PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2007 | 5 | 4 | 996-1006
Tytuł artykułu

Synthesis and isomerism of hydrazones of 2-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-ylthio)acetohydrazide

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
New hydrazones of 2-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-ylthio)acetohydrazide have been obtained and the percentages of anti/syn - conformers were determined. Based on the analyses of 1H NMR spectra, it was concluded that for hydrazones obtained from the 2- hydroxybenzaldehydes and 2’-hydroxycetophenones the ratio between the anti-and syn-conformers depends on the strength of intramolecular hydrogen bond (IMHB) between the nitrogen atom of the imino group and the proton of the 2-hydroxy group. It was shown that increase in IMHB strength results in stabilization of the anti-conformer in solution. [...]
Wydawca

Czasopismo
Rocznik
Tom
5
Numer
4
Strony
996-1006
Opis fizyczny
Daty
wydano
2007-12-01
online
2007-07-31
Twórcy
  • Institute of Chemistry, Vilnius, LT-01108, Lithuania
  • Institute of Chemistry, Vilnius, LT-01108, Lithuania
  • Institute of Chemistry, Vilnius, LT-01108, Lithuania
Bibliografia
  • [1] P. Ponka, J. Borova, J. Neuwirt and O. Fuchs: “Mobilization of iron from reticulocytes. Identification of pyridoxal isonicotinoyl hydrazone as a new iron chelating agent”, FEBS Lett., Vol. 97, (1979), pp. 317–321. http://dx.doi.org/10.1016/0014-5793(79)80111-8[Crossref]
  • [2] D.R. Richardson and P. Ponka: “Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease”, J. Lab. Clinic. Med., Vol. 131, (1998), pp. 306–315. http://dx.doi.org/10.1016/S0022-2143(98)90180-9[Crossref]
  • [3] L.M.W. Vitolo, G.T. Hefter, B.W. Clare and J. Webb: “Iron chelators of the pyridoxal isonicotinoyl hydrazone class part 2. Formation constants with iron(III) and iron(II)”, Inorg. Chim. Acta, Vol. 170, (1990), pp. 171–176. http://dx.doi.org/10.1016/S0020-1693(00)80472-7[Crossref]
  • [4] A.A. Aruffo, T.B. Murphy, D.K. Johnson, N.J. Rose and V. Schomaker: “Structural studies of Fe(III) and Cu(II) complexes of salycylaldehyde benzoyl hydrazone, a synthetic chelating agent exhibiting diverse biological properties”, Inorg. Chim. Acta, Vol. 67, (1982), pp. L25–L27. http://dx.doi.org/10.1016/S0020-1693(00)85021-5[Crossref]
  • [5] A.A. Aruffo, T.B. Murphy, D.K. Johnson, N.J. Rose and V. Schomaker: “Structures of cis-dichloro(methanol)(salicylaldehyde benzoylhydrazonato)iron(III), [FeCl2(C14H11N2O2)(CH4O)], and chloro(salicylaldehyde benzoylhydrazonato) copper(II) monohydrate, [CuCl(C14H11N2O2)]·H2O”, Acta Crystallogr., Vol. C40, (1984), pp. 1164–1169.
  • [6] D.R. Richardson and P. Ponka: “The iron metabolism of the human neuroblastoma cell. Lack of relationship between the efficacy of iron chelation and the inhibition of DNA synthesis”, J. Lab. Clin. Med., Vol. 124, (1994), pp. 660–671.
  • [7] D.R Richardson, E. Tran and P. Ponka: “The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective anti-proliferative agents”, Blood, Vol. 86, (1995), pp. 4295–4306.
  • [8] D.R. Richardson and K. Milnes: “The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective anti-proliferative agents. II. The mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone”, Blood, Vol. 89, (1997), pp. 3025–3038.
  • [9] I.A. Litvinov, O.N. Kataeva, L.V. Ermolaeva, G.A. Vagina, T.V. Troepol’skaya and V.A. Naumov: “Crystal and molecular structure of aroyl-and acetylhydrazones of acet-and benzaldehydes”, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl.Transl.), Vol. 40, (1991), pp. 62–67. http://dx.doi.org/10.1007/BF00959631[Crossref]
  • [10] G. Palla, G. Predieri and P. Domiano: “Conformational behaviour and E/Z isomerization of N-acyl and N-aroylhydrazones”, Tetrahedron, Vol. 42, (1986), pp. 3649–3654. http://dx.doi.org/10.1016/S0040-4020(01)87332-4[Crossref]
  • [11] Ch. Cordier, E. Vauthier, A. Adenier, Y. Lu, A. Massat, 1 and A. Cosse-Barbi: “Salicylaldehyde benzoyl hydrazone: Isomerization due to water. A structural analysis using a combination of NMR, IR, and theoretical investigations”, Struct. Chem., Vol. 15, (2004), pp. 295–307. http://dx.doi.org/10.1023/B:STUC.0000026744.76622.2c[Crossref]
  • [12] A. Rutavichyus, S. Valyulene and Z. Kuodis: “Synthesis and structure of dihydrazones obtained from the dihydrazide of 1,3,4-thiadiazole-2,5-dithioglycolic acid”, Chem. Heterocycl. Compd., Vol. 33, (1997), pp. 118–124. http://dx.doi.org/10.1007/BF02290758[Crossref]
  • [13] A. Rutavichyus and S. Valyulene: “Synthesis and structure of dihydrazones obtained from the dihydrazide of S,S’-(1,3,4-thiadiazole-2,5-diyl)bis(2-mercaptopropionic acid)”, Chem. Heterocycl. Compd., Vol. 34, (1998), pp. 1436–1441. http://dx.doi.org/10.1007/BF02317817[Crossref]
  • [14] A. Rutavicius, S. Valiulene and Z. Kuodis: “Isomerism of hydrazones of (2-benzothiazolylthio)-and (2-benzoxazolylthio)acetic acids”, Chem. Heterocycl. Compd., Vol.31, (1995), pp. 629–633. http://dx.doi.org/10.1007/BF01166343[Crossref]
  • [15] L.A. Fiodorov: NMR spectroscopy of organic analytical reagents and their complexes with metal ions, Nauka, Moscow, 1987(in Russian).
  • [16] James J.P. Stewart: Stewart Computational Chemistry, Version 7.053W, http://OpenMOPAC.net
  • [17] A. Klamt and G. Schüürmann: “COSMO: A New Approach to Dielectric Screening in Solvents with Explicit Expressions for the Screening Energy and its Gradient”, J. Chem. Soc., Perkin Trans., Vol. 2, (1993), pp. 799–805. [Crossref]
  • [18] http://www.acdlabs.com
  • [19] Z. Kuodis, A. Rutavichyus and S. Valiulene: “Salts of 2,5-dimercapto-1,3,4-thiadiazole”, Chem. Heterocycl. Compd., Vol. 36, (2000), pp. 598–602 http://dx.doi.org/10.1007/BF02290852[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-007-0043-7
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.