4-(2,4-dichlorobenzoylamino)benzoic acid | 209741-68-4

• 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: 4-(2,4-dichlorobenzoylamino)benzoic acid
• 英文别名: ChemBridge ID 5272829；4-[(2,4-Dichlorobenzoyl)amino]benzoic acid
• CAS: 209741-68-4
• 化学式: C₁₄H₉Cl₂NO₃
• 分子量: 310.136
• InChiKey: LLSAQUAKECRTPM-UHFFFAOYSA-N

物化性质

• 熔点：
  274-275 °C
• 沸点：
  424.9±45.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,4-dichlorobenzoylamino)benzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以97%的产率得到苯甲酰氯,4-[(2,4-二氯苯甲酰)氨基]-
  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 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 4-(2,4-dichlorobenzoylamino)benzoic acid
  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

• 1,3,4-Oxadiazolethiol as Acyl-transfer Reagent in Acylation of Amines: a One-pot Reaction†
  作者：B. N. Goswami、N. Borthakur、A. C. Ghosh

  DOI：10.1039/a705061e

  日期：——

  Amines are acylated using 5-(2,4-dichlorophenyl)-1,3,4-oxadiazolethiol in the presence of diethyl chlorothiophosphate (DCTP) in good yield.

  胺类化合物在二乙基氯磷酸酯（DCTP）的存在下，使用5-(2,4-二氯苯基)-1,3,4-噁二唑硫醇进行酰化，产率良好。
• 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.