Abstract
The reaction of cyanoacetylhydrazine (1) with 3-(2-bromoacetyl)-2H-chromen-2-one (2) in 1,4-dioxan gave the hydrazidehydrazone derivative (3). The latter compound was cyclized to the 1,3,4-oxadiazine derivative 4, its 4-bromo derivative underwent a series of cross coupling reactions together with [4+2] cycloaddition reactions with either acrylonitrile or ethyl acrylate to afford the pyran derivatives 10a and 10b, respectively. The antitumor evaluation of the newly synthesized products against three cancer cell lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were recorded. Four of the synthesized compounds namely 7c, 10a, 11a and 12b showed high inhibitory effects. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity.
Keywords: Cross coupling, Hydrazide-hydrazone, 1, 3, 4-oxadiazine, coumarin, Anti-tumor.
Current Organic Chemistry
Title:Design, Synthesis and Molecular Modeling Studies of Some Heterocyclic Compounds Derived from the Suzuki-coupling of 6-bromo-1,3,4-oxadiazine Together with their Antitumor and Anti-leishmanial Evaluations
Volume: 17 Issue: 17
Author(s): Rafat M. Mohareb, Sherif M. Sherif and Adel Abou Elkair
Affiliation:
Keywords: Cross coupling, Hydrazide-hydrazone, 1, 3, 4-oxadiazine, coumarin, Anti-tumor.
Abstract: The reaction of cyanoacetylhydrazine (1) with 3-(2-bromoacetyl)-2H-chromen-2-one (2) in 1,4-dioxan gave the hydrazidehydrazone derivative (3). The latter compound was cyclized to the 1,3,4-oxadiazine derivative 4, its 4-bromo derivative underwent a series of cross coupling reactions together with [4+2] cycloaddition reactions with either acrylonitrile or ethyl acrylate to afford the pyran derivatives 10a and 10b, respectively. The antitumor evaluation of the newly synthesized products against three cancer cell lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were recorded. Four of the synthesized compounds namely 7c, 10a, 11a and 12b showed high inhibitory effects. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity.
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Mohareb M. Rafat, Sherif M. Sherif and Elkair Abou Adel, Design, Synthesis and Molecular Modeling Studies of Some Heterocyclic Compounds Derived from the Suzuki-coupling of 6-bromo-1,3,4-oxadiazine Together with their Antitumor and Anti-leishmanial Evaluations, Current Organic Chemistry 2013; 17 (17) . https://dx.doi.org/10.2174/13852728113179990037
DOI https://dx.doi.org/10.2174/13852728113179990037 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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