Anti-tumor and anti-leishmanial evaluations of 1,3,4-oxadiazine, pyran derivatives derived from cross-coupling reactions of ?-bromo-6H-1,3,4- oxadiazine derivatives
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Date
2011
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Type
Article
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Bioorganic and Medicinal Chemistry
19
19
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Abstract
Cyanoacetylhydrazine reacted with the ?-bromoacetophenones 2a,b to give hydrazide-hydrazone derivatives 3a,b. The latter products were cyclized to the 1,3,4-oxadiazine derivatives 4a,b. Bromination of the latter products gave the 6-bromo-6H-1,3,4-oxadiazine derivatives 5a,b which underwent a series of cross-coupling reactions. The antitumor evaluation of the newly synthesized products against the three cancer cells namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of them have high inhibitory effect towards three cell lines which is higher than the standard. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity. � 2011 Published by Elsevier Ltd. All rights reserved.
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Keywords
1,3,4-Oxadiazine, Anti-leishmanial, Anti-tumor, Cross-coupling, Hydrazide-hydrazone, Pyran, 1,3,4 oxadiazine derivative, 2 (4 bromoacetophenon omega yl) 3 (4 bromophenyl) 5 cyano 6 cyanomethylpyran, 2 (4 bromoacetophenon omega yl) 3 (4 nitrophenyl) 5 cyano 6 cyanomethylpyran, 2 (4 nitroacetophenon omega yl) 3 (4 bromophenyl) 5 cyano 6 cyanomethylpyran, 2 (4 nitroacetophenon omega yl) 3 (4 nitrophenyl) 5 cyano 6 cyanomethylpyran, 2 [5 (4 bromophenyl) 6 (4 bromophenylacet omega yl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile, 2 [5 (4 bromophenyl) 6 bromo 6h 1,3,4 oxadiazin 2 yl]acetonitrile, 2 [5 (4 bromophenyl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile, 2 [5 (4 nitrophenyl) 6 (4 bromophenylacet omega yl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile, 2 [5 (4 nitrophenyl) 6 (4 nitrophenylacet omega yl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile, 2 [5 (4 nitrophenyl) 6 bromo 6h 1,3,4 oxadiazin 2 yl]acetonitrile, 2 [5 (4 nitrophenyl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile, amphotericin B, cyanoacetylhydrazido n (4 bromophenyl alpha bromoaceto)hydrazone, cyanoacetylhydrazido n (4 nitrophenyl alpha bromoaceto)hydrazone, doxorubicin, hydrazide derivative, hydrazone derivative, unclassified drug, amastigote, antineoplastic activity, article, bromination, cancer cell, cell strain MCF 7, controlled study, cross coupling reaction, cyclization, cycloaddition, drug structure, growth inhibition, human, human cell, Leishmania donovani, nonhuman, Suzuki reaction, Antineoplastic Agents, Cell Line, Tumor, Cyclization, Drug Screening Assays, Antitumor, Halogenation, Heterocyclic Compounds, Humans, Hydrazones, Leishmania, Parasitic Sensitivity Tests, Pyrans, Leishmania donovani