Structure de la benzoyl-6 dihydro-2,3 benzoxazole-1,3 one-2, C14H9NO3

Mairesse, G.; Boivin, J.C.; Thomas, Daniel J.; Bermann, M.; Bonte, Jean‐Paul; Lesieur, D.

doi:10.1107/s0108270184006636

Cited by 11 publications

(7 citation statements)

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“…6-Methoxy-BOA (23) [36,37] is a product of natural origin found in corn and endowed with insecticide, antimicrobial, and antifungal properties. until phase II as analgesic [38][39][40][41]. S-14080 (24b, Fig.…”

Section: Therapeutic Applicationsmentioning

confidence: 99%

2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

Poupaert

Carato²,

Colacino³

et al. 2005

CMC

185

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The 2(3H)-benzoxazolone heterocycle and its bioisosteric surrogates (such as 2(3H)-benzothiazolinone, benzoxazinone, etc.) have received considerable attention from the medicinal chemists owing to their capacity to mimic a phenol or a catechol moiety in a metabolically stable template. These heterocycles and pyrocatechol have indeed similar pKa's, electronic charge distribution, and chemical reactivity. Therapeutic applications of this template are very broad, and range from analgesic anti-inflammatory compounds (including PPAR-gamma antagonists) to antipsychotic and neuroprotective anticonvulsant compounds. High affinity ligands have been obtained also for dopaminergic (D2 and D4), serotoninergic (5-HT1A and 5-HT-2A), sigma-1 and sigma-2 receptors. Owing to the high number of positive hits encountered with this heterocycle and its congeners, 2(3H)-benzoxazolone template certainly deserves the title of "privileged scaffold" in medicinal chemistry.

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Section: Therapeutic Applicationsmentioning

confidence: 99%

2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

Poupaert

Carato²,

Colacino³

et al. 2005

CMC

185

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“…As the Friedel-Crafts acylation of 2(3H)-benzothiazolone was previously studied and was found to proceed with high regioselectivity in position 6 [23][24][25], the access to the 5-benzoyl derivatives of 2(3H)-benzothiazolone was realized by us using an alternative route (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antioxidant potential of novel synthetic benzophenone analogues

Tzanova

Gerova

Petrov

et al. 2009

European Journal of Medicinal Chemistry

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“…The precise position of acylation was uniquivocally assigned by x-ray single-crystal defraction in the case of 6-benzoyl-2(3H)-benzothiazolone. 4 The assignment of the position of acylation was extended to other compounds by the use of high-field 1 H-NMR. 3 Keywords: 2(3H)-benzothiazolones; 6-benzoyl-2(3H)-benzothiazolones; acylation reaction; benzoyl chloride; benzoylation; zinc chloride 6-Benzoyl-2(3H)-benzothiazolones are obtained by the reaction of 2(3H)-benzothiazolones with benzoic acid in polyphosporic acid as solvent and catalyst or with benzoyl chloride in the mixture AlCl 3 -DMF.…”

Section: Benzoylation Of 2(3h)-benzothiazolones In the Presence Of 8 mentioning

confidence: 99%

Benzoylation of 2(3H)-benzothiazolones in the Presence of 8 Equivalents of Zinc Chloride in N,N-dimethylformamide

Guenadil

Aichaoui

Liacha

2002

Phosphorus, Sulfur, and Silicon and the Related Elements

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Structure de la benzoyl-6 dihydro-2,3 benzoxazole-1,3 one-2, C14H9NO3

Cited by 11 publications

References 0 publications

2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

Synthesis and antioxidant potential of novel synthetic benzophenone analogues

Benzoylation of 2(3H)-benzothiazolones in the Presence of 8 Equivalents of Zinc Chloride in N,N-dimethylformamide

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Structure de la benzoyl-6 dihydro-2,3 benzoxazole-1,3 one-2, C14H9NO3

Cited by 11 publications

References 0 publications

2(3H)-Benzoxazolone and Bioisosters as &#x201C;Privileged Scaffold&#x201D; in the Design of Pharmacological Probes

2(3H)-Benzoxazolone and Bioisosters as &#x201C;Privileged Scaffold&#x201D; in the Design of Pharmacological Probes

Synthesis and antioxidant potential of novel synthetic benzophenone analogues

Benzoylation of 2(3H)-benzothiazolones in the Presence of 8 Equivalents of Zinc Chloride in N,N-dimethylformamide

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Product

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2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes