Robert Wilson Lambert

Synthesis of 3(s)-acylamino-1-[(phenyl)(1h-tetrazol-5-yl)amino]-2-azetidinones

Abstract 1-Phenyl 1 (1-benzyl-1H-tetrazol 5-yl)hydrazine has been synthesised from N1-benzyloxycarbonyl-N2-phenylhydrazide and benzyl isothiocyanate. Coupling with N-(benzyloxycarbonyl)-L-serine 3,4-dihydro-4-oxo 1,2,3-benzotriazin 3-yl ester and cyclisation of the product, using triphenyl phosphine and dimethyl azodicarboxylate, gave a fully protected β-lactam Hydrogenolytic deprotection and acylation gave the title compounds, which are related to Nocardicin A. Fast atom bombardment mass spectra showed (M + H)+ peaks for all the β-ldctams studied.

New Potent and Selective Inhibitors of Herpes Simplex Virus Tbyhidine Kinase

Abstract Analogues of 5-ethyl-2′-deoxyuridine with modifications in the 5′-position have been prepared as potent inhibitors of herpes simplex virus thymidine kinase (HSV TK). The most potent compound in the series is extremely selective for the viral enzyme, antagonises the antiviral activity of acyclovir in vitro and shows a protective effect in virus-infected mice.

Synthesis of 2(r)-[3(s)-acylamino-2-oxo-1 azetidinyloxy]-acetic acids

Abstract The title compounds when constructed from a-aminoxyacetic esters coupled with N-benzyloxycarbonyl-L-serine in the presence of N-ethoxycarbonyl-2-ethoxy L-2-(benzyloxyformamido)-3-hydroxypropionamidooxy acetates. Alternative coupling with N-benzyloxycarbonyl-L-serine 3,4-dihydro-4-oxo-l,2,3-benzotriazin triphenyl phosphine and dimethyl azodicarboxylate gave the fully protected monocyclic β-lactams. In the phenylacetic acid series hydrogenolytic deprotection led to decomposition. However, in the phenylpropionic series the hydrogenolysis product was sufficiently stable to allow acylation by the thiol ester route to the title compound.