The present research work involved the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (1) and benzenesulfonyl chloride (2) under dynamic pH control at 10 using aqueous Na2CO3. This reaction yielded 2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamide (3), which was further substituted at N-position with various alkyl/aryl halides (4a – 4m) in N,N-dimethylformamide and catalytic amount of lithium hydride to obtain N-substituted (2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamides (5a – 5m). The projected structures of the synthesized derivatives were confirmed using various spectral techniques (IR, 1H NMR and EIMS). The synthesized derivatives were screened for antibacterial potential and inhibitory activity against lipoxygenase enzyme.
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References
A. Kleemann, et al., Pharmaceutical Substances: Synthesis, Patents and Applications, 2nd ed., Thieme, Stuttgart (1999).
B. L. Wilkinson, et al., J. Med. Chem., 50, 1651 (2007).
C. Almansa, et al., J. Med. Chem., 47, 5579 (2004).
W. Chu, et al., J. Med. Chem., 50, 3751 (2007).
O. Lukin, et al., J. Am. Chem. Soc., 128, 8964 (2008).
H. Matsunaga, et al., Tetrahedron Lett., 46, 3645 (2005).
Z. Xu, et al., Coord. Chem. Rev., 42, 5747 (2003).
T. W. Green, et al., Protective Groups in Organic Synthesis, Vol. 4, Wiley, New York (2007), p. 224.
A. Alsughayer, et al., J. Biomater. Nanobiotechnol., 2, 144 – 149 (2011).
A. Thakur, et al., Arkivoc, 14, 87 – 102 (2006).
M. S. Al-Said, et al., Eur. J. Med. Chem., 46, 201 – 207 (2011).
M. J. O’Neill, et al., Current Drug Targets – CNS and Neurological Disorders, 3, 181 (2004).
G. L. Ellman, K. D. Courtney, J. R. Andres, and R. M. Featherstone, Biochem. Pharma., 7, 88 – 90 (1961).
A. L. Tappel, Arch. Biochem. Biophys., 44(2), 378 – 395 (1953).
S. Baylac and P. Racine, Int. J. Aromather., 13(2 / 3), 138 – 42 (2003).
M. Kaspday, V. K. Narayanaswamy, M. Raju, and G. K. Rao, Lett. Drug Design & Discovery, 6, 21 – 28 (2009).
H. Jamil, I. U. Haq, B. Mirza, and H. Qayyum, Ann. Clin. Microbiol. Antimicrob., 11, 11 (2012).
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Abbasi, M.A., Farani, S.K., Aziz-ur-Rehman et al. Synthesis of N-Substituted (2,3-Dihydro-1,4-Benzodioxin-6-YL)Benzenesulfonamide Derivatives as Potent Antibacterial Agents and Moderate Enzyme Inhibitors. Pharm Chem J 51, 193–199 (2017). https://doi.org/10.1007/s11094-017-1581-8
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DOI: https://doi.org/10.1007/s11094-017-1581-8