Open AccessSynthesis, antioxidant and antimicrobial properties of novel pyridyl-carbonyl thiazoles as dendrodoine analogs
Author(s) -
Zafer Şahin,
Sevde Nur Biltekin,
Leyla Yurttaş,
Şeref Demirayak
Publication year - 2020
Publication title -
turkish journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.239
H-Index - 46
eISSN - 1303-6130
pISSN - 1300-0527
DOI - 10.3906/kim-2008-8
Subject(s) - chemistry , trolox , antimicrobial , thiazole , dpph , stereochemistry , antioxidant , organic chemistry
Marine compound dendrodoine was first obtained from tunicate species ( Dendrodo grossularia ). It has a five-membered ring, namely, it is a heterocycle thiadiazole, which is found rarely in natural sources . Following its biological activities, novel analogs have been investigated recently. Synthesis of the analogs for this study is realized with uncommon thiazole closure, including methylene-carbonyl condensation. Structures are elucidated by NMR ( 1 , 13 C) and HRMS spectrums. As an alkaloid derivative, antioxidant properties were evaluated with DPPH and FRAP assays and antimicrobial effect with microdilution method. Among the series, 3bc-3cf showed higher antioxidant activity than those having 3 or 4-pyridyl substituents. There is lesser activity for 2-pyridyl activity for 2-pyridyl containing group, which may be a result of intramolecular interactions. No activity was observed against gram-negative bacteria at 250 μg/mL. 3ae and 3ce showed activity at 64 μg/mL against S. aureus and 3ae showed activity at 16 μg/mL against S. epidermidis gram-positive bacteria. Chloramphenicol showed activity against all microorganisms at 8–16 μg/mL. Sixteen original dendrodoine analogs have been defined by close/higher activity compared to dendrodoine analogs and Trolox.