New nordihydroguaiaretic acid derivatives as anti-HIV agents

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• 作者：Jih Ru Hwu ; Ming-Hua Hsu ; Ru Chih C. Huang
• 关键词：Anti-HIV ; NDGA ; Nordihydroguaiaretic acid ; DNA ; HIV Tat-regulated transactivation
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2008
• 出版时间：15 March 2008
• 年：2008
• 卷：18
• 期：6
• 页码：1884-1888
• 全文大小：362 K

文摘

Reaction of nordihydroguaiaretic acid with various alkyl chloride, 1-piperidinecarbonyl chloride, methyl chloroformate, or 1,1′-carbonyldiimidazole under alkaline conditions produced the corresponding phenol ethers, carbamates and carbonates, respectively, in 67–83 % yields. Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found stable in aqueous solution. These new compounds exerted appealing activity against HIV Tat-regulated transactivation in human epithelial cells. The most potent compound meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperdino)ethoxyphenyl])butane tetrakishydrochloride salt (5b) showed IC₅₀ value of 0.88 μM.