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Synthesis and Antibacterial Activities of New 2-(Benzylthio)pyrimidines and 2-(Benzimidazolylmethylthio)pyrimidines Derivatives

Synthesis and Antibacterial Activities of New 2-(Benzylthio)pyrimidines and 2-(Benzimidazolylmethylthio)pyrimidines Derivatives
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摘要 A series of 2-<span style="font-family:Verdana;">(</span><span style="font-family:Verdana;">benzylthio</span><span style="font-family:Verdana;">)</span><span style="font-family:;" "=""><span style="font-family:Verdana;">pyrimidines (</span><b><span style="font-family:Verdana;">6a-l</span></b><span style="font-family:Verdana;">) and</span></span><span style="font-family:Verdana;"> 2-(benzimidazolylmethylthio</span><span style="font-family:Verdana;">)-</span><span style="font-family:;" "=""><span style="font-family:Verdana;">pyrimidines derivatives (</span><b><span style="font-family:Verdana;">6m</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">6n</span></b><span style="font-family:Verdana;">) analogues of ethyl 2-(benzylthio)-6-methyl-</span></span><span style="font-family:Verdana;">4-phenyl-1,4-dihydropyrimidine-5-carboxylates and ethyl 2-(((1H-benzimi</span><span style="font-family:;" "=""><span style="font-family:Verdana;">da</span><span style="font-family:Verdana;">zol-</span></span><span style="font-family:Verdana;">2-yl)methyl)thio)-6-methyl-4-phenyl-1,4-dihydropyri</span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">midine-5-carboxy</span><span style="font-family:Verdana;">l</span><span style="font-family:Verdana;">ates</span><span style="font-family:;" "=""> </span><span style="font-family:Verdana;">were prepared and evaluated for antibacterial activity. These com</span><span style="font-family:;" "=""><span style="font-family:Verdana;">pounds were </span><span><span style="font-family:Verdana;">obtained by condensation of 2-thiopyrimidines (</span><b><span style="font-family:Verdana;">4</span></b><span style="font-family:Verdana;">) with benzyl halides or</span></span><span style="font-family:Verdana;"> 2-</span></span><span style="font-family:;" "=""><span style="font-family:Verdana;">(chloromethyl)-</span><i><span style="font-family:Verdana;">1H</span></i><span style="font-family:Verdana;">-benzimidazole (</span><b><span style="font-family:Verdana;">5</span></b><span style="font-family:Verdana;">) in the presence of a base. All com</span></span><span style="font-family:;" "=""><span style="font-family:Verdana;">pounds were characterized by </span><sup><span style="font-family:Verdana;">1</span></sup><span style="font-family:Verdana;">H, </span><sup><span style="font-family:Verdana;">13</span></sup><span style="font-family:Verdana;">C and HRMS spectra. Out of fourteen, only eight compounds were screened against multi-resistant strains of </span><i><span style="font-family:Verdana;">Escherichia</span></i> <i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;"> and </span><i><span style="font-family:Verdana;">Staphylococcus</span></i> <i><span style="font-family:Verdana;">aureus</span></i><span style="font-family:Verdana;">. The results revealed that all of them were found </span><span style="font-family:Verdana;">to possess significant antibacterial activity against the germs tested.</span><span style="font-family:Verdana;"> Compounds </span><b><span style="font-family:Verdana;">6c</span></b><span style="font-family:Verdana;">, </span><b><span style="font-family:Verdana;">6d</span></b><span style="font-family:Verdana;">, </span><b><span style="font-family:Verdana;">6h</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">6m</span></b><span style="font-family:Verdana;"> were more active on </span><i><span style="font-family:Verdana;">S</span></i><span style="font-family:Verdana;">. </span><i><span style="font-family:Verdana;">aureus</span></i><span style="font-family:Verdana;"> and compounds </span><b><span style="font-family:Verdana;">6h</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">6m</span></b><span style="font-family:Verdana;"> more active on </span><i><span style="font-family:Verdana;">E</span></i><span style="font-family:Verdana;">. </span><i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;">.