Nano Sb{sub 2}O{sub 3} catalyzed green synthesis, cytotoxic activity, and molecular docking study of novel α-aminophosphonates

Journal Article · Mon Apr 15 04:00:00 EDT 2019 · Medicinal Chemistry Research (Print)

DOI:https://doi.org/10.1007/S00044-019-02302-Y· OSTI ID:22936203

Poola, Sreelakshmi; Nadiveedhi, Maheshwara Reddy; Sarva, Santhisudha; Gundluru, Mohan; Nagaripati, Saichaithanya; Shaik, Mahammad Sadik ^[1]; Kotha, Peddanna ^[2]; Chamarthi, Nagaraju

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1. Sri Venkateswara University, Department of Chemistry (India)
2. Sri Venkateswara University, Department of Bio-Chemistry (India)

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{sub 2}O{sub 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, {sup 1}H, {sup 13}C, {sup 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. .

• OSTI ID: 22936203
• Journal Information: Medicinal Chemistry Research (Print), Journal Name: Medicinal Chemistry Research (Print) Journal Issue: 4 Vol. 28; ISSN 1054-2523
• Country of Publication: United States
• Language: English

Related Subjects

60 APPLIED LIFE SCIENCES
ALDEHYDES
AROMATICS
CARBON 13
DOXORUBICIN
HEPATOMAS
HYDROGEN 1
KIDNEYS
MAMMARY GLANDS
NUCLEAR MAGNETIC RESONANCE
PANCREAS
PHOSPHONATES
PHOSPHORUS 31
PHOSPHORUS COMPOUNDS
PROSTATE
PYRIDINE
SYNTHESIS