Synthesis and biological evaluation of 3′,4′,5′-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation

Rao, Yerra Koteswara; Fang, Shih-Hua; Tzeng, Yew‐Min

doi:10.1016/j.bmc.2009.10.022

Cited by 91 publications

(38 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The chalcones were soluble in dimethylsulfoxide, acetone, acetyl acetate, chloroform and dichloromethane. Compounds 3a–3o and 3r were previously cited in the literature [6, 7, 16–21]. Chalcone derivatives 2a, 2b and 2c were previously synthesized by our group [13–15] and 2d, 3p, 3q and 3s are novel compounds.…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic 3,4,5-trimethoxychalcones as mitotic arresters and cell migration inhibitors

Salum¹,

Altei²,

Chiaradia³

et al. 2013

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Based on classical colchicine site ligands and a computational model of the colchicine binding site on beta tubulin, two classes of chalcone derivatives were designed, synthesized and evaluated for inhibition of tubulin assembly and toxicity in human cancer cell lines. Docking studies suggested that the chalcone scaffold could fit the colchicine site on tubulin in an orientation similar to that of the natural product. In particular, a 3,4,5-trimethoxyphenyl ring adjacent to the carbonyl group appeared to benefit the ligand-tubulin interaction, occupying the same subcavity as the corresponding moiety in colchicine. Consistent with modeling predictions, several 3,4,5-trimethoxychalcones showed improved cytotoxicity to murine acute lymphoblastic leukemia cells compared with a previously described parent compound, and inhibited tubulin assembly in vitro as potently as colchicine. The most potent chalcones inhibited the growth of human leukemia cell lines at nanomolar concentrations, caused microtubule destabilization and mitotic arrest in human cervical cancer cells, and inhibited human breast cancer cell migration in scratch wound and Boyden chamber assays.

show abstract

Section: Methodsmentioning

confidence: 99%

Cytotoxic 3,4,5-trimethoxychalcones as mitotic arresters and cell migration inhibitors

Salum¹,

Altei²,

Chiaradia³

et al. 2013

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…In addition, a huge array of hemisynthetic or synthetic chalcone analogues has been created to identify the most efficient structure for the inhibition of proliferation (see Table 1) [9,91,95,145,148,156,179].…”

Section: Effect Of Chalcones On Tumor Progressionmentioning

confidence: 99%

Dietary chalcones with chemopreventive and chemotherapeutic potential

et al. 2011

View full text Add to dashboard Cite

Chalcones are absorbed in the daily diet and appear to be promising cancer chemopreventive agents. Chalcones represent an important group of the polyphenolic family, which includes a large number of naturally occurring molecules. This family possesses an interesting spectrum of biological activities, including antioxidative, antibacterial, anti-inflammatory, anticancer, cytotoxic, and immunosuppressive potential. Compounds of this family have been shown to interfere with each step of carcinogenesis, including initiation, promotion and progression. Moreover, numerous compounds from the family of dietary chalcones appear to show activity against cancer cells, suggesting that these molecules or their derivatives may be considered as potential anticancer drugs. This review will focus primarily on prominent members of the chalcone family with an 1,3-diphenyl-2-propenon core structure. Specifically, the inhibitory effects of these compounds on the different steps of carcinogenesis that reveal interesting chemopreventive and chemotherapeutic potential will be discussed.

show abstract

“…1b) which can be dubbed as mimics of curcumin due to structural similarity such as presence of two phenyl rings and a,b-unsaturated ketone moiety and presence of hydroxyl and methoxy groups in ring B (vanillin ring). Chalcones (1,3-diaryl-2-propen-1-one) exhibit large number of biological activities including anticancer activity (Kamal et al, 2010;Rao et al, 2009;Vogel et al, 2010). Chalcones can be synthesized easily using conventional methods and relish the stature of good safety profile and is pertinent for oral administration.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin

et al. 2015

View full text Add to dashboard Cite

An array of chalcones from vanillin/isovanillin and differently substituted acetophenones were synthesized and assessed for their anticancer activity against A549, MCF7 and MIA PaCa-2 cell lines using MTT assay. Some of the chalcones exhibited good anticancer activity with IC 50 values below 10 lM. Compound 5f with IC 50 values 5.4 ± 0.7, 10.45 ± 2.15 and 13.0 ± 1.68 lM on MIA PaCa-2, A549 and MCF7, respectively, was more potent than curcumin and hence was analyzed for changes in cell morphology, inhibition of cell migration, mechanism of cell death and arrest of cell cycle progression on MIA PaCa-2 cells.

show abstract

Synthesis and biological evaluation of 3′,4′,5′-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation

Cited by 91 publications

References 30 publications

Cytotoxic 3,4,5-trimethoxychalcones as mitotic arresters and cell migration inhibitors

Cytotoxic 3,4,5-trimethoxychalcones as mitotic arresters and cell migration inhibitors

Dietary chalcones with chemopreventive and chemotherapeutic potential

Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin

Contact Info

Product

Resources

About