Molecules 2012, 17(7), 8449-8463; doi:10.3390/molecules17078449
Article

Uses of Cyanoacetylhydrazine in Heterocyclic Synthesis: Novel Synthesis of Pyrazole Derivatives with Anti-tumor Activities

Received: 29 May 2012; in revised form: 22 June 2012 / Accepted: 26 June 2012 / Published: 12 July 2012
(This article belongs to the Section Medicinal Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The reaction of cyanoacetylhydrazine with chloroacetyl chloride gave N'-(2-chloroacetyl)-2-cyanoacetohydrazide. The latter underwent cyclization to afford 1-(5 amino-3-hydroxy-1H-pyrazol-1-yl)-2-chloroethanone, which underwent nucleophilic substitution to give 3-(5-amino-3-hydroxy-1H-pyrazol-1-yl)-3-oxopropanenitrile. The latter two compounds were used as key synthons to synthesize new thiophene, pyran, thiazole and some fused heterocyclic derivatives. The antitumor activity of the newly synthesized compounds was evaluated against three human tumor cells lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) and some of these compounds were found to exhibit much higher inhibitory effects towards the three tumor cell lines than the Gram positive control doxorubicin.
Keywords: pyrazole; thiophene; thiazole; antitumor
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MDPI and ACS Style

Mohareb, R.M.; El-Sayed, N.N.E.; Abdelaziz, M.A. Uses of Cyanoacetylhydrazine in Heterocyclic Synthesis: Novel Synthesis of Pyrazole Derivatives with Anti-tumor Activities. Molecules 2012, 17, 8449-8463.

AMA Style

Mohareb RM, El-Sayed NNE, Abdelaziz MA. Uses of Cyanoacetylhydrazine in Heterocyclic Synthesis: Novel Synthesis of Pyrazole Derivatives with Anti-tumor Activities. Molecules. 2012; 17(7):8449-8463.

Chicago/Turabian Style

Mohareb, Rafat M.; El-Sayed, Nahed N. E.; Abdelaziz, Mahmoud A. 2012. "Uses of Cyanoacetylhydrazine in Heterocyclic Synthesis: Novel Synthesis of Pyrazole Derivatives with Anti-tumor Activities." Molecules 17, no. 7: 8449-8463.

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