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Anti-HIV activity of new pyrazolobenzothiazine 5,5-dioxide-based acetohydrazides

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Abstract

A series of fifteen new 2-[3-(3-chlorophenyl)-5,5-dioxidobenzo[e]pyrazolo[4,3-c][1,2]thiazin-4(2H)-yl]-N′-arylmethyleneacetohydrazides (5a–o) were synthesized and screened for their anti-HIV-1 and cytotoxicity activity. Out of fifteen pyrazolobenzothiazine-based hydrazones, thirteen were found to be active inhibitors of HIV with EC50 values <20 µM. Moreover, the cytotoxicity results showed that most of the compounds were toxic to PBM, CEM and Vero cell lines. This information could be used for structural modifications to acquire good candidates of HIV drugs.

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Acknowledgments

The authors (MA, ZK, SA and MAM) are grateful to Higher Education Commission, Pakistan, and Institute of Chemistry, University of the Punjab, Lahore, for financial assistance. We are also thankful to International Centre for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi, for spectral measurements. This work was also supported in part by NIH grant 2P30-AI-050409 and the Department of Veterans Affairs (RFS), USA. The X-ray coordinate of the compounds has been deposited at Cambridge Crystallographic Data Centre with CCDC numbers 881055.

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Authors and Affiliations

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

    Zunera Khalid, Sana Aslam & Munawar Ali Munawar

  2. Department of Chemistry, Government College Women University, Faisalabad, 38000, Pakistan

    Sana Aslam

  3. Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan

    Matloob Ahmad

  4. Center for AIDS Research, Laboratory of Biochemical Pharmacology, Emory University School of Medicine/Veterans Affairs Medical Center, 1760 Haygood Drive, Atlanta, GA, 30322, USA

    Catherine Montero, Mervi Detorio & Raymond F. Schinazi

  5. Department of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, AB, T2N 1N4, Canada

    Masood Parvez

Authors
  1. Zunera Khalid
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  2. Sana Aslam
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  3. Matloob Ahmad
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  4. Munawar Ali Munawar
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  5. Catherine Montero
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  6. Mervi Detorio
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  7. Masood Parvez
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  8. Raymond F. Schinazi
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Corresponding author

Correspondence to Matloob Ahmad.

Additional information

We dedicate the research article to Prof. Dr. Hamid Latif Siddiqui (Late) who was our beloved teacher (ZK, SA and MA) and he passed away on July 26, 2011.

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Khalid, Z., Aslam, S., Ahmad, M. et al. Anti-HIV activity of new pyrazolobenzothiazine 5,5-dioxide-based acetohydrazides. Med Chem Res 24, 3671–3680 (2015). https://doi.org/10.1007/s00044-015-1411-z

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  • DOI: https://doi.org/10.1007/s00044-015-1411-z

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