Current Topics in Medicinal Chemistry
Michelyne Haroun
a,*
, Christophe Tratrat
a
, Katerina Kositzi
b
, Evangelia Tsolaki
b
, Anthi Petrou
b
,
Bandar Aldhubiab
a
, Mahesh Attimarad
a
, Sree Harsha
a
, Athina Geronikaki
b,*
,
Katharigatta N. Venugopala
a,c
, Heba S. Elsewedy
a
, Marina Sokovic
d
, Jasna Glamoclija
d
and
Ana Ciric
d
a
Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi
Arabia;
b
Aristotle University, School of Pharmacy, Thessaloniki, 54124, Greece;
c
Department of Biotechnology and
Food Technology, Faculty of Applied Sciences, Durban University of Technology, Durban 4001, South Africa;
d
My-
cological Laboratory, Department of Plant Physiology, Institute for Biological Research, Siniša Stanković, University of
Belgrade, Bulevar DespotaStefana 142, 11000, Belgrade, Serbia
A R T I C L E H I S T O R Y
Received: November 13, 2017
Revised: November 17, 2017
Accepted: November 22, 2017
DOI:
10.2174/1568026618666180206101814
Abstract: Background: Thiazole and benzothiazole derivatives, as well as thiazolidinones are very im-
portant scaffolds in medicinal chemistry. Literature has revealed that they possess a wide spectrum of
biological activities including antimicrobial activity.
Objective: The goal of this paper is the designing of new benzothiazole based thiazolidinones and the
evaluation of their biological activities.
Methods: The designed compounds were synthesized using classical organic synthesis methods. The
antimicrobial activity was evaluated using the method of microdilution.
Results: The twelve newly synthesized compounds showed antimicrobial properties. All compounds
appeared to be more active than ampicillin in most studied strains and in some cases, more active than
streptomycin. Antifungal activity, in most cases was also better than the reference drugs ketoconazole
and bifonazole. The prediction of cytotoxicity revealed that the synthesized compounds were not toxic
(LD50 350-1000 mg/kg of body weight). Docking studies on the antibacterial activity confirmed the
biological results.
Conclusion: The twelve new compounds were synthesized and studied for their antimicrobial activity.
The compounds appeared to be promising antimicrobial agents and could be the lead compounds for
new, more potent drugs. According to the docking prediction, the compounds could be MurB inhibitors.
Keywords: Benzothiazole, Thiazolidinone, Antibacterial, Antifungal, Microdilution, Drugs.
1. INTRODUCTION
The term infection describes the entry of microbes in the
body, their installation in places where they are endemic and
the consequent cause of inflammatory reaction through their
toxicity.
Despite that, the discovery of antimicrobial agents during
the 20th centuryhas substantially reduced the threats posed
by infectious diseases. Due to the large number of antibiotics
and chemotherapeutics available, the appearance of resistant
strains led to the urgent need for the development of new
antimicrobials with different modes of action.
Taking into account the growing problem of resistance to
antimicrobials, the World Health Organization in newsletter
*Address correspondence to these authors at the Department of Pharmaceu-
tical Sciences, College of Clinical Pharmacy, King Faisal University,
Al-Ahsa 31982, Saudi Arabia; Tel.: +966550909890,
E-mail: michelineharoun@gmail.com; mharoun@kfu.edu.sa and Aristotle
University of Thessaloniki, School of Pharmacy, Thessaloniki, 54124,
Greece; Tel.: 30 2310997616; E-mail: geronik@pharm.auth.gr
No194 (2015) reported that resistance to antibiotics is no
longer a forecast for the future and that without concerted
action, the world is heading towards a “post-antibiotic era”
in which common infections and minor injuries which have
been treatable for decades, could still be a mortal danger.
Thiazolyl and benzothiazolyl derivatives have been
found to possess analgesic, [1, 2] anti-inflammatory, [3-5]
antioxidant, [5,6], cycloxygenase and lipoxygenase inhibi-
tory [7-9] as well as antimicrobial activities [10-16].
Thiazolidinone is an interesting core responsible for nu-
merous types of biological activities and pharmacological
properties such as antimicrobial, [17-25] anti-inflammatory
and analgesic [26, 27], anti-viral [28-30], antioxidant, [31,
32] anticancer [32-34], antidiabetic [35] and anticonvulsant
[36].
Taking all of these into account and as a continuation of
our attempts in developing new antimicrobial agents [12-16,
20, 21, 24], we hereby, reported the synthesis of 6-
methoxybenzothiazol- 2-thiazolylimino-5-arylidene-4-thiaz-
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Current Topics in Medicinal Chemistry, 2018, 18, 75-87
75
RESEARCH ARTICLE
New Benzothiazole-based Thiazolidinones as Potent Antimicrobial Agents.
Design, Synthesis and Biological Evaluation