADYKININE NON PEPTIDIQUE
  申请人：SCIOS NOVA INC.

  公开号：WO1995007294A1

  公开（公告）日：1995-03-16

  (EN) The invention provides bradykinin antagonist compounds wherein many (or all) of the peptide bonds of bradykinin are eliminated to yield compounds which specifically compete with bradykinin for binding to the bradykinin receptor. More particularly, the invention relates to compounds having, in appropriate spatial arrangement, two positively charged moieties flanking a hydrophobic organic moiety and a moiety which mimics a beta turn conformation.(FR) L'invention concerne des composés antagonistes de la bradykinine dans lesquels de nombreuses liaisons peptidiques de bradykinine (voire leur totalité) sont éliminées de manière à produire des composés pouvant rivaliser avec la bradykinine pour se fixer au récepteur de la bradykinine. L'invention porte, plus particulièrement sur des composés présentant, dans une configuration spatiale appropriée, deux fractions chargées positivement adjacentes à une fraction organique hydrophobe et à une fraction imitant la conformation d'une spire bêta.