Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives.

Łukasz Balewski,Aleksandra Jalińska,Anita Kornicka,Franciszek Sączewski,Karolina Cicha,Maria Gdaniec

doi:10.3390/molecules24224070

Łukasz Balewski, Aleksandra Jalińska + Show 4 more

Open Access

https://doi.org/10.3390/molecules24224070

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Abstract

Isoquinoline derivatives have attracted great interest for their wide biological and fluorescent properties. In the current study, we focused on the synthesis of a series of novel isoquinoline derivatives substituted at position 3 of the heteroaromatic ring. Compounds were obtained in a Goldberg–Ullmann-type coupling reaction with appropriate amides in the presence of copper(I) iodide, N,N-dimethylethylenediamine (DMEDA), and potassium carbonate. The structures of novel isoquinolines were confirmed by IR, NMR, and elemental analysis, as well as X-ray crystallography. In the course of our research work, the visible fluorescence of this class of compounds was observed. The above findings prompted us to investigate the optical properties of the selected compounds.

Highlights

Among heteroaromatic compounds, the isoquinoline scaffold constitutes an important and privileged structural framework, and may be found in several naturally occurring alkaloids [1,2]
Biological activities of isoquinoline derivatives found in nature, as well as those obtained by organic synthetic procedures, have been widely explored
Several compounds with isoquinoline core were found to exhibit anti-tumor or antiproliferative activity serving as a lead structure for the development of potential anticancer drugs [9,10,11,12]

Summary

Introduction

The isoquinoline (benzo[c]pyridine) scaffold constitutes an important and privileged structural framework, and may be found in several naturally occurring alkaloids [1,2]. Biological activities of isoquinoline derivatives found in nature, as well as those obtained by organic synthetic procedures, have been widely explored. It was demonstrated that isoquinoline derivatives exhibit antifungal, antibacterial [6], and anti-malarial activities [7]. Several compounds with isoquinoline core were found to exhibit anti-tumor or antiproliferative activity serving as a lead structure for the development of potential anticancer drugs [9,10,11,12]. Noteworthy is the fact that the isoquinoline ring constitutes an important molecular part of topical anesthetic drug quinisocaine, whereas the 1,2,3,4-tetrahydroisoquinoline moiety is found in the structure of antihypertensive drugs, quinapril and debrisoquine

Methods

Discussion

Conclusion