Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids.
In the present communication, a new series of 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids (2a-p) have been synthesized. Benzaldehyde 4-phenyl-3-thiosemicarbazones substituted (1a-p) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were characterized by IR, (1)H and (13)C NMR. The in vitro anti-Toxoplasma gondii activity of 1a-p and 2a-p was evaluated. The 4-thiazolidinones (2a-p) were screened for their in vitro antimicrobial activity. For anti-Toxoplasma gondii activity, in general, all compounds promoted decreases in the percentage of infected cells leading to parasite elimination. These effects on intracellular parasites also caused a decrease in the mean number of tachyzoites. In addition, most of the 4-thiazolidinones showed more effective toxicity against intracellular parasites, with IC(50) values ranging from 0.05 to 1 mM. According to results of antimicrobial activity, compounds 2f, 2l, and 2p showed best activity against Mycobacterium luteus, 2c was more active against Mycobacterium tuberculosis, and 2g, 2l, and 2n showed same activity as nistatin (standard drug) against Candida sp. (4249).
de Aquino
Thiago M
TM
Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife 50670-901, Brazil.
Liesen
André P
AP
da Silva
Rosa E A
RE
Lima
Vânia T
VT
Carvalho
Cristiane S
CS
de Faria
Antônio R
AR
de Araújo
Janete M
JM
de Lima
José G
JG
Alves
Antonio J
AJ
de Melo
Edésio J T
EJ
Góes
Alexandre J S
AJ
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002175:Candida / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D009161:Mycobacterium / Q000187:drug effects; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013057:Spectrum Analysis; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000494:pharmacology; D014122:Toxoplasma / Q000187:drug effects*
D000890:Anti-Infective Agents; D000981:Antiprotozoal Agents; D053778:Thiazolidines; D013882:Thiosemicarbazones