Arene-fused 1,2-oxazole N-oxides and derivatives. The impact of the N–O dipole and substitution on their aromatic character and reactivity profile. Can it be a useful structure in synthesis? A theoretical insight

Kozielewicz, Paweł; Tzeli, Demeter; Tsoungas, Petros G.; Zloh, Mire

doi:10.1007/s11224-014-0459-6

Cited by 5 publications

(15 citation statements)

References 87 publications

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“…[68] Ab road range of glutamate receptor ligand binding domain (LBD) X-ray structures are available, including those co-crystalized with isoxazole-based agonists, partial agonists, and antagonists. [69] Spectral data are in line with geometry calculations for the isoxazole ring (see Kozielewicz et al [135] ). [69] Spectral data are in line with geometry calculations for the isoxazole ring (see Kozielewicz et al [135] ).…”

Section: Psychoactive Drugs (Psychotropics)supporting

confidence: 72%

“…The LBD dynamics have been analyzed by NMR, fluorescence and infrared spectroscopies. [69] Spectral data are in line with geometry calculations for the isoxazole ring (see Kozielewicz et al [135] ).…”

Section: Psychoactive Drugs (Psychotropics)supporting

confidence: 72%

“…[127][128][129] Chemical moieties isoelectronic to nitric oxide have been shown to elicit NO-like functions. [135] The dipole NÀOb ond is quite short (withint he range of 1.202-1.242 ,a ss hort as in the NO 2 group), af eature commont oh eteroaromatic Noxides. As as mall endogenousm olecule, NO functions as ac hemical messenger,p articularly in vascular endothelium cells and immune and neural systems.…”

Section: The N-oxide Of Isoxazol(in)ementioning

confidence: 97%

“…[133,134] The NÀOe ntity having ad ipole character,i nduces a p density perturbation in the ring (a larger one upon fusion onto ac arbo(hetero)cycle). [135] The dipole NÀOb ond is quite short (withint he range of 1.202-1.242 ,a ss hort as in the NO 2 group), af eature commont oh eteroaromatic Noxides. [135] The ring NÀOb ond is quite stretched (~1.492 ) and it is slightly shorter in fused derivatives.…”

Section: The N-oxide Of Isoxazol(in)ementioning

confidence: 97%

“…[130] Nitric oxide (NO) is known [131] to be implicated in anumber of important processes in living systems, includingn euromodulation and neurotransmission. [135] The ring NÀOb ond is quite stretched (~1.492 ) and it is slightly shorter in fused derivatives. It plays ac riticalr ole in regulating ad iverse range of physiological processes,i ncluding cellular differentiation and apoptosis.…”

Section: The N-oxide Of Isoxazol(in)ementioning

confidence: 99%

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The Isoxazole Ring and Its N‐Oxide: A Privileged Core Structure in Neuropsychiatric Therapeutics

et al. 2017

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Mental disorders are neuropsychiatric conditions that are marked by unusual or irregular thinking, feelings, or behavior, and lead to distress and/or impaired functions. Major psychiatric conditions are depression, anxiety, and psychoses of various types. Their etiopathogeneses, of a primary or secondary origin, are associated with genetic and environmental factors. They are commonly treated with psychoactive drugs (also known as psychotropics), which target serotonin, dopamine, norepinephrine, glutamate, and nuclear receptors (NRs), including retinoic acid receptor-related orphan receptors (RORs) and other receptors in the central nervous system (CNS). Herein we present a diverse array of isoxazole derivatives, among which are some prominent marketed drugs. Some of the derivatives and forms, including N-oxides, are under either (pre)clinical evaluation or patent protection as new generation of psychotropics, and a few have effective blood-brain barrier (BBB) permeability. Various drug-like isoxazol(in)es and their structural features and efficiency, modified through scaffold hopping, are described and discussed in the context of treating neuropsychiatric conditions.

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