Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents
Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents
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DOI：
10.1016/j.ejmech.2017.10.046
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发表时间：
2018-01-01
影响因子：
6.7
通讯作者：
Ammar, Yousry A.
中科院分区：
文献类型：
--
作者：
El Shehry, Mohamed F.;Ghorab, Mostafa M.;Ammar, Yousry A.
在开发新型抗菌剂的尝试中，已经合成了三个带有吡唑部分的喹啉衍生物系列。第一个系列的合成是通过合成4-(喹啉-2-基氧基)苯甲醛和4-(喹啉-2-基氧基)苯乙酮，然后用酮或醛衍生物处理得到相应的查耳酮。后者查耳酮与肼衍生物的环化导致形成新的吡唑啉衍生物。第二个系列的合成是通过合成2-肼基喹啉，然后用甲酰基吡唑处理得到相应的腙基吡唑衍生物。第三系列是通过乙氧基亚乙基、二硫缩醛和亚芳基衍生物处理2-肼基喹啉，得到相应的吡唑衍生物。评估合成化合物的预期抗菌和抗真菌活性；其中，大多数化合物对测试的细菌和真菌菌株表现出有效的抗菌和抗真菌活性。从 MIC 值（0.12-0.98 μg/mL）可以看出，吡唑衍生物 13b 与参比药物相比显示出更好的结果。吡唑衍生物13b在抑制福氏链霉菌生长方面表现出四倍于庆大霉素的效力（MIC 0.12 μg/mL）。此外，化合物13b在抑制棒曲霉(MIC 0.49μg/mL)和白色念珠菌(MIC 0.12μg/mL)生长方面分别显示出两性霉素B的四倍效力。相同的化合物在抑制普通疟原虫生长方面显示出庆大霉素的两倍效力（MIC 0.98 μg/mL），分别与氨苄西林和两性霉素 B 在抑制表皮葡萄球菌（MIC 0.49 μg/mL）和烟曲霉（MIC 0.98 μg/mL）生长方面的效力相当。因此，这些研究表明带有吡唑部分的喹啉衍生物是开发新型抗菌剂和抗真菌剂的有趣支架。 (C) 2017 Elsevier Masson SAS。版权所有。
In an attempt for development of new antimicrobial agents, three series of quinoline derivatives bearing pyrazole moiety have been synthesized. The first series was synthesized through the synthesis of 4-(quinolin-2-yloxy)benzaldehyde and 4-(quinolin-2-yloxy)acetophenone and then treatment with ketone or aldehyde derivatives to afford the corresponding chalcones. Cyclization of the latter chalcones with hydrazine derivatives led to the formation of new pyrazoline derivatives. The second series was synthesized via the synthesis of 2-hydrazinylquinoline and then treatment with formylpyrazoles to afford the corresponding hydrazonyl pyrazole derivatives. The third series was synthesized through the treatment of 2-hydrazinylquinoline with ethoxyethylidene, dithioacetal and arylidene derivatives to afford the corresponding pyrazole derivatives. The synthesized compounds were evaluated for their expected antibacterial and antifungal activities; where, the majority of these compounds showed potent antibacterial and antifungal activities against the tested strains of bacteria and fungi. Pyrazole derivative 13b showed better results when compared with the reference drugs as revealed from their MIC values (0.12-0.98 mu g/mL). The pyrazole derivative 13b showed fourfold potency of gentamycin in inhibiting the growth of S. flexneri (MIC 0.12 mu g/mL). Also, compound 13b showed fourfold potency of amphotericin B in inhibiting the growth of A. clavatus (MIC 0.49 mu g/mL) and C. albicans (MIC 0.12 mu g/mL), respectively. The same compound showed twofold potency of gentamycin in inhibiting the growth of P. vulgaris (MIC 0.98 mu g/mL), equipotent to the ampicillin and amphotericin B in inhibiting the growth of S. epidermidis (MIC 0.49 mu g/mL), A. fumigatus (MIC 0.98 mu g/mL), respectively. Thus, these studies suggest that quinoline derivatives bearing pyrazole moiety are interesting scaffolds for the development of novel antibacterial and antifungal agents. (C) 2017 Elsevier Masson SAS. All rights reserved.