Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities

Viktor A. Zapol’skii
ORCID logo ,
Sandra Kaul
,
Bianka Karge
,
Mark Brönstrup
ORCID logo ,
Mimoza Gjikaj
,
Dieter E. Kaufmann
* ORCID logo
Version 1 : Received: 2 February 2023 / Approved: 3 February 2023 / Online: 3 February 2023 (13:49:18 CET)

A peer-reviewed article of this Preprint also exists.

Zapol’skii, V.A.; Kaul, S.; Karge, B.; Brönstrup, M.; Gjikaj, M.; Kaufmann, D.E. A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities †. Molecules 2023, 28, 2479. Zapol’skii, V.A.; Kaul, S.; Karge, B.; Brönstrup, M.; Gjikaj, M.; Kaufmann, D.E. A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities †. Molecules 2023, 28, 2479.

Abstract

The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[h]quinolines. These heterocycles are easily accessible via a single-step reaction with 1-naphthyl- or 1-anthracenylamine, respectively. Due to steric bulk and high electron density ring closure to benzo[h]quinolines takes place, exclusively. Such highly substituted annelated pyridine systems can be modified in subsequent, selective reactions to build up new N-heterocycles with promising microbiological properties. Antibacterial and antiproliferative assays against four cell mammalian cell lines demonstrate that some of the sulfur-substituted benzo[h]quinolines analogs display potent phenotypic bioactivities in the single-digit micromolar range.

Keywords

synthetic methods; 2-nitroperchlorobutadiene; benzoquinolines; cyclization; amines; sulfides; nucleophilic substitution; oxidation; medicinal chemistry

Subject

Chemistry and Materials Science, Medicinal Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Download PDF Download Supplementary

Comments (0)

We encourage comments and feedback from a broad range of readers. See criteria for comments and our Diversity statement.

Leave a public comment
Send a private comment to the author(s)
* All users must log in before leaving a comment
Views 0
Downloads 0
Comments 0
Metrics 0
Get PDF Supplementary Files Cite Share 0
Bookmark BibSonomy Mendeley Reddit Delicious
×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.
We use cookies on our website to ensure you get the best experience.
Read more about our cookies here.