<abstract xmlns="http://www.w3.org/1999/xhtml"><sec id="j_abm-2018-0015_s_012_w2aab3b7b2b1b6b1aab1c16b1Aa"><h3>Background</h3><p>Infectious diseases, especially those caused by multidrug-resistant bacteria, are becoming a serious problem worldwide because of the lack of effective therapeutic agents. Moreover, most antifungal drugs exhibit low efficacy and high toxicity because of the similarity between fungal and human cells. These issues warrant the search for potential new agents.</p></sec><sec id="j_abm-2018-0015_s_013_w2aab3b7b2b1b6b1aab1c16b2Aa"><h3>Objectives</h3><p>To synthesize potent 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives, improve the synthetic process, elucidate their structures, and determine their antimicrobial activity.</p></sec><sec id="j_abm-2018-0015_s_014_w2aab3b7b2b1b6b1aab1c16b3Aa"><h3>Methods</h3><p>2-Iodoaniline was used as an initial reactant in a 3-step process for the synthesis of 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives, including an acylation reaction, a cyclization reaction, and aldol condensation reactions. The structures of the obtained derivatives were investigated and elucidated using spectral methods. Antimicrobial activity toward 5 bacterial strains and 2 fungal strains was determined using Kirby–Bauer and agar dilution methods.</p></sec><sec id="j_abm-2018-0015_s_015_w2aab3b7b2b1b6b1aab1c16b4Aa"><h3>Results</h3><p>We successfully synthesized 12 novel compounds and elucidated their structures. The derivatives had no antifungal activities. By contrast, they showed remarkable antibacterial activities. Some of them with minimum inhibitory concentrations (MICs) ≤8 μg/mL in both <italic>Staphylococcus aureus</italic> and methicillin-resistant <italic>S. aureus</italic>.</p></sec><sec id="j_abm-2018-0015_s_016_w2aab3b7b2b1b6b1aab1c16b5Aa"><h3>Conclusions</h3><p>A simple and flexible way to synthesize new compounds with a thiazolidin-4-one ring was determined. Some of these new compounds have outstanding effects with low MICs for bacteria. Their further investigation as therapeutic agents is warranted.</p></sec></abstract>

BackgroundInfectious diseases, especially those caused by multidrug-resistant bacteria, are becoming a serious problem worldwide because of the lack of effective therapeutic agents. Moreover, most antifungal drugs exhibit low efficacy and high toxicity because of the similarity between fungal and human cells. These issues warrant the search for potential new agents.ObjectivesTo synthesize potent 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives, improve the synthetic process, elucidate their structures, and determine their antimicrobial activity.Methods2-Iodoaniline was used as an initial reactant in a 3-step process for the synthesis of 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives, including an acylation reaction, a cyclization reaction, and aldol condensation reactions. The structures of the obtained derivatives were investigated and elucidated using spectral methods. Antimicrobial activity toward 5 bacterial strains and 2 fungal strains was determined using Kirby–Bauer and agar dilution methods.ResultsWe successfully synthesized 12 novel compounds and elucidated their structures. The derivatives had no antifungal activities. By contrast, they showed remarkable antibacterial activities. Some of them with minimum inhibitory concentrations (MICs) ≤8 μg/mL in both Staphylococcus aureus and methicillin-resistant S. aureus.ConclusionsA simple and flexible way to synthesize new compounds with a thiazolidin-4-one ring was determined. Some of these new compounds have outstanding effects with low MICs for bacteria. Their further investigation as therapeutic agents is warranted.

Antimicrobial activity of some novel 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives

Can Tho University of Medicine and Pharmacy

Asian Biomedicine

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

BackgroundInfectious diseases, especially those caused by multidrug-resistant bacteria, are becoming a serious problem worldwide because of the lack of...


Structure	Name	R	Bacteria					Fungi
Structure	Name	R	E. coli	P. aeruginosa	E. faecalis	S. aureus	MRSA	C. albicans	A. niger
	2-(2-Iodophenylimino)-5-
3A	(4-methoxybenzylidene)thiazolidin-	4”-OCH₃	−	−	−	>1024	>1024	−	−
	4-one
	2-(2-Iodophenylimino)-5-
3B	(4-chlorobenzylidene)thiazolidin-	4”-Cl	−	−	−	8	4	−	−
	4-one
	2-(2-Iodophenylimino)-5-
3C	(2,4-dichlorobenzylidene)thiazoli-	2”-Cl	−	−	−	>1024	>1024	−	−
	din-4-one	4”-Cl
	2-(2-Iodophenylimino)-5-	4”-OH
3D	(4-hydroxy-3-methoxybenzylidene)	3”-OCH	−	−	−	16	16	−	−
	thiazolidin-4-one	₃
	2-(2-Iodophenylimino)-5-
3E	(4-fluorobenzylidene)thiazolidin-	4”-F	−	−	−	8	8	−	−
	4-one
3F	2-(2-Iodophenylimino)-5-		−	−	−	>1024	>1024	−	−
	benzylidenethiazolidin-4-one
	2-(2-Iodophenylimino)-5-
3G	(4-methylbenzylidene)thiazolidin-	4”-CH₃	−	−	−	>1024	128	−	−
	4-one
	2-(2-Iodophenylimino)-5-
3H	(4-nitrobenzylidene)thiazolidin-	4”-NO₂	−	−	−	8	8	−	−
	4-one
	2-(2-Iodophenylimino)-5-
3I	(2-nitrobenzylidene)thiazolidin-	2”-NO₂	−	−	>1024	8	32	−	−
	4-one
	2-(2-Iodophenylimino)-5-
3J	(2-hydroxybenzylidene)thiazolidin-	2”-OH	−	−	−	>1024	>1024	−	−
	4-one
	2-(2-Iodophenylimino)-5-	2”-OH
3K	(5-bromo-2-hydroxybenzylidene)	5”-Br	−	−	−	64	64	−	−
	thiazolidin-4-one
	2-(2-Iodophenylimino)-5-
3L	(4-dimethylaminobenzylidene)	4”-N(CH₃)₂	−	−	−	−	–	−	−
	thiazolidin-4-one
PC	Cephalexin				32	4	32

Antimicrobial activity of some novel 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives

Article Category: Original article

Published Online: Oct 10, 2018

Page range: 405 - 412

DOI: https://doi.org/10.1515/abm-2018-0015

Keywords
antimicrobial, derivatives, MRSA, synthesis, thiazolidin-4-one

© 2017 Duy Toan Pham et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Scheme 1

Antimicrobial activity of the synthesized compounds, 3A–3L, on various strains of bacteria and fungi

Antimicrobial activity of some novel 2-(2-iodophenylimino)-5-arylidenethiazolidin-4-one derivatives

Article Category: Original article

Published Online: Oct 10, 2018

Page range: 405 - 412

DOI: https://doi.org/10.1515/abm-2018-0015

Keywordsantimicrobial, derivatives, MRSA, synthesis, thiazolidin-4-one

© 2017 Duy Toan Pham et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Scheme 1

Antimicrobial activity of the synthesized compounds, 3A–3L, on various strains of bacteria and fungi

Keywords
antimicrobial, derivatives, MRSA, synthesis, thiazolidin-4-one