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Short Paper | Regular issue | Vol 92, No. 6, 2016, pp.1121-1131
Published online, 28th April, 2016
DOI: 10.3987/COM-16-13464
Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines

Felicia Phei Lin Lim, Koon Kee Kow, Eng Hwa Yeo, Sek Chuen Chow, and Anton V. Dolzhenko*

*School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Subang Jaya, Selangor 47500, Malaysia


Novel fluorinated 4-benzylamino-7-phenylpyrazolo[1,5-a]- [1,3,5]triazin-2-amines were prepared using an efficient and practical approach. The chemoselectivity of condensation of pyrazolylguanidine and trichloroacetonitrile was found to be solvent-dependent and, when conducted in toluene, this reaction afforded 7-phenyl-4-trichloromethylpyrazolo[1,5-a]- [1,3,5]triazin-2-amine as the main product. This key intermediate underwent nucleophilic replacement of the trichloromethyl group with fluorinated benzylamines providing a series of the target compounds. Antiproliferative activity of the prepared compounds against Jurkat T cells was explored using MTS assay. Morphological changes observed in cells treated by the most potent compounds of this series, suggested that these compounds induced apoptosis in cells.