Synthesis and Anticancer Activity of Some New Thiopyrano[2,3-&lt;i&gt;d&lt;/i&gt;]thiazoles Incorporating Pyrazole Moiety

Metwally, Nadia H.; Badawy, Mohamed A.; Okpy, Doha Samir

doi:10.1248/cpb.c14-00885

Cited by 43 publications

(20 citation statements)

References 36 publications

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“…Also, 3,5‐bis‐(2‐fluorobenzylidene)‐4‐piperidone (EF24) is the lead compound displaying potent anti‐inflammatory and anticancer activity both in vitro as well as in vivo . In view of these reports, and in continuation to our work in the synthesis of novel anticancer agents , we design the synthesis of bis‐heterocyclic compounds incorporating biologically active chromene, and pyridazine in one molecule starting from a new key intermediate N , N ′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) 1 to explore the promising anticancer compounds. Also, we investigated the newly synthesized compounds against the hepatocellular carcinoma (HEPG2), human breast cancer (MCF‐7), and human cervical carcinoma (HeLa).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Biological Evaluation of Some Novel Bis‐heterocyclic Compounds Based N,N′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) as Potential Anticancer Agents

Metwally

Abdelrazek

Eldaly

2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Synthesis of unreported hitherto N,N 0 -([1,1 0 -biphenyl]-4,4 0 -diyl)bis(2-cyanoacetamide) as a precursor to synthesize bis-chromenes, bis-thiazole derivatives, and bis-pyridizines. The structures of the newly synthesized compounds were established by their elemental analyses and spectral data. Some of the newly synthesized compounds were tested for in vitro activity against hepatocellular carcinoma, human breast cancer, and human cervical carcinoma cell lines compared with the employed standard antitumor drug (doxorubicin), and the results revealed that the starting N,N 0 -([1,1 0 -biphenyl]-4,4 0 -diyl)bis(2-cyanoacetamide) is more potent activity than doxorubicin against hepatocellular carcinoma and human cervical carcinoma.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Biological Evaluation of Some Novel Bis‐heterocyclic Compounds Based N,N′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) as Potential Anticancer Agents

Metwally

Abdelrazek

Eldaly

2018

Journal of Heterocyclic Chem

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“…showed potent cytotoxicity towards MCF7 (IC 50 : 12.3 μg/ml) and against HEPG2 (IC 50 : 21.4 μg/ml) cell lines. 156 Ferrocenyl-nucleobases are a new class of nucleoside-related molecules that have been recently a subject of interest. 157 The presence of cytotoxic ferrocenyl groups in close vicinity to the nucleobase moiety has shown to impart antibacterial or anticancer activity.…”

Section: Thiophenementioning

confidence: 99%

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

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This review article proposes a comprehensive report of the design strategies engaged in the development of various sulfur-bearing cytotoxic agents. The outcomes of various studies depict that the sulfur heterocyclic framework is a fundamental structure in diverse synthetic analogs representing a myriad scope of therapeutic activities. A number of five-, six-and seven-membered sulfur-containing heterocyclic scaffolds, such as thiazoles, thiadiazoles, thiazolidinediones, thiophenes, thiopyrans, benzothiazoles, benzothiophenes, thienopyrimidines, simple and modified phenothiazines, and thiazepines have been discussed. The subsequent studies of the derivatives unveiled their cytotoxic effects through multiple mechanisms (viz. inhibition of tyrosine kinases, topoisomerase I and II, tubulin, COX, DNA synthesis, and PI3K/Akt and Raf/MEK/ERK signaling pathways), and several others. Thus, our concise illustration explains the design strategy and anticancer potential of these five-and six-membered sulfur-containing heterocyclic molecules along with a brief outline on seven-membered sulfur heterocycles. The thorough assessment of antiproliferative activities with the reference drug allows a proficient assessment of the structure-activity relationships (SARs) of the diversely synthesized molecules of the series.

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“…In the view of these observations and as a part of our ongoing research program aimed to the synthesis of biologically active heterocycles, [ 24–35 ] we report herein the synthesis of some new heterocyclic compounds depending on 2‐cyano‐ N ′‐(4‐(2‐oxo‐2‐phenylethoxy)‐benzylidene)acetohydrazide 2 as a starting compound that underwent reactions with usual chemical reagents delivering various species of heterocyclic compounds besides that antimicrobial activity assessment has been performed for some selected compounds as a biological application.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, reactions, and antimicrobial activity of 2‐cyano‐N′‐(4‐(2‐oxo‐2‐phenylethoxy)benzylidene)acetohydrazide derivatives

Metwally

Abdelrazek

Eldaly

2020

Journal of Heterocyclic Chem

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Knӧvenagel condensation of the starting 2-cyano-N 0-(4-(2-oxo-2-phenylethoxy)benzylidene)acetohydrazide with different aromatic aldehydes produced the comparable arylidenes derivatives. Else way, 2-cyano-N 0-(4-(2-oxo-2-phenylethoxy)benzylidene)-acetohydrazide condensed with o-hydroxybenzaldehydes affording the respective chromenes which latter underwent acid hydrolysis giving the oxo-chromenes analogues. Moreover, the reaction of 2-cyano-N 0-(4-(2-oxo-2phenylethoxy)benzylidene)acetohydrazide with istain yielded the respective indeno [2,1-b]furan derivative that was converted to its oxo-analogue through acid hydrolysis. The treatment of 2-cyano-N 0-(4-(2-oxo-2-phenylethoxy)benzylidene) acetohydrazide with α-halocompounds produced the relevant thiazoles. The enamine 2-cyano-3-(dimethylamino)-N 0-(4-(2-oxo-2-phenylethoxy)benzylidene) acrylohydrazide underwent nucleophilic substitution reaction with guanidine hydrochloride followed by heterocyclization to get the relative aminopyrimidine. Contrarily, the reaction with various 4-arylazo-3,5-diaminopyrazoles provided the relative pyrazolo[1,5-a]pyrimidines. The antimicrobial investigation was carried out for some of the newly synthesized compounds using agar well diffusion method.

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Synthesis and Anticancer Activity of Some New Thiopyrano[2,3-<i>d</i>]thiazoles Incorporating Pyrazole Moiety

Cited by 43 publications

References 36 publications

Synthesis, Molecular Docking, and Biological Evaluation of Some Novel Bis‐heterocyclic Compounds Based N,N′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) as Potential Anticancer Agents

Synthesis, Molecular Docking, and Biological Evaluation of Some Novel Bis‐heterocyclic Compounds Based N,N′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) as Potential Anticancer Agents

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Synthesis, reactions, and antimicrobial activity of 2‐cyano‐N′‐(4‐(2‐oxo‐2‐phenylethoxy)benzylidene)acetohydrazide derivatives

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