94029-36-4

Upstream product

• 2564-02-5 N-(4-bromophenyl)-2-chloroacetamide 
• 106-40-1 4-bromo-aniline 
• 128094-91-7 Bis-2-(chlorosulfonyl)ethyl 2,2'-dithiodiacetate 
• 10021-77-9 2,2'-disulfanediyldiacetylchloride 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Dithiobisacetamides as Novel Urease Inhibitors

Thirty-eight disulfides containing N-arylacetamide were designed and synthesized in an effort to develop novel urease inhibitors. Biological evaluation revealed that some of the synthetic compounds exhibited strong inhibitory potency against both cell-free urease and urease in intact cell with low cytotoxicity to mammalian cells even at concentration up to 250 μM. Of note, 2,2′-dithiobis(N-(2-fluorophenyl)acetamide) (d7), 2,2′-dithiobis(N-(3,5-difluorophenyl)acetamide) (d24), and 2,2′-dithiobis(N-(3-fluorophenyl)acetamide) (d8) were here identified as the most active inhibitors with IC50 of 0.074, 0.44, and 0.81 μM, showing 32- to 355-fold higher potency than the positive control acetohydroxamic acid. These disulfides were confirmed to bind urease without covalent modification of the cysteine residue and to inhibit urease reversibly with a mixed inhibition mechanism. They also showed very good anti-Helicobacter pylori activities with d8 showing a comparable potency to the clinical used drug amoxicillin. The impressive in vitro biological profile indicated their immense potential as therapeutic agents to tackle H. pylori caused infections.

SULFINIC ACIDS AND RELATED COMPOUNDS. 22. DERIVATIVES OF 2-HYDROXYETHANE-SULFINIC ACID

Sodium 2-hydroxyethanesulfinate (3) could be converted to the unstable methyl ester 8 by acidification followed by reaction with diazomethane (although the acid 4, itself, could not be isolated as reported).The ester 8 was esterified with 2,2'-dithioacetyl dichloride (10) to afford the desired convergent synthesis of a disulfide bissulfinate ester (11), but 11 was even less stable than 8; efforts to esterify the sulfinate salt 3 with 10 to give a more stable sulfinate salt counterpart (12) of the ester 11 were unpromising.The salt 12 also was sought by reduction of a sulfonyl chloride 13, which was obtained by coupling 10 with 2-hydroxyethanesulfonyl chloride (2) and for which the structure was confirmed by reaction with p-bromoaniline; 12 evidently was obtained, but greater purity not be obtained than ca. 83-95percent.In other reactions, 2-hydroxyethanesulfonyl chloride (2) reacted with p-bromoaniline, and the hydroxysulfonanilide (6) produced could be esterified with 10 to give 9 by use of special conditions.