Recent advances of cytotoxic chalconoids targeting tubulin polymerization: Synthesis and biological activity

Mirzaei, Hassan; Emami, Saeed

doi:10.1016/j.ejmech.2016.05.067

Cited by 84 publications

(36 citation statements)

References 118 publications

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“…During the recent decades, diverse chalcone derivatives displayed potent anticancer activity by inhibit tubulin polymerization or depolymerization. [6][7][8] Indoles are very commonly skeleton in natural products and synthetic compounds, which have attracted great attention in medicinal chemistry over the past decade. 9,10) It is important to point out that indole moiety is an important pharmacophoric fragment for design and development antitubulin agents as reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anticancer Activity and Molecular Modeling Studies of Novel Chalcone Derivatives Containing Indole and Naphthalene Moieties as Tubulin Polymerization Inhibitors

Wang

Peng

2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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Eighteen novel chalcone derivatives containing indole and naphthalene moieties (2-19) were synthesized and characterized by 1 H-NMR, 13 C-NMR and high resolution (HR)-MS spectra. All compounds were evaluated for their in vitro cytotoxic potential against human hepatocellular carcinoma (HepG2), human colon carcinoma (HCT116) and human breast adenocarcinoma (MCF-7) cell lines. Among them, compound 2, 3, 4 and 7 showed potent activities against tested cancer cell lines. More significantly, compound 7 exhibited the most potent cytotoxic activity against HepG2, HCT116 and MCF-7 with IC 50 values of 0.65, 1.13 and 0.82 µM, respectively. Furthermore, flow cytometry analysis indicated that compound 7 arrested cancer cells in G2/M phase. The compound 7 also displayed significant inhibition of tubulin polymerization (IC 50 3.9 µM). Finally, molecular docking studies were performed to explore the possible interactions between compound 7 and tubulin binding pockets.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Anticancer Activity and Molecular Modeling Studies of Novel Chalcone Derivatives Containing Indole and Naphthalene Moieties as Tubulin Polymerization Inhibitors

Wang

Peng

2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Beside acting as a precursor, epoxy chalcones (23a & 23b) and epoxy chalcone derivatives (24) have been reported for superb anti-cancer activities. The trimethoxy substituents on the epoxy chalcone (23a) are able to inhibit the in vitro growth of human pancreatic cancer cells [135], while epoxy chalcone (23b) having various substituents able to cure hepatocellular carcinoma (HCC) [136,137]. Epoxy chalcone derivatives (24), which conveniently synthesized from the reaction of epoxy chalcone with phenyl hydrazine or hydrazine hydrate and oxirane, exhibited good inhibition against cancer disease [138].…”

Section: Anti-cancermentioning

confidence: 99%

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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Epoxy chalcone is a heterocyclic molecule and an important precursor for the synthesis of biologically active compounds. This mini-review is elucidating the synthetic strategies of chalcone epoxide via one pot and two pot routes including nature of reactants, nature of catalyst and variety of catalyst to improve yield of desired product, biological applications and advantages and drawbacks of these synthetic strategies. One pot route has wide variety of reactants and efficient one is the condensation of aldehyde and ketone. However, two pot route is consisted of chalcone synthesis preceding to epoxy chalcone. The synthetic routes for the preparation of epoxy chalcone and the usage as a precursor for the synthesis of various organic molecules with biological application is comprehensively discussed. This review is outstanding in organic chemistry and pharmaceutical industries to produce new molecules with various applications. Graphic AbstractO O

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“…The 6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (14) was chosen as the starting material. This acid was converted to the aldehyde 15 by treatment BH3•Me2S followed by Dess-Martin oxidation of the intermediate alcohol (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…Among skeletons abundantly present in compounds inhibiting tubulin polymerization of natural or synthetic origen, chalcones and chalconoides occupy an important position [14]. In 2009, a series of chalcones (compounds 6-8) ( Figure 1) were described as CA4 surrogates, among which the αmethyl chalcone 7 showed antiproliferative activity at the nM or subnM range [15,16].…”

Section: -Introductionmentioning

confidence: 99%

Conformational mimetics of the α-methyl chalcone TUB091 binding tubulin: Design, synthesis and antiproliferative activity

Bueno

Tobajas

Quesada

et al. 2018

European Journal of Medicinal Chemistry

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Based on the conformation of the α-methyl chalcone TUB091 in its complex with tubulin, a series of conformational mimetics have been designed and synthesized where the methyl group of the chalcone has been fused to phenyl ring B resulting in 1,2,3,4-tetrahydronaphthalen-2-yl aryl ketones. Among the synthesized compounds, the 5-amino-6-methoxy derivative, with a similar substitution pattern to that of TUB091, showed antiproliferative activity around 20 nM against tumor and endothelial cells. Tubulin binding experiments confirmed its binding to tubulin at the colchicine site with a Kb of 2.4 × 10 M resulting in the inhibition of the in vitro assembly of purified tubulin. Moreover, based on the recently reported complex of combretastatin A4 (CA4) with tubulin, a comparative analysis of the binding mode of CA4 and the α-methyl chalcone to tubulin has been performed.

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Recent advances of cytotoxic chalconoids targeting tubulin polymerization: Synthesis and biological activity

Cited by 84 publications

References 118 publications

Synthesis, Anticancer Activity and Molecular Modeling Studies of Novel Chalcone Derivatives Containing Indole and Naphthalene Moieties as Tubulin Polymerization Inhibitors

Synthesis, Anticancer Activity and Molecular Modeling Studies of Novel Chalcone Derivatives Containing Indole and Naphthalene Moieties as Tubulin Polymerization Inhibitors

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Conformational mimetics of the α-methyl chalcone TUB091 binding tubulin: Design, synthesis and antiproliferative activity

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