Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation

Kumar, C. S. Chidan; Loh, Wan-Sin; Ooi, Chin Wei; Quah, Ching Kheng; Fun, Hoong‐Kun

doi:10.3390/molecules181012707

Cited by 41 publications

(12 citation statements)

References 26 publications

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“…The ability of the test samples, in addition to the standard anti-oxidant butylated hydroxyltoluene (BHT), on DPPH radical scavenging was estimated according to the method described earlier [14,15]. Compounds of different concentrations were prepared in ethanol, 1 mL of each compound solution having different concentrations (10-250 μg/mL).…”

Section: Dpph Radical Scavenging Assaymentioning

confidence: 99%

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Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

Kumar

Chia

Ooi

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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Phenacyl benzoates possess commercial importance due to their various applications in the fields of synthetic and photochemistry, such as photosensitive blocking groups owing to their ease of cleavage under mild conditions. In the present study, a series of ten new 2-(4-bromophenyl)-2-oxoethyl benzoates 2(a-j), with the general formula Br(C 6 H 4 )COCH 2 OCO(C 6 H 5Àn X n ), X ¼ Cl, NO 2 or NH 2 , and n ¼ 1 or 2, have been synthesized by reacting 4-bromophenacyl bromide with various substituted benzoic acids using potassium carbonate in DMF medium at room temperature. These reactions proceeded with ease under mild conditions producing high purity products in good yield. Each product was characterized by mass spectra, elemental analysis and melting points, its 3D structure was confirmed by single-crystal X-ray diffraction studies. The X-ray 3D structures showed the flexibility of the C(¼O)-O-C-C(¼O) connecting bridge in which 7 out of 10 compounds tend to form a torsion angle in the range of 70 to 91°, whereas the rest are slightly twisted with a torsion angles of À160, 163, 176 and 178°. Their molecular conformations are in good agreement with another 22 related structures. These synthesized compounds were screened for their abilities for DPPH radical scavenging and ferric reducing anti-oxidant power. The results indicate that these compounds displayed mild anti-oxidant ability when compared to the standard anti-oxidant BHT.

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Section: Dpph Radical Scavenging Assaymentioning

confidence: 99%

“…The synthesized compounds were screened for ferric reducing power anti-oxidant ability by the method described earlier [14,15]. The method is based on the reduction of ferric (Fe 3þ ) to ferrous (Fe 2þ ), which is accomplished in the presence of antioxidants.…”

Section: Ferric Reducing Anti-oxidant Power (Frap) Assaymentioning

confidence: 99%

Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

Kumar

Chia

Ooi

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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“…Compounds M 2 and M 6 exhibited significant protection activities against TMV at 500 μg/mL, with the values of 68.6% ± 7.7% and 72.3% ± 5.2%, respectively, which were even better than that of Ribavirin (51.8% ± 2.3%). The inactivation activities of compounds M 2 , M 6 , M 8 , M 10 , and M 14 at 500 μg/mL were 82.1% ± 4.1%, 83.2% ± 4.4%, 85.6% ± 2.6%, and 85.1% ± 3.6%, respectively, which were better than that of Ribavirin (72.9% ± 2.4%). Based on the previous bioassays, the 50% effective concentration (EC50) values of protection activities against TMV of the title compounds were tested and presented in Table 2.…”

Section: Antiviral Activity Screening Of Title Compounds Against Tmv mentioning

confidence: 85%

“…Chalcones, belonging to the flavonoid family and obtained from Carthamus tinctorius first, possessed a broad spectrum of biological activities, including antibacterial [9][10][11][12], antifungal [13], anti-Alzheimer's disease [14], anticancer [15], antitrichomonal [16], and anti-trypanosomacruzi [17] activities. It is reported that Verma et al, had reported a series of chalcones derivatives, which were used to control plant viruses [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiviral Bioactivity of Novel 4-Thioquinazoline Derivatives Containing Chalcone Moiety

Wan

et al. 2015

Molecules

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A series of novel 4-thioquinazoline derivatives containing chalcone moiety were designed, synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited moderate to good anti-TMV activity. In particular, compounds M 2 and M 6 possessed appreciable protection activities against TMV in vivo, with 50% effective concentration (EC50) values of 138.1 and 154.8 μg/mL, respectively, which were superior to that of Ribavirin (436.0 μg/mL). The results indicated that chalcone derivatives containing 4-thioquinazoline moiety could effectively control TMV. Meanwhile, the structure-activity relationship (SAR) of the target compounds, studied using the three-dimensional quantitative structure-activity relationship (3D-QSAR) method of comparative molecular field analysis (CoMFA) based on the protection activities against TMV, demonstrated that the CoMFA model exhibited good predictive ability with the cross-validated q 2 and non-cross-validated r 2 values of 0.674 and 0.993, respectively. Meanwhile, the microscale thermophoresis (MST) experimental showed that the compound M 6 may interaction with the tobacco mosaic virus coat protein (TMV CP).

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“…Chalcones are bicyclic flavonoids that consist of two aromatic rings that are linked by an α,β‐unsaturated ketone system . They display several pharmacological activities such as antibacterial, antifungal, antileishmanial, and antitumor . Recently, many derivatives of chalcones were synthesized for evaluation of their cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs

Ketabforoosh

Kheirollahi

Safavi

et al. 2014

Archiv der Pharmazie

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A novel series of chalcones and flavanones discriminated by the presence of a 3,4-dimethoxyphenyl moiety in their structures were synthesized as anti-cancer agents. The cytotoxicity evaluation of the analogs against the MCF-7, MDA-MB-231 (human breast cancer), and SK-N-MC (human neuroblastoma) cell lines demonstrated that the introduction of a halogen on the 3,4-dimethoxyphenyl part of both series and the attachment of a pyrrolidinylethoxy group on the C-7 position of the flavanone derivatives increased their activity. Indeed, 3-halogenated chalcones (1c and 1d) were more potent than the standard drug etoposide against all tested cell lines. Fluorescence microscopy and flow cytometry analyses confirmed that the anti-cancer effect of the most potent compounds 1c and 1d occurs via apoptosis induction.

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Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation

Cited by 41 publications

References 26 publications

Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

Synthesis, Antiviral Bioactivity of Novel 4-Thioquinazoline Derivatives Containing Chalcone Moiety

Synthesis and Anti‐Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs

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