N-cyclohexyl-quinolin-4(1H)-one-3-carboxamide | 283166-82-5

• 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-quinolin-4(1H)-one-3-carboxamide
• 英文别名: 4-oxo-N'-cyclohexyl-1,4-dihydroquinoline-3-carboxamide；N-Cyclohexyl-1,4-dihydro-4-oxo-3-quinolinecarboxamide；N-cyclohexyl-4-oxo-1H-quinoline-3-carboxamide
• CAS: 283166-82-5
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: AULFDYXEUGTVRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 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-(2-氯乙基)吗啉盐酸盐 、 N-cyclohexyl-quinolin-4(1H)-one-3-carboxamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以50%的产率得到N-cyclohexyl-1-(2-(morpholin-4-yl)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：

  2-苯基氨基亚甲基-丙二酸二乙酯 以 二苯醚 为溶剂， 反应 1.5h， 生成 N-cyclohexyl-quinolin-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

• Quinolones:  Novel Probes in Antifilarial Chemotheraphy^,
  作者：Sanjay K. Srivastava、Prem M. S. Chauhan、Amiya P. Bhaduri、Nigar Fatima、Ranjit K. Chatterjee

  DOI：10.1021/jm990438d

  日期：2000.6.1

  Quinolones have been discovered in our laboratory as a new class of antifilarial agents. This has led to the design, synthesis, and antifilarial evaluation of a number of N-substituted quinol-4(1H)-one-3-carboxamide derivatives 4-6. The macrofilaricidal activity of the target compounds was initially evaluated in vivo against Acanthoeilonema viteae by oral administration of 200 mg/kg x 5 days. Among all the synthesized compounds, 13 displayed activity,with the most potent compound (4a) exhibiting 100% macrofilaricidal and 90% microfilaricidal activities. Compound 4e elicited significant macrofilaricidal (80%) response while compound 5c showed 100% sterilization of female worms. Finally, the two most potent macrofilaricidal compounds, namely 4a and 4e, have been screened for their potency against DNA topoisomerase II, and it has been observed that both have the capability to interfere with this enzyme at 10 mu mol/mL concentration. The structure-activity relationship (SAR) associated with position-3 and aryl ring substituents is discussed.