|
NISCAIR ONLINE PERIODICALS REPOSITORY (NOPR) >
NISCAIR PUBLICATIONS >
Research Journals >
Indian Journal of Chemistry -Section A (IJC-A) >
IJC-A Vol.50A [2011] >
IJC-A Vol.50A(09-10) [September-October 2011] >
| Title: | Synthesis of intramolecularly coordinated cyclic selenenate/thioselenenate esters and their glutathione peroxidase-like activity |
| Authors: | Singh, Vijay P
Singh, Harkesh B
Butcher, Ray J |
| Keywords: | Coordination chemistry
Cyclic compounds
Selenenate esters
Thioselenenate esters
Thionation
GPx-like activity
Intramolecular interactions
Secondary interactions |
| Issue Date: | Sep-2011 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | The syntheses and characterization of selenenate
esters, thioselenenate ester and related derivatives are described. The
reactions of n-butyl-4-tert-2,6-di(formyl)phenyl selenide (23) or bis(2,6-diformyl-4-tert-butylphenyl)diselenide (24) with bromine affords a new
selenenate ester, 5-tert-butyl-7-(formyl)benzoxaselenol-3-one
(25), stabilized by ortho-formyl group along with 3,3′-oxybis(5-tert-butyl-3H-benzo[c][1,2]oxoselenole-7-carbaldehyde)
(16). Oxidation of (25) with H2O2
gives
5-tert-butyl-7-(carboxylic)benzoxaselenol-3-one-Se-oxide
(26). However, the direct oxidation
of (23) with H2O2
affords
5-tert-butyl-7-(butylcarboxylate)benzoxaselenol-3-one (27). The synthesis of 5-tert-butyl-7-(methylcarboxylate) benzothia-
selenol-3-one (28) has been accomplished by the
reaction of (26) with thionyl
chloride (SOCl2) with a catalytic amount of
N, N-dimethylformamide. Attempted thionation of 7-nitro-1,2-benzisoselenole(3H)-Se-oxide (20) leads to the isolation of
bis(2-chloromethyl-6-nitrophenyl)diselenide (29). The presence of intramolecular secondary Se···O interactions
in all the esters is confirmed by single crystal X-ray diffraction studies and
computational studies. Glutathione peroxidase-like activity of
(16), (25)-(29) has been
determined by the coupled reductase assay. |
| Page(s): | 1263-1272 |
| CC License: |  CC Attribution-Noncommercial-No Derivative Works 2.5 India |
| ISSN: | 0975-0975(Online); 0376-4710(Print) |
| Source: | IJC-A Vol.50A(09-10) [September-October 2011]
|
|
