Design, Synthesis and Biological Activity of the 4-Thioquinoline Derivative
Affiliation:
1Zaporizhzhia National University, Faculty of Biology, 66, Zhukovs’ky St., Zaporizhzhia, 69095, Ukraine
2Khortytsia National Academy, 59, Naukovemistechko St., Khortytsiaisland, Zaporizhzhia, 69017, Ukraine
3Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany
4VasylStefanykPrecarpathian National University, 57, Shevchenko St., Ivano-Frankivsk, 76018, Ukraine
5Department of Chemistry, PGP College of Arts and Science Paramathi, Namakkal, Tamil Nadu, India
zm311270@gmail.com, vasyl.shupeniuk@pnu.edu.ua
DOI:
https://doi.org/10.23939/chcht17.04.774
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Abstract:
One of the promising areas in the creation of bioregulators is the modeling of compounds that combine several pharmacophores. The design of new highly efficient and low-toxic cytoprotectors is largely based on the derivatives of nitrogen-containing heterocycles, and quinoline plays a significant role among these compounds.
The researchers evaluated the toxicity of the tested compounds in silico, in vitro, and in vivo, which allowed determiningseveral factors that affect the level of toxic action of 4-thioquinoline derivatives and the direction of non-toxic substances in this sequence.
The studied 4-thioquinolines showed a moderate antiradical action in the experiment, inferior to the reference antioxidant Acetylcysteine. The most active compounds are 7-chloro-4-thioquinoline derivatives with propanoic acid residues in the 4th position. 2-(7-chloroquinolin-4-ylthio)propanoic acid and sodium salt of 2-amino-3-((7-chloroquinolin-4-yl)thio)propanoic acid showed the most promising results and their antioxidant action was higher than Tiotriazolin (the comparator) by 27 % and 41 %, respectively.
The studied compounds showed a protective effect under H2O2-induced oxidative stress against male sperm according to the main indicators of sperm fertility. It was found that the compounds withresidues of succinic acid, cysteamine, or cysteine in the molecule structure are not inferior to reference drugs. On average, 2-((7-chloroquinolin-4-yl)thio)succinic acid and 2-((quinolin-4-yl)thio)ethanaminedihydrochloride exceeded the comparison drug Acetylcysteine and were on a par with the effect of Ascorbic acid.
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