Synthesis, antioxidant, antimicrobial, and molecular docking studies of some N-cinnamyl phenylacetamide and N-(3,7-dimethylocta-2,6-dien-1-yl)phenylacetamide derivatives was written by El-Zemity, Saad R.;Badawy, Mohamed E. I.;Esmaiel, Kareem E. E.;Badr, Mai M.. And the article was included in Journal of Molecular Structure in 2022.Category: esters-buliding-blocks This article mentions the following:
A series of N-cinnamyl phenylacetamides I [R = 2-OH, 4-Cl, 4-SO2NH2, etc.] and N-(3,7-dimethylocta-2,6-dien-1-yl)phenylacetamide derivatives II [R1 = 3,5-di-MeC6H3, 2,6-di-MeC6H3, 2-Me,6-EtC6H3, 1-naphthyl] with different active moieties have been designed, synthesized and tested for antioxidant and antimicrobial activity. The synthetic protocol was based on the formation of Schiff bases followed by chloroacetylation of imines. The chem. structures of the compounds were recognized by 1H-NMR, 13C-NMR and MS spectral techniques. Compounds I and II exhibited superior antioxidant activity (IC50 = 9.92-19.06μM) compared to α-tocopherol (IC50 = 26μM). Derivatives II showed excellent antibacterial activities against all the tested strains with MIC values in the range of 10-230μM comparable to those of amoxicillin (80-275μM) against Bacillus cereus (G+), Staphylococcus aureus (G+), Escherichia coli (G-), and Pseudomonas aeruginosa (G-). Besides, the compounds also exhibited candidacidal activity against Candida albicans and Compound II [R1 = 2-Me,6-EtC6H3] was the most active compound (EC50 = 423.62μM). Mol. docking, drug-likeness data, physicochem. properties, and ADMET (absorption, distribution, metabolism, excretion, and toxicity) parameters of the compounds were in silico computed. The derivatives presented good properties for Lipinski’s parameters, poor solubility in the aqueous medium (Log S of -4.06 to -5.97), and PSA <140, indicating good permeability in biol. membranes and gastrointestinal absorption. Mol. docking to the active sites of NADPH oxidase (PDB: 1W6X), penicillin-binding protein 2a (PDB: 1VQQ), and lanosterol 14-alpha demethylase (PDB 1EA1) revealed that most compounds displayed minimal binding energy and have a good affinity toward the active pocket of each enzyme. In the experiment, the researchers used many compounds, for example, (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3Category: esters-buliding-blocks).
(E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Category: esters-buliding-blocks
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics