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Bacterial infections are increasingly difficult to combat as bacteria evolve resistance to antibiotic drugs and have severely compromised the arsenal of antibiotic drugs. On the other hand matrix metalloproteinases (MMPs) play a fundamental role in inflammation and extracellular matrix degradation in physiological and pathological conditions. In search of potent antibiotic, taking coumarin and dihydropyrimidinone as lead compound, a green, eco-friendly and efficient protocol has been developed and synthesized the dihydropyrimidin-2(1 H )-one/thione derivatives of coumarin 3/4 from substituted 4-formylcoumarins 2 and ethylacetoacetate using urea/thiourea in the presence of catalytic amount of ceric ammonium nitrate is reported. All the synthesized compounds were evaluated for their antibacterial activity against four bacterial strains by broth dilution method. The tested compounds have exhibited promising in vitro potency with low MIC values against the drug susceptive S. aureus strain with low MIC values ranging from 0.2 to 6.25 μg/mL. The in vivo anti-inflammatory potency of 3a–e and 4a–e by gelatin zymography is comparable to that of tetracycline. Molecular docking study performed for all the synthesized compounds with S. aureus DNA gyrase and results obtained were quite promising. [ABSTRACT FROM AUTHOR]

• Cyclic ureido based mono/ bis -coumarin 'click triazoles' have been synthesized. • Newly synthesized triazoles inhibited Mycobacterium tuberculosis H37Rv. • Benzimidazolono- bis -coumarinyl triazoles exhibited lower MIC values. • Theophylline/uracil-based mono/ bis -coumarin triazoles exhibited higher MIC values. • Cytotoxicity studies exhibited IC 50 values 10 times higher than Mtb MIC values. Nucleoside bases like uracil, pharmacophoric triazoles and benzimidazolones have been used during the present study to design molecular matrices for antitubercular activity, employing Click Chemistry. Click triazoles 4 / 7 / 10 have been obtained by the reaction of 4-(Azidomethyl)-2 H -chromen-2-ones/quinolin-2(1 H)-ones 3 and propargyl ethers 2/6/9 derived from theophylline/6-methyl uracil/2-benzimidazolone respectively. In addition to spectral data structures have been confirmed by single crystal X-ray diffraction studies in case of uracil bis alkyne (6) and theophylline mono triazole (4c). Theophylline linked mono triazoles, 4 (a-d) and 6-methyl uracil linked bis triazoles, 7 (a-e) have been found to inhibit Mycobacterium tuberculosis H37Rv with MIC values in the range 55.62–115.62 μM. Benzimidazolone bis triazoles, 10 (a-n) showed better activity with MIC in the range 2.33–18.34 μM. Molecular modeling studies using Surflex-Dock algorithm supported our results. [ABSTRACT FROM AUTHOR]