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6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine
In the title molecule {systematic name: N-[3-(diquino[3,2-b;2′,3′-e][1,4]thiazin-6-yl)propyl]-4-methylbenzenesulfonamide}, C(28)H(24)N(4)O(2)S(2), the pentacyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring s...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685109/ https://www.ncbi.nlm.nih.gov/pubmed/23795128 http://dx.doi.org/10.1107/S1600536813013950 |
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author | Jeleń, Małgorzata Shkurenko, Aleksander Suwińska, Kinga Pluta, Krystian Morak-Młodawska, Beata |
author_facet | Jeleń, Małgorzata Shkurenko, Aleksander Suwińska, Kinga Pluta, Krystian Morak-Młodawska, Beata |
author_sort | Jeleń, Małgorzata |
collection | PubMed |
description | In the title molecule {systematic name: N-[3-(diquino[3,2-b;2′,3′-e][1,4]thiazin-6-yl)propyl]-4-methylbenzenesulfonamide}, C(28)H(24)N(4)O(2)S(2), the pentacyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.23 (2)° and that between the two halves of the 1,4-thiazine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolylsulfonylamino)propyl substituent allows for the formation of an intramolecular N—H⋯N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the pentacyclic system. In the crystal, molecules are arranged via π–π stacking interactions into (0-11) layers [centroid–centroid distances = 3.981 (1)–4.320 (1) Å for the rings in the pentacyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, molecules are involved in weak C—H⋯O, which connect the layers, and C—H⋯S hydrogen bonds. The title compound shows promising anticancer activity against renal cancer cell line UO-31. |
format | Online Article Text |
id | pubmed-3685109 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-36851092013-06-21 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine Jeleń, Małgorzata Shkurenko, Aleksander Suwińska, Kinga Pluta, Krystian Morak-Młodawska, Beata Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title molecule {systematic name: N-[3-(diquino[3,2-b;2′,3′-e][1,4]thiazin-6-yl)propyl]-4-methylbenzenesulfonamide}, C(28)H(24)N(4)O(2)S(2), the pentacyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.23 (2)° and that between the two halves of the 1,4-thiazine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolylsulfonylamino)propyl substituent allows for the formation of an intramolecular N—H⋯N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the pentacyclic system. In the crystal, molecules are arranged via π–π stacking interactions into (0-11) layers [centroid–centroid distances = 3.981 (1)–4.320 (1) Å for the rings in the pentacyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, molecules are involved in weak C—H⋯O, which connect the layers, and C—H⋯S hydrogen bonds. The title compound shows promising anticancer activity against renal cancer cell line UO-31. International Union of Crystallography 2013-05-25 /pmc/articles/PMC3685109/ /pubmed/23795128 http://dx.doi.org/10.1107/S1600536813013950 Text en © Jeleń et al. 2013 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 | Organic Papers Jeleń, Małgorzata Shkurenko, Aleksander Suwińska, Kinga Pluta, Krystian Morak-Młodawska, Beata 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine |
title | 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine
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title_full | 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine
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title_fullStr | 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine
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title_full_unstemmed | 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine
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title_short | 6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine
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title_sort | 6-[3-(p-tolylsulfonylamino)propyl]diquinothiazine |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685109/ https://www.ncbi.nlm.nih.gov/pubmed/23795128 http://dx.doi.org/10.1107/S1600536813013950 |
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