Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity

Gerova, Mariana; Stateva, S; Radonova, Elena M.; Kalenderska, Rositsa B.; Rusew, Rusi; Nikolova, Rositsa; Chanev, Christo; Shivachev, Boris; Apostolova, Margarita D.; Petrov, Ognyan

doi:10.1016/j.ejmech.2016.05.012

Cited by 46 publications

(32 citation statements)

References 44 publications

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“…Both compounds reached the retardation maximum at 24 h of treatment (about 80%) followed by sub-G1 enrichment "directly from mitotic arrest". Some cells escaped the cell cycle arrest and underwent cell divisions increasing their DNA content to more than 4N 16 which is consistent with our results.…”

Section: Cell Cycle Distributionsupporting

confidence: 93%

Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives

Garbicz

Mielecki

Wrzesiński

et al. 2018

CCDT

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Among the newly synthesized stilbene derivatives, we selected two as potent anticancer compounds triggering late apoptosis/necrosis in cancerous cells through sub-G1 phase cell cycle arrest. They changed cyclin expression, induced DNA repair mechanisms, enzymes involved in apoptosis and oxidative stress response. Compounds JJR5 and JJR6 can be a base for structure modification(s) to obtain even more active derivatives.

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Section: Cell Cycle Distributionsupporting

confidence: 93%

Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives

Garbicz

Mielecki

Wrzesiński

et al. 2018

CCDT

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“…[38,40] In addition, CA-4 leads to rapid and selectivev ascular dysfunction in solid tumors by attacking endothelial cells within the tumor vasculature. [41] Unfortunately,i ts Z double bond tends to isomerize to the more thermodynamic stable, but less depolymerizing active E configuration. [42] To overcome this shortcoming, al argen umber of modifications for CA-4 have been made ands ome examples are reported below.…”

Section: Natural Anticancer Stilbenesmentioning

confidence: 99%

“…[42] To overcome this shortcoming, al argen umber of modifications for CA-4 have been made ands ome examples are reported below. [41] In ap aper published in 2001, Stivala et al investigated whether antiproliferative properties are dependent on configuration of the molecule: [19] surprisingly,b oth E or Z configured synthetic methylated stilbenes stop mitosis at the Mp hase, whereas only (E)-resveratrol blocks cells at the Sphase. [43] Studies on colorectal cancerc ell proliferation, conducted with as eries of polymethoxystilbenes, led to the unexpected result that the strongeste ffect depends on Z stereochemistry.…”

Section: Natural Anticancer Stilbenesmentioning

confidence: 99%

“…These compounds exhibitedt he most potent growth inhibition in the micromolar range,a gainst most of the human cancer cell lines in the panel. [104] Heteroaromatic stilbene derivatives are also hybrid molecules, [41,105] that combine the anticancer properties of the stilbene moiety with that of acounterpart with documented ability to modulate one or several pathways relevant for cancer pathogenesis. [106] Polypharmacological compounds represent an innovative strategy to obtain an ew chemical entity with multitarget activities.…”

Section: Heteroaromatic Stilbenesmentioning

confidence: 99%

“…It induced mitotic arrest in the G 2 /M phase like CA-4, as confirmed by X-ray studies. [41] The combretastatin-based hybrid 45 ( Figure 11)a nd its analoguesw ere tested in vitro for potentiala ntitumor and cytotoxic activities on HeLa tumor cell line and non-tumor Vero cell line. This derivative showed ah igh potential antitumora ctivity with an IC 50 value in the low micromolar range.…”

Section: (Z)-stilbenesmentioning

confidence: 99%

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Anticancer Activity of Stilbene‐Based Derivatives

et al. 2017

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Stilbene is an abundant structural scaffold in nature, and stilbene-based compounds have been widely reported for their biological activity. Notably, (E)-resveratrol and its natural stilbene-containing derivatives have been extensively investigated as cardioprotective, potent antioxidant, anti-inflammatory, and anticancer agents. Starting from its potent chemotherapeutic activity against a wide variety of cancers, the stilbene scaffold has been subject to synthetic manipulations with the aim of obtaining new analogues with improved anticancer activity and better bioavailability. Within the last decade, the majority of new synthetic stilbene derivatives have demonstrated significant anticancer activity against a large number of cancer cell lines, depending on the type and position of substituents on the stilbene skeleton. This review focuses on the structure-activity relationship of the key compounds containing a stilbene scaffold and describes how the structural modifications affect their anticancer activity.

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Regioselective N‐Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate‐Catalyzed Substitution of Alcohols and Alkyl Group Migrations

et al. 2022

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A catalytic synthetic strategy has been developed combining two protocols, such as, direct nucleophilic substitution of alcohols followed by X‐ to N‐ alkyl group migration (X=O, S) to access N‐functionalized benzoxazolones, benzothiazolethiones, indolinone, benzoimidazolethiones, and pyridinones derivatives. Methyl trifluoromethanesulfonate (MeOTf) was found to catalyze the reaction, which revealed the catalytic property of MeOTf. A mechanism was established through experiments as well as DFT calculations wherein the −OH group of alcohols were converted to the corresponding −OMe groups and in situ generated TfOH. The −OMe groups produced underwent TfOH catalyzed −X alkylation (X=O, S) of the heterocycles followed by −X‐ to −N‐alkyl group migrations in a single step.

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Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity

Cited by 46 publications

References 44 publications

Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives

Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives

Anticancer Activity of Stilbene‐Based Derivatives

Regioselective N‐Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate‐Catalyzed Substitution of Alcohols and Alkyl Group Migrations

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