Synthesis, Antibacterial and Lipoxygenase Inhibition Studies of N-(Alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides
Muhammad A Abbası1, Aziz-ur Rehman1, Sabahat Z Sıddıquı1, Anam Sheeza1, Sumaira Nazır1, Irshad Ahmad2, Rabia Malık2, Syed Aa Shah3, Syed Aa 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 (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
Sulfonamides are biologically active compounds having vast applications in pharmaceutical industry. The present research work was aimed to synthesize biologically active sulfonamides which was triggered by reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) using 10% aqueous Na2CO3 to afford N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (3). Further the parent molecule 3 was reacted with different alkyl/aralkyl halides (4a-e) to achieve N-(alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides (5a-e), using polar aprotic solvent; N,N-dimethylformamide (DMF) and catalytic amount of lithium hydride as base. The characterization of synthesized compounds was conducted by contemporary spectral techniques e.g., IR, 1H-NMR and EI-MS. The screening results against various Gram-positive and Gram-negative bacterial strains revealed that N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (3), N-(2-bromoethyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5a) and N-(2-phenethyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5b) showed good inhibitory activity as compared to standard Ciprofloxacin. Moreover, N-(3-phenylpropyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamide (5c) and N-(4-chlorobenzyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfon-amide (5e) displayed decent inhibition against lipoxygenase enzyme relative to standard Baicalein.
Keywords: 2, 3-Dihydro-1, 4-benzodioxin-6-amine, 1H-NMR, Antibacterial potential, Lipoxygenase.Bazıları üzerinde Sentezi, Antibakteriyel ve Lipoksijenaz Önleme Çalışmaları N-alkil / Aralkil -N-(2,3- Dihidrobenzo [1,4 ] dioksin-6-il) -4–methylbenzenesulfonamides
Muhammad A Abbası1, Aziz-ur Rehman1, Sabahat Z Sıddıquı1, Anam Sheeza1, Sumaira Nazır1, Irshad Ahmad2, Rabia Malık2, Syed Aa Shah3, Syed Aa 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 (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
Sülfonamidler biyolojik olarak, farmasötik endüstrisinde geniş uygulamaları olan aktif bileşiklerdir. Mevcut araştırma çalışmaları (2) vermek üzere 10% sulu Na2CO3 kullanılarak 4-metilbenzensülfonil klorür ile 2,3-dihidro-1,4-benzodioksin-6-amin (1) reaksiyonu ile tetiklenen biyolojik olarak aktif sülfonamidler sentezlenmesi amaçlanmıştır N-(2,3-dihidrobenzo [1,4] dioksin-6-il)-4-metilbenzensülfonamid (3). Bundan başka, ana molekül-3 (N-alkil / aralkil-N- (2,3-dihidrobenzo [1,4] dioksin-6-il) -4-methylbenzenesulfonamides elde etmek için farklı alkil /aralkil halojenürler (4a-e) ile reaksiyona sokuldu Şekil (5a-e), polar aprotik çözücü kullanılarak; N,N-dimetilformamid (DMF) ile baz olarak lityum hidrit ve katalitik miktarda. Sentezlenen bileşiklerin vasıflandırılması güncel spektrum teknikleri, örneğin, IR, 1H-NMR ve EI-MS tarafından gerçekleştirilmiştir. Çeşitli gram-pozitif ve Gram-negatif bakteri türlerine karşı tarama sonucu ortaya koydu N-(2,3-dihidrobenzo[1,4]dioksin-6-il)-4-metilbenzensülfonamid (3), N-(2-bromoetil)-N-(2,3-dihidrobenzo[1,4]dioksin-6-il)-4-metilbenzensülfonamid (5a) ve N-(2-feniletil)-N-(2,3-dihidrobenzo[1,4]dioksin-6-il Standart Siprofloksasin ile karşılaştırıldığında) (5b)-4-metilbenzensülfonamid iyi inhibitör aktivite göstermiştir. Ayrıca, N-(3-fenilpropil)-N-(2,3-dihidrobenzo[1,4] dioksin-6-il)-4-metilbenzensülfonamid (5c) ve N-(4-klorobenzil)-N- (2,3-dihidrobenzo [1,4] dioksin-6-il) -4-metilbenzensülfonamid (5e), standart baicalein için lipoksijenaz enzimi yönüne karşı iyi bir inhibisyon göstermiştir.
Anahtar Kelimeler: 2, 3-Dihidro-1, 4-benzodioksin-6-amin, 1H-NMR, Antibakteriyel potansiyeli, Lipoksijenaz.Corresponding Author: Muhammad A Abbası, Pakistan
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