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Design, synthesis, crystal structure and in vitro cytotoxic properties of a novel Schiff base derived from indole and biphenyl
Author(s) -
Bu Fan-Zhi,
Tan Xue-Jie,
Xing Dian-Xiang,
Wang Chao
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229617009044
Subject(s) - chemistry , molecule , indole test , acetonitrile , stereochemistry , crystal structure , supramolecular chemistry , biphenyl , schiff base , stacking , hydrogen bond , single crystal , crystallography , organic chemistry
A novel and potentially active dihydroorotate dehydrogenase (DHODH) inhibitor, namely 3‐({( E )‐[( E )‐1‐(biphenyl‐4‐yl)ethylidene]hydrazinylidene}methyl)‐1 H ‐indole (BEHI) acetonitrile disolvate, C 23 H 19 N 3 ·2CH 3 CN, has been designed and synthesized. The structure of BEHI was characterized by elemental analysis, Q‐TOF (quadrupole time‐of‐flight) MS, NMR, UV–Vis and single‐crystal X‐ray diffraction. The antitumour activity of the target molecule was evaluated by the MTT method. Results indicated that BEHI exhibited rather potent cytotoxic activity against human A549 (IC 50 = 20.5 µ M ) and mouse breast 4T 1 (IC 50 = 18.5 µ M ) cancer cell lines. Meanwhile, to rationalize its potencies in the target, BEHI was docked into DHODH and the interactions with the active site residues were analyzed. Single‐crystal structure analysis indicated that hydrogen bonds are present only between BEHI and acetonitrile solvent molecules in the asymmetric unit. The interplay of weak π–π stacking and weak C(N)—H…π interactions between neighbouring BEHI molecules play crucial roles in the formation of the final supramolecular frameworks.