New calcium antagonists: synthesis, X-ray analysis, and smooth muscle relaxing effect of 3-[ O -(Benzyl-substituted)-oximino-ethers]-hexahydroazepin-2,3-diones

Oximes of Seven-Membered Heterocyclic Compounds Containing One Heteroatom

“…Beside this O-ethers of azepane oximes are obtained from the corresponding carbonyl compounds and O-alkyl derivatives of hydroxylamine in the presence of pyridine in methanol [43], pyridine in ethanol [9] or sodium acetate in acetic acid [44]. Reaction of oxime of azepan-2-one with dimethyl acetylenedicarboxylate (DMAD) in acetonitrile gives a mixture of Eand Z-isomers of oxime ethers 28 and 29 in the ratio 8:1 [45].…”

Synthesis of new azepanedione oximes

“…The O-aryl-hydroxylamines used for the synthesis of the azepanedione oximes, were prepared according to Garoufalias et al [8] and their physicochemical properties were reported in a previous work [2], l-Benzylazepane-2,3-dione 3-(0-substituted oximes) 8a-f were isolated as mixture of Zand Ε isomers (Table 1) in which the Ε isomer predominates. Ratio of isomers were assessed by NMR spectroscopy on the basis of the chemical shifts observed for protons on carbon adjacent to the oxime double bond [9], In accordance with assignments reported in literature for several oximes and alkylated oximes [10], Ζ isomers are more downfield than their Ε counterparts.…”

“…Through studies of amide or lactame derivatives highlighted the interesting pharmacological properties, in particular actions on central nervous system via stimulation of various ion channels [1], The synthesis of 3-[0-(benzyl)oximinoether] hexahydroazepin-2,3-diones previously reported [2] showed that they are capable to relax both rat trachea and human bronchus. The oximinoether or oxime derivatives exhibited marked antinociceptive and anticonvulsant activities [3], This work describes synthesis and physicochemical properties of l-benzylazepane-2,3-dione 3-(0-substituted oximes) with attribution of their Ζ and Ε configurations and 4-(phenylhydrazono)azepane-2,3-dione 3-(0-substituted oximes) resulting of condensation with various O-arylhydroxylamines from the corresponding azepan-2-ones and 1 -benzylazepan-2-ones.…”