105118-41-0Relevant articles and documents
One-pot synthesis of 2,4-disubstituted thiazoline from β-azido disulfide and carboxylic acid
Liu, Yi,Liu, Jun,Qi, Xiangbing,Du, Yuguo
, p. 7108 - 7113 (2012)
A concise and efficient one-pot four-step synthesis of 2,4-disubstituted thiazoline via a cascade disulfide bond cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction is established. Treatment of various carboxylic acids with β-azido disulfides under this one-pot procedure obtained the desired thiazolines in good to excellent isolated yields.
Stereoselective synthesis of optically active bicyclic β-lactam carboxylic acids that target pilus biogenesis in pathogenic bacteria
Emtenaes, Hans,Carlsson, Marcus,Pinkner, Jerome S.,Hultgren, Scott J.,Almqvist, Fredrik
, p. 1308 - 1314 (2007/10/03)
Optically active bicyclic β-lactams were synthesized, starting from 2-H-Δ2-thiazolines and Meldrum's acid derivatives. Several methods to accomplish an ester hydrolysis without damaging the β-lactam framework were investigated. A rapid CsOH saponification of the β-lactam methyl esters was developed and protonation of the Cs-carboxylates by Amberlite (IR-120 H+) afforded a series of bicycle β-lactam carboxylic acids. Moreover, a convenient method for the synthesis of 2-H-Δ2-thiazolinecarboxylic acid methyl ester 2 was developed. Bicyclic β-lactam carboxylic acids 7a-g and aldehydes 4a-d were screened for their affinity to the bacterial periplasmic chaperone PapD using a surface plasmon resonance technique. β-Lactams substituted with large acyl substituents showed better binding to the chaperone than the native C-terminal peptide PapG8, demonstrating that bicyclic β-lactams constitute a new class of potential bacterial chaperone inhibitors.
