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Issue 2, 2019
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Methoxy substituted 2-benzylidene-1-indanone derivatives as A1 and/or A2A AR antagonists for the potential treatment of neurological conditions

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Abstract

A prior study reported on hydroxy substituted 2-benzylidene-1-indanone derivatives as A1 and/or A2A antagonists for the potential treatment of neurological conditions. A lead compound (1a) was identified with both A1 and A2A affinity in the micromolar range. The current study explored the structurally related methoxy substituted 2-benzylidene-1-indanone derivatives with various substitutions on ring A and B of the benzylidene indanone scaffold in order to enhance A1 and A2A affinity. This led to compounds with both A1 and A2A affinity in the nanomolar range, namely 2c (A1Ki (rat) = 41 nM; A2AKi (rat) = 97 nM) with C4-OCH3 substitution on ring A together with meta (3′) hydroxy substitution on ring B and 2e (A1Ki (rat) = 42 nM; A2AKi (rat) = 78 nM) with C4-OCH3 substitution on ring A together with meta (3′) and para (4′) dihydroxy substitution on ring B. Additionally, 2c is an A1 antagonist. Consequently, the methoxy substituted 2-benzylidene-1-indanone scaffold is highly promising for the design of novel A1 and A2A antagonists.

Graphical abstract: Methoxy substituted 2-benzylidene-1-indanone derivatives as A1 and/or A2A AR antagonists for the potential treatment of neurological conditions

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Supplementary files

Article information


Submitted
28 Oct 2018
Accepted
06 Jan 2019
First published
08 Jan 2019

Med. Chem. Commun., 2019,10, 300-309
Article type
Research Article

Methoxy substituted 2-benzylidene-1-indanone derivatives as A1 and/or A2A AR antagonists for the potential treatment of neurological conditions

H. D. Janse van Rensburg, L. J. Legoabe, G. Terre'Blanche and M. M. Van der Walt, Med. Chem. Commun., 2019, 10, 300
DOI: 10.1039/C8MD00540K

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