Synthesis and Antiprotozoal Properties of 1,2,6‐Thiadiazine 1,1‐Dioxide Derivatives

Herrero, Ana B.; Ochoa, Carmen; Atienza, Juan Carlos; Escario, José Antonio; Gómez‐Barrio, Alicia; Femández, Antonio R. Índez Mart

doi:10.1002/ardp.19923250811

Cited by 19 publications

(18 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…So, compound 2, which showed great activity against the Bolivia strain, was 10,()()() times less effective against the Y strain. This accords with the ineffectiveness of com pound 2 to clear Y strain trypomastigotes from stored infected blood [10]. Screening against amastigote forms of T. cruzi seems to be a more selective method than that against cpimastigotcs.…”

Section: Absorbances Of Controlsabsorbances Of Experimental Groups --mentioning

confidence: 80%

“…1. Compounds 1-4, 3, 6, 7a and 7b have previously been described [10], Compound 5 (m.p. 138-139 °C) has now been synthesized following the procedure described for 3 and 4.…”

Section: Source O F Compoundsmentioning

confidence: 99%

“…Four thiadiazine derivatives that overcame the previous in vitro screening as antitricho monal agents [10] were selected for in vivo as says. Three of them (compounds No.…”

Section: Absorbances Of Controlsabsorbances Of Experimental Groups --mentioning

confidence: 99%

“…Continuing with the biological studies on antitrichomonal and antitrypanosomal prop erties of a new series of thiadiazinc derivatives [10], in vivo tests on mice experimentally in fected with T. vaginalis, and in vitro on amasti gote forms of T. cruzi, were performed. The cytotoxicity of these compounds was assessed by investigating their effects on cell prolifer ation in tissue culture.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Activity Assays of Thiadiazine Derivatives on Trichomonas vaginalis and Amastigote Forms of Trypanosoma cruzi

et al. 1992

View full text Add to dashboard Cite

Eight thiadiazine 1,1-dioxide derivatives were evaluated for antitrichomonal and antitrypanosomal activities. In vivo tests were performed on a murine model for trichomoniasis standardized in our laboratory. The capacity of compounds to clear visceral lesions in experimentally infected animals as well as their effects on the mortality time of mice were used as criteria for activity. One of the thiadiazines (compound 7b) showed an efficacy similar to that obtained with the reference drug metronidazole, although higher doses were required. Its toxicity on cell proliferation in tissue culture was moderate. In vitro assays on amastigote forms of Trypanosoma cruzi were carried out using cultures of Vero cells infected with metacyclic trypomastigotes. For one compound (1) trypanocidal activity resembled that of nifurtimox as assessed by microscopic counts of infected and uninfected cells. Unfortunately, this compound showed a high degree of cytotoxicity on Vero cell cultures.

show abstract

Section: Absorbances Of Controlsabsorbances Of Experimental Groups --mentioning

confidence: 80%

“…1. Compounds 1-4, 3, 6, 7a and 7b have previously been described [10], Compound 5 (m.p. 138-139 °C) has now been synthesized following the procedure described for 3 and 4.…”

Section: Source O F Compoundsmentioning

confidence: 99%

“…Four thiadiazine derivatives that overcame the previous in vitro screening as antitricho monal agents [10] were selected for in vivo as says. Three of them (compounds No.…”

Section: Absorbances Of Controlsabsorbances Of Experimental Groups --mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Activity Assays of Thiadiazine Derivatives on Trichomonas vaginalis and Amastigote Forms of Trypanosoma cruzi

et al. 1992

View full text Add to dashboard Cite

show abstract

“…metronidazole (MW: 171,16 ; Sigma-Aldrich, Madrid, Spain) was used as reference drug at concentrations of 12, 6, and 3 µM. Cytocidal and cytostatic activities were determined in relation with controls as previously reported (Herrero et al, 1992). Briefly, the cytocidal (% CA) or cytostatic (% ca) activities were calculated with respect to the growth rates (GR) as follows:…”

Section: In Vitro Trichomonicidal Activitymentioning

confidence: 99%

Effect of piroxicam, metamizol, and S-adenosylmethionine in a murine model of experimental trichomoniasis

et al. 2005

View full text Add to dashboard Cite

Summary :Biological effects of piroxicam, metamizol, and S-adenosylmethionine (S-AMET) have been tested in NMRI mice infected intraperitoneally with Trichomonas vaginalis. An intraperitoneal treatment during ten preinfection days with piroxicam (10 mg/Kg/day), or metamizol (275 mg/Kg/day), but not with S-AMET (17 mg/Kg/day) induced a significant decrease of abdominal lesions and mortality, assessed by means of a pathogenicity index. The trichomonicidal activity of piroxicam, metamizol, and S-AMET was tested in vitro at the concentration of 300 µM, but found ineffective. These assays have shown the usefulness of the experimental trichomoniasis model for the study of the immunomodulating activity of synthetic drugs. Résumé : EFFETS PHARMACOLOGIQUES DU PIROXICAM,

show abstract

Sulfahydantoins as Tripeptide Constraints: Synthesis and Structure of Chiral Substituted 3-Oxo-1,2,5-thiadiazolidine 1,1-Dioxides

Boudjabi¹,

Dewynter²,

Voyer³

et al. 1999

Eur. J. Org. Chem.

View full text Add to dashboard Cite

A sulfahydantoin (3‐oxo‐1,2,5‐thiadiazolidine 1,1‐dioxides) motif is used as a new type of peptidic constraint to lock two consecutive amide nitrogens by a sulfonyl bridge. The 5‐membered heterocyclic motif was prepared starting from proteogenic and synthetic amino acids and chlorosulfonyl isocyanate. Constrained dipeptides were obtained under alkaline conditions (methoxide or tert‐butoxide) by cyclization of symmetric and dissymmetric sulfamides. The absolute configuration of the chiral centers for the derivative L‐Phe‐D‐Ala, a congener of the series, was established by X‐ray diffraction crystallographic analysis. In addition, the chemo‐, regio‐, and stereoselectivities of the reactions were studied. In the acylated derivatives, the sulfahydantoin constraint induces a unique backbone conformation with coplanarity of two consecutive peptide bonds.

show abstract

Synthesis and Antiprotozoal Properties of 1,2,6‐Thiadiazine 1,1‐Dioxide Derivatives

Cited by 19 publications

References 8 publications

Activity Assays of Thiadiazine Derivatives on <i>Trichomonas vaginalis </i>and Amastigote Forms of <i>Trypanosoma cruzi</i>

Activity Assays of Thiadiazine Derivatives on <i>Trichomonas vaginalis </i>and Amastigote Forms of <i>Trypanosoma cruzi</i>

Effect of piroxicam, metamizol, and S-adenosylmethionine in a murine model of experimental trichomoniasis

Sulfahydantoins as Tripeptide Constraints: Synthesis and Structure of Chiral Substituted 3-Oxo-1,2,5-thiadiazolidine 1,1-Dioxides

Contact Info

Product

Resources

About