A stereoselective approach towards a small library of cytotoxic isomeric sphingoid bases

Carbohydrate Research
Milica FabišíkováJuraj Kuchár

Abstract

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.

Citations

Mar 12, 2019·Organic & Biomolecular Chemistry·Jozef GondaMartina Bago Pilátová

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