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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 31, Number 5
JKCSEZ 31(5)
October 20, 1987 

Synthesis and Antimicrobial Activity of Phenazine Derivatives (Ⅰ)

Phenazine 유도체의 합성과 항균성에 관한 연구 (제 1 보)
Jong Dae Kim, Ho Sik Kim, Sung Wook Han

김종대, 김호식, 한성욱
파라위치에 메톡시, 메틸, 아세틸 및 니트로기를 가진 아닐린유도체를 출발물질로 하여 6-substituted benzofuroxan 유도체를 합성하고, 이들과 4-아미노페놀을 반응시켜 7-Substituted 2-aminophenazine-5,10-dioxides류를 합성하였다. 그리고 benzofuroxan과 4-아미노페놀을 반응시켜 2-Aminophenazine-5,10-dioxide도 합성하였다. 이들 phenazine 유도체의 항균성을 희석법에 의하여 최소 발육저지 농도로서 조사하였는데, 전자를 주는 치환기를 가진 phenazine dioxide 유도체들이 전자를 당기는 치환기를 가진 phenazine dioxide유도체들 보다 항균성이 더 강하였다. 이 사실로부터 phenazine dioxide 유도체에서 치환기의 전자효과와 항균성사이에는 직접적인 연관성이 있다는 것을 알았다.

7-Substituted 2-aminophenazine-5,10-dioxides were synthesized by the reaction of 4-aminophenol with 6-substituted benzofuroxan derivatives which had been obtained from aniline derivatives bearing methoxy, methyl, acetyl, and nitro group at the para position. 2-Aminophenazine-5,10-dioxide was also prepared by the reaction of 4-aminophenol with benzofuroxan. The antimicrobial activities of these phenazine dioxide derivatives were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. It was observed that the antimicrobial activity of the phenazine dioxides bearing electron releasing substituents was stronger than that of those bearing electron withdrawing substituents. From this result, it was concluded that the antimicrobial activity of phenazine dioxide derivative has a direct relationship with the electronic effect of the substituents.

464 - 470
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