Influence of ethylene-oxy spacer group on the activity of linezolid: synthesis of potent antibacterials possessing a thiocarbonyl group.
The influence of an ethylene-oxy spacer element between the heterocycle and the aromatic ring in linezolid is reported. The introduction of such spacer group generated compounds with inferior antibacterial activity. However, the conversion of the acetamide group present in the linezolid analogues to either thiocarbamate or thioacetamide functionality restored the activity. The synthesis of linezolid analogues possessing the ethylene-oxy spacer group along with SAR studies with different heterocycles and preparation of some thiocarbonyl compounds possessing potent antibacterial property are presented.
Selvakumar
N
N
Anti-infectives Discovery Group, Discovery Research, Dr. Reddy's Laboratories Ltd., Miyapur, Hyderabad, 500 049, India. selvakumarn@drreddys.com
Raheem
Mohammed A
MA
Khera
Manoj Kumar
MK
Rajale
Trideep V
TV
Kumar
Magadi Sitaram
MS
Kandepu
Sreenivas
S
Das
Jagattaran
J
Rajagopalan
R
R
Iqbal
Javed
J
Trehan
Sanjay
S
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D005030:Ethylenes / Q000737:chemistry*; D000069349:Linezolid; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013853:Thioacetamide / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000081:Acetamides; D000890:Anti-Infective Agents; D005030:Ethylenes; D023303:Oxazolidinones; D013853:Thioacetamide; C036216:ethylene; D000069349:Linezolid