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Open AccessArticle

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

1
Peptide Chemistry Department, Chemical Industries Research Division, National Research Centre, Dokki 12622, Cairo, Egypt
2
Chemistry Department, College of Science and Arts-Qurayat, Jouf University, Saudi Arabia
3
Photochemistry Department, Chemical Industries Research Division, National Research Centre, Dokki 12622, Cairo, Egypt
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Department of Pharmaceutical Chemistry, Drug Exploration and Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
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Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia
6
Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Div., National Research Centre, Dokki 12622, Cairo, Egypt
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(4), 761; https://doi.org/10.3390/molecules23040761
Received: 16 January 2018 / Revised: 14 March 2018 / Accepted: 20 March 2018 / Published: 27 March 2018
A series of linear dipeptide derivatives (410) 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 410 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. View Full-Text
Keywords: nicotinoyl chloride; amino acids; linear dipeptides; antimicrobial activity; molecular docking studies nicotinoyl chloride; amino acids; linear dipeptides; antimicrobial activity; molecular docking studies
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MDPI and ACS Style

Moustafa, G.; Khalaf, H.; Naglah, A.; Al-Wasidi, A.; Al-Jafshar, N.; Awad, H. 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. Molecules 2018, 23, 761. https://doi.org/10.3390/molecules23040761

AMA Style

Moustafa G, Khalaf H, Naglah A, Al-Wasidi A, Al-Jafshar N, Awad H. 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. Molecules. 2018; 23(4):761. https://doi.org/10.3390/molecules23040761

Chicago/Turabian Style

Moustafa, Gaber; Khalaf, Hemat; Naglah, Ahmed; Al-Wasidi, Asma; Al-Jafshar, Nawal; Awad, Hassan. 2018. "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" Molecules 23, no. 4: 761. https://doi.org/10.3390/molecules23040761

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