758708-96-2Relevant academic research and scientific papers
Potential bacterial biofilm, MRSA, and DHFR inhibitors based on new morpholine-linked chromene-thiazole hybrids: One-pot synthesis and in silico study
Sanad, Sherif M.H.,Mekky, Ahmed E.M.,El-Idreesy, Tamer T.
, (2022)
We report herein the utility of the morpholine-linked benzaldehyde as a key building block in the preparation of two series of new chromene-thiazoles with potential bioactivities. In this regard, a one-pot protocol was developed involving the reaction of the prior aldehyde, 2-cyanothioacetamide and α-bromoketones in dioxane in the presence of triethylamine to give the target hybrids. Thiazole hybrids 9d and 9e, attached to two chromene units at thiazole-C2 and C4, and linked to methyl or methoxy groups, respectively, showed the best antibacterial activity. The previous hybrids exhibited MIC/MBC values of 3.9/7.8 and 1.7/3.5 μM, respectively, against S. aureus, S. mutans and E. coli strains. In addition, the same hybrids gave MIC values of 7.7–32.0 μM and MBC values of 15.5–64.1, μM against MRSA ATCC:33,591 and ATCC:43,300 strains. Furthermore, 9d and 9e gave the best bacterial biofilm inhibitory activity against S. aureus, S. mutans and E. coli strains with IC50 values ranging from 3.9 to 4.6 μM. Also, 9e and 9d displayed superior dihydrofolate reductase enzyme inhibitory activity with IC50 values of 0.122 and 0.131 μM, respectively, compared to the standard sulfadiazine (IC50 value of 0.138 μM). Molecular docking study was used to determine the binding energies of some new hybrids with the previous enzyme. Moreover, physicochemical, pharmacokinetic properties, and drug-likeness of some new hybrids were calculated using SwissADME.
New thiazole and thiazole-chromene hybrids possessing morpholine units: Piperazine-mediated one-pot synthesis of potential acetylcholinesterase inhibitors
Mekky, Ahmed E. M.,Sanad, Sherif M. H.,El-Idreesy, Tamer T.
, p. 3332 - 3344 (2021/08/31)
In the current study, new morpholine-linked thiazoles were prepared by the reaction of salicylaldehyde derivative, thiosemicarbazide, and α-bromoketones. To mediate the previous three-component reaction, the reaction was conducted using two equiv. of piperazine in dioxane at reflux for 5 h. Using the prior protocol, two series of thiazoles, linked to arene or chromene units, were prepared in good to excellent yields. The new thiazoles were examined as potential inhibitors of acetylcholinesterase at a concentration of 50 μM. When compared to donepezil (inhibition percentage of 92.8%), hybrids 11b and 11c, linked to 6-chloro or 6-bromochromen-3-yl units, gave the best inhibition percentages of 72.3 and 71.5%, respectively. Furthermore, when tested at a concentration of 25 μg/mL, the same hybrids demonstrated the highest DPPH antioxidant activity, with inhibition percentages of 84.1 and 83.2%, respectively, when compared to ascorbic acid (inhibition percentage of 89.5%).
