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Efficient Protocol for Novel Hybrid Pyrimidines Synthesis: Antiproliferative Activity, DFT Analyses, and Molecular Docking Studies.
Althobaiti, Ibrahim O; Alserhani, Mjd Saleh Morezeq; Arafa, Wael A A; Ghoneim, Amira A; Hussein, Modather F; Ibrahim, Hamada Mohamed; Mourad, Asmaa K.
Afiliación
  • Althobaiti IO; Chemistry Department, College of Science and Arts, Jouf University, Gurayat 77217, Saudi Arabia.
  • Alserhani MSM; Chemistry Department, College of Science, Jouf University, Sakaka 72341, Aljouf, Saudi Arabia.
  • Arafa WAA; Chemistry Department, College of Science, Jouf University, Sakaka 72341, Aljouf, Saudi Arabia.
  • Ghoneim AA; Chemistry Department, Faculty of Science, Fayoum University, P.O. Box 63514 Fayoum, Egypt.
  • Hussein MF; Chemistry Department, College of Science, Jouf University, Sakaka 72341, Aljouf, Saudi Arabia.
  • Ibrahim HM; Chemistry Department, Faculty of Science, Zagazig University, Zagazig 7120001, Egypt.
  • Mourad AK; Chemistry Department, College of Science, Jouf University, Sakaka 72341, Aljouf, Saudi Arabia.
ACS Omega ; 8(49): 47239-47253, 2023 Dec 12.
Article en En | MEDLINE | ID: mdl-38107937
ABSTRACT
An efficient, microwave/ultrasound-irradiated synthesis of novel chromenopyrimidines has been established. 2-Amino-5-oxo-4-(thiophen-2-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (1) underwent cyclization reactions with various assorted reagents under sustainable conditions to afford a family of fused pyrimidine derivatives. The proposed structures of the designed fused pyrimidines were confirmed by several spectral techniques. Moreover, the targeted pyrimidines were estimated for their in vitro cytotoxic activities toward three carcinoma cell lines breast (MCF7), hepatocyte (HepG2), and lung (A549) cancer cell lines, as well as one noncancerous cell line (MCF-10A). Structure-activity relationship (SAR) analyses revealed that derivatives 3 and 7 exhibited the highest potency in inhibiting the growth of cancer cells tested in vitro. Particularly, 3-amino-4-imino-5-(thiophen-2-yl)-3,4,5,7,8,9-hexahydro-6H-chromeno[2,3-d]pyrimidin-6-one (3) displayed a robust impact with IC50 values ranging from 2.02 to 1.61 µM. Interestingly, compound 3 was observed to have low cytotoxicity toward noncancerous cell (MCF-10A) compared to the standard drug (Doxorubicin). Further, quantum chemical computations of the designed molecules utilizing density functional theory (DFT) were conducted and shown to be compatible with the observed antiproliferative properties. Thorough docking investigations revealed that the assembled compounds possess exceptionally low binding energies toward our three selected proteins 4b3z-Lung, HepG2-2JW2, and 6ENV-MCV-7. Based on these intriguing results, compound 3 could be further evaluated for preclinical screening, potentially paving the way for its utilization as a promising cancer treatment.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: ACS Omega Año: 2023 Tipo del documento: Article País de afiliación: Arabia Saudita Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: ACS Omega Año: 2023 Tipo del documento: Article País de afiliación: Arabia Saudita Pais de publicación: Estados Unidos