ABSTRACT
Breast and cervical cancer account for the majority of cancer-narrated fatalities among women worldwide, necessitating the development of novel, effective therapeutic ways to combat the disease. In this study, we synthesized 6-methoxy naphthalene and anthracene-based acrylamide chalcone (NBA and ABA) and evaluated its activity for cell multiplication inhibition against two cancer cell lines from humans such as MCF-7 (Human Breast) and HeLa (Cervical) by MTT assay. Physiochemical characterization, such as FT-IR and NMR analyses, validated the synthesized NBA and ABA. Both NBA and ABA have shown antiproliferative action against two cancer cell lines, each with IC50 values of 38.46 and 48.25 µg/mL for HeLa cells and 38.02 and 36.35 µg/mL for MCF-7 cell lines. The results suggest that these acrylamide chalcones for cancer therapy at the lowest concentration. NBA and ABA could prevent cervical and breast cancer in-vitro, and their anti-cancer activity was closely related to methoxy-substituted naphthalene, anthracene ring, α, ß-unsaturated carbonyl and amide group. According to docking data, the NBA and ABA have dock scores ranging from -8.7 to -11.44 kcal/mol. The highest dock score for compound ABA was -11.58 kcal/mol and compound NBA was -10.77 kcal/mol with Braf (5VAM) binding site.
Subject(s)
Antineoplastic Agents , Chalcone , Chalcones , Neoplasms , Humans , Female , Chalcone/chemistry , Chalcone/pharmacology , Molecular Structure , Chalcones/chemistry , Chalcones/pharmacology , Structure-Activity Relationship , MCF-7 Cells , HeLa Cells , Acrylamides/pharmacology , Spectroscopy, Fourier Transform Infrared , Drug Screening Assays, Antitumor , Cell Proliferation , Naphthalenes/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Dose-Response Relationship, DrugABSTRACT
Synthesis of spiroindoloquinazolines via one-pot three-component condensation reactions of tryptanthrin, malononitrile or ethylcyanoacetate, and nucleophiles was carried out in MeOH using triethylamine as the base catalyst under reflux conditions. This method has the advantages of short reaction time, excellent yields, and an easy work-up procedure. The structural properties of the compound 4c {2-amino-6-methyl-spiro-[12H]Indolo(2,1-b)quinazoline-12-one]12',4-pyrano(2,3-c)pyrazole]-3-carbonitrile} and the obtained crystal were analyzed by the DFT theoretical calculation method, using the B3LYP 6-311G(d,p) basis set and were found to be in agreement with the experimental results. The importance of biological application and drug design of the same compound was verified by molecular docking studies.
