Many phenothiazine derivatives have been used as drugs. Modifications of the main structural fragment of phenothiazine drugs reveal interesting chemical properties and potent biological activity.¹ Extensive research has been conducted on new methods of synthesizing potentially useful phenothiazine derivatives with pharmacological activity. New applications of phenothiazine derivatives have also been found.²

The reaction of bis-salts (1) with primary aliphatic amines and anilines led to 1-alkyl-4-aminoquinolinium-3-thiolates (2). 1-Alkyl-4-arylaminoquinonolinium-3-thiolates in the presence of oxygen and hydrogen chloride undergo cyclization to 5-alkyl-12H-quino[2,3-b][1,4]benzothiazinium chloride (3).^3,4 This reaction is a new method of synthesizing phenothiazine derivatives.Antibacterial studies of the compounds (3) were conducted on Staphylococcus aureus, Escherichia coli, Enterococcus faecalis and Pseudomonas aeruginosa. Correlations of antibacterial activity tested compounds with chemical structure and lipophilicity were observed.

[1]. Delgado J.N. and Remers W.A., (eds.) Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, 10 ed., Lippincott-Raven Publishers, Philadelphia, 1998, p. 450.

[2]. S. Sharma and A. Kumar, Pharmazie, 2005, 60, 18.

[3]. A. Zięba, A. Maślankiewicz, and K. Suwińska, Eur. J. Org. Chem., 2000, 2947.

[4]. A. Zięba and K. Suwińska, Heterocycles, 68, 495 (2006).

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1. Molecular effects of newly synthesized derivatives of phenothiazine in C-32 and MDA-MD-231 cancer cells
2. Quinolinesulfonamides as potential 5-HT₇ and 5-HT_1A receptor ligands