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Please use this identifier to cite or link to this item: http://hdl.handle.net/10481/47297

Title: N,N′-Disubstituted thiourea and urea derivatives: design, synthesis, docking studies and biological evaluation against nitric oxide synthase
Authors: Chayah, Meriem
Camacho Quesada, Encarnación
Carrión Peregrina, María Dora
Gallo Mezo, Miguel Ángel
Romero, Miguel
Duarte, Juan
Issue Date: 4-Jan-2016
Abstract: The synthesis and biological evaluation of new types of N,N′-disubstituted thiourea and urea derivatives as inhibitors of both neuronal nitric oxide synthase (nNOS) and inducible nitric oxide synthase (iNOS) are described. These compounds have been designed by reduction of the carbonyl group in the thiourea and urea kynurenamine derivatives 3 previously synthesized by our research group. The synthetic route performed to this new family also allows us to obtain the molecules 3 with less synthetic steps and higher global yield. Regarding the biological results, in general, the new derivatives 4a–q inhibit the neuronal NOS isoform better than the inducible one. Furthermore, thioureas exhibit higher inhibition than ureas for both isoenzymes. Among all the tested compounds, 4g shows significant nNOS (80.6%) and iNOS (76.6%) inhibition values without inhibiting eNOS. This molecule could be an interesting starting point for the design of new inhibitors with application in neurological disorders where both isoenzymes are implicated such as Parkinson's disease.
Sponsorship: We are very grateful to Dr. Pedro A. Sánchez-Murcia for his help. This work was partially supported by the Instituto de Salud Carlos III through grant FI11/00432 and by Ministerio de Economía y Competitividad, Instituto de Salud Carlos III (RIC RD12/0042/0011).
Publisher: Royal Society of Chemistry
Keywords: Thiourea
Urea
Nitric oxide synthase
URI: http://hdl.handle.net/10481/47297
ISSN: 2040-2511
Rights : Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License
Citation: Chayah, M.; et al. N,N′-Disubstituted thiourea and urea derivatives: design, synthesis, docking studies and biological evaluation against nitric oxide synthase. MedChemComm, 7: 667-678 (2016). [http://hdl.handle.net/10481/47297]
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