Synthesis of thiosemicarbazone and 4-thiazolidinone derivatives and their in vitro anti-Toxoplasma gondii activity

Tenório, Rômulo P.; Carvalho, Cristiane Suely Melo de; Pessanha, Carla S.; Lima, José Gildo de; Faria, Antônio Rodolfo de; Alves, A. J.; Melo, Édesio José Tenório de; Góes, Alexandre J. S.

doi:10.1016/j.bmcl.2005.03.048

Cited by 109 publications

(58 citation statements)

References 17 publications

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“…This chemical structure showed anti-parasitic effects similar to those described by Tenório et al (14). The best compound was acid [2-(benzylidenehydrazone)-4-oxo-1,3-thiazolidin-5-yl]acetic, that had an The mechanism of action of TSC and TZD compounds is mainly associated with ribonucleotide reductase inhibition, as is that of HU (29), but it may also involve inhibition of other metallic proteins involved in metabolic processes.…”

Section: Discussionsupporting

confidence: 66%

“…This concentration was selected according to the concentration screen (0.1 to 20 mM), and following preliminary experiments and previous studies carried out by Tenório et al (14). HU and sulfadiazine were used as the reference drugs, at 4 and 1 mM, respectively, according our previous data (11,14). All drugs were dissolved in DMSO and added to medium 199.…”

Section: Incubation With the Compoundsmentioning

confidence: 99%

“…HU and thiosemicarbazones are known to inhibit the cell cycle in the G1/S phase, mainly inactivating ribonucleotide reductase, an enzyme that mediates the conversion of ribonucleotides to deoxyribonucleotides (13). Recently, we demonstrated that TSC and analog compounds, 4-thiazolidinones (4-TZD), decreased in vitro infection and eliminated intracellular T. gondii (14). This study used TSC substituted at the arylhydrazone moiety with a nitro substituent at the ortho, meta and para positions, and 4-TZD substituted at the N-3 position with a phenyl, methyl and hydrogen substituent, and with the same groups at the arylhydrazone moiety.…”

Section: Introductionmentioning

confidence: 99%

“…Compounds bearing a heterocyclic 4-TZD have high biological activity including antimicrobial (15), antiviral (16), anti-inflammatory (17), hypnotic (18), and antiprotozoal activity (19,20). Both TSC and TZD compounds reduced infection, but the 4-TZD compounds were more efficient (14).…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis of TSC (1-3) and 4-TZD (4-6) derivatives ( Figure 1) followed the method described by Tenório et al (14). The chemical names of the compounds are the following: compound 1 (benzaldehyde thiosemicarbazone); compound 2 (para-chloro-benzaldehyde thiosemicarbazone); compound 3 (para-nitro-benzaldehyde thiosemicarbazone);…”

Section: Chemistrymentioning

confidence: 99%

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Anti-parasitic action and elimination of intracellular Toxoplasma gondii in the presence of novel thiosemicarbazone and its 4-thiazolidinone derivatives

Carvalho

Melo

2009

Braz J Med Biol Res

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Section: Discussionsupporting

confidence: 66%

Section: Incubation With the Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 3 more Smart Citations

Anti-parasitic action and elimination of intracellular Toxoplasma gondii in the presence of novel thiosemicarbazone and its 4-thiazolidinone derivatives

Carvalho

Melo

2009

Braz J Med Biol Res

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Synthesis and Biological Evaluation of Some 2,4,5‐Trisubstituted Thiazole Derivatives as Potential Antimicrobial and Anticancer Agents

Al-Saadi

Faidallah

Rostom³

2008

Archiv der Pharmazie

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We report on the synthesis and biological evaluation of two series of 2,4,5-polysubstituted thiazoles comprising the acid hydrazide functionality and some derived pharmacophores known to contribute to various chemotherapeutic activities. All newly synthesized compounds were subjected to in-vitro antibacterial and antifungal screening. Of the compounds tested, 13 derivatives displayed inhibitory effect on the growth of three Gram-positive strains while they lack activity against Gram-negative bacteria. Moreover, four compounds were able to exert antifungal activity against C. albicans. Potential antibacterial and antifungal activities were linked to the thiosemicarbazide function 6a-f and those substituted with both the thioureido and thiosemicarbazide moieties 12a-f. Compounds 6f and 12f (R = 4-F-C(6)H(4)) could be considered as the most active members in this investigation with a broad spectrum of antibacterial activity against three types of Gram-positive bacteria, together with an appreciable antifungal activity against C. albicans. Compounds 6d, 6f, and 12f were twice as active as ampicillin against B. subtilis. The best antifungal activity was shown by compound 6d 50% less active than clotrimazole. 17 compounds were selected and tested for their preliminary in-vitro anticancer activity according to the current one-dose protocol of the NCI. Three cell lines, non-small cell lung cancer Hop-92, ovarian cancer IGROV1, and melanoma SK-MEL-2, exhibited some sensitivity against most of the tested compounds. Compound 12f proved to be the most active anticancer member with a broad spectrum of activity against most of the tested subpanel tumor cell lines. Consequently, 12f was carried over to be tested in the five-dose assay.

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An Expedient Method for the Synthesis of Thiosemicarbazones under Microwave Irradiation in Solvent‐free Medium

Zheng

Zhu

et al. 2006

Chin. J. Chem.

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Synthesis of thiosemicarbazone and 4-thiazolidinone derivatives and their in vitro anti-Toxoplasma gondii activity

Cited by 109 publications

References 17 publications

Anti-parasitic action and elimination of intracellular Toxoplasma gondii in the presence of novel thiosemicarbazone and its 4-thiazolidinone derivatives

Anti-parasitic action and elimination of intracellular Toxoplasma gondii in the presence of novel thiosemicarbazone and its 4-thiazolidinone derivatives

Synthesis and Biological Evaluation of Some 2,4,5‐Trisubstituted Thiazole Derivatives as Potential Antimicrobial and Anticancer Agents

An Expedient Method for the Synthesis of Thiosemicarbazones under Microwave Irradiation in Solvent‐free Medium

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