Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole-carboxamides

Abdel‐Aziz, Hatem A.; Elzahabi, Heba S. A.; Dawood, Kamal M.

doi:10.1016/j.ejmech.2010.02.026

Cited by 84 publications

(37 citation statements)

References 46 publications

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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: 94%

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: 94%

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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“…These predictions encouraged us to synthesize hybrid compounds containing N-arylpyrazole combined with chalcone scaffold. Based on the previous findings and in continuation of our interest in the synthesis of bioactive heterocycles including pyrazoles, [15][16][17][18][19][20][21][22][23][24][25] we are dealing in this study with the synthesis of the title compounds using microwave irradiation to evaluate their anti-inflammatory activity.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted Synthesis of Novel 3,4‐Bis‐chalcone‐N‐arylpyrazoles and Their Anti‐inflammatory Activity

Abdel‐Aziz

Al‐Rashood

Eltahir

et al. 2011

J Chinese Chemical Soc

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A series of 3,4-bis-chalcone-N-arylpyrazoles 3a-h was prepared conveniently from diacetyl pyrazoles 2a,b. All reactions were carried out under conventional thermal heating and/or microwave irradiation. The structure of the latter functionally pyrazoles was confirmed under the bases of their IR, mass, 1 H NMR and 13 C NMR. The X-ray diffraction of compound 3e not only confirmed the chemical structure of 3a-h, but also showed the E configuration of their chalcone moieties. Treatment of compound 3e with phenyl hydrazine in presence of acetic acid afforded the tri-pyrazle 4. The anti-inflammatory activity of the newly synthesized compounds was investigated. Some of these compounds showed a moderate activity when compared with indomethacin as a reference drug. The combination between chalcone and pyrazole moieties revealed a variable effect in anti-inflammatory activity.

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“…As part of our research work towards synthesis of heterocycles with broad biologically activities [25][26][27][28][29][30][31], this work aims at synthesis of several new bis-thiazolidinone derivatives to evaluate their antibacterial and antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives

Dawood

Abu-Deif

2013

Eur. J. Chem.

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Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole-carboxamides

Cited by 84 publications

References 46 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

Microwave‐assisted Synthesis of Novel 3,4‐Bis‐chalcone‐N‐arylpyrazoles and Their Anti‐inflammatory Activity

Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives

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