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

✍ Scribed by Zdzisław Brzozowski; Jarosław Sławiński; Anna Kędzia; Ewa Kwapisz; Maria Gdaniec

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 252 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.272

✦ Synopsis

Abstract

magnified image Two series of 4__H__‐pyrido[4,3‐e]‐1,2,4‐thiadiazine derivatives 3, 4, 5 and 7, 8, 9, 10, 11, 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 = Me, Y = O) afforded the corresponding 3‐(R‐amino)‐4‐(2‐hydroxy‐5‐methylphenyl)‐4__H__‐pyrido[4,3‐e]‐1,2,4‐thiadiazine 1,1‐dioxides 13, 14, 15, 16, 17, 18. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data, and X‐ray crystallography. Compounds 3, 4, 5, 7, 8, 9, 10, 12, 13, 14, 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, 12, 13, and 17, 18 at the National Cancer Institute (Bethesda, MD) at a single dose (10 μ__M__) in the full NCI 60 cell panel. J. Heterocyclic Chem., (2009).