Synthesis, Antibacterial and Lipoxygenase Inhibition Studies of N-(Alkyl/aralkyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenesulfonamides
Journal Title: Turkish Journal of Pharmaceutical Sciences - Year 2017, Vol 14, Issue 1
Abstract
Objectives: The present research work was aimed to synthesize some new sulfonamides bearing 1,4-benzodioxin ring, which might have suitable antibacterial potential and can be used as possible therapeutic agents for inflammatory ailments. Materials and Methods: The synthesis was accomplished by the 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. Then these molecules were subjected to screening against various bacterial strains and their inhibitory potential against Lipoxygenase was also ascertained. Results: 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. Conclusion: On the basis of results obtained it can be concluded that the synthesized sulfonamides may provide an overall indispensable basis to introduce new drug candidates for the cure of inflammatory and other associated diseases.
Authors and Affiliations
Muhammad Athar ABBASI, Aziz-ur REHMAN, Sabahat Z SIDDIQUI, Anam SHEEZA, Sumaira NAZIR, Irshad AHMAD, Rabia MALIK, Syed AA SHAH
Keywords
Related Articles
- EP ID EP380934
- DOI 10.4274/tjps.84756
- Views 154
- Downloads 0
In Vitro Cytotoxic and Anti-inflammatory Activities of Tanacetum argenteum (Lam.) Willd. subsp. argenteum Extract
Objectives: The objective of this study was to examine the anti-inflammatory and cytotoxic potential of n-hexane, ethyl acetate, and methanolic extracts of Tanacetum argenteum subsp. argenteum. Materials and Methods: Ta...
Evaluation of Antioxidant Activities and Phenolic Compounds of Scorzonera latifolia (Fisch. & Mey.) DC. Collected from Different Geographic Origins in Turkey
Objectives: The chemical composition of plants is considered to be affected by many parameters. Therefore, the region where the samples are collected is likely to have an influence on the composition of phenolic compoun...
Phytotoxicity, Toxicity on Brine Shrimp and Insecticidal Effect of Chrysophthalmum gueneri Aytac & Anderb. Growing in Turkey
Objectives: The aim of this study was to investigate the probable toxicity on brine shrimp, phytotoxicity, and insecticidal activity of Chrysophthalmum gueneri Aytac & Anderb. Materials and Methods: The MeOH (80%) extrac...
Cytotoxic Activities of Certain Medicinal Plants on Different Cancer Cell Lines
Objectives: In recent years, the use of plants for the prevention and treatment of cancer is gaining more attention due to their diverse range of phytochemical constituents and fewer adverse effects. In this study, four...
Orally-disintegrating Tablets in Fixed-dose Combination Containing Ambroxol Hydrochloride and Salbutamol Sulphate Prepared by Direct Compression: Formulation Design, Development and In Vitro Evaluation
Objectives: To design a formulation and develop ODTs of AMB hydrochloride and salbutamol sulphate in combination for the treatment of respiratory disorders and perform an in vitro evaluation using superdisintegrants in c...