(±)-trans-Dihydronarciclasine and (±)-trans-dihydrolycoricidine analogues modified in their ring A: Evaluation of their anticancer activity and a SAR study

Gábor Varró, Péter Pálchuber, Balázs Pogrányi, András Simon, L. Hegedûs, István Kádas

Research output: Contribution to journalArticle

Abstract

A series of (±)-trans-dihydronarciclasine and (±)-trans-dihydrolycoricidine derivatives with variously substituted ring A was synthesised and evaluated for their antiproliferative activity against 60 human tumour cell lines (NCI60), representing leukemia, melanoma, and cancers of the lung, colon, brain, ovary, breast, prostate, as well as kidney in vitro. Among the 13 alkaloids screened, (±)-trans-dihydronarciclasine showed the highest potency as a cytotoxic molecule. A structure–activity relationship (SAR) study indicated that the presence of a hydroxy group at position 7 and a rigid, 1,3-benzodioxole scaffold were essential for the antiproliferative activity.

Original languageEnglish
Pages (from-to)76-89
Number of pages14
JournalEuropean Journal of Medicinal Chemistry
Volume173
DOIs
Publication statusPublished - Jul 1 2019

Fingerprint

Tumor Cell Line
Alkaloids
Scaffolds
Colonic Neoplasms
Tumors
Prostate
Ovary
Melanoma
Lung Neoplasms
Brain
Leukemia
Breast
Cells
Derivatives
Kidney
Molecules
dihydronarciclasine
trans-dihydrolycoricidine
1,3-benzodioxole
In Vitro Techniques

Keywords

  • (±)-trans-Dihydronarciclasine
  • Alkaloids
  • Anticancer activity
  • Structure–activity relationship (SAR)

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

(±)-trans-Dihydronarciclasine and (±)-trans-dihydrolycoricidine analogues modified in their ring A : Evaluation of their anticancer activity and a SAR study. / Varró, Gábor; Pálchuber, Péter; Pogrányi, Balázs; Simon, András; Hegedûs, L.; Kádas, István.

In: European Journal of Medicinal Chemistry, Vol. 173, 01.07.2019, p. 76-89.

Research output: Contribution to journalArticle

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AU - Pogrányi, Balázs

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AU - Hegedûs, L.

AU - Kádas, István

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