Synthesis and cellular characterization of novel isoxazolo- and thiazolohydrazinylidene-chroman-2,4-diones on cancer and non-cancer cell growth and death

Jashari, Ahmed; Imeri, Faik; Ballazhi, Lulzime; Shabani, Agim; Mikhova, B.M.; Dräger, Gerald; Popovski, Emil; Huwiler, Andrea

doi:10.1016/j.bmc.2014.03.026

Cited by 25 publications

(26 citation statements)

References 34 publications

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“…This procedure has already been described in detail in a previous study (18). Briefl y, cooled solutions (-10 °C) of the heterocyclic amines (10 mmol) in a mixture of water (10 mL) and HCl (6 mol L -1 , 40 mL) were slowly added to the aqueous solution of NaNO 2 (0.14 g mL -1 ) and stirred vigorously.…”

Section: Synthetic Procedures and Characterization Of Synthesized Compmentioning

confidence: 99%

“…Their structures were evaluated using spectroscopic techniques, including FTIR (Perkin-Elmer System 2000 FTIR, USA), 1 H NMR, 13 C NMR and 2D NMR (Bruker-250 DRX Spectrometer, USA, using standard Bruker Topspin so ware) and MS (MS -Q-TOF premierspectrometer (ESI mode), Waters (USA). X-ray crystallography was done on Agilent SuperNova Dual, Cu at zero, Atlas diff ractometer (Agilent Technologies, USA) (18,30).…”

Section: Synthetic Procedures and Characterization Of Synthesized Compmentioning

confidence: 99%

“…Eight 3-substituted coumarin derivatives that combine the coumarin core and fi ve membered heterocycles in hydrazinyldiene-chroman-2,4-diones (Table I, 1a-h) were previously synthesized by Jashari et al (18). FTIR and NMR studies confi rmed the presence of C=O at position 2 in the coumarin ring and substitution of the hydrogen at position 3 with isoaxozoles and thiazoles via a hydralazinylidene linker.…”

Section: Structure and Characteristics Of The Isoxazolo-and Thiazolo mentioning

confidence: 99%

“…In order to fi nd new coumarin structure based drugs with anticancer activity, with special focus on (metastatic) breast cancer, we have synthesized compounds that combine the coumarin core and fi ve membered heterocycles (isoxazoles and thiazoles) in hydrazinylidiene-chroman-2,4-diones (18). Based on the »hard and so (Lewis) acids and bases« (HSAB) concept that electrophiles a ack the coumarine ring (19), the eight heterocyclic amines, isoxazoles and thiazoles, were derivatized to obtain diazonium ions which would be further used as electrophiles to a ack the coumarine ring at position 3.…”

mentioning

confidence: 99%

“…Similar results were obtained when antiproliferative eff ects on prostate cancer (LnCaP) and monocytic leukemia (U937) cell lines were evaluated. Reduced cell viability accompanied by increased apoptosis was shown by PARP cleavage and reduced activity of survival kinase Akt (18).…”

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confidence: 99%

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Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

et al. 2015

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Potential antiproliferative effect of isoxazolo-and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastasesThe study highlights the current progress in the development of coumarin scaffolds for drug discovery as novel anticancer agents in metastatic breast cancer. Eight compounds, combining the coumarin core and five membered heterocycles (isoxazoles and thiazoles) in hydrazinyldiene--chroman-2,4-diones, were characterized in terms of a potential antiproliferative effect on bone (SCP1833) and lung (SCP4175) metastatic breast cancer cell lines using the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide assay. Cell viability was evaluated after 48 and 72 h of treatment and the 50 % inhibitory concentrations were determined. The results demonstrated dose-and time-dependent activity, with the most potent molecules having a thiazole moiety, without or with additional methyl group(s) attached to the carbon(s) at position(s) 5 and/or 4 in the thiazole ring. These molecules possessed significantly higher potency against both test cell lines compared to 4-hydroxycoumarin.

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Section: Synthetic Procedures and Characterization Of Synthesized Compmentioning

confidence: 99%

Section: Synthetic Procedures and Characterization Of Synthesized Compmentioning

confidence: 99%

Section: Structure and Characteristics Of The Isoxazolo-and Thiazolo mentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

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Advances of antitumor drug discovery in traditional Chinese medicine and natural active products by using multi‐active components combination

Wang

Zheng

Tang³

et al. 2023

Medicinal Research Reviews

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The antitumor efficacy of Chinese herbal medicines has been widely recognized. Leading compounds such as sterols, glycosides, flavonoids, alkaloids, terpenoids, phenylpropanoids, and polyketides constitute their complex active components. The antitumor monomers derived from Chinese medicine possess an attractive anticancer activity. However, their use was limited by low bioavailability, significant toxicity, and side effects, hindering their clinical applications. Recently, new chemical entities have been designed and synthesized by combining natural drugs with other small drug molecules or active moieties to improve the antitumor activity and selectivity, and reduce side effects. Such a novel conjugated drug that can interact with several vital biological targets in cells may have a more significant or synergistic anticancer activity than a single‐molecule drug. In addition, antitumor conjugates could be obtained by combining pharmacophores containing two or more known drugs or leading compounds. Based on these studies, the new drug research and development could be greatly shortened. This study reviews the research progress of conjugates with antitumor activity based on Chinese herbal medicine. It is expected to serve as a valuable reference to antitumor drug research and clinical application of traditional Chinese medicine.

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Antiproliferative and antioxidative effects of novel hydrazone derivatives bearing coumarin and chromene moiety

et al. 2016

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Synthesis and cellular characterization of novel isoxazolo- and thiazolohydrazinylidene-chroman-2,4-diones on cancer and non-cancer cell growth and death

Cited by 25 publications

References 34 publications

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

Advances of antitumor drug discovery in traditional Chinese medicine and natural active products by using multi‐active components combination

Antiproliferative and antioxidative effects of novel hydrazone derivatives bearing coumarin and chromene moiety

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