Synthesis of 2,3-dihidropyrido[1,2,3-de]-1,4-benzoxazinium chloride and some of its derivatives substituted in the carbocyclic ring

Kovel'man, I. R.; Tochilkin, A. I.; Volkova, O. A.; Dubinskii, V. Z.

doi:10.1007/bf02219390

Cited by 3 publications

(1 citation statement)

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“…The application of the Appel reaction conditions, in which the alcohol reacts with carbon tetrachloride in the presence of triphenylphosphine also not allowed to obtain the desired products. Instead, spectroscopic data (HRMS) confirmed the formation of a resonance-stabilized structure of the tricyclic oxazaquinolinium salts 5a–10a [58]. Finally, to obtain compounds 5–10 , a reaction of quinoline derivatives 1 or 2 with 1-azido-2-bromoethane, 1-azido-3-bromopropane or 1-azido-4-bromobutane as donors of desired groups was carried out.…”

Section: Resultsmentioning

confidence: 99%

8-Hydroxyquinoline Glycoconjugates: Modifications in the Linker Structure and Their Effect on the Cytotoxicity of the Obtained Compounds

et al. 2019

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Small molecule nitrogen heterocycles are very important structures, widely used in the design of potential pharmaceuticals. Particularly, derivatives of 8-hydroxyquinoline (8-HQ) are successfully used to design promising anti-cancer agents. Conjugating 8-HQ derivatives with sugar derivatives, molecules with better bioavailability, selectivity, and solubility are obtained. In this study, 8-HQ derivatives were functionalized at the 8-OH position and connected with sugar derivatives (D-glucose or D-galactose) substituted with different groups at the anomeric position, using copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC). Glycoconjugates were tested for inhibition of the proliferation of cancer cell lines (HCT 116 and MCF-7) and inhibition of β-1,4-galactosyltransferase activity, which overexpression is associated with cancer progression. All glycoconjugates in protected form have a cytotoxic effect on cancer cells in the tested concentration range. The presence of additional amide groups in the linker structure improves the activity of glycoconjugates, probably due to the ability to chelate metal ions present in many types of cancers. The study of metal complexing properties confirmed that the obtained glycoconjugates are capable of chelating copper ions, which increases their anti-cancer potential.

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Section: Resultsmentioning

confidence: 99%