Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines

作者: Anna V Dolzhenko , Bee Jen Tan , Gigi Ngar Chee Chiu , Wai Keung Chui , Anton V Dolzhenko

DOI: 10.1016/J.JFLUCHEM.2015.03.010

关键词:

摘要: Abstract New fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5- a ][1,3,5]triazin-5-amines were designed as potential anticancer agents and practical method for their preparation was developed. The reaction of benzhydrazide with cyanoguanidine followed by intramolecular cyclocondensation resulted in the formation triazolylguanidine, which upon condensation trichloroacetonitrile afforded key intermediate – 2-phenyl-7-trichloromethyl-1,2,4-triazolo[1,5- ][1,3,5]triazin-5-amine. In mild conditions, this underwent nucleophilic displacement trichloromethyl group series benzylamines providing target compounds. Antiproliferative activity prepared compounds against lung breast cancer cells explored. Together effect, some demonstrated anti-angiogenic properties.

参考文章(24)
Danièle Bonnet-Delpon, Jean-Pierre Bégué, Bioorganic and Medicinal Chemistry of Fluorine ,(2008)
Svetlana A. Kalinina, Dmitrii V. Kalinin, Anton V. Dolzhenko, A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines Tetrahedron Letters. ,vol. 54, pp. 5537- 5540 ,(2013) , 10.1016/J.TETLET.2013.07.158
Joshua Seitz, Jacob G. Vineberg, Edison S. Zuniga, Iwao Ojima, Fluorine-Containing Taxoid Anticancer Agents and Their Tumor-Targeted Drug Delivery Journal of Fluorine Chemistry. ,vol. 152, pp. 157- 165 ,(2013) , 10.1016/J.JFLUCHEM.2013.05.013
Anton V. Dolzhenko, Dmitrii V. Kalinin, Svetlana A. Kalinina, Synthesis of novel trichloromethyl substituted azolo[1,3,5]triazines Heterocycles. ,vol. 85, pp. 2515- 2522 ,(2012) , 10.3987/COM-12-12542
Hriday Bera, Min Huey Lee, Lingyi Sun, Anton V. Dolzhenko, Wai Keung Chui, Synthesis, anti-thymidine phosphorylase activity and molecular docking of 5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ones. Bioorganic Chemistry. ,vol. 50, pp. 34- 40 ,(2013) , 10.1016/J.BIOORG.2013.07.004
Fabrício Gava Menezes, Hugo Gallardo, César Zucco, Recentes aplicações sintéticas de compostos orgânicos tricloro(bromo)metila substituídos Química Nova. ,vol. 33, pp. 2233- 2244 ,(2010) , 10.1590/S0100-40422010001000037
Anton V. Dolzhenko, Svetlana A. Kalinina, Dmitrii V. Kalinin, A novel multicomponent microwave-assisted synthesis of 5-aza-adenines RSC Advances. ,vol. 3, pp. 15850- 15855 ,(2013) , 10.1039/C3RA41932K
Felicia Phei Lin Lim, Anton V. Dolzhenko, 4-Amino-substituted pyrazolo[1,5-a][1,3,5]triazin-2-amines: a new practical synthesis and biological activity Tetrahedron Letters. ,vol. 55, pp. 6684- 6688 ,(2014) , 10.1016/J.TETLET.2014.10.057
Anton V Dolzhenko, Bee Jen Tan, Anna V Dolzhenko, Gigi Ngar Chee Chiu, Wai Keung Chui, None, Synthesis and biological activity of fluorinated 7-aryl-2-pyridyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amines. Journal of Fluorine Chemistry. ,vol. 129, pp. 429- 434 ,(2008) , 10.1016/J.JFLUCHEM.2008.02.007