Synthesis and Biological Screening of N-(Dimethylphenyl Substituted)-N-Ethyl/Benzyl-4-Chlorobenzenesulfonamide Derivatives

Aziz‐ur‐Rehman, I. Ahmad, M. Abbasi, S. Z. Siddiqui, K. Nafeesa, A. Sattar, Irshad Ahmed, S. Afzal
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Abstract

In the undertaken research, a number of N-dimethylphenyl substituted derivatives of N-ethyl/benzyl-4-chlorobenzenesulfonamide, (6a-f & 7a-f) was synthesized and also estimated for their biological potential. The reaction of 4-chlorobenzenesulfonyl chloride with different dimethyl substituted phenyl amine (2a-f) in the presence of basic aqueous media yielded N-[(Dimethyl substituted) phenyl]-4-chlorobenzenesulfonamides (3a-f). The targeted compounds 6a-f & 7a-f were synthesized by the reaction of compounds 3a-f with electrophiles, ethyl bromide/benzyl chloride in the presence of base NaH and polar aprotic solvent (DMF). The structures of the compounds were elucidated through H-NMR, IR and mass spectral data. The synthesized compounds (6a-f & 7a-f) were screened against Gram-negative & Gram-positive bacteria and also subjected for enzyme inhibition potential against lipoxygenase and chymotrypsin enzymes and almost all the compounds exhibited moderate to good activities.
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N-(二甲基苯基取代)-N-乙基/苄基-4-氯苯磺酰胺衍生物的合成及生物学筛选
在进行的研究中,合成了n -乙基/苄基-4-氯苯磺酰胺(6a-f和7a-f)的若干n -二甲基苯基取代衍生物,并对其生物潜力进行了估计。4-氯代苯磺酰氯与不同的二甲基取代苯胺(2a-f)在碱性水介质存在下反应生成N-[(二甲基取代)苯基]-4-氯代苯磺酰胺(3a-f)。在碱NaH和极性非质子溶剂(DMF)存在下,化合物3a-f与亲电试剂、溴乙基/氯化苄反应合成了目标化合物6a-f和7a-f。通过H-NMR、IR和质谱数据对化合物的结构进行了表征。合成的化合物(6a-f和7a-f)对革兰氏阴性菌和革兰氏阳性菌进行了筛选,并对脂氧合酶和糜凝胰蛋白酶进行了酶抑制,几乎所有化合物都表现出中等至良好的活性。
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