Nano Sb2O3 catalyzed green synthesis, cytotoxic activity, and molecular docking study of novel α-aminophosphonates

• Published in: Medicinal chemistry research 2019-04, Vol.28 (4), p.528-544
• Main Authors: Poola, Sreelakshmi, Nadiveedhi, Maheshwara Reddy, Sarva, Santhisudha, Gundluru, Mohan, Nagaripati, Saichaithanya, Shaik, Mahammad Sadik, Kotha, Peddanna, Chamarthi, Nagaraju, Cirandur, Suresh Reddy
• Format: Article
• Language: English
• Subjects: Adenocarcinoma; Aldehydes; Antimony trioxide; Aromatic compounds; Beta cells; Biochemistry; Biomedical and Life Sciences; Biomedicine; Biotechnology; Breast cancer; Cancer; Catalysts; Cell Biology; Cell proliferation; Cervical cancer; Cervix; Chemical synthesis; Cytotoxicity; Doxorubicin; ErbB-2 protein; Hepatocellular carcinoma; Molecular docking; NMR; Nuclear magnetic resonance; Original Research; Pancreatic cancer; Pancreatic carcinoma; Pharmacology/Toxicology; Phosphonates; Prostate; Pyridines; Substitutes; Sulforhodamine; Tumor cell lines
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-019-02302-y

Green synthesis of a series of novel dialkyl (aryl substituted)(2-fluoro-4-((2-methylcarbamoyl)pyridine-4-yl)oxy)phenyl)amino)methyl)phosphonates is accomplished by a simple and an efficient one pot three component reaction of 3-(4-amino-3-fluorobenzyl)- N -methylbenzamide with different substituted aromatic aldehydes and dialkyl phosphite in the presence of nano Sb 2 O 3 catalyst under solvent free conditions at 40–50 °C to obtain the title compounds. Excellent isolated product yields are obtained (85–95%) with high purity within shorter reaction times (30–60 min). The title compounds are characterized by IR, 1 H, 13 C, 31 P-NMR and mass spectral data. The synthesized compounds are screened for their anticell-proliferation activity on seven cell lines, Control cells–HEK293 (human embryonic kidney), DU-145 (human prostate adenocarcinoma), MCF-7 (human ER+/PR+/Her2− breast cancer), MDA-MB-231 (human ER−/PR−/Her2− breast cancer), Mia-Paca-2 (human pancreatic carcinoma), HeLa (human cervical cancer) cells as well as HepG2 (human hepatocellular carcinoma) cancer cell lines using Sulforhodamine B (SRB) assay method. Docking studies were carried out for all these synthesized compounds against topoisomerase-II by using Auto dock method. Doxorubicin was taken as standard. Compounds 4a , 4c , 4d , 4e , 4h , 4i , 4k , and 4l exhibited higher cytotoxic activity than the standard doxorubicin.