New nordihydroguaiaretic acid derivatives as anti-HIV agents

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

Research output: Contribution to journalArticle

26 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

Fingerprint

Masoprocol
Anti-HIV Agents
Chlorides
Salts
Nitrogen Compounds
Derivatives
Ethers
Carbamates
Carbonates
Phenol
Solubility
Transcriptional Activation
Inhibitory Concentration 50
Nitrogen
Epithelial Cells
HIV
meso-2,3-dimethyl-1,4-bis(3,4-(2-(piperdino)ethoxyphenyl))butane tetrakishydrochloride
methyl chloroformate

All Science Journal Classification (ASJC) codes

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

Cite this

Hwu, Jih Ru ; Hsu, Ming-Hua ; Huang, Ru Chih C. / New nordihydroguaiaretic acid derivatives as anti-HIV agents. In: Bioorganic and Medicinal Chemistry Letters. 2008 ; Vol. 18, No. 6. pp. 1884-1888.
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New nordihydroguaiaretic acid derivatives as anti-HIV agents. / Hwu, Jih Ru; Hsu, Ming-Hua; Huang, Ru Chih C.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 18, No. 6, 15.03.2008, p. 1884-1888.

Research output: Contribution to journalArticle

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