Cargando…

Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)

The title compound, C(24)H(32)N(4)O(8)S, (I), crystallizes as a zwitterion. The terminal amine N atom of the [(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl] side chain is protonated, while the 1,2,5-thia­diazo­lidin-3-one 1,1-dioxide N atom is deprotonated. The side chain is turned o...

Descripción completa

Detalles Bibliográficos
Autores principales: Ruddraraju, Kasi Viswanatharaju, Hillebrand, Roman, Barnes, Charles L., Gates, Kent S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438830/
https://www.ncbi.nlm.nih.gov/pubmed/26029383
http://dx.doi.org/10.1107/S2056989015003850
_version_ 1782372398674214912
author Ruddraraju, Kasi Viswanatharaju
Hillebrand, Roman
Barnes, Charles L.
Gates, Kent S.
author_facet Ruddraraju, Kasi Viswanatharaju
Hillebrand, Roman
Barnes, Charles L.
Gates, Kent S.
author_sort Ruddraraju, Kasi Viswanatharaju
collection PubMed
description The title compound, C(24)H(32)N(4)O(8)S, (I), crystallizes as a zwitterion. The terminal amine N atom of the [(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl] side chain is protonated, while the 1,2,5-thia­diazo­lidin-3-one 1,1-dioxide N atom is deprotonated. The side chain is turned over on itself with an intra­molecular N—H⋯O hydrogen bond. The 1,2,5-thia­diazo­lidin-3-one 1,1-dioxide ring has an envelope conformation with the aryl-substituted N atom as the flap. Its mean plane is inclined by 62.87 (8)° to the aryl ring to which it is attached, while the aryl rings of the biphenyl unit are inclined to one another by 20.81 (8)°. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, forming slabs lying parallel to (010). Within the slabs there are C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π inter­actions present.
format Online
Article
Text
id pubmed-4438830
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-44388302015-05-30 Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B) Ruddraraju, Kasi Viswanatharaju Hillebrand, Roman Barnes, Charles L. Gates, Kent S. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(24)H(32)N(4)O(8)S, (I), crystallizes as a zwitterion. The terminal amine N atom of the [(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl] side chain is protonated, while the 1,2,5-thia­diazo­lidin-3-one 1,1-dioxide N atom is deprotonated. The side chain is turned over on itself with an intra­molecular N—H⋯O hydrogen bond. The 1,2,5-thia­diazo­lidin-3-one 1,1-dioxide ring has an envelope conformation with the aryl-substituted N atom as the flap. Its mean plane is inclined by 62.87 (8)° to the aryl ring to which it is attached, while the aryl rings of the biphenyl unit are inclined to one another by 20.81 (8)°. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, forming slabs lying parallel to (010). Within the slabs there are C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π inter­actions present. International Union of Crystallography 2015-03-04 /pmc/articles/PMC4438830/ /pubmed/26029383 http://dx.doi.org/10.1107/S2056989015003850 Text en © Ruddraraju et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Ruddraraju, Kasi Viswanatharaju
Hillebrand, Roman
Barnes, Charles L.
Gates, Kent S.
Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)
title Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)
title_full Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)
title_fullStr Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)
title_full_unstemmed Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)
title_short Crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B)
title_sort crystal structure of 5-{4′-[(2-{2-[2-(2-ammonio­eth­oxy)eth­oxy]eth­oxy}eth­yl)carbamo­yl]-4-meth­oxy-[1,1′-biphen­yl]-3-yl}-3-oxo-1,2,5-thia­diazo­lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1b (ptp1b)
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438830/
https://www.ncbi.nlm.nih.gov/pubmed/26029383
http://dx.doi.org/10.1107/S2056989015003850
work_keys_str_mv AT ruddrarajukasiviswanatharaju crystalstructureof542222ammonioethoxyethoxyethoxyethylcarbamoyl4methoxy11biphenyl3yl3oxo125thiadiazolidin2ide11dioxideapotentialinhibitoroftheenzymeproteintyrosinephosphatase1bptp1b
AT hillebrandroman crystalstructureof542222ammonioethoxyethoxyethoxyethylcarbamoyl4methoxy11biphenyl3yl3oxo125thiadiazolidin2ide11dioxideapotentialinhibitoroftheenzymeproteintyrosinephosphatase1bptp1b
AT barnescharlesl crystalstructureof542222ammonioethoxyethoxyethoxyethylcarbamoyl4methoxy11biphenyl3yl3oxo125thiadiazolidin2ide11dioxideapotentialinhibitoroftheenzymeproteintyrosinephosphatase1bptp1b
AT gateskents crystalstructureof542222ammonioethoxyethoxyethoxyethylcarbamoyl4methoxy11biphenyl3yl3oxo125thiadiazolidin2ide11dioxideapotentialinhibitoroftheenzymeproteintyrosinephosphatase1bptp1b