Synthesis and Antifungal Activity Against <i>Candida</i> Strains of Mesoionic System Derived From 1,3-Thyazolium-5-thiolate

Peixoto, Isabelle N.; Souza, Helivaldo D. S.; Lira, Bruno F.; Silva, Daniele F.; Lima, Edeltrudes O.; Barbosa-Filho, José M.; Athayde-Filho, Petrônio F. de

doi:10.5935/0103-5053.20160063

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Articles • J. Braz. Chem. Soc. 27 (10) • Oct 2016 • https://doi.org/10.5935/0103-5053.20160063 copy

Synthesis and Antifungal Activity Against Candida Strains of Mesoionic System Derived From 1,3-Thyazolium-5-thiolate

Authorship SCIMAGO INSTITUTIONS RANKINGS

A series of ten new compounds have been synthetized in satisfactory yields (85-95%) through the treatment of isopropyl mesoionic 1,3-thiazolium-5-thiolate with 2-chloro-N-arylacetamides and characterized by elemental analysis, infrared (IR), ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopies. The newly synthesized compounds were evaluated as new drug candidates in in silico study and for their antifungal activity against several strains of Candida albicans. In silico study indicates that no compound has potential to be a new drug while four compounds showed medium to strong activity with minimum inhibitory concentration (MIC) range of 256-1024 µg mL^-1.

Keywords:
isopropyl mesoionic derivatives; antifungal activity; in silico

Compound	Lipinski’s parameter					log S	TPSA / Å²	%ABS	Drug likeness	Drug score
Compound	HBA	HBD	MW	milog P	nViol	log S	TPSA / Å²	%ABS	Drug likeness	Drug score
7a	3	1	528	4.75	1	–7.06	86.52	79.41	–0.47	–0.27
7b	5	1	573	4.71	1	–7.52	132.30	63.35	–14.00	0.18
7c	3	1	556	5.67	2	–7.56	86.52	79.41	0.96	0.22
7d	3	1	542	5.20	2	–7.41	86.52	79.41	–0.22	0.25
7e	3	1	606	5.56	2	–7.90	86.52	79.41	–0.79	0.11
7f	3	1	562	5.43	2	–7.80	86.52	79.41	1.62	0.29
7g	3	1	570	6.26	2	–7.93	86.52	79.41	1.08	0.25
7h	4	1	558	4.81	1	–7.08	95.75	75.97	0.02	0.27
7i	5	1	591	4.80	1	–7.84	132.30	63.35	–10.20	0.17
7j	5	1	607	5.32	2	–8.26	132.30	63.35	–7.60	0.16

Compound	Minimum inhibitory concentration / (µg mL^-1)
	Candidastrains
	C. albicans ATCC 76645	C. albicans ATCC 76485	C. albicans LM 178	C. albicans LM 615	C. albicans LM 37
7a	+	+	+	+	+
7b	+	+	+	+	+
7c	256	256	256	256	256
7d	256	256	256	256	256
7e	+	+	+	+	+
7f	256	512	256	256	512
7g	256	256	256	256	512
7h	+	+	+	+	+
7i	+	+	+	+	+
7j	+	+	+	+	+
Control medium	–	–	–	–	–
Fluconazole	–	–	–	–	–
Control yeast	+	+	+	+	+

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