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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...

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Autores principales: Jeleń, Małgorzata, Shkurenko, Aleksander, Suwińska, Kinga, Pluta, Krystian, Morak-Młodawska, Beata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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
title_full 6-[3-(p-Tolyl­sulfonyl­amino)­prop­yl]diquino­thia­zine
title_fullStr 6-[3-(p-Tolyl­sulfonyl­amino)­prop­yl]diquino­thia­zine
title_full_unstemmed 6-[3-(p-Tolyl­sulfonyl­amino)­prop­yl]diquino­thia­zine
title_short 6-[3-(p-Tolyl­sulfonyl­amino)­prop­yl]diquino­thia­zine
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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