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Synthesis and antioxidant studies of novel N-substituted benzyl/phenyl-2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl)acetamides

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Abstract

Two new series of twenty-two N-substituted benzyl/phenyl-2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl)acetamides were synthesized by synergism of the dihydropyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide moiety with side chain of carboxamides. The routes of formation for these products have been discussed. All the compounds were characterized by NMR, mass and elemental analysis. Structures of compounds 6d and 6l have been elucidated by X-ray crystallography. The synthesized compounds were screened to the preliminary evaluation for their anti-oxidant activities and most of the compounds were found to possess moderate to significant radical scavenging activity. Furthermore, these compounds could be useful as a template for future development through modification or derivatization to design more potent biologically active compounds.

Graphical Abstract

[Two series of novel carboxamides based upon pyrazolobenzothiazine ring system have been synthesized and evaluated for antioxidant activity. Many compounds were found to be good scavengers of superoxide anion radical. Moreover, the compounds may also possess the bioactivities of parent ring system and thus, are useful as template for further development of new bioactive molecules.]

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Acknowledgments

The authors (MA and HLS) are grateful to Higher Education Commission, Pakistan for financial assistance and for funding the research visit of MA to the University of Manchester. We are also thankful to School of Chemistry, University of Manchester, Manchester, UK, and International Centre for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi and Institute of Chemistry, University of the Punjab for research facilities, spectral measurements and antioxidant studies.

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Authors and Affiliations

  1. Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan

    Matloob Ahmad

  2. Department of Chemistry, Govt. College University, Faisalabad, Pakistan

    Matloob Ahmad

  3. Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan

    Hamid Latif Siddiqui & Sana Aslam

  4. School of Chemistry and Manchester Interdisciplinary Biocentre, University of Manchester, Manchester, M1 7DN, UK

    John M. Gardiner

  5. Department of Chemistry, University of Calgary, 2500 University Drive N.W, Calgary, AB, T2N 1N4, Canada

    Masood Parvez

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  1. Matloob Ahmad
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  2. Hamid Latif Siddiqui
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  3. John M. Gardiner
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  4. Masood Parvez
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  5. Sana Aslam
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Correspondence to Hamid Latif Siddiqui.

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Ahmad, M., Siddiqui, H.L., Gardiner, J.M. et al. Synthesis and antioxidant studies of novel N-substituted benzyl/phenyl-2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl)acetamides. Med Chem Res 22, 794–805 (2013). https://doi.org/10.1007/s00044-012-0062-6

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  • DOI: https://doi.org/10.1007/s00044-012-0062-6

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