156578-98-2

Upstream product

• 1433218-68-8 N-(2-bromoethyl)-N-(4-cyano-2-iodophenyl)-4-methylbenzenesulfonamide 
• 1449225-55-1 N-(4-cyano-2-iodophenyl)-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 33348-34-4 4-amino-3-iodobenzonitrile 
• 1433218-50-8 C₁₆H₁₄N₂O₂S₂ 
• 185540-73-2 3-(2-Chloro-ethylsulfanyl)-4-(toluene-4-sulfonylamino)-benzoic acid methyl ester 
• 185540-71-0 4-Amino-3-(2-chloro-ethylsulfanyl)-benzoic acid 
• 1571-66-0 4-amino-3-mercaptobenzoic acid hydrochloride 
• 185540-74-3 4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]thiazine-7-carboxylic acid methyl ester 

Downstream Products

• 185540-75-4 (S)-2-{[4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]thiazine-7-carbonyl]-amino}-pentanedioic acid diethyl ester 
• 156578-99-3 (S)-2-{[4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]thiazine-7-carbonyl]-amino}-hexanedioic acid dimethyl ester 

Relevant academic research and scientific papers

Efficient access to 1,4-benzothiazine: Palladium-catalyzed double C-S bond formation using Na2S2O3 as sulfurating reagent

A novel Pd-catalyzed double C-S bond formation coupling reaction has been developed. This protocol, in which Na2S2O3 was used as sulfurating reagent in metal-catalyzed reactions, provides an efficient method for the synthe

Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety

Novel methotrexate (MTX) derivatives bearing dihydro-2H-1,4- benzothiazine or dihydro-2H-1,4-benzoxazine were synthesized and tested for in vitro antiproliferative activities against human synovial cells (hSC) and human peripheral blood mononuclear cells (hPBMC) obtained from patients with rheumatoid arthritis and healthy volunteers, respectively. In vivo antiarthritic activities of these derivatives were also evaluated in a rat adjuvant arthritis model. N-[[4-[(2,4-Diaminopteridin-6-yl)methyl]-3,4- dihydro-2H-1,4-benzothiazin-7-yl]carbonyl]-L-glutamic acid (3c) exhibited more potent antiproliferative activities in hSC and hPBMC than MTX in vitro. Antiproliferative activities of N-[[4-[(2,4-diaminopteridin-6-yl)methyl]- 3,4-dihydro-2H-1,4-benzoxazin-7-yl]carbonyl]-L-homoglutamic acid (3b) and N- [[4-[(2,4-diaminopteridin-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7- yl]carbonyl]-L-homoglutamic acid (3d) (MX-68) were comparable to that of MTX in these in vitro assays. Compounds 3b,d (MX-68) significantly suppressed progression of the adjuvant arthritis in a dose-dependent manner ranging from 0.5 to 2.5 mg/kg (po). In addition, 3d (MX-68) completely suppressed this progression at the dose of 2.5 mg/kg (po). Importantly, 3d (MX-68) having benzothiazine and homoglutamate, as expected, did not undergo polyglutamation, a process which may be responsible for the associated side effects of MTX. These results suggest that 3d (MX-68) is a potent and safe candidate antirheumatic agent, absent of the side effects of MTX.