Abstract
Phenothiazines are a large group of heterocyclic, aromatic molecules with nitrogen and sulphur between two benzene rings. Their derivatives, N-alkylphenothiazines have supstitutient on heterocyclic nitrogen atom which gives them different properties. Also, a series of these molecules have substitution on carbon atom at place 2 of phenothiazine benzene ring. Alkylphenothiazines contain aminoalkyl substituent and their alkyl, acyl and sulphonil derivatives, as well as monocyclic and bicyclic heterocycles attached at thiazine nitrogen atom or directly linked to benzene ring. The N-alkylphenothiazines have been known as antipsychotic drugs, but they also possess antibacterial, antifungal, anticancer activity, and ability to react with macromolecules and to coordinate to the metals. Metal complexes with N-alkylphenothiazines are biological active compounds with different antimicrobial activities and cytotoxic effect against tumor cell lines. Their large field of application of N-alkylphenothiazines is very attractive in terms of synthesis of new related derivatives, metal complexes, studying their properties and applications. This article presents a review of the literature and a contemporary view at N-alkylphenothiazines - their synthesis and application, as well as their metal complexes which have promising biological effects.
Highlights
Phenothiazines are a large group of heterocyclic, aromatic molecules with nitrogen and sulphur between two benzene rings
The N-alkylphenothiazines as ligands are used in metal complexes, but biological properties of these complexes are investigated in recent years
This review shows current importance of the N-alkylphenothiazines and reveals their metal complexes as potent pharmacological group which can be a rich source of new compounds having desirable biological activities
Summary
The N-alkylphenothiazines are heterocyclic aromatic compounds with nitrogen and sulphur atoms and substituents on aromatic ring and nitrogen. The first phenothiazines, thionine and methylene blue (Fig. 2) were synthesized in reaction of p-phenylendiamine/p-aminodimethylaniline with sulphur in hydrochloric acid solution, in the middle of the 19th century [2] In that time, these compounds with phenothiazine ring had an application in aniline dye industry. These molecules have antipsychotic, antiemetic, anthelmintic, antibacterial, antifungal and insecticidal properties, and they represent promising anticancer drugs [1,2,3,4,5,6,7,8] These activities represent the result of the interaction of phenothiazines with biological systems through their pharmacophoric substituent, the multicyclic ring system (π-π interaction, intercalation in DNA) or the lipophilic character allowing the penetration through the biological membranes. R1 Phenothiazines with an aliphatic side chain (CH2)3–N(CH3) (CH2)3–N(CH3) (CH2)3–N(CH3) CH2–CH(CH3)–N(CH3) Phenothiazines with a piperidine side chain
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