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.

MSAR Home
→
MSA University Academic Research
→
Research Papers, Articles and Books Chapters.
→
Faculty Of Pharmacy Research Paper
→
View Item

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.

Full Text link: https://t.ly/ZEKZB

Date issued: 2011

Scientific Journal Rankings: Click Here

Doi: https://doi.org/10.1016/j.bmc.2011.02.051 PubMed ID 21435889

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.