29814-12-8Relevant articles and documents
Analgesic Effects of 5-Alkyloxy-4-amino-2(5H)-furanones as Cholecystokinin-2 Antagonists
Lattmann, Eric,Sattayasai, Jintana,Schwalbe, Carl H.,Boonprakob, Yodchai,Dunn, Simon,Fajana, Feyisayo,Lattmann, Pornthip
, p. 456 - 465 (2016)
4-Amino-2(5H)-furanones were synthesized in high yields over two synthetic steps from readily available mucochloric acid. These 5-alkyloxy-4-amino-2(5H)-furanones were screened in a [125]I-CCK-8 radioligand receptor binding assay for CCK2 affinity and novel active ligands in the nanomolar range were identified. SAR was optimized leading to the cyclohexyl derivative 25 with an IC50 of 27 nM. Furanone 18 was obtained as a stable crystalline material with an IC50 of 85 nM, but had a higher CCK2 selectivity. It was subsequently tested in the isolated Guinea pig ileum assay with sulfated CCK8, and the CCK antagonizing properties of the ligand were confirmed. The CCK2 selective antagonist 18 was found to potentiate analgesia in the tail flick assay in mice, for the strong opiate morphine, the partial opiate agonist tramadol and the tricyclic antidepressant desimipramine. 4-Amino-2(5H)-furanones were synthesized and screened in a [125]I-CCK-8 radioligand receptor binding assay for CCK2 affinity. SAR optimization led to furanone 18 (IC50 = 85 nM). It was confirmed as antagonist in the isolated Guinea pig ileum assay and it was found to potentiate analgesia in the tail flick assay in mice, with morphine, tramadol, and desimipramine at 0.5 mg/kg.
NOVEL 4-AMINO-2(5H)-FURANONES
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Page 21-22, (2008/06/13)
The present invention relates to compounds of formula (I): wherein X is selected from hydrogen, a halogen, a substituted or unsubstituted cyclic and heterocyclic moiety, substituted or unsubstituted, linear or branched alkyl, alkyloxy, alkylcarbonyl, alky
7-Chloro-7-cyanobicyclooctan-8-one (Prepared from Chlorocyanoketene)
Fishbein, Paul L.,Moore, Harold W.
, p. 3283 - 3288 (2007/10/02)
The synthesis of 7-chloro-7-cyanobicyclooctan-8-one is described.This compound was prepared in 73percent yield from the cycloaddition of chlorocyanoketene to cyclohexene.The ketene, in turn, was generated from the thermolysis of 4-azido-3-chloro-5-isopropoxy-2(5H)-furanone.