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Synthesis and in vitro antimicrobial evaluation of benzothiazolylindenopyrazoles

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Abstract

In the present study, a series of benzothiazolylindenopyrazoles 5a‒o has been efficiently synthesized by refluxing a solution of 2-(3-substitutedbenzoyl)-(1H)-indene-1,3(2H)-diones 1a–c and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles 4a–e in presence of dry ethanol and glacial acetic acid in good yields. The newly synthesized derivatives 5a‒o were well characterized by using different physical and spectral techniques (FTIR, 1H NMR, 13C NMR and HRMS). All the derivatives 5a‒o were subjected to their preliminary antimicrobial assay against two Gram-positive bacterial strains [Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443)], two Gram-negative bacterial strains [Escherichia coli (MTCC 1652) and Pseudomonas aeruginosa (MTCC 424)], and two fungal strains [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)] employing serial dilution method using Ciprofloxacin and Fluconazole as standard drugs for bacterial and fungal strains, respectively. Among all the tested derivatives, 5m (MIC = 0.0255 µmol/mL) and 5o (MIC = 0.0232 µmol/mL) exhibited maximal inhibition against fungal strain C. albicans. Overall, the investigation revealed that the titled compounds were found more potent against C. albicans.

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Acknowledgements

The authors are highly thankful to the University Grants Commission, New Delhi, India [Sr.No. 2061610093 Ref.No.19/06/2016(i)EU-V, dated 26-12-2016] and Council of Scientific & Industrial Research, New Delhi [CSIR no. 09/752(0104)/2019-EMR-I] for providing financial support.

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  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, 125001, Haryana, India

    Satbir Mor, Mohini Khatri & Ravinder Punia

  2. Department of Chemistry, Maharshi Dayanand University, Rohtak, 124001, Haryana, India

    Komal Jakhar

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Mor, S., Khatri, M., Punia, R. et al. Synthesis and in vitro antimicrobial evaluation of benzothiazolylindenopyrazoles. Med Chem Res 32, 47–56 (2023). https://doi.org/10.1007/s00044-022-02988-7

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