N-[5-(2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamino)pentyl]-4-fluorobenzamide hydrochloride | 1400976-12-6

• 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-[5-(2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamino)pentyl]-4-fluorobenzamide hydrochloride
• CAS: 1400976-12-6
• 化学式: C₂₄H₂₆FN₃O*ClH
• 分子量: 427.949
• InChiKey: OJDKFKVSJAHWDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.02
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 在 N-甲基吗啉 、 盐酸 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 sodium iodide 、 三氯氧磷 、 苯酚 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.03h， 生成 N-[5-(2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamino)pentyl]-4-fluorobenzamide hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Activity of New 2,3-dihydro-1H-cyclopenta[b]- quinoline Derivatives as Acetylcholinesterase Inhibitors

  摘要：

  本研究介绍了 4-氟苯甲酸和 2,3-二氢-1H-环戊并[b]喹啉衍生物的合成及其对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）抑制作用的生物学评价。 所获分子的合成涉及活化的 4-氟苯甲酸和 2,3-二氢-1H-环戊并[b]喹啉的氨基衍生物之间的缩合反应。根据埃尔曼分光光度法进行了抑制胆碱酯酶的生物测试。结果发现，与他克林相比，化合物 4b 和 4e 的活性较低。然而，化合物 4d、4g 和 4h 的活性与他克林相似。化合物 4a、4c 和 4f 在抑制 AChE 方面的活性高于他克林。与他克林相比，除化合物 4b 外，所有合成化合物对 AChE 的选择性都较高，而对 BChE 的选择性较低。与他克林相比，化合物 4b 对 AChE 具有相似的选择性，而对 BChE 则具有更高的选择性。

  DOI：

  10.2174/157018012801319454

文献信息

• New cyclopentaquinoline derivatives with fluorobenzoic acid induce G1 arrest and apoptosis in human lung adenocarcinoma cells
  作者：Paulina Olszewska、Jacek Szymański、Elżbieta Mikiciuk-Olasik、Paweł Szymański

  DOI：10.1016/j.ejphar.2014.02.003

  日期：2014.4

  Non-small cell lung cancer accounts for 80-85% of all lung cancer cases and is the leading cause of cancer death indicating inefficient current treatment. Act dine derivatives interact with DNA and inhibit topoisomerase leading to cell growth arrest or cell death. The aim of this study was to evaluate the effects of new synthesized sixteen 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives (cyclopentaquinoline), a member of acridine-based compounds, On the survival and growth of human lung adenocarcinoma, A549 cells. Anticancer activity of eight new cyclopentaquinoline derivatives with hydrazinonicotinic acid (compounds 1-8) and eight with fluorobenzoic acid (compounds 9-16) were screened using WST-1 assay. Interestingly, cyclopentaquinoline derivatives with fluorobenzoic moiety were found to have a higher anticancer activity than derivatives with hydrazinonicotinic acid. Four out of eight rested compounds with fluorobenzoic acid inhibited 50% cancer cell growth at concentration below 20 mu M. Moreover, the efficacy of cyclopentaquinoline derivatives containing fluorobenzoic acid correlated with increasing number of carbon atoms in the aliphatic chain. The most effective compounds (6, 15, 16) were selected to determine molecular mechanisms of their anticancer action. The results indicated that inhibition of A549 cell growth by compounds 15 and 16 was associated with a cell cycle arrest at G0/1 phase and with induction of caspase 3-dependent apoptosis. Compound 6 also caused A549 cells death due to apoptosis, however, it had no significant effect on a cell cycle progression. These findings suggest that cyclopentaquinoline derivatives containing fluorobenzoic acid with 8 and 9 carbon atoms in aliphatic chain may be promising candidate for treatment of lung cancer. (C) 2014 Elsevier B.V. All rights reserved.