title: Synthesis and structure-activity relationships of some 6 beta-acrylamido penicillins.
abstract: Syntheses are described for penicillins (4b approximately 4i, 5a and 5b) which possess a 6 beta-(2-heteroaryl-3-substituted)-propenamido side-chain of fixed geometry. In vitro results for these compounds against a range of Gram-positive and Gram-negative bacteria showed in most cases good stability against both penicillinase and TEM-1 beta-lactamase; analogues (4b approximately 4i) bearing a 2-(2-aminothiazol-4-yl) unit showed the best intrinsic activity, the cyclohexyl compound (4b) being the most promising. The 1-acetoxyethyl ester (6) of 4b was also prepared; in experimental animal studies the in vivo properties of this compound compared favourably with cefuroxime axetil and are reported together with selected in vivo data for the other compounds.
authors: Department of Synthetic Chemistry, SmithKline Beecham Pharmaceuticals, Tonbridge, Kent, U.K.
authors: R K
authors: RK
authors: Anderson
authors: P C
authors: PC
authors: Chapman
authors: S C
authors: SC
authors: Cosham
authors: J S
authors: JS
authors: Davies
authors: T J
authors: TJ
authors: Grinter
authors: M A
authors: MA
authors: Harris
authors: D J
authors: DJ
authors: Merrikin
authors: C A
authors: CA
authors: Mitchell
authors: R J
authors: RJ
authors: Ponsford
authors: C F
authors: CF
authors: Smith
mesh_terms: D000818:Animals; D001419:Bacteria / Q000187:drug effects; D051379:Mice; D010406:Penicillins / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D012453:Saimiri; D013329:Structure-Activity Relationship
chemical_list: D010406:Penicillins