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Outstanding effect of the conformational restriction of isoquinolines: hints for the development of optimized antimicrobial agents

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Abstract

Conformational restriction constitutes a useful strategy of molecular modification for the design of new potential drug candidates. Herein we present the planning, antimicrobial evaluation, and establishment of structure–activity relationship (SAR) data for some isoxazole (3a–k, 8a–c, and 9a–c) and pyrazole (5a–h) derivatives. These derivatives were structurally designed by conformational restriction followed by bioisosteric exchange of previously described antimicrobial isoquinolines (1a–c). Some of these more conformationally restricted derivatives present improved properties as new antibacterial drug candidates.

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Abbreviations

CLSI:

Clinical and Laboratory Standards Institute

DMSO:

Dimethyl sulfoxide

MIC:

Minimal inhibition concentration

RPMI:

Roswell Park Memorial Institute

SAR:

Structure–activity relation

SI:

Selectivity index

TLC:

Thin-layer chromatography

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Acknowledgments

This work was supported by grants from Project Global d’Université Mohammed Premier/LCM, Brazilian Research National Council (CNPq) and by Brazilian National Institute of Research in Dengue (INCT-Dengue).

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Authors and Affiliations

  1. Department of Pharmaceutical Microbiology, Gazi University, Ankara, Turkey

    Berrin Ozcelik

  2. Department of Chemistry, Dhote Bandu Science College, Gondia, 441614, India

    Javed Sheikh

  3. Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Eastern Mediterranean University, Gazimagosa, Famagusta, The Northern Cyprus

    Ilkay E. Orhan

  4. Department of Chemistry, RTM Nagpur University, Nagpur, 440033, India

    Harjeet Juneja

  5. Laboratoire Chimie Organique, Faculté des Sciences Dhar El Mehraz, Fès, Morocco

    Brahim Bennani & Abdelali Kerbal

  6. Centre for Health Science, Federal University of Pernambuco, Recife, Brazil

    S. M. T. Cavalcanti & Ana C. L. Leite

  7. Laboratoire Chimie Matériaux, FSO, Université Med. Premier, Oujda, Morocco

    Taibi Ben Hadda

Authors
  1. Berrin Ozcelik
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  2. Javed Sheikh
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  3. Ilkay E. Orhan
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  4. Harjeet Juneja
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  5. Brahim Bennani
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  6. Abdelali Kerbal
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  7. S. M. T. Cavalcanti
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  8. Ana C. L. Leite
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  9. Taibi Ben Hadda
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Corresponding authors

Correspondence to Javed Sheikh or Taibi Ben Hadda.

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Ozcelik, B., Sheikh, J., Orhan, I.E. et al. Outstanding effect of the conformational restriction of isoquinolines: hints for the development of optimized antimicrobial agents. Res Chem Intermed 39, 2955–2962 (2013). https://doi.org/10.1007/s11164-012-0808-2

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  • DOI: https://doi.org/10.1007/s11164-012-0808-2

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