1331965-83-3Relevant academic research and scientific papers
Multivalent agents containing 1-substituted 2,3,4-trihydroxyphenyl moieties as novel synthetic polyphenols directed against HIV-1
Flores, Aida,Camarasa, Maria Jose,Perez-Perez, Maria Jesus,San-Felix, Ana,Balzarini, Jan,Quesada, Ernesto
, p. 5278 - 5294 (2014/07/08)
The synthesis and the assessment of the anti-HIV activity of a set of molecules inspired by the multivalent structures of some naturally-occurring polyphenols (tannins) are reported. Different multibranched scaffolds have been derived from pentaerythritol as the central core which distribute spatially synthetic polyphenolic subunits based on 1-substituted 2,3,4-trihydroxyphenyl moieties. A tetrapodal compound (13b) bearing four N-(2,3,4-trihydroxyphenyl) amide groups, exhibits remarkable selective activity against HIV-1 with EC 50 values in the micromolar scale, in the same range as those reported for the most representative anti-HIV tannins. Preliminary SAR studies emphasize the importance of the 1-substituted 2,3,4-trihydroxyphenyl moiety, the presence of an amide as the linker and the multivalent architecture of these molecules, since the anti-HIV activity increases with the number of polyphenolic moieties. The data support the interest in synthetic polyphenols and represent a promising starting point for further design and development of selective HIV-1 inhibitors.
Synthesis and evaluation of C-ring aromatized analogues of phenanthridone alkaloids
Lee, Seokwoo,Hwang, Soonho,Yu, Shuai,Jang, Wonyoung,Lee, Yun Mi,Kim, Sanghee
, p. 1065 - 1070 (2012/07/14)
Phenanthridone alkaloids are envisaged as an attractive lead for the development of anticancer agents. We have prepared a series of aromatized analogues on the basis of the structure of this class of alkaloids with the hope of finding the simplified compounds with comparable activities. The obtained analogues were evaluated for their cytotoxic effect against several cancer cell lines and found to be virtually inactive. These observations together with molecular modeling studies strongly suggest that the stereochemistries of hydroxyl groups in C-ring of phenanthridone alkaloids are crucial to biological effects.
