PMID: 9168238May 20, 1997Paper

Tetrahydronaphthalene lignan compounds as potent anti-HIV type 1 agents

AIDS Research and Human Retroviruses
H HaraH Kaji

Abstract

Anti-HIV-1 activity of tetrahydronaphthalene (THN) derivatives of lignan compounds was studied. THN derivatives prevented cell death caused by HIV-1 infection in MT-4 cells. They also inhibited giant cell formation by HIV-1 in Sup-T1 cells, and p24 production in HIV-1-infected H9 cells. The 50% effective concentration (ED50) of the most active compound, 1737 [5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,3,3a,4,9,9a-hexahydron aphtho[2,3-c]thiophene], for inhibition of the cytopathic effects of HIV-1 infection ranged from 0.15 to 0.8 microM. The 50% cytotoxic concentration (CC50) of compound 1737 measured by the viability of MT-4 cells was 58 microM, indicating a selective index (CC50/ED50) of 70-400. Substitution of the phenyl ring with other structures markedly decreased cytotoxicity but did not affect the antiviral activity of the compounds. This resulted in compounds with a high selective index. One such compound was 1738 [7-methoxy5,6-methylenedioxy-4-(4-benzyloxy-3-methoxyphenyl)1,3,3a ,4,9,9a-hexahydronaphtho[2,3-c]thiophene], with a selective index higher than 770. The time-of-addition experiment indicated that these compounds acted at or near the reverse transcription step of the HIV-1 life cycle. THN derivatives inhib...Continue Reading

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Citations

Feb 26, 2004·Bioorganic & Medicinal Chemistry·Michael WambergClaus Nielsen
Jun 11, 2008·Antimicrobial Agents and Chemotherapy·Anneleen HombrouckMyriam Witvrouw
Aug 11, 2004·Toxicon : Official Journal of the International Society on Toxinology·M GordalizaM A Gómez-Zurita
May 16, 2014·Medicinal Research Reviews·Ying-Qian LiuKuo-Hsiung Lee
Aug 8, 2015·Evidence-based Complementary and Alternative Medicine : ECAM·Ivonne Alejandre-GarcíaMaría Luisa Villarreal
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