Thioureides of 2-(phenoxymethyl)benzoic acid 4-R substituted: A novel class of anti-parasitic compounds

Müller, Joachim; Limban, Carmen; Lundström‐Stadelmann, Britta; Missir, Alexandru Vasile; Chiriţă, Ileana Cornelia; Chifiriuc, Mariana Carmen; Nițulescu, George Mihai; Hemphill, Andrew

doi:10.1016/j.parint.2008.12.003

Cited by 36 publications

(33 citation statements)

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“…Acyl thiourea derivatives have been increasingly important with a wide diversity of applications in heterocyclic chemistry, metal complexes, molecular electronics and exhibit an array of biological activities [5][6][7][8][9]. Some of them are employed as fungicidal, antiviral, antimicrobial [10], parasiticidal [11], antitumoral [12] and pesticidal agent [13][14][15]. Indeed cytotoxicity studies using HeLa cancer cell lines have demonstrated that some of these platinum acyl thioureas show cytotoxic behavior, with the antiproliferative effects being dependent on the nature/type of the substituent in the acyl thiourea ligand [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

Plutı́n

Mocelo

Alvarez

et al. 2014

Journal of Inorganic Biochemistry

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Section: Introductionmentioning

confidence: 99%

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

Plutı́n

Mocelo

Alvarez

et al. 2014

Journal of Inorganic Biochemistry

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“…Literature survey reveals many N-acyl-thiourea derivatives with wide application as herbicides (Hackmann, 1960), insecticides (Aly et al, 2007;Jirman and Resetova, 1986), parasiticidals (Müller et al, 2009), antitumoral (Faidallah et al, 2007), antimicrobials, and antifungals (Balotescu et al, 2007). Giving attention to the possible synergetic antimicrobial effects of both thiourea and pyrayole moieties presence in an organic compound and following the promising model of various phenoxymethylbenzoic acids thioureides (Limban et al, 2000(Limban et al, , 2004(Limban et al, , 2008a we synthesized a series of N-(1-methyl-1H-pyrazole-4-carbonyl)-thiourea derivatives and tested their antimicrobial potential.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial screening of N-(1-methyl-1H-pyrazole-4-carbonyl)-thiourea derivatives

et al. 2010

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In the search of bioactive molecules in the class of functionally 4-substituted pyrazolic compounds, a series of N-(1-methyl-1H-pyrazole-4-carbonyl)-thiourea derivatives were prepared by addition of various substituted anilines to 1-methyl-1H-pyrazole-4-carbonyl isothiocyanate. The new thioureides and the intermediary compounds were characterized by spectroscopic data and elemental analyses and were evaluated for antibacterial and antifungal activities.

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“…Tested compounds include other benzimidazole derivatives such as flubendazole, itraconazole, and methiazole, as well as other anti-infective agents such as arthemether, caspofungin, ivermectin, miltefosine, rifampin, trimethoprim-sulfamethoxazole, amphotericin B (29), isoprinosine and derivatives (20), nitazoxanide, nitazoxanide and albendazole in combination (36,37), alpha-difluoromethyl-ornithine (24), genistein and derivatives (26), p38 mitogen-activated protein kinase inhibitors (5), thioureides (25), and anticancer agents such as 2-methoxyestradiol (32) and doxorubicin and cyclosporine (21,22). Although some of these compounds showed promising activities in vitro and, to some extent, also in the rodent models (for recent reviews, see references 7 and 8), these findings have not translated into clinical applications.…”

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confidence: 99%

In Vitro and In Vivo Efficacies of Mefloquine-Based Treatment against Alveolar Echinococcosis

Küster

Lundström‐Stadelmann

Hermann

et al. 2011

Antimicrob Agents Chemother

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Alveolar echinococcosis (AE) is caused by the metacestode stage of the fox tapeworm Echinococcus multilocularis and causes severe disease in the human liver, and occasionally in other organs, that is fatal when treatment is unsuccessful. The present chemotherapy against AE is based on mebendazole and albendazole. Albendazole treatment has been found to be ineffective in some instances, is parasitostatic rather than parasiticidal, and usually involves the lifelong uptake of large doses of drugs. Thus, new treatment options are urgently needed. In this study we investigated the in vitro and in vivo efficacy of mefloquine against E. multilocularis metacestodes. Treatment using mefloquine (20 M) against in vitro cultures of metacestodes resulted in rapid and complete detachment of large parts of the germinal layer from the inner surface of the laminated layer within a few hours. The in vitro activity of mefloquine was dependent on the dosage. In vitro culture of metacestodes in the presence of 24 M mefloquine for a period of 10 days was parasiticidal, as determined by murine bioassays, while treatment with 12 M was not. Oral application of mefloquine (25 mg/kg of body weight administered twice a week for a period of 8 weeks) in E. multilocularis-infected mice was ineffective in achieving any reduction of parasite weight, whereas treatment with albendazole (200 mg/kg/day) was highly effective. However, when the same mefloquine dosage was applied intraperitoneally, the reduction in parasite weight was similar to the reduction seen with oral albendazole application. Combined application of both drugs did not increase the treatment efficacy. In conclusion, mefloquine represents an interesting drug candidate for the treatment of AE, and these results should be followed up in appropriate in vivo studies.In humans, infection with the larval stage of Echinococcus multilocularis causes alveolar echinococcosis (AE), a mainly hepatic disease, which is fatal if not treated appropriately. E. multilocularis metacestodes proliferate asexually by forming small daughter vesicles, leading to a parasite mass that exhibits tumor-like properties and progressively infiltrates the neighboring tissue (8). The treatment options for AE are surgery and/or chemotherapy. Surgery is, of course, an invasive procedure, and feasibility depends on the location of the metacestode tissue. In addition, care must be taken to remove the entire parasite mass (otherwise, recurrences are certain), and there is the risk of metastasis formation caused by accidental dissemination of small daughter vesicles or even parasitic cells. Surgery is always accompanied by pre-and postoperative chemotherapy. In cases where surgery is not possible, chemotherapy remains the only option. For chemotherapeutical treatment of AE, the only two drugs licensed to date are the benzimidazole carbamate derivatives albendazole and mebendazole (42). However, therapy using these drugs does not result in parasiticidal activity in vivo or in vitro, and treatment failures and/or the occu...

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Thioureides of 2-(phenoxymethyl)benzoic acid 4-R substituted: A novel class of anti-parasitic compounds

Cited by 36 publications

References 20 publications

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

Synthesis and antimicrobial screening of N-(1-methyl-1H-pyrazole-4-carbonyl)-thiourea derivatives

In Vitro and In Vivo Efficacies of Mefloquine-Based Treatment against Alveolar Echinococcosis

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