Year : 2017  |  Volume : 16  |  Issue : 2  |  Page : 71-77

Synthesis and antimicrobial activity of substituted 1,4-bis-spiro[benzocycloheptene-6(5h),3′(3h-pyrazol)-5-one]-benzene under microwave irradiation and molecular docking study

Department of the Chemistry of Natural and Microbial Products, National Research Centre, Dokki, Egypt

Correspondence Address:
Fatma A.A. El-Hag
Department of the Chemistry of Natural and Microbial Products, National Research Centre, 33 El Bohoth St, PO Box 12622, Dokki, Giza
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Source of Support: None, Conflict of Interest: None

DOI: 10.4103/1687-4315.214206

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Background and objective Spiropyrazole derivatives are one of the most bioactive spiro compounds that play a vital role in drug discovery, such as antibacterial, anti-inflammatory, antifungal, antiviral, analgesic, and antidepressant activities. Moreover, microwave as an energy source enhances the reaction rates and improves the regioselectivity. The aim of this study was to synthesize the spiropyrazole derivative compounds. Molecular docking was performed. Materials and methods 1,3-Dipolar cycloaddition of 6,6′-(1,4-phenylene-bis(methanylylidene))-bis(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one) to a variety of nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl halides) under microwave irradiation proceeded regioselectively affording spiro[benzo[7]-annulene-6,3′-pyrazol]-4′-yl)phenyl)-spiro[benzo[7]annulene-6,3′-pyrazol]-5(7H)-ones. The structure of the newly synthesized compounds was confirmed on the basis of spectral data and elemental analyses. The antimicrobial activity of the bis(spiropyrazoles) derivatives was tested for antimicrobial activity. Molecular docking was performed and analyzed with the molecular modeling environment program. Results and conclusion Compound 7f has high potency against all fungi (except Candida albicans) and bacterium species (except Pseudomonas aeruginosa) compared with the reference drug fungicide amphotericin B and the standard bactericides ampicillin and gentamicin. Docking of the most active antibacterial compounds 7f and 7g against the dihydropteroate synthase enzyme gave comparable scores for hydrogen bond interaction (−22.9123, −17.5995 kcal/mol(and binding mode to the reference antibiotic sulfamethoxazole (−13.00 kcal/mol).

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