19283-70-6Relevant articles and documents
Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate
Gayler, Kevin M.,Lambert, Kyle M.,Wood, John L.
, p. 3154 - 3159 (2019)
The 2,5-diketopiperazine (DKP) moiety is a core feature of many natural products and medicinally relevant scaffolds. As part of our efforts directed towards a total synthesis of penicisulfuranol B, we have developed and report herein: (1) the preparation of an N-hydroxy diketopiperazine intermediate accessible via a molybdenum-mediated oxidation of a parent diketopiperazine, and (2) further synthetic studies leading to a novel spirocyclic dihydrobenzofuran-containing diketopiperazine.
Synthetic studies on naturally occurring coumarins. I. A convenient synthesis of 5,8-dimethoxy- and 7,8-dimethoxycoumarins
Ishii,Kenmotsu,Dopke,Harayama
, p. 1770 - 1772 (1992)
The coumarin isolated from Artemisia carvifolia Wall was proved synthetically to be 7,8-dimethoxycoumarin and not 5,8-dimethoxycoumarin as previously proposed. 3,4-Dimethoxy- and 3,6-dimethoxysalicylaldehydes gave the corresponding coumarins in good yield by the method using phosphorane reagent in N,N-diethylaniline under reflux.
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.
