74985-80-1

Upstream product

• 868-59-7 ethyl cysteinate hydrochloride 
• 64-17-5 ethanol 
• 56-89-3 L-cystine 
• 10389-65-8 di-t-butoxycarbonyl-L-cystine 
• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 220168-55-8 benzyl N-(4-nitrobenzoyloxy)benzohydroxamate 
• 220168-41-2 benzyl N-(4-methoxybenzoyloxy)benzohydroxamate 
• 220168-45-6 N-(benzyloxy)-N-((4-chlorobenzoyl)oxy)benzamide 
• 220168-43-4 N-(benzyloxy)-N-((4-methylbenzoyl)oxy)benzamide 
• 220168-39-8 benzyl N-(benzoyloxy)benzohydroxamate 

Downstream Products

• 98303-77-6 C₂₆H₃₂N₂O₉S₂ 
• 23926-58-1 N,N'-bis(benzyloxycarbonyl)-L-cystine diethyl ester 

Relevant academic research and scientific papers

Reaction of N-acyloxy-N-alkoxyamides with biological thiol groups

Mutagenic N-acyloxy-N-alkoxyamides 1 react with thiols by an SN2 process at nitrogen with displacement of carboxylate. They react with glutathione 4 in [D6]DMSO/D2O and methyl and ethyl esters of cysteine hydrochloride, 11 and 12, in [D4]methanol but the intermediate N-alkoxy-N-(alkylthio)amides undergo a rapid substitution reaction at sulfur by a second thiol molecule to give hydroxamic esters and disulfides. Arrhenius activation energies and entropies of activation obtained for a series of different N-benzyloxy-N-(4-substitutedbenzoyloxy)benzamides 13-17 were similar to those found for the SN2 reaction of the same series with N-methylaniline. Entropies of activation were strongly negative in keeping with polar separation and attendant solvation in the transition state, and in keeping with this, bimolecular reaction rate constants at 298K correlated with Hammett σ constants with a positive ρ-value of 1.1. The structure of model N-methoxy-N-(methylthio)acetamide has been computed at the B3LYP/6-31G(d) level and exhibits properties atypical of other anomeric amides with more electronegative atoms at nitrogen. Relative to N,N-bisoxyl substitution, the combination of a sulfur and an oxygen atom at the amide nitrogen results in a relatively small reduction in amide resonance.

COMPOUNDS AS L-CYSTINE CRYSTALLIZATION INHIBITORS AND USES THEREOF

A method of preventing or inhibiting L-cystine crystallization is disclosed, using the compounds of formula I: [in-line-formulae]R1a—[O]v-(-A-L-)m-A-[O]v—R1b [/in-line-formulae] wherein A, L, R1a, R1b, m, and v are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of conditions that are causally related to L-cystine crystallization, such as comprising (but not limited to) kidney stones.

COMPOUNDS AS L-CYSTINE CRYSTALLIZATION INHIBITORS AND USES THEREOF

A method of preventing or inhibiting L-cystine crystallization using the compounds of formula (I) is disclosed, wherein A, L, R1a, R1b, and m are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of conditions that are causally related to L-cystine crystallization, such as comprising (but not limited to) kidney stones.