4-(2,4-dichlorobenzoylamino)-3-methoxybenzoyl chloride | 867288-89-9

• 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)-3-methoxybenzoyl chloride
• 英文别名: 4-[(2,4-Dichlorobenzoyl)amino]-3-methoxybenzoyl chloride
• CAS: 867288-89-9
• 化学式: C₁₅H₁₀Cl₃NO₃
• 分子量: 358.608
• InChiKey: LBHXONQGKIGBEC-UHFFFAOYSA-N

物化性质

• 沸点：
  434.9±45.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-dichlorobenzoylamino)-3-methoxybenzoyl chloride 、 trans-decahydroquinoline 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以83%的产率得到2,4-dichloro-N-[2-methoxy-4-((4aRS,8aSR)-octahydroquinoline-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 在 lithium hydroxide 、 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 4-(2,4-dichlorobenzoylamino)-3-methoxybenzoyl chloride
  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

• 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.