Pyrimidine containing furanose derivative having antifungal, antioxidant, and anticancer activity

BACKGROUND: A series of 6-(substituted aldehyde)-3,4-dihydro-1-(tetrahydro-3,4-dihydroxy-5-(hydroxymethyl) furan-2-yl)-4-phenylpyrimidine-2(1H)-one derivative (6A-6P) was synthesized from the 6-(substituted aldehyde)-4-phenylpyrimidine-2(1H)-one derivative (5A-5P) through following reaction mechanisms Claisen-Schmidt, Cyclization, and Satos fusion. The structures of the synthesized compounds were elucidated by I.R.,(1)H-NMR, elemental analysis, and mass spectroscopic techniques. RESULT: The synthesized compounds were screened for in vitro antifungal activity at 25, 50, 100, and 200 μg/ml concentrations. Among them, compounds 6P, 6D, and 6M exhibited significant antifungal activity that was carried out by cup plate method against fungal strain which was collected from IMTECH Chandigarh, India, against standard drug fluconazole. Compounds have been further evaluated by measuring zone of inhibition and percent inhibition. The synthesized compounds were screened for in vitro antioxidant activity using the DPPH assay, based on the AAI and antioxidant activity unit (AAU), using a combination relation between DPPH concentration and absorbance. The antioxidant strength of compounds was compared against ascorbic acid. Among them, compounds 6K, 6F, 6E, 6G, 6H, and 6M exhibited significant antioxidant activity and 6J have less active compound. The data of these synthesized compounds were submitted to the National Institute of Health, USA, under the drug discovery program of National Cancer Institute (NCI) and screened for anticancer activity at a single high dose (10(−5) M) in full NCI 60 cell lines. The selected compounds have shown potent significant anticancer activity in the NCI 60 cell line screening. CONCLUSION: A new series of pyrimidine analogues that contain furanose moiety were synthesized by Satos fusion and characterized. The synthesized compounds screened for their in vitro antioxidant, antifungal activity, as well as anticancer activity given by the derivative which has chloro, methoxy, nitro, and chloro substitution having furanose contain pyrimidine derivative that showed the most potent activity. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13588-014-0003-0) contains supplementary material, which is available to authorized users.