Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products

Abstract

Known methods of synthesis of dihydropyrimidines and their oxidized products were modified, the impact of hydrogen bonds on stabilization of preferred tautomer and biological activities were studied.

Synthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative

“…Finally, K. pneumoniae was the least sensitive to 4, with a MIC value of 500 µg/mL, the same value obtained with ceftriaxone, but higher than that exhibited by cefotaxime (250 µg/mL). The antibacterial activity of some dihydropyrimidine derivatives was also evaluated in previous work from our research group [53]. In comparison with compound 16 from the mentioned study, 4 showed improved antibacterial activity against all bacterial strains.…”

“…In comparison with compound 16 from the mentioned study, 4 showed improved antibacterial activity against all bacterial strains. For instance, 16 was not active against K. pneumonia [53], while all the bacterial strains tested were susceptible to 4. The improvement of the antibacterial effect of 4 may be related to its chemical structure.…”

“…The control containing DMSO did not affect the growth of the above mentioned gram-positive and gram-negative bacteria. The minimum inhibitory concentration (MIC) of the compounds against the test cultures (S. aureus, E. coli, A. baumannii, P. aeruginosa, and K. pneumonia) was determined using the microdilution method and the resazurin dye, after an initial screening [53]. The results were compared to those obtained with the control antibiotics (cefotaxime and ceftriaxone).…”

“…Overall, these advantages have encouraged scientists to optimize synthetic methods to produce dihydropyrimidines, searching for innovative catalysts and constructing new molecules from different building blocks by employing the Biginelli reaction. To gain a deeper insight into the stereochemistry, conformation, and non-covalent interactions between molecules, which are key factors affecting activity, various methods have been used, leading to the development, enhancement and enrichment of their chemistry [51][52][53]. Furthermore, theoretical calculations have been frequently used to predict and/or explain their activities by finding the relationship between the structure of the investigated molecule and its biological effect [54,55].…”

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

“…Huseynzada et al reported Biginelli synthesis catalyzed by Cu(OTf) 2 of dihydropyrimidines, their regioselective oxidation, and their antibacterial properties [ 102 ]. Compounds 93 and 94 showed the highest inhibitory effect against A. baumanii and S. aureus , with a value of 62.5 μg mL −1 ( Figure 11 ).…”