[1]
Alvar, J.; Vélez, I.D.; Bern, C.; Herrero, M.; Desjeux, P.; Cano, J.; Jannin, J.; den Boer, M. WHO leishmaniasis control team. PLoS One, 2012, 7e35671
[2]
World Health Organization. Control of the Leishmaniases, report of a WHO expert committee. World Health Organ. Tech. Rep. Ser., 2010, 949, 1-186.
[3]
Hotez, P.J.; Molyneux, D.H.; Fenwick, A.; Kumaresan, J.; Sachs, S.E.; Sachs, J.D.; Savioli, L. Control of neglected tropical diseases. N. Engl. J. Med., 2007, 357, 1018-1027.
[4]
Du, R.; Hotez, P.J.; Al-Salem, W.S.; Acosta-Serrano, A. Socioeconomic inequalities in neglected tropical diseases: A systematic review. PLoS Negl. Trop. Dis., 2016, 10(5)e0004546
[5]
Mishra, J.; Saxena, A. Chemotherapy of leishmaniasis: Past, present and future. Curr. Med. Chem., 2007, 14, 1153-1169.
[6]
Momeni, A.Z.; Reiszadae, M.R.; Aminjavaheri, R. Treatment of cutaneous leishmaniasis with a combination of allopurinol and low dose meglumine antimoniate. Int. J. Dermatol., 2002, 41, 441-443.
[7]
Palumbo, E. Current treatment for cutaneous leishmaniasis: A review. Am. J. Ther., 2009, 16, 178-182.
[8]
Croft, S.L.; Sundar, S.; Fairlamb, A.H. Drug resistance in leishmaniasis. Clin. Microbiol. Rev., 2006, 19, 111-126.
[9]
Natera, S.; Machuca, C.; Padrón-Nieves, M.; Romero, A.; Díaz, E.; Ponte-Sucre, A. Leishmania spp: Proficiency of drug-resistant parasites. Int. J. Antimicrob. Agents, 2007, 29, 637-642.
[10]
Frézard, F.; Demicheli, C.; Ribeiro, R.R. Pentavalent antimonials: New perspectives for old drugs. Molecules, 2009, 14, 2317-2336.
[11]
Salas, J.M.; Romero, M.A. Sánchez. M.P.; Quirós, M. Metal complexes of 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Coord. Chem. Rev., 1999, 195, 1119-1142.
[12]
Fischer, G. Recent progress in 1,2,4-triazolo[1,5-a]pyrimidine chemistry. Adv. Heterocycl. Chem., 2008, 95, 143-219.
[13]
Astakhov, A.V.; Sokolov, A.N.; Pyatakov, D.A.; Shishkina, S.V.; Shishkin, O.V.; Chernyshev, V.M. Reactivity of 2-amino-1,2,4-triazolo[1,5-a]pyrimidines with various saturation of the pyrimidine ring towards electrophiles. Chem. Heterocycl. Compd., 2016, 51, 1039-1047.
[14]
Botros, S.; Khamil, O.M.; Kamel, M.M.; El-Dash, Y.S. Synthesis, characterization and cytotoxicity of substituted [1]Benzothieno[3,2-e][1,2,4]triazolo [4,3-a]pyrimidines. Acta Chim. Slov., 2017, 64(1), 102-116.
[15]
Wang, S.; Zhao, L.J.; Zheng, Y.C.; Shen, D.D.; Miao, E.F.; Qiao, X.P.; Zhao, L.J.; Liu, Y.; Huang, R.L.; Yu, B.; Liu, H.M. Design, synthesis and biological evaluation of [1,2,4]triazolo[1,5-a]pyrimidines as potent lysine specific demethylase 1 (LSD1/KDM1A) inhibitors. Eur. J. Med. Chem., 2017, 125, 940-951.
[16]
Birr, E.J. Synthesis of triazolopyrimidine compounds. Wiss. Z. Phot., 1952, 47, 2-27.
[17]
Bulow, C.; Haas, K. Synthetische Versuche zur Darstellung von Derivaten des heterokondensierten, heterocyclischen 1.3-Triazo-7.0′-pyrimidins. Chem. Ber., 1909, 42, 4638-4644.
