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Synthesis, antimicrobial, anti-proliferative activities, molecular docking and DFT studies of novel pyrazolo[5,1-c][1, 2, 4]triazine-3-carboxamide derivatives.
Fahim, Asmaa M; Ismael, Eman H I; Elsayed, Ghada H; Farag, Ahmad M.
Afiliación
  • Fahim AM; Department of Green Chemistry, National Research Center, Dokki, Cairo, Egypt.
  • Ismael EHI; Department of Organometallic and Organ Metalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt.
  • Elsayed GH; Hormones Department, National Research Centre, Dokki, Cairo, Egypt.
  • Farag AM; Department of Chemistry, Faculty of Science, Cairo University, Giza, Cairo, Egypt.
J Biomol Struct Dyn ; 40(19): 9177-9193, 2022.
Article en En | MEDLINE | ID: mdl-34106038
ABSTRACT
In this investigation, we studied the reactivity of 5-aminouracil (1) with ethyl cyanoacetate (2) utilizing microwave irradiation to afford the corresponding 2-cyano-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide (3) in excellent yield. The electrophilic azo-coupling reaction of acetamide 3 with aromatic diazonium salts afforded the corresponding hydrazone derivatives 4a-d. The Michael addition cyclization of hydrazone in pyridine to give pyrazolo[5,1-c][1, 2, 4]triazine-3-carboxamide 5a-d derivatives. The obtained compounds were elucidated against antimicrobial activity and antitumor activity breast cancer cells (MCF-7) and liver cancer cells (HepG2) utilized MTT assay. Compounds 5b, 5c and 5d revealed more inhibitory influence on MCF7 and HepG2 growth than the reference drug doxorubicin (Dox) after 48 h incubation. Furthermore, molecular docking studies were carried out on one of the most effective compound 4-amino-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-7-(4-fluorophenyl) pyrazole [5,1-c][1, 2, 4]triazine-3-carboxamide (5c) (TFC) with (PDB 3t88), (PDB 2wje) , (PDB 4ynt), (PDB 1tgh), (PDB 4hdq) and (PDB 3pxe) which attached with different proteins with different energies and shortage bond distance. Also; the comprehensive theoretical and experimental mechanical studies of compound TFC and TMC were compatible with FTIR and 1H NMR spectral data. The optimized molecular structure of TFC with FTIR was examined via DFT/ B3LYP/6-31G (d) level.Communicated by Ramaswamy H. Sarma.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antiinfecciosos / Antineoplásicos Idioma: En Revista: J Biomol Struct Dyn Año: 2022 Tipo del documento: Article País de afiliación: Egipto

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antiinfecciosos / Antineoplásicos Idioma: En Revista: J Biomol Struct Dyn Año: 2022 Tipo del documento: Article País de afiliación: Egipto