4-[(2,4-二氯苯甲酰基)氨基]苯甲酸乙酯 | 199180-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(2,4-二氯苯甲酰基)氨基]苯甲酸乙酯
• 英文名称: 4-(2,4-dichlorobenzoylamino)benzoic acid ethyl ester
• 英文别名: ChemBridge ID 5257899；Ethyl 4-[(2,4-dichlorobenzoyl)amino]benzoate
• CAS: 199180-10-4
• 化学式: C₁₆H₁₃Cl₂NO₃
• mdl: MFCD00018373
• 分子量: 338.19
• InChiKey: IXGUADNRLBSRDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2,4-二氯苯甲酰基)氨基]苯甲酸乙酯 在 sodium hydroxide 、 草酰氯 、 PS-DIEA resin 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2,4-dichloro-N-[4-[(2R,6S)-2,6-dimethylpiperidine-1-carbonyl]phenyl]benzamide
  参考文献：
  名称：

  Perhydroquinolylbenzamides as Novel Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  High-throughput screening identified 5 as a weak inhibitor of 11 beta-HSD1. Optimization of the structure led to a series of perhydroquinolylbenzamides, some with low nanomolar inhibitory potency. A tertiary benzamide is required for biological activity and substitution of the terminal benzamide with either electron-donating or -withdrawing groups is tolerated. The majority of the compounds show selectivity of > 20 to > 700-fold over 11 beta-HSD2. Analogues which showed >50% inhibition of 11 beta-HSD1 at 1 mu M in an cellular assay were screened in an ADX mouse model. A maximal response of > 70% reduction of liver corticosterone levels was observed for three compounds; 9m, 25 and 49.

  DOI：

  10.1021/jm058228q
• 作为产物：
  描述：

  2,4-二氯苯甲酰氯 、 苯佐卡因 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到4-[(2,4-二氯苯甲酰基)氨基]苯甲酸乙酯
  参考文献：
  名称：

  Perhydroquinolylbenzamides as Novel Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  High-throughput screening identified 5 as a weak inhibitor of 11 beta-HSD1. Optimization of the structure led to a series of perhydroquinolylbenzamides, some with low nanomolar inhibitory potency. A tertiary benzamide is required for biological activity and substitution of the terminal benzamide with either electron-donating or -withdrawing groups is tolerated. The majority of the compounds show selectivity of > 20 to > 700-fold over 11 beta-HSD2. Analogues which showed >50% inhibition of 11 beta-HSD1 at 1 mu M in an cellular assay were screened in an ADX mouse model. A maximal response of > 70% reduction of liver corticosterone levels was observed for three compounds; 9m, 25 and 49.

  DOI：

  10.1021/jm058228q

文献信息

• Insertion of Benzene Rings into the Amide Bond: One-Step Synthesis of Acridines and Acridones from Aryl Amides
  作者：Didier G. Pintori、Michael F. Greaney

  DOI：10.1021/ol902568x

  日期：2010.1.1

  Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines

  描述了使用反应性中间体苯炔将苯环插入酰胺键。用O-三氟苯基硅烷硅烷苯并炔前体处理后，芳族酰胺会顺利插入，从而以高至优异的收率生产出多种用途的氨基二苯甲酮产品。该方法完全不含金属，并已在生物活性a啶和cr啶的合成中得到了例证。
• Perhydroquinolylbenzamides as Novel Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1
  作者：Gary M. Coppola、Paivi J. Kukkola、James L. Stanton、Alan D. Neubert、Nicholas Marcopulos、Natalie A. Bilci、Hua Wang、Hollis C. Tomaselli、Jenny Tan、Thomas D. Aicher、Douglas C. Knorr、Arco Y. Jeng、Beatriz Dardik、Ricardo E. Chatelain

  DOI：10.1021/jm058228q

  日期：2005.10.1

  High-throughput screening identified 5 as a weak inhibitor of 11 beta-HSD1. Optimization of the structure led to a series of perhydroquinolylbenzamides, some with low nanomolar inhibitory potency. A tertiary benzamide is required for biological activity and substitution of the terminal benzamide with either electron-donating or -withdrawing groups is tolerated. The majority of the compounds show selectivity of > 20 to > 700-fold over 11 beta-HSD2. Analogues which showed >50% inhibition of 11 beta-HSD1 at 1 mu M in an cellular assay were screened in an ADX mouse model. A maximal response of > 70% reduction of liver corticosterone levels was observed for three compounds; 9m, 25 and 49.