[18]
Caballero, A.B.; Rodríguez-Diéguez, A.; Vidal, I.; Dobado, J.A.; Castillo, O.; Lezama, L.; Salas, J.M. Insights on the binding ability of a new adenine analog: 7-amine-1,2,4-triazolo[1,5-a]pyrimidine. Synthesis and magnetic study of the first copper(ii) complexes. Dalton Trans., 2012, 41(6), 1755-1764.
[19]
Méndez-Arriaga, J.M.; Oyarzabal, I.; Escolano, G.; Rodríguez-Diéguez, A.; Sánchez-Moreno, M.; Salas, J.M. In vitro leishmanicidal and trypanocidal evaluation and magnetic properties of 7-amino-1,2,4-triazolo[1,5-a]pyrimidine Cu (II) complexes. J. Inorg. Biochem., 2018, 180, 26-32.
[20]
Caballero, A.B.; Rodríguez-Diéguez, A.; Quirós, M.; Lezama, L.; Salas, J.M. New copper(II), nickel(II) and zinc(II) complexes with1,2,4-triazolo[1,5-a]pyrimidines and the chelating ligand 1,3-propanediamine:An unexpected coordination behavior for the 7-amine-derivative. Inorg. Chim. Acta, 2011, 378(1), 194-201.
[21]
Méndez-Arriaga, J.M.; Esteban-Parra, G.M.; Juárez, M.J.; Rodríguez-Diéguez, A.; Sánchez-Moreno, M.; Salas, J.M. Antiparasitic activity against trypanosomatid diseases and novel metal complexes derived from the first time characterized 5-phenyl-1,2,4-triazolo[1,5-a]pyrimidi-7(4H)-one. J. Inorg. Biochem., 2017, 175, 217-224.
[22]
Magán, R.; Marín, C.; Rosales, M.J.; Salas, J.M.; Sánchez-Moreno, M. Therapeutic potential of new Pt(II) and Ru(III) triazole-pyrimidine complexes against Leishmania donovani. Pharmacology, 2005, 73, 41-48.
[23]
Martinez, A.; Carreon, T.; Iniguez, E.; Anzellotti, A.; Sanchez, A.; Tyan, M.; Sattler, A.; Herrera, L.; Maldonado, R.A.; Sanchez-Delgado, R.A. Searching for new chemotherapies for tropical diseases: Ruthenium–clotrimazole complexes display high in vitro activity against Leishmania major and Trypanosoma cruzi and low toxicity toward normal mammalian cells. J. Med. Chem., 2012, 55, 3867-3877.
[24]
Navarro, P.; Sanchez-Moreno, M.; Marín, C.; García-España, E.; Ramírez-Macías, I.; Olmo, F.; Rosales, M.J.; Gómez-Contreras, C.; Yunta, M.J.R.; Gutierrez-Sanchez, R. In vitro leishmanicidal activity of pyrazole-containing polyamine macrocycles which inhibit the Fe-SOD enzyme of leishmania infantum and Leishmania braziliensis species. Parasitology, 2014, 141, 1031-1043.
[25]
Fandzloch, M.; Méndez-Arriaga, J.M.; Sánchez-Moreno, M.; Wojtczak, A.; Jezierska, J.; Sitkowski, J.; Wisniewska, J.; Salas, J.M.; Łakomska, I. Strategies for overcoming tropical disease by ruthenium complexes with purine analog: Application against Leishmania spp. and Trypanosoma cruzi. J. Inorg. Biochem., 2017, 176, 144-155.
[26]
Sánchez-Delgado, R.A.; Anzellotti, A. Metal complexes as chemotherapeutic agents against tropical diseases: trypanosomiasis, malaria and leishmaniasis. Mini Rev. Med. Chem., 2004, 4(1), 23-30.
[27]
Łakomska, I.; Fandzloch, M. Application of 1,2,4-triazolo[1,5-a]pyrimidines for the design of coordination compounds with interesting structures and new biological properties. Coord. Chem. Rev., 2016, 328, 221-241.
[28]
Salas, J.M.; Caballero, A.B.; Esteban-Parra, G.M.; Méndez-Arriaga, J.M. Leishmanicidal and trypanocidal activity of metal complexes with 1,2,4-triazolo[1,5-a]pyrimidines: insights on their therapeutic potential against leishmaniasis and chagas disease. Curr. Med. Chem., 2017, 24(25), 2796-2806.
