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Updated: May 10, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
6-[3-(p-Tolyl-sulfonyl-amino)-prop-yl]diquino-thia-zine
Małgorzata Jeleń1, Aleksander Shkurenko, Kinga Suwińska
1Department of Organic Chemistry, The Medical University of Silesia, ul. Jagiellońska 4, PL-41 200 Sosnowiec, Poland.
Abstract:
In the title mol-ecule {systematic name: N-[3-(diquino[3,2-b;2',3'-e][1,4]thia-zin-6-yl)prop-yl]-4-methyl-benzene-sulfon-amide}, C28H24N4O2S2, the penta-cyclic 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-thia-zine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolyl-sulfonyl-amino)-propyl substituent allows for the formation of an intra-molecular N-H⋯N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the penta-cyclic system. In the crystal, mol-ecules are arranged via π-π stacking inter-actions into (0-11) layers [centroid-centroid distances = 3.981 (1)-4.320 (1) Å for the rings in the penta-cyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, mol-ecules are involved in weak C-H⋯O, which connect the layers, and C-H⋯S hydrogen bonds. The title compound shows promising anti-cancer activity against renal cancer cell line UO-31.
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