</span></span> A series of 2-<span style="font-family:Verdana;">(</span><span style="font-family:Verdana;">benzylthio</span><span style="font-family:Verdana;">)</span><span style="font-family:;" "=""><span style="font-family:Verdana;">pyrimidines (</span><b><span style="font-family:Verdana;">6a-l</span></b><span style="font-family:Verdana;">) and</span></span><span style="font-family:Verdana;"> 2-(benzimidazolylmethylthio</span><span style="font-family:Verdana;">)-</span><span style="font-family:;" "=""><span style="font-family:Verdana;">pyrimidines derivatives (</span><b><span style="font-family:Verdana;">6m</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">6n</span></b><span style="font-family:Verdana;">) analogues of ethyl 2-(benzylthio)-6-methyl-</span></span><span style="font-family:Verdana;">4-phenyl-1,4-dihydropyrimidine-5-carboxylates and ethyl 2-(((1H-benzimi</span><span style="font-family:;" "=""><span style="font-family:Verdana;">da</span><span style="font-family:Verdana;">zol-</span></span><span style="font-family:Verdana;">2-yl)methyl)thio)-6-methyl-4-phenyl-1,4-dihydropyri</span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">midine-5-carboxy</span><span style="font-family:Verdana;">l</span><span style="font-family:Verdana;">ates</span><span style="font-family:;" "=""> </span><span style="font-family:Verdana;">were prepared and evaluated for antibacterial activity. These com</span><span style="font-family:;" "=""><span style="font-family:Verdana;">pounds were </span><span><span style="font-family:Verdana;">obtained by condensation of 2-thiopyrimidines (</span><b><span style="font-family:Verdana;">4</span></b><span style="font-family:Verdana;">) with benzyl halides or</span></span><span style="font-family:Verdana;"> 2-</span></span><span style="font-family:;" "=""><span style="font-family:Verdana;">(chloromethyl)-</span><i><span style="font-family:Verdana;">1H</span></i><span style="font-family:Verdana;">-benzimidazole (</span><b><span style="font-family:Verdana;">5</span></b><span style="font-family:Verdana;">) in the presence of a base. All com</span></span><span style="font-family:;" "=""><span style="font-family:Verdana;">pounds were characterized by </span><sup><span style="font-family:Verdana;">1</span></sup><span style="font-family:Verdana;">H, </span><sup><span style="font-family:Verdana;">13</span></sup><span style="font-family:Verdana;">C and HRMS spectra. Out of fourteen, only eight compounds were screened against multi-resistant strains of </span><i><span style="font-family:Verdana;">Escherichia</span></i> <i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;"> and </span><i><span style="font-family:Verdana;">Staphylococcus</span></i> <i><span style="font-family:Verdana;">aureus</span></i><span style="font-family:Verdana;">. The results revealed that all of them were found </span><span style="font-family:Verdana;">to possess significant antibacterial activity against the germs tested.</span><span style="font-family:Verdana;"> Compounds </span><b><span style="font-family:Verdana;">6c</span></b><span style="font-family:Verdana;">, </span><b><span style="font-family:Verdana;">6d</span></b><span style="font-family:Verdana;">, </span><b><span style="font-family:Verdana;">6h</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">6m</span></b><span style="font-family:Verdana;"> were more active on </span><i><span style="font-family:Verdana;">S</span></i><span style="font-family:Verdana;">. </span><i><span style="font-family:Verdana;">aureus</span></i><span style="font-family:Verdana;"> and compounds </span><b><span style="font-family:Verdana;">6h</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">6m</span></b><span style="font-family:Verdana;"> more active on </span><i><span style="font-family:Verdana;">E</span></i><span style="font-family:Verdana;">. </span><i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;">.</span></span>
作者 Achi Patrick-Armand Coulibali Siomenan Zon Doumade Timotou Adéyolé Bolou Eric Touré Daouda Sissouma Drissa Adjou Ané Achi Patrick-Armand;Coulibali Siomenan;Zon Doumade;Timotou Adéyolé;Bolou Eric;Touré Daouda;Sissouma Drissa;Adjou Ané(Laboratoire de Constitution et Réaction de la Matière, UFR Sciences des Structures de la Matière et Technologie, Université Félix Houphou&#235t Boigny de Cocody, Abidjan, C&#244te d’Ivoire;Département de Mathématiques-Physique-Chimie, UFR des Sciences Biologiques, Université Peleforo Gon Coulibaly, Korhogo, C&#244te d’Ivoire;Centre National de Floristique, Université Félix Houphou&#235t-Boigny de Cocody, Abidjan, C&#244te d’Ivoire;Département de Biochimie-Génétique, UFR des Sciences Biologiques, Université Peleforo Gon Coulibaly, Korhogo, C&#244te d’Ivoire)
出处 《Open Journal of Medicinal Chemistry》 CAS 2021年第3期27-39,共13页 药物化学期刊(英文)
关键词 2-Thiopyrimidine Benzylthiouracil BENZIMIDAZOLE Antibacterial Activity 2-Thiopyrimidine Benzylthiouracil Benzimidazole Antibacterial Activity
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