[29]
Łakomska, I.; Fandzloch, M.; Wojtczak, A. Dimeric ruthenium-triazolopyrimidine complex: Synthesis and structural characterization. Inorg. Chem. Commun., 2014, 49, 24-26.
[30]
Caballero, A.B.; Rodríguez-Diéguez, A.; Quirós, M.; Salas, J.M.; Huertas, O.; Ramírez-Macías, I.; Sánchez-Moreno, M. Triazolopyrimidine compounds containing first-row transition metals and their activity against the neglected infectious Chagas disease and leishmaniasis. Eur. J. Med. Chem., 2014, 85, 526-534.
[31]
Rodríguez-Arce, E.; Machado, I.; Rodríguez, B.; Lapier, M.; Zúñiga, M.C.; Maya, J.D.; Olea-Azar, C.; Otero, L.; Gambino, D. Rhenium(I) tricarbonyl compounds of bioactive thiosemicarbazones: Synthesis, characterization and activity against Trypanosoma cruzi. J. Inorg. Biochem., 2017, 170, 125-133.
[32]
Marutescu, L.; Calu, M.; Chifiriuc, C.; Bleotu, C.; Daniliuc, C.G.; Falcescu, D.; Kamerzan, C.M.; Badea, M.; Olar, R. Synthesis, Physico-chemical characterization, crystal structure and influence on microbial and tumor cells of some Co(II) complexes with 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine. Molecules, 2017, 22, 1233.
[33]
Bruker Apex2, Instructions manual. Bruker AXS Inc., Madison, Wisconsin, USA 2004.
[34]
Sheldrick, G.M. SADABS, Program for Empirical Adsorption Correction; Institute for Inorganic Chemistry, University of Gottingen: Germany, 1996.
[35]
Sheldrick, G.M. Crystal structure refinement with SHELXS. Acta Cryst., 2015, C71, 3-8.
[36]
Romero, M.A.; Salas, J.M.; Quirós, M.; Sánchez, M.P.; Romero, J.; Martín, D. Structural and magnetic studies on a bromine-bridged copper(II) dimer with 5,7-Dimethyl[1,2,4]triazolo[1,5-a]pyrimidine. Inorg. Chem., 1994, 33, 5477-5481.
[37]
Romero, M.A.; Salas, J.M.; Quirós, M. Cobalt(II) complexes of 5,7-dimethyl[1,2,4]-triazolo-[1,5-a]-pyrimidine. Spectroscopic characterization, XRD study and antimicrobial activity. Transition Met. Chem., 1993, 18, 595-598.
[38]
González, P.; Marín, C.; Rodríguez-González, I.; Hitos, A.B.; Rosales, M.J.; Reina, M.; Díaz, J.G.; González-Coloma, A.; Sánchez-Moreno, M. Cobalt(II) complexes of 5,7-dimethyl[1,2,4]-triazolo-[1,5-a]-pyrimidine. Spectroscopic characterization, XRD study and antimicrobial activity. Int. J. Antimicrob. Agents, 2005, 25, 136-141.
[39]
Bradford, M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 1976, 72, 248-254.
[40]
Beyer, W.F.; Fridovich, I. Assaying for superoxide dismutase activity: Some large consequences of minor changes in conditions. Anal. Biochem., 1987, 161, 559-566.
[41]
Salas, J.M.; Romero, M.A.; Rahmani, A.; Faure, R. Dichlorobis(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-N3)zinc(II). Acta Cryst., 1994, C50, 510-512.
[42]
Chilton, N.F.; Anderson, R.P.; Turner, L.D.; Soncini, A.; Murray, K.S. PHI: A powerful new program for the analysis of anisotropic monomeric and exchange-coupled polynuclear d- and f-block complexes. I. Comput. Chem., 2013, 34, 1164-1175.
[43]
Rojo, T.; Arriortua, N.I.; Ruiz, J.; Darriet, J.; Villeneuve, G.; Beltran-Porter, D. Magnetostructural correlations in parallel square-planar chloride bridged copper(II) dimers: structure, dynamic nuclear magnetic resonance study, and magnetic properties of [Cu2(terpy)2Cl2][PF6]2. Dalton Trans., 1987, 285-291.
[44]
Torres-García, P.; Luna-Giles, F.; Bernalte-García, A.; Platas-Iglesias, C.; Esteban-Gómez, D.; Viñuelas-Zahínos, E. Effects of the substituents of pyrazole/thiazine ligands on the magnetic properties of chloro-bridged Cu(II) complexes. New J. Chem., 2017, 41, 8818-8827.
