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Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton

by Pinter, Matthias , Iwan, Dominika , Wojaczyńska, Elżbieta , Senfter, Daniel , Madlener, Sibylle , Samadaei, Mahzeiar , Kochel, Andrzej , Kamińska, Karolina , Wojaczyński, Jacek , Rohr-Udilova, Nataliya

in 2-azabicycloalkane / Alkanes - chemical synthesis / Alkanes - chemistry / Alkanes - pharmacology / Amines - chemical synthesis / Amines - chemistry / Amines - pharmacology / Antibiotics / Bioavailability / Biological activity / Cancer / Carcinoma, Hepatocellular - drug therapy / Carcinoma, Hepatocellular - pathology / chiral sulfonamide / Chromatography / cytotoxic activity / Cytotoxicity / Humans / Liver cancer / Liver Neoplasms - drug therapy / Liver Neoplasms - pathology / Medical research / Molecular Structure / Stereoisomerism / Sulfonamides - chemical synthesis / Sulfonamides - chemistry / Sulfonamides - pharmacology

2020

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Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton

2020

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Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton

2020

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Journal Article

Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton

Pinter, Matthias,

Iwan, Dominika,

Wojaczyńska, Elżbieta,

Senfter, Daniel,

Madlener, Sibylle,

Samadaei, Mahzeiar,

Kochel, Andrzej,

Kamińska, Karolina,

Wojaczyński, Jacek,

Rohr-Udilova, Nataliya

2020

Overview

A series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from aza-Diels–Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic activity of the obtained bicyclic derivatives was evaluated using human hepatocellular carcinoma (HCC), medulloblastoma (MB), and glioblastoma (GBM) cell lines. Chosen compounds were shown to notably reduce cell viability as compared to nonmalignant cells.

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Publisher

MDPI AG,MDPI

Subject

2-azabicycloalkane

/ Alkanes - chemical synthesis

/ Alkanes - chemistry

/ Alkanes - pharmacology

/ Amines - chemical synthesis

/ Amines - chemistry

/ Amines - pharmacology