Ultrasound promoted stereoselective synthesis of 2,3-dihydrobenzofuran appended chalcones at ambient temperature

In the present investigation, an ultrasound promoted the synthesis of a series of (E)-3-(2,3-dihydrobenzofuran 5-yl)-1-(aryl)prop-2-en-1-one derivatives from 2,3-dihydrobenzofuran-5-carbaldehyde and various aromatic ketones under clean conditions. The application of ultrasound irradiation in organic reactions is one of the incredible tools of green chemistry as reactions can be carried out rapidly under neat conditions. A library of a novel (E)-3-(2,3-dihydrobenzofuran-5-yl)-1-(aryl)prop-2-en-1-one chalcone derivatives were synthesized in good to excellent yield under ultrasonic irradiation. The structures of all synthesized chalcone derivatives synthesized in this study have been established by using FT-IR, 1HNMR, 13CNMR, and HRMS techniques. The stereochemistry around C=C in the chalcones was shown to be trans by 1H NMR(Jab= 15.5Hz). The benefits of the present synthesis include mild reaction conditions, high yield, purification by non-chromatographic strategy and short reaction times, demonstrating the significance of this protocol in terms of waste reduction and energy efficiency

Computational study: Synthesis, spectroscopic (UV–vis, IR, NMR), antibacterial, antifungal, antioxidant, molecular docking and ADME of new (E)-5-(1-(2-(4-(2,4-dichlorophenyl)thiazol-2-yl)hydrazineylidene)ethyl)-2,4-dimethylthiazole

In this paper, we describe the synthesis of a novel (E)-5-(1-(2-(4-(2,4-dichlorophenyl)thiazol-2-yl)hydrazineylidene)ethyl)-2,4-dimethylthiazole (DCPTHT) via multicomponent reaction between 1-(2,4-dimethylthiazol-5-yl)ethan-1-one, thiosemicarbazide and 2-bromo-1-(2,4-dichlorophenyl)ethan-1-one. The structure of DCPTHT was confirmed on the basis of FT-IR, 1HNMR and 13C NMR characterizations. The molecular structure of the novel thiazole derivative was examined using density functional theory (DFT) simulations at the B3LYP/6-311G (d,p) level of theory. Molecular simulations were made for total energy, HOMO and LUMO energy, and Mulliken atomic charges. In a dimethyl sulfoxide solvent, the electronic absorption spectra were acquired, and TD-DFT calculations were used to discuss the band assignments. By correlating the experimental and simulated spectra, NMR assignments and interpretations were also established. Remarkably, antibacterial and antifungal screening was used to examine the biological profile of DCPTHT. Antibacterial screening was performed against E. coli, B. subtilis, P. aeruginosa, and MRSA while the antifungal screening was performed against A. niger and C. albicans. It was found that the newly synthesized thiazole derivative demonstrated potent antifungal activity on the investigated fungal species. Molecular docking study against cytochrome P450 14α-sterol demethylase (CYP51) (PDB id: 5v5z). Furthermore, ADME predictions are also discussed. The molecular docking studies revealed mostly hydrophobic and van der Waals interactions with different amino acid residues

Synthesis, antibacterial, antifungal, antioxidant, cytotoxicity and molecular docking studies of thiazole derivatives

The emergence of numerous pandemics and microbial resistance has necessitated the development of novel heterocyclic compounds with potent biological effects. Five new (E)-2-((5-(1H-benzo[d]imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazineyl)-4-(aryl)thiazole derivatives (9a-e) were synthesized through a one pot multicomponent reaction involving 5-(1H-benzo[d]imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, thiosemicabazide and various substituted phenacyl bromides. FT-IR, 1H NMR, and 13C NMR spectroscopic techniques were used to characterize the newly synthesized benzimidazole-pyrazole clubbed thiazole hybrids. The synthesized compounds were screened for antibacterial activity against E. coli, B. subtilis, B. megaterium, and S. aureus and antifungal activity against A. niger, A. oryzae, Rhizophus spp., and C. albicans. All newly synthesized compounds exhibited potent antibacterial action against all tested strains. Besides, % radical scavenging activity was also evaluated and results showed good antioxidant potential of the synthesized compounds. The cytotoxicity study revealed that synthesized compounds has no to less toxicity as compared to standard Triton X 100. Molecular docking simulations against DNA gyrase (PDB: 4URO) revealed binding interactions and MESP plots confirmed the binding locations