Synthesis and Crystal of Methyl 6,6-dihydropenicillanate S,S-dioxide

Abstract

6,6-dihydropenicillanate S,S-dioxide 5 was prepared and determined by X-ray crystallography. Single-crystal X-ray diffraction analysis reveals that the molecular structure of compound 5b is enantiomerically pure. The crystal belongs to orthorhombic, space group P2 1 2 1 2 1 , with unit cell parameters a = 6.5366 Å, b = 10.7649(9) Å, c = 15.5879(13) Å, V = 1096.86(16) Å 3 , D x = 1.491 g cm −3 , Z = 4, T = 296(2)K, F(000) = 520, R 1 = 0.0401, and wR 2 = 0.1200. Absolute structure parameter is 0.02(10).

Penicillin Derivatives Inhibit the SARS-CoV-2 Main Protease by Reaction with Its Nucleophilic Cysteine

“…Considering the importance of the penicillin V sulfone benzyl ester C6 side chain on inhibitor potency, the corresponding C6 mono- and dibromo-substituted penicillin sulfones 26 – 32 were prepared because such substitutions alter the reaction outcome of β-lactams with nucleophilic serine β-lactamases. − The C6 mono- and dibrominated penicillins were synthesized from 6-APA ( 22 ) as reported − and investigated for M pro inhibition using the SPE-MS assay (Table ).…”