Journals / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 5

Synthesis and in vitro cytotoxic activity of novel pyrazolo[1,5-$a$]pyrimidines and related Schiff bases

Pages
1102–1113
Publication Date
2015-05-01
DOI
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c} and Schiff bases \textbf{11b}--\textbf{f} were investigated for their cytotoxicity against four human cancer cell lines (colon HCT116, lung A549, breast MCF-7, and liver HepG2) according to SRB assay and the structure--activity relationship was discussed.

📌 3 Key Takeaways

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Objective & Hypothesis:The reaction of 5-amino-3-(4-methoxyphenylamino)-$N$-aryl-1$H$-pyrazole-4-carboxamides \textbf{1a}--\textbf{c} with ethyl acetoacetate \textbf{2} and 2-(4-fluorobenzylidene)malononitrile \textbf{6} yielded pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c}, respectively.
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Key Findings & Data:On the other hand, Schiff bases \textbf{11a}--\textbf{f} were obtained upon treatment of carboxamides \textbf{1a}--\textbf{c} with some selected aldehydes \textbf{10a }and\textbf{ b}.
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Conclusion & Impact:Pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c} and Schiff bases \textbf{11b}--\textbf{f} were investigated for their cytotoxicity against four human cancer cell lines (colon HCT116, lung A549, breast MCF-7, and liver HepG2) according to SRB assay and the structure--activity relationship was discussed.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:5-Aminopyrazole · pyrazolopyrimidines · ferrocenyl-2-carboxaldehyde

Abstract

The reaction of 5-amino-3-(4-methoxyphenylamino)-$N$-aryl-1$H$-pyrazole-4-carboxamides \textbf{1a}--\textbf{c} with ethyl acetoacetate \textbf{2} and 2-(4-fluorobenzylidene)malononitrile \textbf{6} yielded pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c}, respectively. On the other hand, Schiff bases \textbf{11a}--\textbf{f} were obtained upon treatment of carboxamides \textbf{1a}--\textbf{c} with some selected aldehydes \textbf{10a }and\textbf{ b}. The newly synthesized compounds were characterized and confirmed by analytical and spectroscopic data (IR, MS, $^{1}$H NMR, and $^{13}$C NMR). Pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c} and Schiff bases \textbf{11b}--\textbf{f} were investigated for their cytotoxicity against four human cancer cell lines (colon HCT116, lung A549, breast MCF-7, and liver HepG2) according to SRB assay and the structure--activity relationship was discussed.

Özet

The reaction of 5-amino-3-(4-methoxyphenylamino)-$N$-aryl-1$H$-pyrazole-4-carboxamides \textbf{1a}--\textbf{c} with ethyl acetoacetate \textbf{2} and 2-(4-fluorobenzylidene)malononitrile \textbf{6} yielded pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c}, respectively. On the other hand, Schiff bases \textbf{11a}--\textbf{f} were obtained upon treatment of carboxamides \textbf{1a}--\textbf{c} with some selected aldehydes \textbf{10a }and\textbf{ b}. The newly synthesized compounds were characterized and confirmed by analytical and spectroscopic data (IR, MS, $^{1}$H NMR, and $^{13}$C NMR). Pyrazolo[1,5-$a$]pyrimidines \textbf{5a}--\textbf{c} and \textbf{9a}--\textbf{c} and Schiff bases \textbf{11b}--\textbf{f} were investigated for their cytotoxicity against four human cancer cell lines (colon HCT116, lung A549, breast MCF-7, and liver HepG2) according to SRB assay and the structure--activity relationship was discussed.

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Cite This Article

HASSAN, A. S., HAFEZ, T. S., OSMAN, S. A. M., ALI, M. M. (2015). Synthesis and in vitro cytotoxic activity of novel pyrazolo[1,5-$a$]pyrimidines and related Schiff bases. Turkish Journal of Chemistry, Cilt: 39 - Sayı: 5, 1102–1113. https://ajindex.com/articles/184584

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