N,N-Diisopropyl-4-(2-oxo-1,2-dihydro-quinolin-6-yl)-benzamide | 327057-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N-Diisopropyl-4-(2-oxo-1,2-dihydro-quinolin-6-yl)-benzamide
• 英文别名: 4-(2-oxo-1H-quinolin-6-yl)-N,N-di(propan-2-yl)benzamide
• CAS: 327057-78-3
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: JMNQQDJAIPRXDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-Diisopropyl-4-(2-oxo-1,2-dihydro-quinolin-6-yl)-benzamide 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、3.0 MPa 条件下， 反应 2.5h， 生成 N,N-Diisopropyl-4-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-benzamide
  参考文献：
  名称：

  6-Substituted 1H-quinolin-2-ones and 2-methoxy-quinolines: Synthesis and evaluation as inhibitors of steroid 5α reductases types 1 and 2

  摘要：

  A Negishi-type coupling reaction between 6-bromo-2-methoxyquinoline (la) and various 4-bromo-N,N-dialkyl-benzamides gave access to 6-substituted 2-methoxy-quinolines 1-3 and 1H-quinolin-2-ones 4-12. Most of these compound proved to be inhibitors of steroid 5a reductases with activity and selectivity both being strongly dependent on the features of the heterocycle and the size of the N,N-dialkylamide substituent. The most active inhibitor for the human type 2 isozyme was 6-[4-(N,N-diisopropylcarbamoyl)phenyl]-1H-quinolin-2-one 4 (K-i 800 +/- 85 nM), showing mostly competitive inhibitory patterns. A type 1 selective inhibitor could be identified with 6-[4-(N,N-diisopropylcarbamoyl)phenyl]-N (5, IC50 510 nM). (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01167-3
• 作为产物：
  描述：

  6-溴喹啉-2-酮 在 盐酸 、 叔丁基锂 、 sodium methylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 25.17h， 生成 N,N-Diisopropyl-4-(2-oxo-1,2-dihydro-quinolin-6-yl)-benzamide
  参考文献：
  名称：

  6-Substituted 1H-quinolin-2-ones and 2-methoxy-quinolines: Synthesis and evaluation as inhibitors of steroid 5α reductases types 1 and 2

  摘要：

  A Negishi-type coupling reaction between 6-bromo-2-methoxyquinoline (la) and various 4-bromo-N,N-dialkyl-benzamides gave access to 6-substituted 2-methoxy-quinolines 1-3 and 1H-quinolin-2-ones 4-12. Most of these compound proved to be inhibitors of steroid 5a reductases with activity and selectivity both being strongly dependent on the features of the heterocycle and the size of the N,N-dialkylamide substituent. The most active inhibitor for the human type 2 isozyme was 6-[4-(N,N-diisopropylcarbamoyl)phenyl]-1H-quinolin-2-one 4 (K-i 800 +/- 85 nM), showing mostly competitive inhibitory patterns. A type 1 selective inhibitor could be identified with 6-[4-(N,N-diisopropylcarbamoyl)phenyl]-N (5, IC50 510 nM). (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01167-3

文献信息

• APOCRINE CELL LINE
  申请人：Unilever PLC

  公开号：EP2126053B1

  公开（公告）日：2010-11-17