Design,Synthesis, Antioxidant,and Anti‐Breast Cancer Activities of Novel Diethyl(alkyl/aryl/heteroarylamino)(4‐(pyridin‐2‐yl)phenyl)methylphosphonates |
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Authors: | Sthanikam Siva Prasad Krishnammagari Suresh Kumar Soora Harinath Jayaprakash Balam Satheesh Krishna Chereddy Syama Sundar Pasupuleti Visweswara Rao Tirumalasetty Munichandra Babu Wudayagiri Rajendra Cirandur Suresh Reddy |
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Institution: | 1. Department of Chemistry, Sri Venkateswara University, Tirupati, India;2. Human Genome Centre, School of Medical Sciences, Universiti Sains Malaysia, Kubang Kerian, Kelantan, Malaysia;3. Division of Molecular Biology, Department of Zoology, Sri Venkateswara University, Tirupati, India |
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Abstract: | A series of new diethyl(alkyl/aryl/heteroarylamino)(4‐(pyridine‐2‐yl)phenyl)methylphosphonates ( 4a–t ) were synthesized via three‐component Kabachnik–Field's reaction of 4‐(pyridin‐2‐yl)benzaldehyde, diethylphosphite and various primary amines, catalyzed by cupric acetate monohydrate Cu(OAc)2 · H2O] under solvent‐free and microwave irradiation conditions. Their computational docking analysis supported them as good therapeutic agents to the breast cancer aromatase enzyme and ascertained 4a , 4h , 4m , 4n , and 4t as potential molecules with good binding affinities varying from ?9.0 to ?9.6 kcal/mol and containing the 4‐(pyridine‐2‐yl)phenyl moiety as a pharmacophore. Their in vitro screening performed for the anti‐cell proliferation activity against MBC‐MCF7 cells by MTT and Trypan blue assays confirmed 4m , 4n , and 4q as promising compounds to sustain a low percentage of cell viability at 20 µg/mL concentration. These compounds were also evaluated for their antioxidant activity by the DPPH method and the results established that compounds 4m , 4n , and 4q show around 10% higher activity than the standard antioxidant ascorbic acid. |
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Keywords: | α ‐Aminophosphonates Anti‐breast cancer activity Antioxidant activity Kabachnik‐Field's reaction Molecular docking |
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