Design, synthesis, crystal structure andin vitrocytotoxic properties of a novel Schiff base derived from indole and biphenyl

Abstract

A novel and potentially active dihydroorotate dehydrogenase (DHODH) inhibitor, namely 3-({(E)-[(E)-1-(biphenyl-4-yl)ethylidene]hydrazinylidene}methyl)-1H-indole (BEHI) acetonitrile disolvate, CHN·2CHCN, 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 = 20.5 µM) and mouse breast 4T (IC = 18.5 µM) 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.

Mechanochemical conversion of nano potassium hydrogen terephthalate to thallium analogue nanoblocks with strong hydrogen bonding and straight chain metalophillic interactions

“…It is possible to improve physical and chemical properties of CPs, by adjusting the nature and interactions among the individual components . The design of crystalline architectures employing an understanding of the intermolecular interactions available to molecular subunits is the basis for crystal engineering, a key field straddling solid‐state molecular assembly and structural analysis, whose importance lies in its capability for allowing control of crystal properties and functions as well as its structure . Much progress has been made using simple systems composed of covalent or strong hydrogen bond coordination compounds with peripheral hydrogen bonding substituents have been used to assemble infinite frameworks of one, two, and three dimensions .…”

Synthesis, structure and antiproliferative and optical activities of two new biphenyl-derived Schiff bases

“…As stated in our previous article (Bu et al, 2017), all Schiff bases were readily prepared by similar two-step condensation reactions (see Fig. 1).…”

“…was conducted and modified as described in the literature (Zhao et al, 2010;Cheng et al, 2016;Bu et al, 2017). The cells (8000 cells) were seeded on 96-well microtitre plates in F12K medium with 10% FBS and incubated overnight.…”

“…We have reported a novel Schiff base derived from indole and biphenyl (see 3-BEHI in Scheme 1) (Bu et al, 2017). Compared with Brequinar sodium, this Schiff base shows weaker lung A549 and breast 4T 1 cancer cell inhibitory activities (IC 50 = 20.5 and 18.5 mM, respectively).…”

Theoretical insight into the disordered structure of (Z)-2-[(E)-(4-methoxybenzylidene)hydrazinylidene]-1,2-diphenylethanone: the role of noncovalent interactions

“…We have investigated the design and synthesis of various Schiff bases (Bu et al, 2017;Ma et al, 2017a;Liu et al, 2015;Tan et al, 2014Tan et al, , 2015. In the process of the single-crystal structure characterization of (Z)-2-[(E)-(4-methoxybenzylidene)hydrazinylidene]-1,2-diphenylethanone (MHDE), we found a global positional disorder.…”