Abstract
A series of new α-aminophosphonates containing potential anticancer active 4-chloro-6- methylpyrimidin-2-amino pharmacophore were synthesized.
Background: α-Aminophosphonates are of growing interest to the 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 enrich its activity.
Objective: Erstwhile many of the reported α-aminophosphonates impregnated with bioactive heterocycles like quinazoline, chromene, pyrazole, furan and thiophene were used as anticancer drugs, and we are intended to enhance the anticancer potentiality of α-aminophosphonates by substituting a new 4-chloro-6-methylpyrimidin-2-yl group into its structure, specifically on nitrogen atom.
Methods: Title compounds were synthesized by Kabachnik-Fields reaction by using sulfated Titania, a solid acid catalyst that is encompassed with high density of Lewis acidic reaction sites. The series of synthesized compounds were screened for in vitro anti-cancer activity and their ADMET, QSAR and drug properties studied.
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 that are 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.
Graphical Abstract
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