86712-41-6Relevant academic research and scientific papers
Regioselective reactivity of some 5,7-dimethoxyindoles
Condie, Glenn C.,Channon, Michelle F.,Ivory, Andrew J.,Kumar, Naresh,Black, David StC.
, p. 4989 - 5004 (2005)
The reactivity of some 5,7-dimethoxyindoles with respect to electrophiles has been investigated. The favoured sites for reaction are C3 and C4 and regioselectivity can be controlled by the judicious arrangement of electron-withdrawing substituents. Results of formylation, acylation, the Mannich reaction, bromination and nitration are described.
HIV-1 integrase strand-transfer inhibitors: Design, synthesis and molecular modeling investigation
De Luca, Laura,De Grazia, Sara,Ferro, Stefania,Gitto, Rosaria,Christ, Frauke,Debyser, Zeger,Chimirri, Alba
supporting information; experimental part, p. 756 - 764 (2011/03/20)
This study is focused on a new series of benzylindole derivatives with various substituents at the benzene-fused ring, suggested by our 3D pharmacophore model developed for HIV-1 integrase inhibitors (INIs). All synthesized compounds proved to be active in the nanomolar range (6-35 nM) on the strand-transfer step (ST). In particular, derivative 4-[1-(4-fluorobenzyl)- 5,7-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid (8e), presenting the highest best-fit value on pharmacophore model, showed a potency comparable to that of clinical INSTIs GS 9137 (1) and MK-0518 (2). The binding mode of our molecules has been investigated using the recently published crystal structure of the complex of full-length integrase from the prototype foamy virus in complex with its cognate DNA (PFV-IN/DNA). The results highlighted the ability of derivative 8e to assume the same binding mode of MK-0518 and GS 9137.
