Abstract
The thermal decomposition of [RuCl2(η6-p-cymene)]2 (1) and its biologically active N-alkylphenothiazine compounds of composition L[RuCl3(η6-p-cymene)] where L = CPH+ (2), TFH+·HCl (3), and TRH+ (4) (chlorpromazine hydrochloride, CP·HCl; trifluoperazine dihydrochloride, TF·2HCl; and thioridazine hydrochloride, TR·HCl, respectively) has been studied. The crystal and molecular structure of compound 3 was determined earlier by single crystal X-ray diffraction analysis. The thermal data were collected by simultaneous TG/DSC measurements. For evolved gas detection, the qualitative reaction of chlorides with AgNO3 in an acidic solution was applied. The measurements were carried out in the temperature range to 700 °C in nitrogen atmosphere. Compounds of L[RuCl3(η6-p-cymene)] crystallize with water or water/2-propanole. On the basis of thermal data, the trend in the solvent bonding energies was assessed.
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References
Therrien B. Functionalised η6-arene ruthenium complexes. Coord Chem Rev. 2009;253:493–519.
Zhou Z, Sun Y. Water-soluble chiral aminosulfonamides as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation. Catal Commun. 2009;10:1685–8.
Dann SE, Durran SE, Elsegood MRJ, Smith MB, Staniland PM, Talib S, Dale SH. Supramolecular chemistry of half-sandwich organometallic building blocks based on RuCl2(p-cymene)Ph2PCH2Y. J Organomet Chem. 2006;691:4829–42.
Allardyce CS, Dyson PJ, Ellis DJ, Salter PA, Scopelitti R. Synthesis and characterisation of some water soluble ruthenium(II)-arene complexes and an investigation of their antibiotic and antiviral properties. J Organomet Chem. 2003;668:35–42.
Vock CA, Ang WH, Scolaro C, Phillips AD, Lagopoulos L, Juillerat-Jeanneret L, Sava G, Scopelitti R, Dyson PJ. Development of ruthenium antitumor drugs that overcome multidrug resistance mechanisms. J Med Chem. 2007;50:2166–75.
Kandioller W, Hartinger CG, Nazarov AA, Kasser J, John R, Jakupec MA, Arion VB, Dyson PJ, Keppler BK. Tuning the anticancer activity of maltol-derived ruthenium complexes by derivatization of the 3-hydroxy-4-pyrone moiety. J Organomet Chem. 2009;694:922–9.
Ban TA. Academic psychiatry and the pharmaceutical industry. Prog Neuropsychopharmacol Biol Psychiatr. 2006;30:429–41.
Pluta K, Morak-Mlodavska B, Jelen M. Recent progress in biological activities of synthesized phenothiazines. Eur J Med Chem. 2011;46:3179–89.
Bisi A, Meli M, Gobbi S, Rampa A, Tolomeo M, Dusonchet L. Multidrug resistance reverting activity and antitumor profile of new phenothiazine derivatives. Bioorg Med Chem. 2008;16:6474–82.
Aaron JJ, Seye MDG, Trajkovska S, Motohashi N. Bioactive phenothiazines and benzo[α]phenothiazines: Spectroscopic studies, and biological and biomedical properties and applications. Top Heterocycl Chem. 2009;16:153–231.
Krstić M, Sovilj SP, Grgurić-Šipka S, Radosavljević Evans I, Borozan S, Santibanez JF, Kocić J. New ruthenium(II) complexes with N-alkylphenothiazines: Synthesis, structure, in vivo activity as free radical scavengers and in vitro cytotoxicity. Eur J Med Chem. 2010;45:3669–76.
Krstić M, Sovilj SP, Grgurić-Šipka S, Radosavljević Evans I, Borozan S, Santibanezd JF. Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines. Eur J Med Chem. 2011;46:4168–77.
Holló B, Krstić M, Sovilj SP, Pokol G, Mészáros Szécsényi K. Thermal decomposition of new ruthenium(II) complexes containing N-alkylphenothiazines. J Therm Anal Calorim. 2011;105:27–32.
Jensen SB, Rodger SJ, Spicer MD. Facile preparation of η 6-p-cymene ruthenium diphosphine complexes. Crystal structure of [(η 6-p-cymene)Ru(dppf)Cl]PF6. J Organomet Chem. 1998;556:151–8.
http://webbook.nist.gov/, chemistry, 24.7.2011.
Uivarosi V, Badea M, Olar R, Marinescu D, Nicolescu TO, Nitulescu GM. Thermal degradation behavior of some ruthenium complexes with fluoroquinolone derivatives as potential antitumor agents. J Therm Anal Calorim. 2011;105:645–50.
Ocakoglu K, Emen FM. Thermal analysis of cis-(dithiocyanato)(1,10-phenanthroline-5,6-dione)(4,40-dicarboxy-2,20-bipyridyl)ruthenium(II) photosensitizer. J Therm Anal Calorim. 2011;104:1017–22.
Lide DR (Editor-in-Chief). CRC handbook of chemistry and physics, 84th edn, 2003–2004. Boca Raton: CRC Press; 1915. p. 4–80.
Acknowledgements
The study was financed by the Ministry of Science and Technological Development of the Republic of Serbia (Grant No. 172014). K. Mészáros Szécsényi thanks Secretariat for Science and Technological Development, Autonomous Province of Vojvodina, Republic of Serbia (No. 114-451-02011/2007-02) and the CEEPUS II program (CII-CZ-0212-04-1011) for the financial support.
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Holló, B., Krstić, M., Sovilj, S.P. et al. Thermal decomposition of new chlorido(p-cymene) ruthenium(II) complexes containing N-alkylphenothiazines. J Therm Anal Calorim 111, 1927–1932 (2013). https://doi.org/10.1007/s10973-011-1969-8
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DOI: https://doi.org/10.1007/s10973-011-1969-8