[45]
Boča, R. Zero-field splitting in metal complexes. Coord. Chem. Rev., 2004, 248, 757-815. and references cited therein.
[46]
Titiš, J.; Boča, R. Magnetostructural D correlations in hexacoordinated cobalt(II) complexes. Inorg. Chem., 2011, 50, 11838-11845.
[47]
Colacio, E.; Ruiz, J.; Ruiz, E.; Cremades, E.; Krzystek, J.; Carretta, S.; Cano, J.; Guidi, T.; Wernsdorfer, W.; Brechin, E.K. Slow magnetic relaxation in a CoII–YIII Single‐ion magnet with positive axial zero-field splitting. Angew. Chem. Int. Ed., 2013, 52, 9130-9134.
[48]
Herchel, R.; Vahovska, L.; Potočňak, I.; Travniček, Z. Slow magnetic relaxation in octahedral cobalt(II) field-induced single-ion magnet with positive axial and large rhombic anisotropy. Inorg. Chem., 2014, 53, 5896-5898.
[49]
Smolko, L.; Černák, J.; Dušek, M.; Miklovič, J.; Titiš, J.; Boča, R. Three tetracoordinate Co(II) complexes [Co(biq)X2] (X = Cl, Br, I) with easy-plane magnetic anisotropy as field-induced single-molecule magnets. Dalton Trans., 2015, 44, 17565-17571.
[50]
Idešicová, M.; Titiš, J.; Krzystek, J.; Boča, R. Zero-field splitting in pseudotetrahedral Co(II) complexes: A Magnetic, high-frequency and -field EPR, and computational study. Inorg. Chem., 2013, 52, 9409-9417.
[51]
Caballero, A.B.; Salas, J.M.; Sánchez-Moreno, M. Metal based therapeutics for leishmaniasis. In: Leishmaniasis – Trends in Epidemiology, Diagnosis and Treatment, in Leishmaniasis: Trends in Epidemiology, Diagnosis and Treatment; David M. , Claborn, Ed.; IntechOpen Chapter 20, 2014.
[52]
Tavares, J.; Ouaissi, A.; Kong Thoo Lin, P.; Loureiro, I.; Kaur, S.; Roy, N.; Cordeiro da Silva, A. Bisnaphthalimidopropyl derivatives as inhibitors of Leishmania SIR2 related protein 1. ChemMedChem, 2010, 5, 140-147.
[53]
Cleghorn, L.A.; Woodland, A.; Collie, I.T.; Torrie, L.S.; Norcross, N.; Luksch, T.; Mpamhanga, C.; Walker, R.G.; Mottram, J.C.; Brenk, R.; Frearson, J.A.; Gilbert, I.H.; Wyatt, P.G. Identification of Inhibitors of the Leishmania cdc2-Related protein kinase CRK3. ChemMedChem, 2011, 6, 2214-2224.
[54]
Toro, M.A.; Sánchez-Murcia, P.A.; Moreno, D.; Ruiz-Santaquiteria, M.; Alzate, J.F.; Negri, A.; Camarasa, M.J.; Gago, F.; Velázquez, S.; Jiménez-Ruiz, A. Probing the dimerization interface of Leishmania infantum trypanothione reductase with site-directed mutagenesis and short peptides. ChemBioChem, 2013, 14(10), 1212-1217.
[55]
Ruiz-Santaquiteria, M.; Sánchez-Murcia, P.A.; Toro, M.A.; de Lucio, H.; Gutiérrez, K.J.; de Castro, S.; Carneiro, F.A.C.; Gago, F.; Jiménez-Ruiz, A.; Camarasa, M.J.; Velázquez, S. First example of peptides targeting the dimer interface of Leishmania infantum trypanothione reductase with potent in vitro antileishmanial activity. Eur. J. Med. Chem., 2017, 135, 49-59.
[56]
Miller, A.F. Superoxide dismutases: Active sites that save, but a protein that kills. Curr. Opin. Chem. Biol., 2004, 8, 162-168.
[57]
Turrens, J.F. Oxidative stress and antioxidant defenses: a target for the treatment of diseases caused by parasitic protozoa. Mol. Asp Med., 2004, 25, 211-220.
21
2