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Journals / Turkish Journal of Pharmaceutical Sciences / 2015 / Cilt: 12 - Sayı: 3

Bazı N-(fenetil)-4-acetamidobenzenesulfonamide türevlerinin Sentezi ile Antibakteriyel ve Lipoksijenaz İnhibitör Çalışmaları

Synthesis, Antibacterial and Lipoxygenase Inhibition Studies on Some N-(4-{[(Alkyl/aralkyl)(phenethyl)amino]sulfonyl}phenyl) acetamides

A Muhammad ABBASI
Rabia KHIZER
Aziz-ur REHMAN
Z Sabahat SIDDIQUI
Kaniz RUBAB
Rabia MALIK
Irshad AHMAD
A. Syed Adnan SHAH
Pages
257–266
DOI
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Moreover, N-­-(4-­-{[(4-­-chlorobenzyl)(phenethyl)amino]sulfonyl}phenyl) acetamide (5c) proved to be a possible inhibitor of lipoxygenase enzyme having IC50 of 135.31±0.81 µM relative to Baicalein which was taken as a reference.

📌 3 Key Takeaways

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Objective & Hypothesis:In the present study, 2-phenyl-1-ethanamine (phenethyl amine;1) was reacted with 4-acetamido benzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to achieve N-{4- [(phenethylamino)sulfonyl]phenyl}acetamide (3) which was further reacted with different alkyl/aralkyl halides, 4a-f, in polar aprotic solvent, N,N-dimethylformamide (DMF) and sodium hydride as base to afford various N-substituted derivatives of 3.
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Key Findings & Data:Structural elucidation of N-{4-[(phenethylamino)sulfonyl] phenyl}acetamide derivatives, 5a-f, was done by IR,1 H-NMR and mass spectral analysis.
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Conclusion & Impact:Moreover, N-­-(4-­-{[(4-­-chlorobenzyl)(phenethyl)amino]sulfonyl}phenyl) acetamide (5c) proved to be a possible inhibitor of lipoxygenase enzyme having IC50 of 135.31±0.81 µM relative to Baicalein which was taken as a reference.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

In the present study, 2-phenyl-1-ethanamine (phenethyl amine;1) was reacted with 4-acetamido benzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to achieve N-{4- [(phenethylamino)sulfonyl]phenyl}acetamide (3) which was further reacted with different alkyl/aralkyl halides, 4a-f, in polar aprotic solvent, N,N-dimethylformamide (DMF) and sodium hydride as base to afford various N-substituted derivatives of 3. Structural elucidation of N-{4-[(phenethylamino)sulfonyl] phenyl}acetamide derivatives, 5a-f, was done by IR,1 H-NMR and mass spectral analysis. Parent molecule 3, as well as N-substituted derivatives 5a, 5b, 5e and 5f revealed good to moderate antibacterial potential against various Gram-positive and Gram-negative bacterial strains as compared to standard, ciprofloxacin. Moreover, N-­-(4-­-{[(4-­-chlorobenzyl)(phenethyl)amino]sulfonyl}phenyl) acetamide (5c) proved to be a possible inhibitor of lipoxygenase enzyme having IC50 of 135.31±0.81 µM relative to Baicalein which was taken as a reference.

Özet

Bu çalışmada 2- fenil-1-etanamin (1), N-{[(4-fenetil)aminosülfonil] fenil}-asetamit (3) elde etmek üzere 10% sulu Na2CO3 mevcudiyetinde 4-asetamidobenzensülfonil klorür (2) ile reaksiyona sokulmuş, sonrasında 3 numaralı bileşiğin N-sübstitüe türevlerini elde etmek üzere polar protik solvan DMF ve baz olarak da sodium hidrür kullanılarak farklı alkil halojenürlerle (4a-f) muamele edilmiştir. N-{4[(fenetilamino)sülfonil]fenil}asetamid (5a-f) türevlerinin yapı aydınlatılması IR,1H-NMR ve mass spektral analizlerle yapılmıştır. Ana bileşik (3) ve N- sübstitüe türevlerinin (5a, 5b, 5e ve 5f) çeşitli gram-pozitif ve gram-negatif bakteri türlerine karşı antibakteriyel potansiyelleri standart, siprofloksasin ile karşılaştırıldığında orta-iyi bulunmuştur. Ayrıca, N-(4-{[(4-klorobenzil)(fenetil)amino]sülfonil}fenil)asetamid (5c) bileşiğinin baicalein referans alındığında IC50=135.31±0.81 µM değeri ile olası lipoksijenaz inhibitörü olduğu da kanıtlanmıştır

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Cite This Article

ABBASI, A. M., KHIZER, R., REHMAN, A., SIDDIQUI, Z. S., RUBAB, K., MALIK, R., AHMAD, I., SHAH, A. S. A. (2015). Bazı N-(fenetil)-4-acetamidobenzenesulfonamide türevlerinin Sentezi ile Antibakteriyel ve Lipoksijenaz İnhibitör Çalışmaları. Turkish Journal of Pharmaceutical Sciences, Cilt: 12 - Sayı: 3, 257–266. https://ajindex.com/articles/403740

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