New nordihydroguaiaretic acid derivatives as anti-HIV agents

Jih Ru Hwu; Ming Hua Hsu; Ru Chih C. Huang

doi:10.1016/j.bmcl.2008.02.018

New nordihydroguaiaretic acid derivatives as anti-HIV agents

Jih Ru Hwu, Ming Hua Hsu, Ru Chih C. Huang

Department of Chemistry

Research output: Contribution to journal › Article

27 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1884-1888
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2008.02.018
Publication status	Published - 2008 Mar 15

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Hwu, J. R., Hsu, M. H., & Huang, R. C. C. (2008). New nordihydroguaiaretic acid derivatives as anti-HIV agents. Bioorganic and Medicinal Chemistry Letters, 18(6), 1884-1888. https://doi.org/10.1016/j.bmcl.2008.02.018

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abstract = "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.",

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