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
Mohareb R.M.; Schatz J.
Date issued:
2011
Series Info:
Bioorganic and Medicinal Chemistry
19
Type:
Article
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
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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