Synthesis and Antimicrobial Activity of New Thiazolidine-Based
Heterocycles as Rhodanine Analogues
Naglaa A. Abdel Hafez,
Mohamed A. Elsayed,
Manal M. El-Shahawi,
Ghada E. A. Awad,
and Korany A. Ali
Applied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt
Chemistry Department, Faculty of Science, Ain Shams University, Abbasia, Cairo 11566, Egypt
Chemistry of Natural and Microbial Products Department, National Research Centre, Dokki, Giza 12622, Egypt
Center of Excellence, Advanced Materials and Nanotechnology Group, National Research Centre, Dokki,
Giza 12622, Egypt
Received September 5, 2017
Published online 11 January 2018 in Wiley Online Library (wileyonlinelibrary.com).
A new series of compounds containing thiazole nucleus as Rhodanine analogues have been synthesized.
The new compounds were prepared from the reactions of the thiosemicarbazones (3a,b) with a series of
α-halo carbonyl compounds to give the corresponding Rhodanine analogues. The thiosemicarbazones deriv-
atives (3a,b) were reacted also with hydrazonoyl chlorides to afford the corresponding tri-substituted and
tetra-substituted thiazoles. The structures of the newly synthesized compounds were conﬁrmed by elemental
analysis and spectral data. The biological activities of the new synthesized Rhodanine analogues’ were eval-
uated for their antimicrobial activities. The results showed that some of these compounds showed excellent
activity against two fungal strains, including Aspergillus niger and Aspergillus ﬂavus, in addition to three
yeast strains, including Saccharomyces cervesi, Candida albicans NRRL Y-477, and Candida Pathological
specimen compared with the ketoconazol, as the reference drug.
J. Heterocyclic Chem., 55, 685 (2018).
Thiosemicarbazones are a class of organic compounds
that used for many decades in medicinal chemistry as they
developed as antimicrobial, anticonvulsant, antihelminthic,
and anticancer activities [1–5]. On the other hand,
thiosemicarbazones consider as a good precursors for the
preparation of new class of thiazoles. Moreover, thiazoles
as Rhodanine analogues (Fig. 1), in many publications,
exhibited a wide range of biological activities such as
anti-inﬂammatory , antimicrobial [7,8], anti-apoptotic
, antioxidant , and anticancer  properties.
On the other hand, dimethoxy phenyl is an important
scaffold in pharmaceutical chemistry with a wide
range of registered drugs due to their biological activity.
For example, 2,5-dimethoxy-4-chloroamphetamine is a
psychedlis drug under a class of drugs known as
As part of our targets to synthesize biologically active
heterocycles [13,14] and our ongoing interests in the
chemistry of hydrazonoyl halides and α-halo carbonyl
compounds, we have prepared new series of Rhodanine
analogues containing the dimethoxy phenyl scaffold
and investigated their biological activities as antifungal
RESULTS AND DISCUSSION
The starting materials for this study, 3,4-dimethoxy
acetophenone thiosemicarbazones (3a,b), were prepared
from the reaction of 3,4-dimethoxyacetophenone with the
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