Peter F. Misco

4-Thiazolidinones: Novel Inhibitors of the Bacterial Enzyme MurB

4-Thiazolidinones were synthesized and evaluated for their ability to inhibit the bacterial enzyme MurB. Selected 4-thiazolidinones displayed activity against the enzyme in vitro. This activity, coupled with the design principles of the thiazolidinones, supports the postulate that 4-thiazolidinones may be recognized as diphosphate mimics by a biological selector.

Facile, highly stereoselective synthesis of 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3t'-dideoxy nucleosides via a furanoid glycal intermediate

Abstract Regiospecific and highly Stereoselective electrophilic addition reactions to the furanoid glycal 10 have been used as key steps in the synthesis of ddA and d4T antiviral nucleosides.

New oxidatively removable carboxy protecting groups

Abstract 2,6-Dimethoxybenzyl esters are readily oxidized by 2,3-dichloro-5,6-dicyano benzoquinone (DDQ) to generate the corresponding carboxylic acids. Phenyl esters substituted with hydroxy, methoxy and dimethylamino groups are also efficiently oxidized by ceric ammonium nitrate (CAN) under pH control conditions.

Phosphonate Isosteres of 2′,3′-Didehydro-2,3-dideoxynucleoside Monophosphates: Synthesis and Anti-HIV Activity

Abstract Phosphonate analogues of d4T and d4A monophosphates have been synthesized using stereocontrolled addition of dimethyl hydroxymethylphosphonate to furanoid glycals. The new phosphonates exhibited a potent activity against HIV.

Synthesis of a Phosphonate Isostere of Acycylovir Monophosphate: A Herpesvirus Active Phosphonate Nucleotide Analogue

A novel synthetic methodology for the acyclic acetal functionality was developed. The rationally designed phosphonate analogue (3) of acyclovir monophosphate was active against herpesvirus

Synthesis of a phosphonate isostere of ganciclovir monophosphate: A highly cytomegalovirus active phosphonate nucleotide analogue

Abstract A novel synthetic methodology for the hydroxymethyl substituted acyclic acetal functionality was developed, The rationally designed phosphonate analogue 3 of ganciclovir monophosphate was highly active against human cytomegalovirus.

Synthesis and anti-MRSA Activity of Novel Cephalosporin Derivatives

Abstract Cephalosporin derivatives containing a unique combination of lipophilic C-7 sidechains and polar C-3 thiopyridinium groups were synthesized and found to exhibit potent anti-MRSA activity in vitro and in vivo. The optimum C-7 sidechains utilized were 2,5-dichlorophenylthioacetamido and 2,6-dichloropyrid-4-ylthioacetamido. The C-3 thiopyridinium rings were substituted at nitrogen with amino acid and pyruvic acid groups that were designed to confer aqueous solubility as required for IV formulation. This paper describes the characteristics of these novel cephalosporins and highlights synthetic methods developed to allow their practical, large-scale syntheses.

Me3Al-TMSOSO2CF3 a new reagent for conversion of carbonyl to geminal dimethyl functionality : regiospecific synthesis of alkylated a ring of arotinoids

Abstract Regiospecific synthesis of alkylated A ring of arotinoids has been achieved by using Me 3 Al-TMSOSO 2 CF 3 as a key reagent for conversion of carbonyl to a geminal dimethyl functionality.

Phosphonate Isosteres of Acyclovir and Ganciclovir Honophosphates Synthesis and Anti-Herpesvirus Activity

Abstract Isosteric phosphonate analogues of acyclovir and ganciclovir monophosphates were synthesized. The new phosponates exhibited good anti-herpes activity.

Synthesis and Biological Activities of Phosphonylalkylpurine Derivatives

Abstract Syntheses and biological activities of 2-phosphonylmethoxy-ethyl (PME) purine analogs are described.