Abstract
The aim of the research was to investigate the anti-bacterial potential of some N-substituted sulfonamides bearing benzodioxane moiety. The synthesis was started by reaction of N-2,3-dihydrobenzo[1,4]dioxin-6-amine with 4-acetamidobenzene-1-sulfonyl chloride in the presence of 10% aqueous Na2CO3 solution to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-acetamidobenzenesulfonamide, which was further reacted with alkyl/aralkyl halides in DMF and lithium hydride as a base to afford N-substituted-N-(2,3dihydro-[1,4]-benzodioxin-6-yl)-4-acetamidobenzenesulfonamides. All the synthesized compounds were characterized by spectral data (IR, 1H NMR, EI-MS, and HR-MS). The compounds were tested for antibacterial activity and most of them exhibited potent therapeutic potential against various Gram-negative and Gram-positive strains.
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Dauban, P. and Dodd, R.H., Org. Lett., 2000, vol. 2, pp. 2327–2329.
Roush, W.R., Cheng, J., Knapp-Reed, B., AlvarezHernandez, A., McKerrow, J.H., Hansell, E., and Engel, J.C., J. Am. Chem. Soc., 1998, vol. 120, pp. 10994–10995.
Tougu, V., Curr. Med. Chem., 2001, vol. 1, pp. 155–170.
Hartman, G.D., Halczenko, W., Prugh, J.D., Smith, R.L., Sugrue, M.F., Mallorga, P., Michelson, S.R., Randall, W.C., Schwam, H., and Sondey, J.M., J. Med. Chem., 1992, vol. 35, pp. 3027–3033.
Cremlyn, R., An Introduction to Sulphur Chemistry, New York: Wiley, 1996.
Lukin, O., Gramlich, V., Kandre, R., Zhun, I., Felder, T., Schalley, C.A., and Dolgonos, G., J. Am. Chem. Soc., 2008, vol. 128, pp. 8964–8974.
Isik, K. and Kocak, F.O., Microbiol. Res., 2009, vol. 164, pp. 49–58.
Caballero, D., Torres-Lapasio, J.R., Baeza-Baeza, J.J., and Garcia-Alvarez-Coque, M.C., J. Liq. Chromatogr. Rel. Technol., 2001, vol. 24, pp. 117–131.
Mallesha, L. and Mohana, K.N., Eur. J. Chem., 2011, vol. 2, pp. 193–199.
Vazquez, M.T., Rosell, G., and Pujol, M.D., Eur. J. Med. Chem., 1997, vol. 32, pp. 529–534.
Ahmed, A., Khan, S.A., and Alam, T., Pharmazie, 2003, vol. 58, pp. 173–176.
Chapleo, C.B., Myers, P.L., Butler, C.M., Doxey, J.C., Roach, A.G., and Smith, C.F.C., J. Med. Chem., 1983, vol. 26, pp. 823–831.
Khan, S.A., Ahmed, B., and Alam, T., Pak. J. Pharm. Sci., 2006, vol. 19, pp. 290–294.
Davis-Searles, P.R, Nakanishi, Y., Kim, N.C., Graf, T.N., Oberlies, N.H., and Wani, M.C., Cancer Res., 2005, vol. 65, pp. 4448–4457.
Arai, A., Kessler, M., and Xiao, P., Brain Res., 1994, vol. 638, pp. 343–346.
Neill, M.J.O., Bleakman, D., and Zimmerman, D.M., Curr. Drug Targets: CNS Neurol. Disord., 2004, vol. 3, pp. 181–194.
Avihai, Y., Rachel, O., Tzofit, K., Sima M., Daniel, S., Alex, A., Alina, S., Efrat, B.Z., Nili, S., Osnat, B.K., Alexander, K., Vered, B., and Oren, M.B., Bioorg. Med. Chem. Lett., 2012, vol. 22, pp. 6460–6468.
Martin, J.W., Kyle, R.B., Henrike, V., James, M.B., Thomas, D., William, L., Lewis, C.C., William, J.I., Matthew, G.V.H., Min, S., Douglas, S.A., Craig, J.T., and Matthew, B.B., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 6322–6327.
Irshad, M., Abbasi, M.A., Aziz-Ur-Rehman, Siddiqui, S.Z., Ashraf, M., Ejaz, S.A., Lodhi, M.A., and Jamal, S.B., J. Chem. Soc. Pak., 2014, vol. 36, pp. 660–673.
Doran, K., Jihae, B., Jiho, S., Hyeyoung, B., Hyeyoung, M., and Kyung, H.M., Bioorg. Med. Chem. Lett., 2014, vol. 24, pp. 3823–3825.
Kaspady, M., Narayanaswamy, V.K., Raju, M., and Rao, G.K., Lett. Drug Des. Discov., 2009, vol. 6, pp. 21–28.
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Abbasi, M.A., Tariq, S., Aziz-ur-Rehman et al. Synthesis of some new N-substituted-N-(2,3-Dihydro-[1,4]benzodioxin-6-yl)-4-acetamidobenzenesulfonamides as valuable antibacterial agents. Russ J Bioorg Chem 42, 198–209 (2016). https://doi.org/10.1134/S1068162016020023
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DOI: https://doi.org/10.1134/S1068162016020023