IJARP SJIF(2018): 4.908

International Journal of Advanced Research and Publications!

A Novel Synthesis Of Fused Pyrazolopyrimidine: Pyrazolo-Triazolo-Pyrimidine For Anticancer Evalution.

Volume 3 - Issue 8, August 2019 Edition
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A.Y. Hassan, Mona. S. Kadh, N.M. Saleh, E.S. Abou-Amra.
pyrazolo [3,4-d] pyrimidine,pyrazolotriazolopyrimidine,anticanceractivity.
Some novel fused pyrazolo-triazolo-pyrimidine (2- 5)were designed and prepared via reaction of 5-amino-6-hydrazineyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1) with some electrophilic and nucleophilic reagents. The structures of target compounds were confirmed by elemental analyses and spectral data. The newly synthesized compounds were selected by the NCI – Maryland-U.S.A. and were tested for their anticancer activity in an initial single high dose in the full NCI 60 cell line panel.
[1] M. Chauhan, & R. Kumar, “Medicinal attributes of pyrazolo[3,4-d]pyrimidines: A review,” Bioorganic & Medicinal Chemistry, 21(18), 5657–5668, 2013.

[2] E. R. El-Bendary, & F. A. Badria, “Synthesis, DNA-binding, and Antiviral Activity of Certain Pyrazolo[3,4-d]pyrimidine Derivatives,” Archiv Der Pharmazie, 333(4), 99–103, 2000.

[3] J.-H. Chern, K.-S. Shia, T.-A. Hsu, C.-L. Tai, C.-C. Lee, Y.-C. Lee, S.-R. Shih,“Design, synthesis, and structure–activity relationships of pyrazolo[3,4-d]pyrimidines: a novel class of potent enterovirus inhibitors,” Bioorganic & Medicinal Chemistry Letters, 14(10), 2519–2525, 2004.

[4] L. Ballell, R.A. Field, G.A.C. Chung, &R.J.Young, Bioorganic & Medicinal Chemistry Letters,17, 1736, 2007.

[5] S. Alcaro, A. Artese, M. Botta, A.T. Zizzari, F. Orallo, F. Ortuso, M. Yáñez, “Hit Identification and Biological Evaluation of Anticancer Pyrazolopyrimidines Endowed with Anti-inflammatory Activity,” ChemMedChem, 5(8), 1242–1246, 2010.

[6] K. R. A. Abdellatif, & R.B. Bakr, “New advances in synthesis and clinical aspects of pyrazolo[3,4- d]pyrimidine scaffolds,” Bioorganic Chemistry, 78, 341–357, 2018.

[7] S. Gupta, L.M. Rodrigues, A.P. Esteves, A.M.F. Oliveira-Campos, M.S.J. Nascimento, N. Nazareth, H. Cidade, M.P. Neves, E. Fernandes, &M. Pinto, et al,“Synthesis of N-aryl-5-amino-4-cyanopyrazole derivatives as potent xanthine oxidase inhibitors.” European Journal of Medicinal Chemistry, 43(4), 771–780, 2008.

[8] A. F. Eweas, S.A. Swelam, O.A. Fathalla, N.M. Fawzy, & S.I. Abdel-Moez,“Synthesis, anti-microbial evaluation, and molecular modeling of new pyrazolo[3,4-d]pyrimidine derivatives,” Medicinal Chemistry Research, 21(11), 3848–3857, 2011.

[9] S.B. Yewale, S.B. Ganorkar, K.G. Baheti, & R.U. Shelke, “Novel 3-substituted-1-aryl-5-phenyl-6-anilinopyrazolo[3,4-d]pyrimidin-4-ones:Docking, synthesis and pharmacological evaluation as a potential anti-inflammatory agents,” Bioorganic & Medicinal Chemistry Letters, 22(21), 6616–6620, 2012.

[10] S. Kobayashi, “The Synthesis and Xanthine Oxidase Inhibitory Activity of Pyrazolo[3, 4-d]pyrimidines,” CHEMICAL & PHARMACEUTICAL BULLETIN, 21(5), 941–951, 1973.

[11] N. Boechat, L.C.S. Pinheiro, T.S. Silva, A.C.C. Aguiar, A.S. Carvalho, M.M. Bastos, C.C.P. Costa, S. Pinheiro, A.C. Pinto, & J.S. Mendonça, et al, “New Trifluoromethyl Triazolopyrimidines as Anti-Plasmodium falciparum Agents,” Molecules, 17(7), 8285–8302, 2012.

[12] A. Rashad, M. Hegab, R. Abdel-Megeid, M. Ali, & F. Abdel-Megeid, “Synthesis and Antitumor Evaluation of Some Newly Synthesized Pyrazolopyrimidine and Pyrazolotriazolopyrimidine Derivatives,” Phosphorus, Sulfur, and Silicon and the Related Elements, 185(1), 74–83, 2010.

[13] M.M. Kandeel, A. M. Kamal, E.K.A. Abdelall, & H.A.H. Elshemy, “Synthesis of novel chromene derivatives of expected antitumor activity” European Journal of Medicinal Chemistry, 59, 183–193, 2013.

[14] B. Cacciari, C. Bolcato, G. Spalluto, K.-N. Klotz, M. Bacilieri, F. Deflorian, & S. Moro, “Pyrazolo-triazolo-pyrimidines as adenosine receptor antagonists: A complete structure–activity profile,” Purinergic Signalling, 3(3), 183–193, 2006.

[15] E. Al-Afaleq, & S. Abubshait,“Heterocyclic o-Aminonitriles: Preparation of Pyrazolo[3,4-d]-pyrimidines with Modification of the Substituents at the 1- Position,” Molecules, 6(7), 621–638, 2001.

[16] A. Monks, D, Scudiero, P. Skehan, R, Shoemaker, K. Paull, D. Vistica, H. Curtis, L. John, C. Paul, V-W. Anne, G-G. Marcia, C. Hugh, M. Joseph & M. Boyd,“Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines’’ JNCI Journal of the National Cancer Institute, 83(11), 757–766, 1991.