313335-40-9Relevant academic research and scientific papers
Inhibitors of HIV-1 attachment. Part 4: A study of the effect of piperazine substitution patterns on antiviral potency in the context of indole-based derivatives
Wang, Tao,Kadow, John F.,Zhang, Zhongxing,Yin, Zhiwei,Gao, Qi,Wu, Dedong,Parker, Dawn DiGiugno,Yang, Zheng,Zadjura, Lisa,Robinson, Brett A.,Gong, Yi-Fei,Blair, Wade S.,Shi, Pei-Yong,Yamanaka, Gregory,Lin, Pin-Fang,Meanwell, Nicholas A.
body text, p. 5140 - 5145 (2010/03/31)
4-Fluoro- and 4-methoxy-1-(4-benzoylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione (2 and 3, respectively) have been characterized as potent inhibitors of HIV-1 attachment that interfere with the interaction of viral gp120 with the host cell receptor C
Modification and structure-activity relationship of a small molecule HIV-1 inhibitor targeting the viral envelope glycoprotein gp120
Wang, Jingsong,Le, Nhut,Heredia, Alonso,Song, Haijing,Redfield, Robert,Wang, Lai-Xi
, p. 1781 - 1786 (2007/10/03)
This paper describes selected modification and structure-activity relationship of the small molecule HIV-1 inhibitor, 4-benzoyl-1 -[(4-methoxy-1-H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (BMS-378806). The results revealed: i) that both the presence and configuration (R vs. S) of the 3-methyl group on the piperazine moiety are important for the antiviral activity, with the 3-(R)-methyl derivatives showing the highest activity; ii) that the electronegativity of the C-4 substituent on the indole or azaindole ring seems to be important for the activity, with a small, electron-donating group such as a fluoro or a methoxy group showing enhanced activity, while a nitro group diminishes the activity; iii) that the N-1 position of the indole ring is not eligible for modification without losing activity; and iv) that bulky groups around the C-4 position of the indole or azaindole ring diminish the activity, probably due to steric hindrance in the binding. We found that a synthetic bivalent compound with two BMS-378806 moieties being tethered by a spacer demonstrated about 5-fold enhanced activity in an nM range against HIV-1 infection than the corresponding monomeric inhibitor. But the polyacrylamide-based polyvalent compounds did not show inhibitory activity at up to 200 nM. The Royal Society of Chemistry 2005.
Antiviral indoleoxoacetyl piperazine derivatives
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, (2008/06/13)
This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.
