One pot synthesis of pyrimidine and bispyrimidine derivatives and their evaluation for anti-inflammatory and analgesic activities

A number of pyrimidine derivatives (1–10) have been synthesized by condensation of 4-isothiocyanato-4-methylpentan-2-one with furfurylamine, histamine, 1-(3-aminopropyl)imidazole, 1-(3-aminopropyl)-2-pyrrolidinone, 2-aminobenzonitrile and 3-isothiocyanatobutanal with 1-(3-aminopropyl)-2-pyrrolidinone and 2-hydrazinopyridine under different reaction conditions. Various bispyrimidine derivatives (11–15) were obtained by condensation of 4-isothiocyanato-4-methylpentan-2-one with 2,4,8,10-tetraoxaspiro[5,5]undecane3,9-dipropamine (11′), 1,4-bis(3-aminopropyl)piperazine (13′), 3,5-diamino 1,2,4-triazole (15′) and 3-isothiocyanatobutanal with 2,4,8,10-tetraoxaspiro[5,5]undecane 3,9-dipropamine, 1,4-bis(3-aminopropyl)piperazine. All these compounds were characterized by correct FT-IR, 1H NMR, MS and elemental analysis. These compounds were screened for anti-inflammatory and analgesic activities. Anti-inflammatory activity of 3 is comparable while analgesic activity was found to be better than that of standard drug.

Condensation of 4-isothiocyanato-4-methyl pentan-2-one and 3-isothiocyanatobutanal with various amines and diamines gave pyrimidine (1–10) and bispyrimidine derivatives (11–15). On screening for anti-inflammatory and analgesic activities compound-3 exhibited anti-inflammatory activity comparable to ibuprofen and analgesic activity better than ibuprofen.Figure optionsDownload as PowerPoint slide