New nordihydroguaiaretic acid derivatives as anti-HIV agents

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1884-1888
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number6
DOIs
Publication statusPublished - 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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