关键词: 大黄酸, 结构修饰, 抑菌活性, 初步构效关系

Abstract: Based on carboxyl amidation of rhein(1), a series of derivatives of rhein were synthesized by structure modification of C7 of anthraquinone mother nucleus. And the antibacterial activity and structure-activity relationship of the derivatives were preliminary discussed. The derivatives of rhein were respectively rhein piperidine amide(2), 7-hydroxymethyl-rhein piperidine amide(3), 7-bromomethyl-rhein piperidine amide(4), 7-(4-morpholino)methyl-rhein piperidine amide(5a), 7-(pyrrolidin-1-yl)methyl-rhein piperidine amide(5b), 7-(1-methyl-4-piperazinyl)methyl-rhein piperidine amide(5c). The structures of the compounds were characterized by IR, ¹H NMR, ¹³C NMR, MS. The minimal inhibitory concentrations (MIC) of the compounds obtained were tested and the MIC of compounds 5a and 5b against E.coli reached 0.78 and 0.39 mg/L respectively. Their antibacterial activity were stronger than that of rhein(MIC 3.13 mg/L) obviously, even stronger than that of the kanamycin(MIC 1.56 mg/L); and the MIC of compound 5a against S. aureus reached 1.56 mg/L, which was similar to that of rhein. The preliminary analysis of structure effective relationship showed that if none replace heterocyclic groups were introduced into substituent of C7 of the mother nucleus, the antibaterial activity on E.coli would be stronger.

Key words: rhein, structure modification, antibacterial activity, preliminary structure-activity relationship