Sunday, 18 September 2016

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

General procedure for the preparation of ten newly synthetized compounds - 2-(p-chlorophenyl)-3-methyl-4- (p-isopropylphenyl)-1,3-thiazolium-5-(N-arylacetamide)thio chloridrates 7a-j Mesoionic 2-(p-chlorophenyl)-3-methyl-4-(pisopropylphenyl)-1,3-thiazolium-5-thiolate 5 (278 mmol) was dissolved in hot ethanol and then 2-chloro-Narylacetamides 6a-j (278 mmol) were added. The system was refluxed for 4 h and then concentrated at reduced pressure, giving a yellow-orange solid.

R1, R2 =H, H

2-(p-Chlorophenyl)-3-methyl-4-(p-isopropylphenyl)-1,3- thiazolium-5-(N-phenylacetamide)thio chloridrate 7a Yield: 92.13%;

m.p.: 130-132 °C; anal. calcd.: C, 60.58; H, 4.69; N, 5.43; S, 12.44; found: C, 60.60; H, 4.70; N, 5.42; S, 12.42;

IR (KBr) νmax / cm-1 3181 (NH), 3003 (CHAr.), 2958 (CHAlif.), 1680 (C=O), 1599, 1551, 1491 (C=C and C=N of aromatic and heterocyclic rings), 1442 (C–N of N–CH3), 1404 (C–N), 1092 (C–Cl), 1001, 922 (CHAr.), 756 (NH), 557, 537 (C–C);

1 H NMR (200 MHz, CDCl3) delta
1.30 (d, 6H, J 6.9 Hz, H-16, H-16’),
2.98 (sept, 1H, H-15), 3.79 (s, 2H, H-17),
3.84 (s, 3H, H-10), 7.09 (t, 2H, J 7.3 Hz, H-23),
7.28-7.34 (m, 4H, H-13, H-13’, H-21, H-25),
7.60 (d, 2H, J 8.1 Hz, H-8, H-8’),
7.73 (d, 2H, J 7.9 Hz, H-12, H-12’),
7.86-7.93 (t, 4H, J 7.3 Hz, H-7, H-7’, H-22, H-24),
11.02 (s, 1H, H-19);

13C NMR (50 MHz, CDCl3)
delta 170.21 (C-2), 166.81 (C-18), 152.68 (C-14),
140.28 (C-4), 138.93 (C-9), 132.04 (C-20), 131.64 (C-7, C-7’), 130.89 (C-12, C-12’),
130.27 (C-8, C-8’), 128.69 (C-22, C-24), 127.54 (C-13, C-13’),
124.09 (C-23), 123.79 (C-11), 123.59 (C-6),
120.28 (C-21, C-25), 42.24 (C-17), 40.92 (C-10), 34.21 (C-15), 23.76 (C-16, 16’).

Peixoto IN, Souza HDS, Lira BF, Silva DF, Lima EO, Barbosa-Filho JM, et al. Synthesis and Antifungal Activity AgainstCandida Strains of Mesoionic System Derived From 1,3-Thyazolium-5-thiolate. J. Braz. Chem. Soc. 2016;27(10):1807-1813

J. Braz. Chem. Soc. 2016, 27(10), 1807-1813

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

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

Ten new mesoionic derivatives from the 1,3-thiazolium-5-thiolate system with substituted acetamides were synthesized, had their potential as new drug evaluated in an in silico study and in their activity as antifungal against strains of Candida albicans.

Published online: February 26, 2016

Petrônio Filgueiras Athayde-Filho

Petrônio F. de Athayde-Filho
Universidade Federal da Paraíba

Universidade Federal da Paraíba

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