497058-33-0Relevant academic research and scientific papers
Exploration of benzofuran-based compounds as potent and selective Plasmodium falciparum glycogen synthase kinase-3 (PfGSK-3) inhibitors
Moolman, Chantalle,van der Sluis, Rencia,Beteck, Richard M.,Legoabe, Lesetja J.
, (2021/04/09)
Plasmodium falciparum glycogen synthase kinase-3 (PfGSK-3) has been identified as a potential target for the development of novel drugs against multi-drug resistant malaria. A series of benzofuran-based compounds was synthesised and evaluated as inhibitors of recombinantly expressed and purified PfGSK-3 and human glycogen synthase kinase-3 beta (HsGSK-3β). Of this series, five compounds (5k, 5m, 5p, 5r, 5s) preferentially inhibited PfGSK-3, with four of these compounds exhibiting IC50 values in the sub-micromolar range (0.00048–0.440 μM). Evaluation of the structure-activity relationships required for PfGSK-3 selective inhibition indicated that a C6-OCH3 substitution on ring A is preferred, while the effect of the ring B substituent on activity, in decreasing order is: C4′-CN > C4′-F > C3′-OCH3 > C3′,4′-diCl. To date, development of PfGSK-3 inhibitors has been limited to the 4-phenylthieno[2,3-b]pyridine class. Chalcone-based scaffolds, such as the benzofurans described herein, are promising new hits which can be explored for future design of PfGSK-3 selective inhibitors.
Synthesis and evaluation of methoxy substituted 2-benzoyl-1-benzofuran derivatives as lead compounds for the development adenosine A1 and/or A2A receptor antagonists
Aucamp, Janine,Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Terre'Blanche, Gisella
, (2019/12/25)
A series of fourteen methoxy substituted 2-benzoyl-1-benzofuran derivatives were synthesised and their affinities determined for adenosine A1 and A2A receptors via radioligand binding assays to establish the structure activity relationships pertinent for A1 and A2A affinity. Compound 3j (6,7-dimethoxybenzofuran-2-yl)(3-methoxyphenyl)methanone exhibited A1 affinity (A1Ki (rat) = 6.880 μM) as well as A2A affinity (A2AKi (rat) = 0.5161 μM). Compounds 3a–b & 3i–k exhibited selective affinity towards A1 with Ki values below 10 μM. The results indicate that C6,7-diOCH3 substitution on ring A in combination with meta (C3′)–OCH3 substitution on ring B is beneficial for A1 and A2A affinity and activity. Compounds 3a–b & 3j–k showed low cytotoxicity. Upon in vitro and in silico evaluation, compound 3j may be considered lead-like (i.e. a molecular entity suitable for optimization) and, thus, of value in the design of novel, potent and selective adenosine A1 and A2A receptor antagonists.
A new synthetic route of 2-aroyl- and 2-benzyl-benzofurans and their application in the total synthesis of a metabolite isolated from dorstenia gigas
Correa, Christian,Cruz, Maria Del Carmen,Jimnez, Fabiola,Zepeda, L. Gerardo,Tamariz, Joaqun
experimental part, p. 991 - 999 (2009/04/06)
The Lewis acid-catalyzed cyclization of the (Z)-3-(dimethylamino)-2- aryloxy-1-arylprop-2-en-1-ones 4ah leads to a regioselective and short synthesis of 2-aroylbenzofurans 2ah. The WolffKishner reduction of the latter yielded a series of substituted 2-ben
Cyclic and acyclic propenones for treating CNS disorders
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Page/Page column 20, (2008/06/13)
The invention relates to novel cyclic and non-cyclic propenone derivatives as well as their pharmaceutically acceptable slats. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are useful as medicaments.
