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.