Crystal structures of (<i>E</i>)-3-(4-hydroxybenzylidene)chroman-4-one and (<i>E</i>)-3-(3-hydroxybenzylidene)-2-phenylchroman-4-one

Suchojad, Kamil; Dołęga, Anna; Adamus-Grabicka, Angelika; Budzisz, Elżbieta; Małecka, Magdalena

doi:10.1107/s2056989019015639

Cited by 2 publications

(4 citation statements)

References 42 publications

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“…Additionally, it is worth mentioning that compound 2 has higher values for all tested cytotoxic activities compared to 8 ( Table 3); this is associated with its more extended spatial structure, in which a bulky phenyl substituent is attached in the C2 position. A similar trend is observed for benzylideneflavanone and benzylidenechromanone analogues [13]. However, taking into account the structure 2 and 10, which are similar and differ only the position of methoxy group in phenyl fragment cytotoxic activity is different.…”

Section: X-ray Single-crystal Structure Of 2 Andsupporting

confidence: 72%

“…Elemental analyses were performed at the Faculty of Chemistry (University of Lodz) using a Vario Micro Cube analyzer by Elemental (Langenselbold, Germany). 1 H-(600 MHz) and 13 C-NMR spectra (150 MHz) were recorded at the University of Lodz Faculty of Chemistry on an Avance III 600 MHz instrument (Bruker, Billerica, MA, USA). The samples were dissolved in deuterated DMSO and CDCl 3 .…”

Section: General Informationmentioning

confidence: 99%

“…Next steps were the same as for the synthesis of compound Figure S10). 13 HL-60 used in this work came from the ATCC American Type Culture Collection (Manassas, VA, USA), whereas the NALM-6 cell line was purchased from the German Collection of Microorganisms and Cell Cultures (Braunschweig, Germany). The leukaemia cells and colon adenocarcinoma were cultured in RPMI 1640 medium (Invitrogen, Grand Island, NY, USA) supplemented with 10% fetal bovine serum (FBS; Invitrogen) and gentamicin (25 µg/mL; KRKA, Novo Mesto, Slovenia).…”

Section: Synthesis Of (E)-3-benzylidene-chroman-4-one (7)mentioning

confidence: 99%

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Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

et al. 2020

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A series of 3-benzylidenechrmanones 1, 3, 5, 7, 9 and their spiropyrazoline analogues 2, 4, 6, 8, 10 were synthesized. X-ray analysis confirms that compounds 2 and 8 crystallize in a monoclinic system in P21/n space groups with one and three molecules in each asymmetric unit. The crystal lattice of the analyzed compounds is enhanced by hydrogen bonds. The primary aim of the study was to evaluate the anti-proliferative potential of 3-benzylidenechromanones and their spiropyrazoline analogues towards four cancer cell lines. Our results indicate that parent compounds 1 and 9 with a phenyl ring at C2 have lower cytotoxic activity against cancer cell lines than their spiropyrazolines analogues. Analysis of IC50 values showed that the compounds 3 and 7 exhibited higher cytotoxic activity against cancer cells, being more active than the reference compound (4-chromanone or quercetin). The results of this study indicate that the incorporation of a pyrazoline ring into the 3-arylideneflavanone results in an improvement of the compounds’ activity and therefore it may be of use in the search of new anticancer agents. Further analysis allowed us to demonstrate the compounds to have a strong inhibitory effect on the cell cycle. For instance, compounds 2, 10 induced 60% of HL-60 cells to be arrested in G2/M phase. Using a DNA-cleavage protection assay we also demonstrated that tested compounds interact with DNA. All compounds at the concentrations corresponding to cytotoxic properties are not toxic towards red blood cells, and do not contribute to hemolysis of RBCs.

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Section: X-ray Single-crystal Structure Of 2 Andsupporting

confidence: 72%

Section: General Informationmentioning

confidence: 99%

Section: Synthesis Of (E)-3-benzylidene-chroman-4-one (7)mentioning

confidence: 99%

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Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

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“…A comparison of the logP value (theoretical) with the contribution of various contacts to the Hirshfeld surface found that theoretical lipophilicity (logP) is also inversely proportional to the percentage contribution of the CÁ Á ÁC contacts to the Hirshfeld surface. This analysis has been extended by similar flavonoid compounds and benzylidenochromanone derivatives available from our previous research (Kupcewicz et al, 2013;Adamus-Grabicka et al, 2018;Suchojad et al, The cytotoxic activity (expressed as log 1 IC 50 ) against the HL-60, NALM-6, WM-115 and COLO-205 cancer cell lines.…”

Section: Hirshfeld Surfacementioning

confidence: 99%

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

et al. 2020

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The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzylidene-2-phenylchroman-4-one, C22H16O2, I, (E)-3-(4-methylbenzylidene)-2-phenylchroman-4-one, C23H18O2, II, (E)-3-(3-methylbenzylidene)-2-phenylchroman-4-one, C23H18O2, III, (E)-3-(4-methoxybenzylidene)-2-phenylchroman-4-one, C23H18O3, IV, (E)-3-benzylidenechroman-4-one, C16H12O2, V, and (E)-3-(4-methoxybenzylidene)chroman-4-one, C17H14O3, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their intermolecular interaction preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C...C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C...H contacts to the Hirshfeld surface.

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Crystal structures of (E)-3-(4-hydroxybenzylidene)chroman-4-one and (E)-3-(3-hydroxybenzylidene)-2-phenylchroman-4-one

Cited by 2 publications

References 42 publications

Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

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