Synthesis and Antimicrobial Activity of 1,4-Naphthoquinones Derivatives with [1,2,4]-Triazole-3-thione Substitution

Synthesis of condensed nitrogen-containing heterocycles of substituted 1,4-naphthoquinone

“…=218-220 0 Ñ, I×,  cì -1 : 3450, 3364 (NÍ 2 ); 3325(NÍ); 1683, 1550(Ñ=Î). 1 Ðåçóëüòàòè òà îáãîâîðåííÿ Äî öüîãî ÷àñó ñèíòåçè ãåòåðîöèêë³â íà îñ-íîâ³ 1,4-íàôòîõ³íîíó âèêîíóâàëèñü ç³ ñòîðîíè áåíçîëüíîãî öèêëó [5][6][7]. Ââåäåííÿ NÍ 2 -ãðóïè â 7-÷è 6-ïîëîaeåííÿ íàôòîõ³íîíó äàëî ìîae-ëèâ³ñòü ñèíòåçó ð³çíîìàí³òíèõ ãåòåðîöèêë³â ç³ ñòîðîíè áåíçîëüíîãî öèêëó [8].…”

Primary screening of the biological activity of heterocyclic aminoderivatives of 2,3-dichloro-1,4-naphtoquinone

“…That is why heterocyclic amino derivatives of naphthoquinone, which have a wide range of pharmacological activity, in particular, antibacterial [1,2] antifungal [3], anticancer [4,5], antiviral, anti-inflammatory and regenerating [6], occupy an important place among development of new drug substances.…”

“…It has been reported that some heterocyclic amino derivatives of naphthoquinone have antifungal activity [3]. Synthetic thiol derivatives containing 1,4-naphthoquinone have been reported as potent antimicrobial and anticancer agents [2,10]. However, the toxicity of naphthoquinone compared to antibacterial activity often prevents their use as drugs for the treatment of infectious diseases [12,13].…”

Interaction of 5-Substituted 1,4-Naphthoquinones and Amino Thiotriazoles: Reaction Ways and Regioselectivity

“…Condensation of such heterocycle with various pharmacophore fragments, including 1,4-quinoid, enables design of thiadiazine systems with potential antimicrobial, anti-inflammatory and anti-tumor activities [1][2][3][4][5][6][7][8][9]. Thiotriazole molecule is a bifunctional nucleophile and has two reactive centers.…”

“…Due to the presence of thionethiol tautomerism in the molecule S-nucleophilic center activation can be held by shifting a tautomeric equilibrium. So, in nonpolar solvents the thione form of bifunctional nucleophile prevails, and in polar solventsthiol tautomeric form [8,10]. The nature and arrangement of substituent in quinones have a strong steering effect in the reaction.…”