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Antimicrobial/antioxidant activity and POM analyses of novel 7-o-β-d-glucopyranosyloxy-3-(4,5-disubstituted imidazol-2-yl)-4H-chromen-4-ones

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Abstract

A series of 7-o-β-d-glucopyranosyloxy-3-(4,5-disubstituted imidazol-2-yl)-4H-chromen-4-ones 4 were synthesized and tested for in vitro antibacterial/antifungal and antioxidant activity. The synthesized compounds o-β-d-glucoside of 7-hydroxyl-3-imidazolyl-4H-chromen-4-ones showed good antibacterial/antifungal activity as well as antioxidant activity. The results suggest that aglycone as well as their o-glucosides could be promising candidates for new combined antifungal/antibacterial as well as antioxidant agents (3 in 1). Experimental data and Petra/Osiris/Molinspiration (POM) analyses, respectively, show high bioactivity against various microorganisms at a very low concentration without any side effect, suggesting that series 2–4 is a potential antimicrobial inhibitor and further it deserves to be validated for in vivo studies.

Graphical Abstract

7-Hydroxy-3-(4,5-disubstituted imidazol-2-yl)-4H-chromen-4-ones and their o-β-d-glucosides were synthesized and evaluated for in vitro antimicrobial and antioxidant activity. The compounds were also subjected to high-throughput POM bioinformatics to study the bioavailability.

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Acknowledgments

The authors are thankful to the Director, SAIF, Chandigarh, and the Head, Department of Chemistry, IIT-Pawai, Mumbai, for providing necessary spectral analysis, and the Head, Department of Chemistry, R. T. M. Nagpur University, Nagpur, for providing necessary laboratory facilities. Prof. Siham Lahsasni would like to extend his sincere appreciation to the Deanship of Scientific at King Saud University for its funding of this computational research through the Research Group Project No. RGP-VPP-222.

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Authors and Affiliations

  1. Organic Research Lab-1, Department of Chemistry, Rashtrasant Tukdoji Maharaj Nagpur University, Nagpur, 440033, India

    Kishor Hatzade, Vijay Taile & Vishwas Ingle

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

    Kishor Hatzade, Javed Sheikh & Ajay Ghatole

  3. Department of Chemistry, FSA, Adiyaman University, Adiyaman, 02040, Turkey

    Murat Genc

  4. Department of Chemistry, Science College, King Saud University, Riyadh, Kingdom of Saudi Arabia

    Siham Lahsasni

  5. Laboratoire Chimie Matériaux, FSO, Université Mohammed 1ER, Oujda, 60000, Morocco

    Taibi Ben Hadda

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  1. Kishor Hatzade
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Correspondence to Kishor Hatzade.

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Hatzade, K., Sheikh, J., Taile, V. et al. Antimicrobial/antioxidant activity and POM analyses of novel 7-o-β-d-glucopyranosyloxy-3-(4,5-disubstituted imidazol-2-yl)-4H-chromen-4-ones. Med Chem Res 24, 2679–2693 (2015). https://doi.org/10.1007/s00044-015-1326-8

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