Substituted pyrido[3,2-b]oxazin-3(4H)-ones: synthesis and evaluation of antinociceptive activity

Savelon, L.; Bizot-Espiard, Jean-Guy; Caignard, D. H.; Pfeiffer, Bruno; Renard, Pierre; Viaud, Marie-Claude; Guillaumet, Gérald

doi:10.1016/s0968-0896(97)10005-0

Cited by 17 publications

(7 citation statements)

References 31 publications

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“…For general background to 2-iodo-5-hydroxypyridine derivatives and their applications, see: Cho et al (2003); Hegmann et al (2003); Savelon et al (1998); Wang et al (2012). For the synthesis of the title compound, see: Hutchinson et al (2001); Seton et al (2001 Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 6-ethoxypyridin-1-ium-2-olate

et al. 2014

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In the title compound, C7H9NO2, all non-H atoms are essentially coplanar [r.m.s. deviation = 0.032 Å]. The largest deviation from the plane of the pyridine ring is 0.105 (6) Å for the terminal C atom of the ethoxy group. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers. These dimers are further linked by C—H⋯π interactions and weak π–π interactions between pyridine rings [centroid–centroid distance = 4.023 (1) Å].

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Section: Related Literaturementioning

confidence: 99%

Crystal structure of 6-ethoxypyridin-1-ium-2-olate

et al. 2014

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“…Last years search focused on new analgesic drugs devoid of side effects. A large number of heteropolycyclic compounds were reported and among them several oxazinones displayed particular interest [10,11,12]. In addition, antinociceptive properties of compounds containing an arylpiperazinyl [13,14,15] or an alkylamino moiety [14,16,17] are very often reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Analgesic Effects of 5-[4-(Arylpiperazin-1-yl)alkylamino]-4-benzyl-3-methyl-1,2-oxazin-6-ones

Bebot¹,

Rubat²,

Coudert³

et al. 2011

Arzneimittelforschung

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A series of 5-[4-(arylpiperazin-1-yl)alkylamino]-4-benzyl-3-methyl-1,2-oxaz in-6-ones was synthesized and evaluated for analgesic activity. The structures of these new oxazine derivatives were confirmed by IR, 1H-NMR spectra and by elemental analysis. The three most active compounds, 3c, 3e and 3g possessed significant antinociceptive effects in the phenylbenzoquinone-induced wrigthing test (PBQ-test) in mice, with ED50 values ranging from 19.7 to 68.0 mg/kg i.p. In addition these compounds presented a low toxicity (LD50 > 800 mg/kg i.p.) and did not significantly reduce the spontaneous locomotor activity of mice. They interacted in a synergistic manner with morphine but nevertheless each compound presented its own profile. Thus the analgesic activity of 3c and 3e was naloxone sensitive, suggesting in mu opioidergic mechanism. Otherwise 3c and 3d analgesia was attenuated by oral administration of yohimbine and therefore seemed to be mediated via noradrenergic pathway. Finally, 5-hydroxytryptophan associated to carbidopa only potentiated 3e analgesia, demonstrating an involvement of a serotoninergic mechanism.

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“…1a-c The members of this family are used for treating Parkinson's disease, 1d-e ischemia reperfusion, 2 selective potassium channel openers, 3 antinociceptive, 4 antidepressant 5 and antifungal agent. 6 In addition the fluorescent properties of 1,4-oxazinones are valuable as laser dyes 7 and coupling agent for oxidative hair dyes.…”

Section: Introductionmentioning

confidence: 99%