63368-35-4Relevant academic research and scientific papers
Arylethenylbenzofuroxan derivatives as drugs for chagas disease: Multigram batch synthesis ysubg a wuttug#bideb process
Porcal, Williams,Merlino, Alicia,Boiani, Mariana,Gerpe, Alejandra,Gonzalez, Mercedes,Cerecetto, Hugo
, p. 156 - 162 (2013/01/03)
In the present work, we developed robust processes for the preparation of new antitrypanosomal benzofuroxans, E and Z isomers of 5-arylethenylbenzo[1,2-c] 1,2,5-oxadiazole p1N-oxide 1-6, in muhigram batch through Wittig-Boden conditions as the key synthetic step. In these conditions, the generation of the benzofurazans, as secondary byproduct, was minimized.
Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and structure-activity relationships
Porcal, Williams,Hernandez, Paola,Aguirre, Gabriela,Boiani, Lucia,Boiani, Mariana,Merlino, Alicia,Ferreira, Ana,Maio, Rossanna Di,Castro, Ana,Gonzalez, Mercedes,Cerecetto, Hugo
, p. 2768 - 2781 (2008/02/08)
In vitro growth inhibitory activity of 21 new 5-ethenylbenzofuroxan derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, was studied. The designed compounds possess the previously described exigencies for optimal anti-parasite activity, the 5-ethenylbenzofuroxanyl moiety with different substituents. The synthetic key for preparing the derivatives was the Wittig procedure, that when 5-formylbenzofuroxan was used as the electrophile the corresponding deoxygenated products were marginally generated. Four of the new derivatives displayed remarkable in vitro activities against the epimastigote form of three strains of T. cruzi, Tulahuen 2, CL Brener, and Y. While the three deoxygenated analogues biologically assayed resulted inactives. Unspecific cytotoxicity was evaluated using human macrophages and active derivatives were not toxic at a concentration at least 13 times that of its IC50 against T. cruzi (CL Brener strain). From the preliminary structure-activity relationship studies lipophilicity and electronic requirements were found relevant to anti-T. cruzi activity. Active compounds are more lipophilic than inactive ones and it was also identified that an optimum value of R Swain-Lupton's descriptor is required for optimal activity.
Electrochemical Stability of Catechols with a Pyrene Side Chain Strongly Adsorbed on Graphite Electrodes for Catalytic Oxidation of Dihydronicotinamide Adenine Dinucleotide
Jaegfeldt, Hans,Kuwanw, Theodore,Johansson, Gillis
, p. 1805 - 1814 (2007/10/02)
The electrochemical stability and reactivity of 4-catechol (PSCH2) and 4-catechol (PECH2) strongly adsorbed on graphite electrodes were investigated as a function of the applied potential at pH 7.0.The surface coverage of these compounds ranged from 0.1 x 10-9 to 2.7 x 10-9 mol/cm2.The ''modified'' electrodes exhibited deactivation which could be explained by second-order reactions between the catechols and the electrochemically produced quinones coupled with a second-order reaction between the quinones.The ethano compound showed a much larger decay rate, probably because of free rotation around the saturated bond connecting the pyrene part and the catechol group.The deactivation was apparently not associated with decomposition of the compounds.The catechols in the oxidized form could catalytically oxidize NADH.The overpotential for NADH oxidation was thus decreased from 410 to 150 mV vs.SCE at pH 7.0.However, the catalytic current was found to decrease exponentially with increasing number of scans.The rate of this deactivation of the catalytic electrode was found to be inversely proportional to the coverage of immobilized mediator.The deactivation could be explained by a chemical coupling reaction between the mediator and NADH, forming a complex which gradually blocked off the surface of the electrode.The probable nature of the complex makes it unlikely that ''capping'' of active sites, e.g., the 2, 5, and 6 positions, on the catechol ring would effectively prevent the blocking and, hence, deactivation of the catalytic electrodes.
