Synthesis, Antibacterial and Lipoxygenase Inhibition Studies on Some N-(4-{[(Alkyl/aralkyl)(phenethyl)amino]sulfonyl}phenyl)acetamides
Muhammad A Abbası1, Rabia Khızer1, Aziz-ur Rehman1, Sabahat Z Siddiqui1, Kaniz Rubab1, Rabia Malik2, Irshad Ahmad2, Syed Adnan A. Shah3, Syed Adnan A. Shah41Department Of Chemistry, Government College University, Lahore-54000, Pakistan2Department Of Pharmacy, The Islamia University Of Bahawalpur, Bahawalpur-63100, Pakistan
3Faculty Of Pharmacy, Universiti Teknologi Mara, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
4Atta-ur-rahman Institute For Natural Products Discovery (aurıns), Level 9, Ff3, Universiti Teknologi Mara, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
In the present study, 2-phenyl-1-ethanamine (phenethyl amine; 1) was reacted with 4-acetamidobenzenesulfonyl 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,1H-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.
Keywords: Phenethyl amine, 4-acetamidobenzenesulfonyl chloride, Antibacterial activity, LipoxygenaseBazı Sentez, Antibakteriyel ve Lipoksijenaz Önleme Çalışmaları N-(fenetil)-4-acetamidobenzenesulfonamide N-ikame edilmiş türevleri
Muhammad A Abbası1, Rabia Khızer1, Aziz-ur Rehman1, Sabahat Z Siddiqui1, Kaniz Rubab1, Rabia Malik2, Irshad Ahmad2, Syed Adnan A. Shah3, Syed Adnan A. Shah41Department Of Chemistry, Government College University, Lahore-54000, Pakistan2Department Of Pharmacy, The Islamia University Of Bahawalpur, Bahawalpur-63100, Pakistan
3Faculty Of Pharmacy, Universiti Teknologi Mara, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
4Atta-ur-rahman Institute For Natural Products Discovery (aurıns), Level 9, Ff3, Universiti Teknologi Mara, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
In the present study, 2-phenyl-1-ethanamine (phenethyl amine; 1) was reacted with 4-acetamidobenzenesulfonyl 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,1H-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.
Anahtar Kelimeler: Phenethyl amine, 4-acetamidobenzenesulfonyl chloride, Antibacterial activity, LipoxygenaseCorresponding Author: Muhammad A Abbası, Pakistan
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