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...
Autores principales: | , , , |
---|---|
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 |