Abstract
As a continuation of our project aimed at searching for new chemotherapeutic agents against American trypanosomiasis (Chagas disease), new selenocyanate derivatives were designed, synthesized and biologically evaluated against the clinically more relevant dividing form of Trypanosoma cruzi, the etiologic agent of this illness. In addition, in order to establish the role of each part of the selenocyanate moiety, different derivatives, in which the selenium atom or the cyano group were absent, were conceived, synthesized and biologically evaluated. In addition, in order to study the optimal position of the terminal phenoxy group, new regioisomers of WC-9 were synthesized and evaluated against T. cruzi. Finally, the resolution of a racemic mixture of a very potent conformationally rigid analogue of WC-9 was accomplished and further tested as growth inhibitors of T. cruzi proliferation. The results provide further insight into the role of the selenocyanate group in its antiparasitic activity.
References
Jan 1, 1973·Annual Review of Microbiology·Z Brener
Jul 18, 1997·Journal of Medicinal Chemistry·A J SchvartzapelE G Gros
May 23, 1998·Journal of Medicinal Chemistry·G M CinqueE G Gros
May 5, 2000·Journal of Medicinal Chemistry·S H SzajnmanJ B Rodriguez
Mar 22, 2001·Advanced Drug Delivery Reviews·C A LipinskiP J Feeney
Aug 23, 2002·Journal of Medicinal Chemistry·Eleonora ElhalemJuan B Rodriguez
May 23, 2003·Antimicrobial Agents and Chemotherapy·Julio A UrbinaRoberto Docampo
Oct 30, 2004·Chirality·Ashraf Ghanem, Hassan Y Aboul-Enein
Jul 24, 2007·Bioorganic & Medicinal Chemistry Letters·Guadalupe García LiñaresJuan B Rodriguez
Sep 19, 2008·Journal of the American Chemical Society·Brett P ForsStephen L Buchwald
Aug 12, 2009·Organic Letters·Brijesh BhayanaStephen L Buchwald
Nov 11, 2009·Journal of the American Chemical Society·Debabrata Maiti, Stephen L Buchwald
Nov 11, 2009·Acta Tropica·Julio A Urbina
Jan 2, 2013·International Journal for Parasitology. Drugs and Drug Resistance·Frederick S Buckner, Julio A Urbina
Jan 16, 2013·European Journal of Medicinal Chemistry·Marion RecherJuan B Rodriguez
May 17, 2013·Organic Letters·Nicholas C Bruno, Stephen L Buchwald
Oct 5, 2013·European Journal of Medicinal Chemistry·Pablo D ElicioJuan B Rodriguez
Feb 18, 2014·Acta Crystallographica. Section D, Biological Crystallography·Chia-I LiuAndrew H-J Wang
Apr 29, 2015·ChemMedChem·María N ChaoJuan B Rodriguez
Sep 4, 2015·Chemistry : a European Journal·Kévin JouvinLukas J Goossen
Jul 5, 2016·Expert Opinion on Therapeutic Patents·Juan B RodriguezSergio H Szajnman
Aug 16, 2016·Journal of Medicinal Chemistry·Katarzyna MacegoniukŁukasz Berlicki
Oct 1, 2016·Chemical Reviews·Paula Ruiz-Castillo, Stephen L Buchwald
Nov 26, 2016·ChemMedChem·María N ChaoJuan B Rodriguez
Sep 15, 2017·PLoS Neglected Tropical Diseases·Jonathan D AlpernWilliam M Stauffer
Nov 7, 2017·Bioorganic & Medicinal Chemistry·María N ChaoJuan B Rodriguez
Apr 29, 2018·Nature Communications·Michael J CapperS Samar Hasnain