Synthesis, Molecular Docking Studies, In Vitro Antimicrobial and Antifungal Activities of Novel Dipeptide Derivatives Based on N-(2-(2-Hydrazinyl-2-oxoethylamino)-2-oxoethyl)-Nicotinamide

Abstract

A series of linear dipeptide derivatives (4–10) were prepared and evaluated as antimicrobial agents via the synthesis of N-(2-(2-hydrazinyl-2-oxoethylamino)-2-oxoethyl) nicotinamide (4). Compound 4 was reacted with 4-chlorobenzaldehyde or 4-hydroxybenzaldehyde, to give the hydrazones 5 and 6, respectively. On the other hand, Compound 4 was coupled with phenylisocyanate or methylisothiocyanate to give Compounds 7 and 8, respectively. The latter compounds (7 and 8) were coupled with chloroacetic acid to give oxazolidine (9) and thiazolidine (10), respectively. The newly synthesized dipeptide compounds were confirmed by means of their spectral data. The antimicrobial activity of the newly synthesized compounds 4–10 was evaluated by agar well diffusion, and they showed good activity. Compounds 4, 5, and 9 gave the most promising activity in this study. Most of the tested compounds possessed MIC values ranging from 50 to 500 µg/mL. Furthermore, docking studies were carried out on enoyl reductase from E. coli and cytochrome P450 14 α-sterol demethylase (Cyp51) from Candida albicans active sites. The MolDock scores of the seven tested compounds ranged between −117 and −171 and between −107 and −179, respectively.

In vitroanticancer potentiality and molecular modelling study of novel amino acid derivatives based onN1,N3-bis-(1-hydrazinyl-1-oxopropan-2-yl) isophthalamide

“…In our previous studies of amino acid and peptide derivatives, gave a good antimicrobial properties, anti-inflammatory, analgesic agents 44–48 and anticancer activities 26–28 , 49 , as well as, pyrazoloderivatives as anticancer agents 50 . Thus, our study aims to conjugate l -alanine and isophthalic acid.…”

Synthesis, Docking, Computational Studies, and Antimicrobial Evaluations of New Dipeptide Derivatives Based on Nicotinoylglycylglycine Hydrazide

“…In all biological kingdoms, CYP51 orthologs are located and united into one (CYP51) family (despite very low identity sequence of amino acid across phylogeny) [ 23 ]. Depending on these observations and in continuation of our previous studies for anti-microbial and anticancer agents [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ], this study was aimed at synthesizing a series of novel dipeptide compounds that were hypothesized to affect systemic anti-microbial measurements.…”

Anticancer Activities of Newly Synthesized Chiral Macrocyclic Heptapeptide Candidates

“…Additionally, peptides comprise a major group of pharmaceutical drugs with potential anticancer effects [7]. Previous reports showed that chemical synthesis of peptides proved successful in obtaining new derivatives with potent antimicrobial, anti-inflammatory [8][9][10][11][12][13][14][15][16], and anticancer properties [17][18][19][20][21]. In our previous works, we were able to synthesize, chemically characterize, and biologically evaluate different bis-amino acid and peptide conjugates of dipicolinic acid [22].…”