Abstract
A novel and mild protocol for the synthesis of phosphonotripeptide 16 were achieved from novel formylpyrazolofuran 3, benzyl carbamate 5, triphenyl phosphite 6 by Birum-Oleksyszyn reaction using copper (II) trifliate as Lewis acid catalyst in dry dichloromethane at room temperature which synthesis of novel N-benzyloxy-α-aminophosphonate 7 . A mechanism for this condensation reaction is proposed. Cleavage of the N-benzyloxy carbonyl group under acid hydrolysis afford the free α-aminophosphonate 9 in quantitative yield. This in turn, by reaction with N-phthaloylglycine 12 via TUBU to phthalimido group 13.Cleavage of phthalimido group under hydrazinedihydrochloride afford free peptide 14 .the result phosphonotripeptide 16 obtained by the reaction of free peptide with bioactive cyclic moiety-COCl 15. The structures of all new compounds were established by IR,1HNMR and mass spectral data. Also anti-cancer, anti-inflammatory and biochemical activities of all these compounds were reported.
Highlights
Phosphonotripeptides have been found to exhibit a wide range of biological activities .to the best of our knowledge there are no papers reports on the preparation of Phosphonotripeptide biconjugates
We focused on formyl pyrazolofuran because it is important class of compounds and attracted widespread
The general method for synthesis of diphenyl α-aminophosphate is the three component reaction of formyl pyrazolo furan, carbamate and triphenylphosphite in organic solvent by one pot Birum-Oleksyszyn reaction [4] according to Scheme 1.α-aminophosphate converted by the deprotection with the appropriate acid condition into the respective free α-aminophosphonate, this is in turn, by reaction with N-protected phthalloyl glycine [5] via TUBU to phthalimido group [6] which by the cleavage of phthalimido group turn to free peptide via hydrazinedihydrochloride [7].The novel phosphinotripeptide afforded by the coupling of N-protected acid chloride with phosphonodipeptide[8]
Summary
Phosphonotripeptides have been found to exhibit a wide range of biological activities .to the best of our knowledge there are no papers reports on the preparation of Phosphonotripeptide biconjugates. We focused on formyl pyrazolofuran because it is important class of compounds and attracted widespread. Attention due to their pharmacological properties, being reported to have a large spectrum of biological effects, anti-cancer [1,2,3]. The general method for synthesis of diphenyl α-aminophosphate is the three component reaction of formyl pyrazolo furan, carbamate and triphenylphosphite in organic solvent by one pot Birum-Oleksyszyn reaction [4] according to Scheme 1.α-aminophosphate converted by the deprotection with the appropriate acid condition into the respective free α-aminophosphonate , this is in turn, by reaction with N-protected phthalloyl glycine [5] via TUBU to phthalimido group [6] which by the cleavage of phthalimido group turn to free peptide via hydrazinedihydrochloride [7].The novel phosphinotripeptide afforded by the coupling of N-protected acid chloride with phosphonodipeptide[8]
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