Abstract

The work reports ultrasound promoted facile synthesis of novel ten α-aminophosphonate derivatives coupled with indole-2,3-dione moiety, namely diethyl(substituted phenyl/heteryl)(2-(2-oxoindolin-3ylidene)hydrazinyl)methylphosphonates derivatives 4(a-j). The derivatives 4(a-j) were synthesized through one-pot three component Kabachnik-Fields reaction, by stirring at room temperature in presence of Cerric Ammonium Nitrate (CAN) as a catalyst, to give the final compounds in better yields and in shorter reaction time. Isatin, chemically known as 1-H-indole-2,3-dione, and its derivatives possess a broad range of biological and pharmacological properties. Isatin is widely used as starting material for the synthesis of a broad range of heterocyclic compounds and as substrates for drug synthesis. The α-amino phosphonate derivatives constitute an important class of organophosphorus compounds on account of their versatile biological activity. The general low mammalian toxicity of these compounds made them attractive for use in agriculture and medicine. Considering the importance of the two pharmacophores, promoted us to club both the pharmacophores in a single molecule using green synthetic protocol. The structures of the ultrasound synthesized compounds were confirmed by spectral analysis like IR, 1H NMR, 13C NMR, 31P NMR and MS.

Highlights

  • Isatin-based hydrazones have been identified as inhibitors of the protein tyrosine phosphatase Shp2, which plays an important role in cell signaling, cell proliferation, differentiation and migration [15].The marketed anticancer drug Sunitinib [16] and Oratinib contains 2-oxoindolin-3-ylidene moiety where as Ilmofosin and Edelfosin contains phosphonate moiety and a recently marketed anticancer drug, Toceranib phosphate [17] contains 2-oxoindol-3-ylidene as well as phosphonates moiety

  • Ultrasound assisted method gives better yield in 15-20 minutes against 3-4 hrs required for conventional method. αAminophosphonate derivatives 4(a-j) were synthesized by reacting 3-hydrazonoindolin-2-one (1), substituted/heteryl aldehydes 2(a-j) and triethylphosphite(3) via one pot synthetic step in presence of Cerric Ammonium Nitrate (CAN) as a catalyst

  • CAN catalyst being water soluble can be removed after completion of reaction

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Summary

Introduction

[13].Isatin, chemically known as 1-H-indole-2,3dione, and its derivatives possess a broad range of biological and pharmacological properties and are widely used as starting materials for the synthesis of a broad range of heterocyclic compounds and as substrates for drug synthesis. It is used for the inhibition of pro-apoptotic jurkat T cells. 3hydrazonoindolin-2-one (1) was synthesized by reacting indole-2,3-dione (isatin) (1mmol) with hydrazine hydrate (1mmol) in the presence of glacial acetic acid as a catalyst by conventional method in methanol using molecular sieves and by ultrasonication method by replacing methanol with ethanol.

Experimental Chemistry
Conclusion

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