Synthesis, structure and luminescence of novel co-crystals based on bispyridyl-substituted α , β -unsaturated ketones with coformers

Li, Hongjuan; Wang, Lei; Zhao, Juanjuan; Jun, Sun Hee; Sun, Jiliang; Wang, Chunhua; Hou, Gui‐Ge

doi:10.1016/j.molstruc.2014.09.008

Cited by 10 publications

(6 citation statements)

References 32 publications

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“…Recently, some symmetric or dissymmetric N -substituted-3,5- bis (arylidene)-4-piperidone derivatives as anticancer agents were reported by our group 15,16 . In addition, some bispyridyl-substituted BAPs and their pharmaceutical co-crystals with the interesting luminescent properties 17 and the improved anticancer activities were reported. The results showed that the improvement of anticancer activities should be related to the synergistic effect between BAPs and gallic acid 18 .…”

Section: Introductionmentioning

confidence: 99%

Hydroxyl-substituted double Schiff-base condensed 4-piperidone/cyclohexanones as potential anticancer agents with biological evaluation

Zhang

Chen

Hou

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel hydroxyl-substituted double Schiff-base 4-piperidone/cyclohexanone derivatives, 3a–e, 4a–e, 5a–d, and 6a–c, were synthesized and fully characterized by 1H NMR, IR and elemental analysis. The cytotoxicity against human carcinoma cell lines A549, SGC7901, HePG2, HeLa, K562, THP-1 and non-malignant LO2 cell lines were evaluated. The results showed 4-piperidinone derivatives displayed better cytotoxicity than cyclohexanone derivatives, especially for 3,4,5-trihydroxyphenyl-substituted BAP 5c. The western blot and flow cytometry results proved 5c can effectively promote cell apoptosis through up-regulating Bax protein and down-regulating Bcl-2 protein expression. Molecular docking modes showed that 5c could reasonably bind to the active site of Bcl-2 protein through strong intermolecular hydrogen bonds and significant hydrophobic effect. In vivo, 5c can effectively suppress the growth of HepG2 xenografts without apparent body weight changes. This study indicates that 5c can be a potential anticancer agent for early treatment of liver cancers.

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Section: Introductionmentioning

confidence: 99%

Hydroxyl-substituted double Schiff-base condensed 4-piperidone/cyclohexanones as potential anticancer agents with biological evaluation

Zhang

Chen

Hou

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Recently, we have reported many novel symmetric and unsymmetric BAPs (such as BAP 6d, see Scheme 1) as antitumour agents (Li et al, 2015(Li et al, , 2018Sun et al, 2016;Chen et al, 2016;Liu et al, 2016;Yao et al, 2018). We hypothesize that by changing the N-methyl substituent into N-benzenesulfonyl substituents in BAPs, the configuration of the BAPs would change markedly and this might improve the antitumour and anti-inflammatory activities of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

Bai

Zhang

et al. 2018

Acta Crystallogr C

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of the olefinic double bonds. Molecules of both (4) and (6) are connected by hydrogen bonds into one-dimensional chains. In (5) and (7), pairs of adjacent molecules embrace through intermolecular hydrogen bonds to form a bimolecular combination, which are further extended into a two-dimensional sheet. The anti-inflammatory activity data reveal that (4)-(7) significantly inhibit LPS-induced interleukin (IL-6) and tumour necrosis factor (TNF-) secretion. Most importantly, (6) and (7), with strong electron-withdrawing substituents, display more potential inhibitory effects than (4) and (5).

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“…Similarly, three quaternary ammonium cations of 6c also are linked through O–H···Br and C–H···Br bonds from bromine anions in Figure b. It is different that they generate an infinite zigzag chain through intermolecular H‐bonding interactions in 6c . In Figure b, the complicated hydrogen bonds are formed from quaternary ammonium cations and bromine anions.…”

Section: Resultsmentioning

confidence: 99%

Quaternary ammonium salts substituted by 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol as novel antibacterial agents with low cytotoxicity

et al. 2017

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Twenty-one novel 5-phenyl-1,3,4-oxadiazole-2-thiol (POT) substituted N-hydroxyethyl quaternary ammonium salts (6a-g, 7a-g, 8a-g) were prepared and characterized by FTIR, NMR, and elemental analysis. Compounds 6a, 6c, and 8a were confirmed by X-ray single-crystal diffraction. They display the unsurpassed antibacterial activity against Staphylococcus aureus, α-H-tococcus, Escherichia coli, P. aeruginosa, Proteus vulgaris, Canidia Albicans, especially 6g, 7g, 8g with dodecyl group. Compounds 8a-d with N,N-dihydroxyethyl and POT groups display unsurpassed antibacterial activity and non-toxicity. The structure-activity relationships indicate that POT and flexible dihydroxyethyl group in QAS are necessary for antibacterial activity and cytotoxicity. SEM and TEM images of E. coli morphologies of 8d show the antibacterial agents can adhere to membrane surfaces to inhibit bacterial growth by disrupting peptidoglycan formation and releasing bacterial cytoplasm from cell membranes.

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Synthesis, structure and luminescence of novel co-crystals based on bispyridyl-substituted α , β -unsaturated ketones with coformers

Cited by 10 publications

References 32 publications

Hydroxyl-substituted double Schiff-base condensed 4-piperidone/cyclohexanones as potential anticancer agents with biological evaluation

Hydroxyl-substituted double Schiff-base condensed 4-piperidone/cyclohexanones as potential anticancer agents with biological evaluation

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

Quaternary ammonium salts substituted by 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol as novel antibacterial agents with low cytotoxicity

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