Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity

Subtel’na, Ivanna; Atamanyuk, Dmytro; Szymańska, Ewa; Kieć‐Kononowicz, Katarzyna; Zimenkovsky, Borys; Vasylenko, Olexandr; Gzella, Andrzej

doi:10.1016/j.bmc.2010.05.073

Cited by 93 publications

(78 citation statements)

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“…The appearance of the ylidene proton of compounds 4a-c, 4f-h at δ= 7.78-7.86 confirmed the formation of Z-isomers. 9,15,[23][24][25][26][27][28] On the other hand, the ylidene proton of compounds 4d and 4i were revealed at δ= 8.00-8.16, slightly downfield shifted than the other synthesized analogues, which could be attributed to the anisotropic effect of the hydroxyl group oriented at the o-position of the arylidene function. Furthermore, reaction of 4-thiazolidinones 3a, b with formaldehyde and the appropriate heteroalicyclic amines (pyrrolidine, piperidine, morpholine and N-methylpiperazine) through Mannich reaction yielded 5a-h.…”

Section: Resultsmentioning

confidence: 90%

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Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Hanna

George

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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2-(5-Arylidene-4-oxo-3-phenyl-thiazolidin-2-ylidene)-3-oxo-propionitriles 4a-j were prepared via condensation of aromatic aldehydes with 4-thiazolidinones 3a, b. The latter was obtained via electrophilic attack of phenylisothiocyanate on 3-oxo-propionitriles 1a, b followed by reaction with chloroacetyl chloride under basic condition. Additionally, 2-(5-heteroalicyclic methylene) analogues 5a-h were prepared via Mannich reaction of the appropriate secondary amines and formaldehyde with 4-thiazolidinones 3a, b. Many of the synthesized compounds exhibited promising antitumor properties against colon HCT116 and breast T47D cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explain the observed antitumor properties.Key words thiazolidinone; quantitative structure-activity relationship; antitumor activity; 3-oxo-propionitrile; HCT116; T47D Cancer ranks second in diseases leading to mortality, following only cardiovascular diseases. One-quarter of all deaths in the United States are caused by cancer.1) Out of the many cancer diseases, breast cancer is the most prevalent cancer in women and represents the second highest leading cause of cancer death in this population after lung cancer.2) Colorectal cancer is the third most common cancer in both men and women, 91% of cases are diagnosed in individuals 50 years of age and older. 1) Chemotherapy is widely used to treat and control cell growth and limit the spread of cancer cells to other sites. Although, there is a success with certain forms of cancer, drug therapy has only limited impact against the three major killers: carcinoma of lung, breast and colorectal system. Therefore, there is a need to develop novel antitumor agents to treat and combat this disease.Several promising antitumor agents containing thiazolidine and thiazolidinone scaffolds have been identified to have a broad range of anticancer activities.3-14) Previously, we reported promising antitumor properties of a variety of 5-arylidene thiazolidinone derivatives Ia-c (Fig. 1) exhibiting considerable cytotoxic activity against colon HCT116 cancer cell lines compared with Doxorubicin (reference standard, IC 50 =0.00686 mM).15) In continuation of these previous findings and in order to optimize novel antitumor active agents possessing the same thiazolidinone core, it is intended in the present work to perform some modifications in the adopted structures via inserting heteroalicyclic amines (morpholinyl or piperidinyl functions, 4a-j) instead of the aromatic amines Ia-c due to their hydrophilic properties. Moreover, a series of heteroalicyclic methylene containing compounds 5a-h will be also prepared replacing the arylidene moiety of Ia-c (Fig. 1). Additionally, many morpholine and piperidine containing compounds were known as anticancer active agents that exerted their actions via inhibition of different targets such as phosphatidylinositol 3-kinases (PI3Ks) and histone deacetylase (HDAC). [16][17][18][19][20] Moreover, the piperidine deriva...

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Section: Resultsmentioning

confidence: 90%

“…[3][4][5][6][7][8][9][10][11][12][13][14] Previously, we reported promising antitumor properties of a variety of 5-arylidene thiazolidinone derivatives Ia-c ( Fig. 1) exhibiting considerable cytotoxic activity against colon HCT116 cancer cell lines compared with Doxorubicin (reference standard, IC 50 =0.00686 mM).…”

mentioning

confidence: 99%

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Hanna

George

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The compound described in this paper was synthesized by the reaction protocols typically used for obtaining 2-arylamino-1,3-thiazolidin-4-one derivatives [23]. The starting 2-carbethoxymethylthio-2-thiazolidin-4-one was obtained by the reaction of 2-thioxothiazolidin-4-one triethylammonium salt with ethyl chloroacetate in acetone.…”

Section: Methodsmentioning

confidence: 99%

Conformational space and vibrational spectra of 2-[(2,4-dimethoxyphenyl)amino]-1,3-thiazolidin-4-one

et al. 2014

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In this work we present the results of a study of the X-ray structure of 2-[(2,4-dimethoxyphenyl)amino]-1,3-thiazolidin-4-one. Using the FTIR spectra in solid state and results of ab initio calculations we explain the issue of the tautomerism of this molecule. The compound is shown to exist as the 2-amino tautomer rather 2-imino tautomer. Here we consider eight possible tautomers. On the basis of the vibrational spectra we can eliminate five possible tautomers, as not existing in the solid state. As the most possible tautomeric form we have found keto 2-amino form.Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-014-2366-6) contains supplementary material, which is available to authorized users.

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“…In addition, enzalutamide which is a derivative of 2-thioxoimidazolidinone has been approved for the treatment of castration resistant prostate cancer (Jung et al, 2010;Bassetto et al, 2016). Moreover, an interesting study suggested with experimental results that although the sulfur atom in 2-thioxoimidazolidinones was removed and replaced by arylamino group forming their analogues, 4-imidazolones, 2-arylamino-4-imidazolones exhibited a potent cytotoxic activity against different cell lines as prostate and breast cancer cell lines (Subtel'na et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular docking and cytotoxicity evaluation of some novel 5-arylidene-3-(substituted phenyl)-2-(p-tolylamino)-4-imidazolones

2017

J App Pharm Sci

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Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity

Cited by 93 publications

References 48 publications

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

Conformational space and vibrational spectra of 2-[(2,4-dimethoxyphenyl)amino]-1,3-thiazolidin-4-one

Design, synthesis, molecular docking and cytotoxicity evaluation of some novel 5-arylidene-3-(substituted phenyl)-2-(p-tolylamino)-4-imidazolones

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