Facile green in situ hemisynthesis of new chiral chromeno-pyrimidine derivatives: antibacterial, antioxidant activities and molecular docking study.
Ramzi MaadadiAbbes BenmeracheRafik MenacerBorhane Eddine Cherif ZianiZahia KaboucheLiza SaherKhaldoun BachariDominique HarakatPublished in: Natural product research (2023)
A hemisynthesis ' in situ ' reaction of (thio)barbituric acids with an α,β-unsaturated aldehyde using perillaldehyde from Ammodaucus leucotrichus essential oil, afforded chromeno-pyrimidine derivatives B-1 and B-2 . The reaction was carried out in water and water/ethanol medium without a catalyst. The obtained pyrimidines were identified by their spectral 1 H, 13 C, Dept-135, HMBC, HSQC, COSY, and NOESY 2D. The antioxidant activity of both compounds was evaluated using different in vitro methods (DPPH, ABTS, and CUPRAC). The hemisynthesized molecules exhibited a bacteriostatic effect against ten tested gram (+) and gram (-) strains. According to the molecular docking analysis, B-1 showed lower binding energies compared to B-2 against (PDB: 1HD2) and (PDB: 1KZN) targets, which is in agreement with the ABTS and E. Coli assays. Furthermore, a probable promising anti-HIV activity was noticed against reverse transcriptase (PDB: 2RKI), a key enzyme for HIV replication. The ADME properties calculations showed no Lipinski's rule violation for both compounds.
Keyphrases
- molecular docking
- essential oil
- molecular dynamics simulations
- antiretroviral therapy
- hiv positive
- hiv testing
- hiv infected
- human immunodeficiency virus
- gram negative
- escherichia coli
- hepatitis c virus
- density functional theory
- hiv aids
- men who have sex with men
- ionic liquid
- reduced graphene oxide
- highly efficient
- multidrug resistant
- oxidative stress
- south africa
- optical coherence tomography
- anti inflammatory
- high throughput
- room temperature
- metal organic framework
- structure activity relationship
- quantum dots
- gold nanoparticles
- electron transfer
- computed tomography
- capillary electrophoresis
- transcription factor
- wound healing
- data analysis