Guanidine dicycloamine-based analogs: green chemistry synthesis, biological investigation, and molecular docking studies as promising antibacterial and antiglycation leads.

Autor: El-Remaily MAEAAA; Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt. msremaily@yahoo.com., Aboelez MO; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Sohag University, Sohag, 82524, Egypt. drmoustafaaboelez@yahoo.com., Ezelarab HAA; Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University, Minia, 61519, Egypt., Selim HMRM; Department of Pharmaceutical Sciences, Faculty of Pharmacy, AlMaarefa University, Diriyah, Riyadh, Saudi Arabia. hmustafa@um.edu.sa.; Department of Microbiology and Immunology, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt. hmustafa@um.edu.sa., Taha EA; Department of Chemistry, Faculty of Pharmacy, October 6 University, 6 October City, Giza, Egypt., Mohamed SK; The Environment and School of Healthcare Science, Manchester Metropolitan University, Manchester, UK., Soliman AM; Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt., Abdallah MS; The Environment and School of Healthcare Science, Manchester Metropolitan University, Manchester, UK., Fawy MA; Department of Zoology, Faculty of Science, South Valley University, Qena, 83523, Egypt., Hassany MA; Department of Internal Medicine, Faculty of Medicine, Aswan University, Aswan, Egypt., Ahmed N; The Environment and School of Healthcare Science, Manchester Metropolitan University, Manchester, UK., Alsaggaf AT; Department of Chemistry, Taibah University, Madinah, Saudi Arabia., El Hamd MA; Department of Pharmaceutical Chemistry, College of Pharmacy, Shaqra University, 11961, Shaqra, Saudi Arabia. aboelhamdmohamed@su.edu.sa.; Department of Pharmaceutical Analytical Chemistry, Faculty of Pharmacy, South Valley University, Qena, 83523, Egypt. aboelhamdmohamed@su.edu.sa., Kamel MS; Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt. mim_chem2@yahoo.com.
Jazyk: angličtina
Zdroj: Molecular diversity [Mol Divers] 2024 Feb 07. Date of Electronic Publication: 2024 Feb 07.
DOI: 10.1007/s11030-024-10816-w
Abstrakt: Dicyandiamide (DCD) reacted with amino acids 1a-f to produce biguanides 2 and 4 and guanidine pyrazolones 3, 5, 6, 7, and 8, according to the reaction. DCD exhibited the following reactions: imidodicarbonimidicdiamide 9, diazocan-2-ylguanidine 10, methyl biguanidylthion 11, N-carbamothioylimidodicarbonimidicdiamide 12, 2-guanidinebenzoimidazole 13a, 2-guanidinylbenzoxazole 13b, and 2-guanidinylbenzothiazol 13c. These reactions were triggered by 6-amino caproic acid, thioacetamide, thiourea, o-aminophenol, o-aminothiophenol, and anthranilic acid, respectively. Compound 2 had the least antimicrobial activity, while compound 13c demonstrated the most antibacterial impact against all bacterial strains. Furthermore, in terms of antiglycation efficacy (AGEs), 12, 11, and 7 were the most effective AGE cross-linking inhibitors. Eight and ten, which showed a considerable inhibition on cross-linking AGEs, come next. Compounds 4 and 6 on the other hand have shown the least suppression of AGE production. The most promising antiglycation scaffolds 8, 11, and 12 in the Human serum albumin (HAS) active site were shown to be able to adopt crucial binding interactions with important amino acids based on the results of in silico molecular docking. The most promising antiglycation compounds 8, 11, and 12 were also shown to have better hydrophilicity, acceptable lipophilicity, gastrointestinal tract absorption (GIT), and blood-brain barrier penetration qualities when their physicochemical properties were examined using the egg-boiled method.
(© 2024. The Author(s), under exclusive licence to Springer Nature Switzerland AG.)
Databáze: MEDLINE
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