Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring

Tapia, Ricardo A.; Alegría, Luz; Pessoa, Carlos D; Salas, Cristian O.; Cortés, Manuel; Valderrama, Jaime A.; Sarciron, Marie‐Elisabeth; Pautet, F.; Walchshofer, Nadia; Fillion, H.

doi:10.1016/s0968-0896(03)00122-6

Cited by 49 publications

(29 citation statements)

References 20 publications

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“…Thiazole derivatives have been used to prepare various drugs that are important for antimicrobial (31), antibacterial (32,33), antifungal (32), antiinflammatory (34), and antitubercular (35) treatment, and some of the thiazole derivatives are used as antiprotozoals (36).…”

mentioning

confidence: 99%

Evaluation of the Anti-Schistosoma mansoni Activity of Thiosemicarbazones and Thiazoles

Santiago

Oliveira

Filho

et al. 2014

Antimicrob Agents Chemother

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f Schistosomiasis is a chronic and debilitating disease caused by a trematode of the genus Schistosoma and affects over 207 million people. Chemotherapy is the only immediate recourse for minimizing the prevalence of this disease and involves predominately the administration of a single drug, praziquantel (PZQ). Although PZQ has proven efficacy, there is a recognized need to develop new drugs as schistosomicides since studies have shown that repeated use of this drug in areas of endemicity may cause a temporary reduction in susceptibility in isolates of Schistosoma mansoni. Hydrazones, thiosemicarbazones, phthalimides, and thiazoles are thus regarded as privileged structures used for a broad spectrum of activities and are potential candidates for sources of new drug prototypes. The present study determined the in vitro schistosomicidal activity of 10 molecules containing these structures. During the assays, parameters such motility and mortality, oviposition, morphological changes in the tegument, cytotoxicity, and immunomodulatory activity caused by these compounds were evaluated. The results showed that compounds formed of thiazole and phthalimide led to higher mortality of worms, with a significant decline in motility, inhibition of pairing and oviposition, and a mortality rate of 100% starting from 144 h of exposure. These compounds also stimulated the production of nitric oxide and tumor necrosis factor alpha (TNF-␣), thereby demonstrating the presence of immunomodulatory activity. The phthalyl thiazole LpQM-45 caused significant ultrastructural alterations, with destruction of the tegument in both male and female worms. According to the present study, phthalyl thiazole compounds possess antischistosomal activities and should form the basis for future experimental and clinical trials.

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mentioning

confidence: 99%

Evaluation of the Anti-Schistosoma mansoni Activity of Thiosemicarbazones and Thiazoles

Santiago

Oliveira

Filho

et al. 2014

Antimicrob Agents Chemother

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“…All tested compounds at the two doses (15 acetic acid in mice (Table V). Compound 2a was the most potent in this respect, inhibiting the number of abdominal writhes by 97.3% at high dose (30 mg kg -1 ), compared to saline as the negative control group.…”

Section: Screening For Sedative Activitymentioning

confidence: 99%

Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives

Wardakhan

Abdel-Salam²,

Elmegeed³

2008

Acta Pharmaceutica

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Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivativesThis study was aimed at the synthesis of fused benzothiophene derivatives containing heterocyclic moiety. The reaction of the tetrahydrobenzo[b]thiophene derivatives1a,bwith ethoxycarbonylisothiocyanate afforded the thiourea derivatives2a,b.Cyclization of the latter products gave the annulated benzo[b]thienopyrimidine derivatives3a,b.Compounds2a,band3aunderwent a series of heterocyclization reactions through the reaction with some chemical reagents to give the new benzo[b]thienopyrimidine derivatives5a,bto8a-c.Also, this work was extended to study the potential role of the novel synthesized thiourea derivative2aand benzo[b]thienopyrimidine derivatives3a, 5b, 6aand8bas antidepressant, sedative or analgesic agents at two doses (15 or 30 mg kg-1body mass). Some compounds (2a, 3aand5b) showed mild antidepressant activity in the forced-swimming test. No compound showed sedative effect. Visceral pain evoked byi.p.injection of acetic acid in mice was significantly inhibited by all compounds at a high doses.

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“…By example, they appear to vary in their susceptibility to sterol-biosynthesis inhibitors (Urbina, 1997). Various compounds of the acridine family (9-amino-6-chloro-2-methoxyacridine series and their unsubstituted bisacridine derivatives) have shown a potent toxicity towards Leishmania parasites (Di Giorgio et al, 2003;Grisard et al, 2000;Murray, 2000;Tapia et al, 2003a). Chalcones, or 1, 3-diaryl-2-propen-1-ones, are natural or synthetic compounds belonging to the flavonoid family.…”

Section: Molecular Modeling Studymentioning

confidence: 99%

“…Some heterocyclic quinones have been reported to be active in vitro against virulent strains of Leishmania sp. (Tournaire et al, 1996;Valderrama et al, 1999;Tapia et al, 2003a;Tapia et al, 2002b;Tapia et al, 2003b), it is why we have explored the antileishmanial activity of various quinonic compounds. We have performed in vitro tests in order to identify three-dimensional structural similarities between these compounds that may explain their potency against L. donovani, or L. major or both strains.…”

Section: Molecular Modeling Studymentioning

confidence: 99%

Antileishmanial activity of polycyclic derivatives

et al. 2005

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Summary :33 polycyclic derivatives have been studied and tested on Leishmania donovani and L. major promastigotes. Their antileishmanial activity was assessed in vitro and an assay of their cytotoxicity was realized on human myelomonocytic cell line. The reference molecules used in the assays were amphotericin B and pentamidine. Among the compounds tested, 29 possess an antileishmanial activity; 25 of those were more active against L. donovani than amphotericin B, and nine were as effective as amphotericin B against L. major. Many synthesized derivatives were more active against L.donovani than against L. major. The cytotoxicity studies have shown that among the thirty-three derivatives tested, 12 molecules have an IC 50 towards THP-1 cells about equal than that reference drugs, the 21 other derivatives are much less toxic. A 3D QSAR study was undertaken and has permitted to predict activity against L. donovani and L. major and to highlight critical area to optimize activity against the two species. Résumé

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Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring

Cited by 49 publications

References 20 publications

Evaluation of the Anti-Schistosoma mansoni Activity of Thiosemicarbazones and Thiazoles

Evaluation of the Anti-Schistosoma mansoni Activity of Thiosemicarbazones and Thiazoles

Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives

Antileishmanial activity of polycyclic derivatives

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