Synthesis, DFT Calculations, and Biological Studies of New 2-Cyano-3-(Naphthalene-1-yl) Acryloyl Amide Analogues as Anticancer Agents.
Chem Biodivers
; 21(10): e202401023, 2024 Oct.
Article
de En
| MEDLINE
| ID: mdl-39015085
ABSTRACT
A set of novel naphthalene derivatives was synthesized via investment of the electrophilic reaction center of the easily obtainable starting substance, 2-cyano-3-(naphthalen-1-yl)acryloyl chloride (1), with various nitrogen nucleophiles and assessed as potential antitumor agents. The chemical structures of these derivatives were completely specified using several spectral and elemental analyses. The antiproliferative efficacy of the discovered compounds against the human cancer cell lines HepG2 and MCF-7 was investigated. Compounds 12b and 9 have more potent anticancer activity versus MCF-7 breast cancer. DFT calculations for the synthesized compounds were studied to determine molecular geometry, frontier orbital analysis, and molecular electrostatic potential. Compound 2 has the lowest energy gap, the highest softness, and the lowest hardness molecule. Also, the electrophilicity values of the studied molecules provide evidence for their biological effectiveness, as compound 9 had significant antiproliferative activity and a high value of electrophilicity (ω) (0.190â
eV).
Mots clés
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Tests de criblage d'agents antitumoraux
/
Prolifération cellulaire
/
Théorie de la fonctionnelle de la densité
/
Amides
/
Naphtalènes
/
Antinéoplasiques
Limites:
Humans
Langue:
En
Journal:
Chem Biodivers
Sujet du journal:
BIOQUIMICA
/
QUIMICA
Année:
2024
Type de document:
Article
Pays d'affiliation:
Égypte
Pays de publication:
Suisse