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El-Sawy ER, Ebaid MS, Abo-Salem HM, et al. Synthesis and biological activity of novel series of 4-methoxy, and 4,9-dimethoxy-5-substituted furo[2,3-g]-1,2,3-benzoxathiazine-7,7-dioxide derivatives. J Adv Res. 2013;5(3):337-46doi: 10.1016/j.jare.2013.05.004.
El-Sawy, E. R., Ebaid, M. S., Abo-Salem, H. M., El-Hallouty, S., Kassem, E. M., & Mandour, A. H. (2014). Synthesis and biological activity of novel series of 4-methoxy, and 4,9-dimethoxy-5-substituted furo[2,3-g]-1,2,3-benzoxathiazine-7,7-dioxide derivatives. Journal of advanced research, 5(3), 337-46. https://doi.org/10.1016/j.jare.2013.05.004
El-Sawy, Eslam R, et al. "Synthesis and biological activity of novel series of 4-methoxy, and 4,9-dimethoxy-5-substituted furo[2,3-g]-1,2,3-benzoxathiazine-7,7-dioxide derivatives." Journal of advanced research vol. 5,3 (2014): 337-46. doi: https://doi.org/10.1016/j.jare.2013.05.004
El-Sawy ER, Ebaid MS, Abo-Salem HM, El-Hallouty S, Kassem EM, Mandour AH. Synthesis and biological activity of novel series of 4-methoxy, and 4,9-dimethoxy-5-substituted furo[2,3-g]-1,2,3-benzoxathiazine-7,7-dioxide derivatives. J Adv Res. 2014 May;5(3):337-46. doi: 10.1016/j.jare.2013.05.004. Epub 2013 May 21. PMID: 25685501; PMCID: PMC4294728.
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J Adv Res. 2014 May;5(3):337-46. doi: 10.1016/j.jare.2013.05.004. Epub 2013 May 21.

Synthesis and biological activity of novel series of 4-methoxy, and 4,9-dimethoxy-5-substituted furo[2,3-g]-1,2,3-benzoxathiazine-7,7-dioxide derivatives.

Journal of advanced research

Eslam R El-Sawy, Manal S Ebaid, Heba M Abo-Salem, Salwa El-Hallouty, Emad M Kassem, Adel H Mandour

Affiliations

  1. Chemistry Department of Natural Compounds, National Research Centre, 12311 Dokki, Giza, Egypt.
  2. Pharmacognosy Department, National Research Centre, 12311 Dokki, Giza, Egypt.
  3. Therapeutical Chemistry Department, National Research Centre, 12311 Dokki, Giza, Egypt.

PMID: 25685501 PMCID: PMC4294728 DOI: 10.1016/j.jare.2013.05.004

Abstract

A novel series of 4-methoxy, and 4,9-dimethoxy-5-substituted furo[2,3-g]-1,2,3-benzoxathiazine-7,7-dioxide derivatives 3a,b, 10a-g and 11a-g were prepared in good yields via the reaction of 4-methoxy (1a) and 4,7-dimethoxy-5-acetyl-6-hydroxybenzofurans (1b) and their α,β-unsaturated keto derivatives 6a-g and 7a-g with chlorosulfonyl isocyanate (CSI). On the other hand, N-chlorosulfonyl carbamate derivatives 4a,b, 12a,b and 13a,b were prepared and allowed to react with piperidine to give the corresponding N-piperidinosulfonyl carbamate derivatives 5a,b, 14a,b and 15a,b, respectively. Sixteen new target compounds 3a,b, 10a-g, and 11a-g were tested for their DPPH radical-scavenging, and in vitro antiproliferative activity against A-549, MCF7 and HCT-116 cancer cell lines. Compounds 10a, 11c, 11e, and 11g showed moderate DPPH radical-scavenging activity compared to ascorbic acid at 100 μg/mL. 4,9-Dimethoxy-5-substituted styrylfuro[3,2-g]-1,2,3-benzoxathiazine-7,7-dioxides 11a, 11b, and 11c were found to be highly active against A-549 and HCT-116 cancer cell lines with IC50 values ranging from 0.02 to 0.08 μmol/mL compared to doxorubicin with IC50 = 0.04 and 0.06 μmol/mL, respectively.

Keywords: Anticancer activity; Benzofuran; Benzoxathiazin-7,7-dioxide; Chlorosulfonyl isocyanate (CSI); DPPH radical-scavenging activity

References

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