| dc.contributor.author |
Georgiadis, MP |
en |
| dc.contributor.author |
Couladouros, EA |
en |
| dc.contributor.author |
Delitheos, AK |
en |
| dc.date.accessioned |
2014-06-06T06:42:18Z |
|
| dc.date.available |
2014-06-06T06:42:18Z |
|
| dc.date.issued |
1992 |
en |
| dc.identifier.issn |
00223549 |
en |
| dc.identifier.uri |
http://dx.doi.org/10.1002/jps.2600811117 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/548 |
|
| dc.subject.other |
2 methyl 6 [(4 nitrobenzoyl)oxy] 2 [4 (phenylthio)phenyl] 2h pyran 3(6h) one |
en |
| dc.subject.other |
2h pyran 3(6) one derivative |
en |
| dc.subject.other |
6 hydroxy 2h pyran 3(6h) one |
en |
| dc.subject.other |
6 methoxy 2 methyl 2 [4 (phenylthio)phenyl] 2h pyran 3(6h) one |
en |
| dc.subject.other |
antiinfective agent |
en |
| dc.subject.other |
unclassified drug |
en |
| dc.subject.other |
antibacterial activity |
en |
| dc.subject.other |
antimicrobial activity |
en |
| dc.subject.other |
article |
en |
| dc.subject.other |
drug synthesis |
en |
| dc.subject.other |
gram positive bacterium |
en |
| dc.subject.other |
minimum inhibitory concentration |
en |
| dc.subject.other |
priority journal |
en |
| dc.subject.other |
staphylococcus aureus |
en |
| dc.subject.other |
streptococcus |
en |
| dc.subject.other |
structure activity relation |
en |
| dc.subject.other |
Anti-Infective Agents |
en |
| dc.subject.other |
Microbial Sensitivity Tests |
en |
| dc.subject.other |
Pyrones |
en |
| dc.subject.other |
Structure-Activity Relationship |
en |
| dc.subject.other |
Support, Non-U.S. Gov't |
en |
| dc.title |
Synthesis and antimicrobial properties of 2H-pyran-3(6H)-one derivatives and related compounds |
en |
| heal.type |
journalArticle |
en |
| heal.identifier.primary |
10.1002/jps.2600811117 |
en |
| heal.publicationDate |
1992 |
en |
| heal.abstract |
The synthesis of several derivatives of 2H-pyran-3(6H)-ones and their Michael adducts is described. Phenylthio, benzenesulfonyl, p- acetylaminobenzenesulfonyl, and p-bromophenyl substituents are beneficial for activity against gram-positive bacteria. 2-[4-(Phenylthio)phenyl]-2-methyl- 6-methoxy-2H-pyran-3(6H)-one (8a) showed a minimum inhibitory concentration of 1.56 μg/mL against Staphylococcus aureus ATCC 2593, and 2-[4- (phenylthio)phenyl]-2-methyl-6-[(p-nitrobenzoyl)oxy]-2H-pyran-3(6H)-one (9) showed a minimum inhibitory concentration of 0.75 μg/mL against Streptococcus sp. C203M. In general, derivatives of 6-hydroxy-2H-pyran- 3(6H)-ones with substituents at C-2 and C-6 showed significant activity against gram-positive bacteria. More specifically, the bulkier the C-2 substituent, the greater the antibacterial activity. Michael adducts of thiols (13) showed activity, which may be due to a retro-Michael reaction. In conclusion, the α,β-enone system is essential for the activity of 6- hydroxy-2H-pyran-3(6H)-ones, and the size and nature of substituents at C-2 are associated with antimicrobial activity. |
en |
| heal.journalName |
Journal of Pharmaceutical Sciences |
en |
| dc.identifier.issue |
11 |
en |
| dc.identifier.volume |
81 |
en |
| dc.identifier.doi |
10.1002/jps.2600811117 |
en |
| dc.identifier.spage |
1126 |
en |
| dc.identifier.epage |
1131 |
en |