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A stereoselective approach towards a small library of cytotoxic isomeric sphingoid bases.
Fabisíková, Milica; Martinková, Miroslava; Gonda, Jozef; Jacková, Dominika; Bago Pilátová, Martina; Kuchár, Juraj.
Afiliación
  • Fabisíková M; Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Safárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic.
  • Martinková M; Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Safárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic. Electronic address: miroslava.martinkova@upjs.sk.
  • Gonda J; Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Safárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic.
  • Jacková D; Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Safárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic.
  • Bago Pilátová M; Institute of Pharmacology, Faculty of Medicine, P.J. Safárik University, SNP 1, 040 66, Kosice, Slovak Republic.
  • Kuchár J; Institute of Chemical Sciences, Department of Inorganic Chemistry, P.J. Safárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic.
Carbohydr Res ; 468: 51-63, 2018 Oct.
Article en En | MEDLINE | ID: mdl-30149268
Two approaches to a small library of cytotoxic dihydrosphingosine analogues are described. [3,3]-Sigmatropic rearrangements along with an OCM reaction were used as the key steps for the construction of the two isodihydrosphingosines ent-6 and 10, whereas the functional group manipulations, including Grubbs' metathesis chemistry, were applied to known isothiocyanate scaffolds 15 and 16 to provide access to the enantiomeric forms of ent-6 and 10 and diastereomeric isophytosphingosines ent-7.HCl and 14. Cell viability experiments revealed that the target isomeric sphingoid bases were more potent than the traditional anticancer agent cisplatin, with IC50 values in the low micromolar range for the most active compounds.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Esfingosina / Antineoplásicos Límite: Humans Idioma: En Revista: Carbohydr Res Año: 2018 Tipo del documento: Article Pais de publicación: Países Bajos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Esfingosina / Antineoplásicos Límite: Humans Idioma: En Revista: Carbohydr Res Año: 2018 Tipo del documento: Article Pais de publicación: Países Bajos