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Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases

Here, the synthesis and glycosidase inhibition properties of the two first known 3-ethyloctahydro-1H-indole-4,5,6-triols are reported. This study shows the transformation of d-glucose into polyhydroxylated 1-(2-nitrocyclohexane) acetaldehydes, followed by a protocol involving the formation of the az...

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Autores principales: Estévez, Juan C., González, Marcos A., Villaverde, M. Carmen, Hirokami, Yuki, Kato, Atsushi, Sussman, Fredy, Reza, David, Estévez, Ramón J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631223/
https://www.ncbi.nlm.nih.gov/pubmed/30934879
http://dx.doi.org/10.3390/ph12020047
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author Estévez, Juan C.
González, Marcos A.
Villaverde, M. Carmen
Hirokami, Yuki
Kato, Atsushi
Sussman, Fredy
Reza, David
Estévez, Ramón J.
author_facet Estévez, Juan C.
González, Marcos A.
Villaverde, M. Carmen
Hirokami, Yuki
Kato, Atsushi
Sussman, Fredy
Reza, David
Estévez, Ramón J.
author_sort Estévez, Juan C.
collection PubMed
description Here, the synthesis and glycosidase inhibition properties of the two first known 3-ethyloctahydro-1H-indole-4,5,6-triols are reported. This study shows the transformation of d-glucose into polyhydroxylated 1-(2-nitrocyclohexane) acetaldehydes, followed by a protocol involving the formation of the azacyclopentane ring. Results of inhibitory potency assays and docking calculations show that at least one of them could be a lead for optimization in the search for compounds that behave like folding chaperones in lysosomal storage diseases.
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spelling pubmed-66312232019-08-19 Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases Estévez, Juan C. González, Marcos A. Villaverde, M. Carmen Hirokami, Yuki Kato, Atsushi Sussman, Fredy Reza, David Estévez, Ramón J. Pharmaceuticals (Basel) Article Here, the synthesis and glycosidase inhibition properties of the two first known 3-ethyloctahydro-1H-indole-4,5,6-triols are reported. This study shows the transformation of d-glucose into polyhydroxylated 1-(2-nitrocyclohexane) acetaldehydes, followed by a protocol involving the formation of the azacyclopentane ring. Results of inhibitory potency assays and docking calculations show that at least one of them could be a lead for optimization in the search for compounds that behave like folding chaperones in lysosomal storage diseases. MDPI 2019-03-29 /pmc/articles/PMC6631223/ /pubmed/30934879 http://dx.doi.org/10.3390/ph12020047 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Estévez, Juan C.
González, Marcos A.
Villaverde, M. Carmen
Hirokami, Yuki
Kato, Atsushi
Sussman, Fredy
Reza, David
Estévez, Ramón J.
Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases
title Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases
title_full Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases
title_fullStr Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases
title_full_unstemmed Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases
title_short Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases
title_sort chain-branched polyhydroxylated octahydro-1h-indoles as potential leads against lysosomal storage diseases
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631223/
https://www.ncbi.nlm.nih.gov/pubmed/30934879
http://dx.doi.org/10.3390/ph12020047
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