Enzo Perrotta

Design, synthesis and biological activity of carbohydrate-containing peptidomimetics as new ligands for the human tachykinin NK-2 receptor.

Enantiopure cycloadducts between glycals and alkyl or aryl heterodienes were selected as small, rigid, nonpeptide molecules able to superimpose to the structure of the cyclopeptide tachykinin NK-2 antagonist 1. The presence of three aromatic groups in the pyranose ring resulted essential for NK-2 affinity, while an increase in activity was shown by the corresponding sulfoxides.

SOLID-PHASE AMINO-ZINC-ENOLATE CYCLIZATION FOR THE SYNTHESIS OF 3-SUBSTITUTED PROLINES

Abstract Preparation of 3-substituted prolines was achieved by extension to Solid Phase Organic Synthesis (SPOS) of the amino-zinc-enolate cyclization we have recently described. 1 Functionalizations of proline at C-3 were considered by nucleophilic substitutions of an iodo derivative obtained on the resin.

Unusual reductive cleavage of 7-oxa-bicyclo[2,2,1]heptane system for the synthesis of tetrahydrofuran derivatives

Abstract An unusual reductive cleavage of a CC bond adjacent to the ethereal bridge in the 7-oxa-bicyclo[2,2,1]heptane system led to some valuable tetrahydrofuran derivatives and, in particular, to tetrahydrofuranyl glycine derivatives.

Enantioselective syntheses of orthogonally protected tricarballylic acid esters

Abstract 3( S ) and 3( R )-Benzyloxycarbonyl-pentanedioic acid mono- tert -butyl esters ( 6 ) were obtained as enantiopure orthogonally protected tricarballylic acid (TCA) esters. These were synthesised by alkylation of the sodium enolate derived from chiral but-3-enoyloxazolidinone imides ( 3 ) with tert -butyl bromoacetate; following the hydrolysis to remove the chiral auxiliary, benzyl esterification afforded the 2-allyl succinic acid diesters ( 4 ) that were converted to protected TCA esters after oxidation of the double bond.

Synthesis of new penem dithiocarbamates

Abstract Penem dithiocarbamates, 10 were synthesized from the alcohol 6 , in high yields and favourable ratio between the penem and the undesired penam isomers. In vitro antibacterial activity showed a dependence on polarity and steric hindrance of the side chain at C-2. Best results were obtained with the piperazino derivatives 10 l–n , while catechol 10 p did not show the expected improvements in anti-pseudomonal activity.

Synthesis and antibacterial activity of men 10700, a new penem antibiotic

The new penem antibiotic Men 10700 (3), bearing an amino acid derived amide as C-2 side chain, was synthesized. Men 10700 exhibited high potency and a broad spectrum of activity against Gram positive and Gram negative microorganisms.

Synthetic approaches towards 4-(silylmethyl)-2-azetidinones

Differently substituted 4-(silylmethyl)-2-azetidinones were prepared starting form the corresponding 4-acetoxy-2-azetidinones with silylmethylmagnesium chlorides. The same kind of β-lactams were synthesized «via» cycloaddition of allylsilanes and chlorosulfonyl isocyanate (CSI)

Insertion of 2-carboxysuccinate and tricarballylic acid fragments into cyclic-pseudopeptides: new antagonists for the human tachykinin NK-2 receptor.

A series of cyclic pseudopeptides were synthesized containing the sequence -Trp-Phe-(D)-PhePsiCH2NH-, the terminal ends of which were bound to 2-carboxy succinate or enantiomerically enriched tricarballylic acid to give the final cyclic structures. These two molecules and their subsequent derivatives were screened for h-NK2 receptor binding and functional antagonist activity on the rabbit urinary bladder.

2-(Iodomethyl) penems as useful substrates in the Wittig olefination: Synthesis of 2-arylethenyl penems

Abstract Wittig olefination at room temperature on the new (2-iodomethyl) penems 4 gave a series of (2-arylethenyl) penems 5 with different E/Z selectivity depending on the position and electronic effect of the substituent on the aryl aldehyde.