Synthesis of New 4-Chloro-6-Methylpyrimidin-2-yl-Aminophosphonates as Potential DU145 and A549 Cancer Cell Inhibitors

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Author(s): Gajjala Raghavendra Reddy, Chinta Raveendra Reddy, Gopireddy Venkata Subba Reddy, Pasupuleti Visweswara Rao, Meenakshisundaram Swaminathan, Cirandur Suresh Reddy*.

Journal Name: Letters in Drug Design & Discovery

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A series of new α-aminophosphonates containing a potential anticancer active 4-chloro-6-methylpyrimidin-2-amino pharmacophore were synthesized.

Background: α-Aminophosphonates are ever appealing to the interest of researchers due to their biological activities. Besides aminophosphoryl functionality which is responsible for the vital activity, incorporation of a captivating pharmacophore on it will definitely enriches its activity.

Objective: Erstwhile many of the reported α-aminophosphonates impregnated with bioactive heterocycles like quinazoline, chromene, pyrazole, furan and thiophene are anticancer drugs, we are intended to enhance the anticancer potentiality of α-aminophosphonates by substituting a new 4-chloro-6-methylpyrimidin-2-yl group in to its structure, specifically on nitrogen atom.

Method: Title compounds were synthesized by Kabachnik-Fields reaction by using sulfated titania, a solid acid that is encompassed with high density of Lewis acidic reaction sites as catalyst. The series of compounds synthesized were screened for in vitro anti-cancer activity and studied their ADMET, QSAR and drug properties.

Results: Structures of all the title compounds synthesized in high yields were confirmed by spectral & elemental analyses. Their anti-cancer screening studies on various cell lines and evaluation of other properties revealed their potentiality towards the inhibition of growth of DU145 & A549 cell lines.

Conclusion: The substitution of 4-chloro-6-methylpyrimidin-2-amino moiety on to the amino functionality of the α-aminophosphonates is a critical task invariably due to the substitutions of the NH2 located on α-carbon. As such, this substitution had increased the scope for growth inhibition of DU145 and A549 cancer cells.

Keywords: Kabachnik-Fields Reaction, 4-chloro-6-methylpyrimidin-2-amine, sulfated Titania, DU145 cell lines, A549 cell lines, in vitro anti-cancer activity, QSAR studies, ADMET Properties.

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(E-pub Ahead of Print)
DOI: 10.2174/1570180816666190329223207
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