3323-42-0

Upstream product

• 91525-55-2 3'-methoxybenzenesulphenanilide 
• 103929-99-3 2'-phenylthio-5'-methoxybenzenesulphenanilide 
• 110-83-8 cyclohexene 
• 33358-37-1 (4-methoxy-2-nitrophenyl)(phenyl)sulfane 
• 108-98-5 thiophenol 
• 10298-80-3 2-chloro-5-methoxynitrobenzene 
• 536-90-3 m-Anisidine 

Downstream Products

• 195073-73-5 3-Bromo-N-(5-methoxy-2-phenylsulfanyl-phenyl)-propionamide 
• 195073-78-0 (3-Bromo-propyl)-(5-methoxy-2-phenylsulfanyl-phenyl)-amine 

Relevant academic research and scientific papers

New spermine and spermidine derivatives as potent inhibitors of trypanosoma cruzi trypanothione reductase

Several spermine and spermidine derivatives containing 2-amino diphenylsulfide substituents were prepared and tested for their inhibiting effects on Trypanosoma cruzi trypanothione reductase. IC50 values were assessed between 0.3 and 3 μM. Compound 32 (K(i) = 0.4 μM) is the most potent TR inhibitor described so far.

BORON TRIFLUORIDE PROMOTED REACTION OF BENZENESULPHENANILIDES WITH ALKENES

The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides.The benzenesulphenanilides (1) investigated generally afford arylaminosulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (1e and f), which largely lead to decomposition products under comparable conditions.In all cases examined, the addition proceeds with trans-stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides.The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.

Acid-promoted Decomposition of Benzenesulphenanilides and N-Aryl Bis(benzenesulphen)amides

The decomposition of 4'-substituted benzenesulphanilides (1a-d) in the presence of trifluoroacetic acid (0.6 equiv.) leads to N-arylbis(benzenesulphen)amides (6a-d) in variable yields, depending on the 4'-substituent, in addition to disulphide (4) and anilines (3a-d), whereas products arising from sulphenylation of the N-aryl ring result from 3'-methoxybenzenesulphenanilide (1g).The 4'-nitro- and 3'-nitro-benzenesulphenanilides (1e,f) react with a slight excess of trifluoroacetic acid to give only (4), the thiosulphonate (5), and aniline (3e,f).The findings are interpreted in terms of possible nucleophilic attack at the S-N bond of a protonated sulphenanilide by the nitrogen or the N-aryl ring of another sulphenanilide unit, according to the nature of the substituent and its position, with displacement of aniline (3).The reaction of (1a-d) with 1.5 equiv. of trifluoroacetic acid leads to complete disappearance of the initially formed amides (6a-d) with concomitant formation of phenazines (9) and/or p-quinone di-imines (8).Similar results are obtained by using boron trifluoride-diethyl ether.Di-imines (8) and phenazines (9) are explained on the basis of a mechanism initially involving nucleophilic attack by (1) and/or (6) and/or (3) at the ortho and para positions of an intermediate cation, possibly (18A) or (18B), and loss of the disulphide (4).