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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 30, Number 1
JKCSEZ 30(1)
February 20, 1986 

Synthesis and Antimicrobial Properties of Surfactants Containing Phenazine Ring (Ⅲ)

Phenazine Ring을 가진 계면활성제의 합성과 그 항균성 (제3보)
Jong Dae Kim, Ho Sik Kim, Sung Wook Han

김종대, 김호식, 한성욱
Aniline과 n-alkyl alcohol류로 부터 6-alkylbenzofuroxan을 얻고 이것과 4-aminophenol을 반응시켜 butyl, hexyl, octyl기를 가진 7-Alkyl-2-aminophenazine-5,10-dioxide를 합성하였다. 그리고 benzofuroxane과 4-aminophenol을 반응시켜 2-aminophenazine-5,10-dioxide도 합성하였다. 생성물들은 IR, NMR, 원소분석등으로 확인하였다. 이들 phenazine 유도체의 수용액에 대한 표면장력을 측정하였는데 alkyl기의 탄소수가 증가할수록 표면장력이 저하됨을 알았다. 또한 항균성을 희석법에 의하여 조사하였는데 alkyl기의 탄소수가 4개인 butyl 유도체의 경우가 가장 항균성이 강했으며, alkyl기가 없는 2-aminophenazine-5,10-dioxide보다는 alkyl기가 치환된 2-aminophenazine-5,10-dioxide의 향균성이 더 강하다는 것을 알았다.

7-Alkyl-2-aminophenazine-5,10-dioxides bearing butyl, hexyl and octyl group were synthesized by the reaction of 4-aminophenol with 6-alkylbenzofuroxans which had been obtained from aniline and n-alkyl alcohols. And 2-aminophenazine-5,10-dioxide was prepared by the reaction of 4-aminophenol with benzofuroxan. Infrared, nuclear magnetic resonance spectrophotometers, and elemental analyzer were employed to identify the products concerned with the synthetic processes. Surface tension of aqueous solutions of these phenazine derivatives was determined by surface tensiometer and it was found that the surface tension decreased with an increase of the number of carbon in the alkyl group. Antimicrobial activities were evaluated in terms of minimum inhibitory concentration by a dilution method. The butyl derivative showed the highest activity among these derivatives. It was observed that the antimicrobial activity of these alkyl substituted 2-aminophenazine-5,10-dioxides was stronger than that of 2-aminophenazine-5,10-dioxide.

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