Syntheses and Biological Activities of 7-(Substituted triazolo thioethoxy)flavone Derivatives†

doi:10.7503/cjcu20140423

Abstract

Abstract:

Flavone and 1,2,4-triazole derivatives have many different biological activities. According to the active groups combination principle, sixteen 7-(substituted triazolo thioethoxy)flavone derivatives were synthesized by means of the condensation reaction of 7-bromoethoxy flavone, which was synthesized from 7-hydroxy flavone and 1,2-dibromoethane, with four types of 1,2,4-triazole compounds, such as 3-substituted-4-phenylallylideneamino-1,2,4-triazol-5-thiones, 3-substituted-4-phenyl-5-mercapto-1,2,4-triazoles, 3-(α-naphthylmethene)-5-mercapto-1,2,4-triazole and 3-mercapto-5-phenylallylideneamino-1,2,4-triazole. These new compounds were characterized via IR, ¹H NMR, MS and elementary analysis. Their scavenging effects on the superoxide radical(), hydroxyl radical(·OH) and DPPH· radical and their total reduction activities were compared, and the in vitro antimicrobial activities were also tested. The results showed that at the concentration of 0.5 mg/mL, some of the title compounds had scavenging effects on DPPH·, among which 7-(5-phenylmethylene-4-phenylallylideneamino-1,2,4-triazol-3-thioethoxy)flavone(1i) had stronger effect than the others, and the title compound had relatively antibacterial activity, among which 7-(5-phenylmethylene-4-phenyl-1,2,4-triazol-3-thioethoxy)flavone(2c) had stronger effect on E. coli, S. aureus and A. niger than the others.

Key words: Triazole, Flavone, Antioxidation, Antibacterial

CLC Number:

O629
Q946

TrendMD:

DUAN Zhifang, FU Li, LI Chongbi. Syntheses and Biological Activities of 7-(Substituted triazolo thioethoxy)flavone Derivatives^†[J]. Chem. J. Chinese Universities, 2015, 36(1): 102.

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