N-cyclohexyl-7-chloroquinolin-4(1H)-one-3-carboxamide | 913534-02-8

• 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-cyclohexyl-7-chloroquinolin-4(1H)-one-3-carboxamide
• 英文别名: N-cyclohexyl-7-chloroquinolin-4(1H)-on-3-carboxamide；7-chloro-4-oxo-N'-cyclohexyl-1,4-dihydroquinoline-3-carboxamide；7-chloro-N-cyclohexyl-4-oxo-1H-quinoline-3-carboxamide
• CAS: 913534-02-8
• 化学式: C₁₆H₁₇ClN₂O₂
• 分子量: 304.776
• InChiKey: ITAGNEYRFJVQMS-UHFFFAOYSA-N

物化性质

• 熔点：
  132-135 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  514.9±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-7-chloroquinolin-4(1H)-one-3-carboxamide 、 N-(2-氯乙基)吗啉盐酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以52%的产率得到N-Cyclohexyl-7-chloro-1-[2-(4-morpholinyl)ethyl]quinolin-4(1H)-one-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New 1,8-Naphthyridin-4(1H)-on-3-carboxamide and Quinolin-4(1H)-on-3-carboxamide Derivatives as CB₂ Selective Agonists

  摘要：

  On the basis of docking studies carried out using the recently published cannabinoid receptor models,(35) new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives were designed, synthesized, and tested for their affinities toward the cannabinoid CB1 and CB2 receptors. Compound 10, which presented p-fluorobenzyl and carboxycycloheptylamide substituents bound in the 1 and 3 positions of the 1,8-naphthyiridine-4-one nucleus, showed a high CB2 affinity with a K-i of 1.0 nM. The substitution of the naphthyridine-4-one nucleus with the quinoline-4-one system determined a general increase in CB2 affinity. In particular, the N-cyclohexyl-7-chloro-1-(2-morpholin-4-ylethyl) quinolin-4(1H)-on-3-carboxamide (40) possessed a remarkable affinity, with K-i of 3.3 nM, which was also accompanied by a high selectivity for the CB2 receptor (K-i(CB1)/K-i(CB2) ratio greater than 303). Moreover, the [S-35]GTP gamma binding assay and functional studies on human basophils indicated that the 1,8-naphthyridin-4(1H)-on-3-carboxamide derivatives behaved as CB1 and CB2 receptor agonists.

  DOI：

  10.1021/jm0603466
• 作为产物：
  描述：

  3-氯苯胺 以 二苯醚 、 乙醇 为溶剂， 反应 4.5h， 生成 N-cyclohexyl-7-chloroquinolin-4(1H)-one-3-carboxamide
  参考文献：
  名称：

  4-oxoquinoline-3-carboxamide 衍生物的合成、细胞毒性和机理评估：寻找新的潜在抗癌药物。

  摘要：

  作为继续寻找新的潜在抗癌候选物的一部分，我们描述了一系列 4-oxoquinoline-3-carboxamide 衍生物作为新型抗癌剂的合成、细胞毒性和机制评估。使用 MTT 比色法测定了化合物 10-18 对三种癌细胞系的抑制活性。筛选显示，与临床使用的标准化疗药物阿霉素相比，衍生物 16b 和 17b 对胃癌细胞系具有显着的细胞毒活性，但对正常细胞系没有活性。有趣的是，当测试 16b 和 17b 对血细胞的毒性时，没有观察到溶血活性。

  DOI：

  10.3390/molecules19056651

文献信息

• New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists
  作者：Clementina Manera、Maria Grazia Cascio、Veronica Benetti、Marco Allarà、Tiziano Tuccinardi、Adriano Martinelli、Giuseppe Saccomanni、Elisa Vivoli、Carla Ghelardini、Vincenzo Di Marzo、Pier Luigi Ferrarini

  DOI：10.1016/j.bmcl.2007.09.089

  日期：2007.12

  A series of new 1,8-naphthyridine and quinoline derivatives were synthesized and evaluated for their cannabinoid receptor affinity. In particular, compounds 2, 5, 11, and 13 showed a high CB2 affinity and CB2 versus CB1 selectivity, in agreement with molecular modeling studies. Furthermore, compound 2 also exhibited in vivo antinociceptive effects. (c) 2007 Elsevier Ltd. All rights reserved.