Synthesis and anti‐HIV activity of <i>n</i>‐(3‐amino‐3,4‐dihydro‐4‐oxopyrimidin‐2‐yl)‐4‐chloro‐2‐mercapto‐5‐methylbenzenesulfonamide derivatives

2013

A series of 6′‐chloro‐1′,1′‐dioxo‐2′H‐spiro[benzo[d][1,3,7]oxadiazocine‐4,3′‐(1,4,2‐benzodithiazine)]‐2,6(1H,5H)‐dione derivatives 2a, 2b and 3a, 3b have been synthesized starting from 3‐aminobenzodithiazines 1a, 1b and isatoic anhydride. Subsequent reactions of 2a with 3‐chlorophenyl isocyanate gave condensation products 4 and 5. Compound 2a was also converted into 3‐(2‐aminobenzamido)‐6‐chloro‐7‐methyl‐1,1‐dioxo‐1,4,2‐benzodithiazine derivatives 6, 7, 8, 9, 10. The mechanisms of the reactions are discussed.

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Series of 6‐Chloro‐1,1‐dioxo‐1,4,2‐benzodithiazine Derivatives with Potential Biological Activity

2013

On the Reaction Products of 4‐Substituted 3‐Pyridinesulfonamides with Some Benzenesulfonyl Chloride Derivatives

Szafrański

2013

in Wiley Online Library (wileyonlinelibrary.com).The reactions of 4-substituted 3-pyridinesulfonamides 1a-e with benzenesulfonyl chlorides 2a-f in acetonitrile were investigated. Depending on the structure of arylsulfonyl chlorides and the reaction conditions the following four types of products were obtained in good yields: 3-sulfamoyl-4-R-1-arylpyridinium chlorides 3-8; 1,10-bis(3-nitrobenzenesulfonylimino)deca-2,4,6,8-tetraene-2,9-disulfonamides 9-12; 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides 13-14; and 4-methoxy-3-[N-(2,5-dichlorophenyl)sulfonyl] sulfonamidates 15 and 16. The mechanisms of these reactions were discussed.

Application of 3‐methylthiopyrido[4,3‐e]‐1,4,2‐dithiazine 1,1‐dioxide to the synthesis of novel series of 4H‐pyrido[4,3‐e]‐1,2,4‐thiadiazine derivatives with potential biological activity

Kędzia

et al. 2009

Two series of 4H-pyrido[4,3-e]-1,2,4-thiadiazine derivatives 3-5 and 7-12 were synthesized by the reactions of 3-methylthiopyrido[4,3-e]-1,4,2-dithiazine 1,1-dioxide 1 with 2-or 6-hydrazinoazines and 2-aminophenols or 2-aminothiophenol, respectively. Aminolysis of 8 (R ¼ Me, Y ¼ O) afforded the corresponding 3-(R-amino)-4-(2-hydroxy-5-methylphenyl)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides 13-18. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data, and X-ray crystallography. Compounds 3-5, 7-10, 12-15, and 17-18 were screened in vitro for antibacterial activity. Moreover, preliminary in vitro anticancer assay was performed for compounds 3, 7, 10, 11-13, and 17-18 at the National Cancer Institute (Bethesda, MD) at a single dose (10 lM) in the full NCI 60 cell panel.