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Fluorinated hydrazonoyl chlorides as precursors for synthesis of antimicrobial azoles
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-11-28 , DOI: 10.1002/jhet.4198 Sami A. Al‐Hussain 1 , Fatimah Alshehrei 2 , Magdi E. A. Zaki 1 , Marwa F. Harras 3 , Thoraya A. Farghaly 4, 5 , Zeinab A. Muhammad 6
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-11-28 , DOI: 10.1002/jhet.4198 Sami A. Al‐Hussain 1 , Fatimah Alshehrei 2 , Magdi E. A. Zaki 1 , Marwa F. Harras 3 , Thoraya A. Farghaly 4, 5 , Zeinab A. Muhammad 6
Affiliation
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Hydrazonoyl halides have been known for their ability to react with different reagents to afford wide range of bioactive heterocyclic systems as thiazoles and imidazopyrazoles. This research work focused on the synthesis of two new fluorinated hydrazonoyl chlorides and used them in synthesis of novel series of thiazole derivatives and two imidazopyrazole systems. The mechanistic pathways and the structures of all synthesized derivatives were discussed and assured based on the available spectral data. The results of antimicrobial activity of the tested thiazoles and imidazopyrazoles showed that some derivatives have moderate to no activity against tested fungi and bacteria strains. Only one derivative namely 2‐(2‐(3‐fluoro‐4‐methylphenyl)hydrazono)‐7‐(2‐oxoindolin‐3‐ylidene)‐2,7‐dihydro‐3H‐imidazo[1,2‐b]pyrazole‐3,6(5H)‐dione is the most active against Candida albicans (CA) with IZD = 20 mm, which was equipotent to ketoconazole. Furthermore, docking simulation was carried out to predict the binding pattern of the new compounds in the ATP binding site of the DNA gyrase B enzyme. The results of the docking simulation revealed that compounds 9a‐e, 12, and 13a,b fit well in the ATP binding site of DNA gyrase B with docking score values ranging from −5.883 to −6.833 kcal/mol.
中文翻译：
氟化酰氯作为合成抗菌唑的前体
众所周知，卤酰酰卤能与不同的试剂反应以提供广泛的生物活性杂环系统，如噻唑和咪唑并吡唑。这项研究工作集中于两种新型氟化new酰氯的合成，并将它们用于新型噻唑衍生物系列和两种咪唑并吡唑体系的合成。基于可获得的光谱数据，讨论并确保了所有合成衍生物的机理途径和结构。测试的噻唑和咪唑并吡唑的抗菌活性结果表明，某些衍生物对测试的真菌和细菌菌株具有中等至无活性。只有一个衍生物即2-（2-（3-氟-4-甲基苯基）亚肼基）-7-（2- oxoindolin -3-亚基）-2,7-二氢-3 ħ -咪唑并[1,2-b ]吡唑-3,6（5 H）-二酮对白色念珠菌（CA）的活性最高，IZD = 20 mm，与酮康唑相当。此外，进行对接模拟以预测新化合物在DNA回旋酶B酶的ATP结合位点的结合模式。对接模拟的结果表明，化合物9a-e，12和13a，b非常适合DNA促旋酶B的ATP结合位点，对接得分范围为-5.883至-6.833 kcal / mol。
更新日期：2020-11-28
中文翻译：
氟化酰氯作为合成抗菌唑的前体
众所周知，卤酰酰卤能与不同的试剂反应以提供广泛的生物活性杂环系统，如噻唑和咪唑并吡唑。这项研究工作集中于两种新型氟化new酰氯的合成，并将它们用于新型噻唑衍生物系列和两种咪唑并吡唑体系的合成。基于可获得的光谱数据，讨论并确保了所有合成衍生物的机理途径和结构。测试的噻唑和咪唑并吡唑的抗菌活性结果表明，某些衍生物对测试的真菌和细菌菌株具有中等至无活性。只有一个衍生物即2-（2-（3-氟-4-甲基苯基）亚肼基）-7-（2- oxoindolin -3-亚基）-2,7-二氢-3 ħ -咪唑并[1,2-b ]吡唑-3,6（5 H）-二酮对白色念珠菌（CA）的活性最高，IZD = 20 mm，与酮康唑相当。此外，进行对接模拟以预测新化合物在DNA回旋酶B酶的ATP结合位点的结合模式。对接模拟的结果表明，化合物9a-e，12和13a，b非常适合DNA促旋酶B的ATP结合位点，对接得分范围为-5.883至-6.833 kcal / mol。
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