A novel and efficient synthesis of 1, 2, 3,4-tetrahydropyrimidine carboxamide derivatives by Biginelli reaction and their in vitro antibacterial activity

Abstract

Introduction and Aim: An efficient aspect of two step synthesis of tetrahydro pyrimidine carboxamide derivatives were developed by Biginelli reaction. The two-step synthesized 1,2,3,4-tetrahydropyrimidinecarboxamide compounds were evaluated by In-vitro studies like antifungal and bacterial activities. Few compounds were shown excellent zone of inhibition against fungal and Microbial activities. In this study showed significant effect of antifungal and bacterial action against tetrahydro pyrimidine derivatives. Materials and Methods: In this procedure to synthesize 1,2,3,4-tetrahydropyrimidinecarboxamide derivatives, ethyl acetoacetate, cytosine, para-toluene sulphonic acid and ethanol were used. Results: The synthesized compounds of 1,2,3,4-tetrahydropyrimidine carboxamide derivatives through Biginelli reaction used an efficient catalyst such as para-toluene sulphonic acid and solvent ethanol. In this study tested compounds have developed into two step protocol for synthesis of diversely substituted novel pyrimidines. Conclusion: In this study the synthesized 1,2,3,4-tetrahydropyrimidine carboxamide (THPC) shows significant inhibiting action against Gram +ve, Gram –ve bacterial and fungal growth.

Advances in Biginelli reaction: A comprehensive review

“…In 2021, Thirunavukkarasu and co-workers synthesized tetrahydropyrimidine carboxamide derivatives in two steps via Biginelli reaction. 34 Tetrahydropyrimidine-5-carboxamide derivatives were obtained in a moderately good yield using para-toluene sulphonic acid (PTSA) as a catalyst, and a mixture of 3-oxo-N-(2-oxo-1,-2-dihydropyrimidin-4-yl)butanamide, arylaldehyde, and urea/thiourea as model substrates in ethanol as a solvent (Scheme 13). Tetrahydropyrimidine derivatives exhibit strong inhibitory effects against Gram-positive bacteria, Candida albicans, and fungi, while specific variants display excellent activity against both Gram-positive and Gram-negative bacteria.…”

“…In 2021, Thirunavukkarasu and co‐workers synthesized tetrahydropyrimidine carboxamide derivatives in two steps via Biginelli reaction 34 . Tetrahydropyrimidine‐5‐carboxamide derivatives were obtained in a moderately good yield using para ‐toluene sulphonic acid (PTSA) as a catalyst, and a mixture of 3‐oxo‐N‐(2‐oxo‐1,2‐dihydropyrimidin‐4‐yl)butanamide, arylaldehyde, and urea/thiourea as model substrates in ethanol as a solvent (Scheme 13).…”

Catalytic role in Biginelli reaction: Synthesis and biological property studies of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines

“…[95] 3.5 | Antioxidant properties As shown in this study, the pyrimidine administered in the form of substituted indole-3-yl and furan linked at the fourth position of the pyrimidine-ring exhibits antibacterial, antioxidant, and antifungal properties, which result in remarkable antifungal, free radical scavenging, and antibacterial effects. [96] 3.6 | DNA binding studies acids, it showed a significant DNA groove binder with a binding energy of −21.32 kJ/mol. [97] 3.7 | Antitubercular properties nitrates.…”

“…As shown in this study, the pyrimidine administered in the form of substituted indole‐3‐yl and furan linked at the fourth position of the pyrimidine‐ring exhibits antibacterial, antioxidant, and antifungal properties, which result in remarkable antifungal, free radical scavenging, and antibacterial effects. [ 96 ]…”