Tag: M.W=150-200

Kim, Su Jeong published the artcileThe tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold, Related Products of isoxazole, the publication is Bioorganic & Medicinal Chemistry (2018), 26(14), 3882-3889, database is CAplus and MEDLINE.

Thirteen (Z)-4-(substituted benzylidene)-3-phenylisoxazol-5(4H)-ones were designed to confirm the geometric effect of the double bond of the β-phenyl-α, β-unsaturated carbonyl scaffold on tyrosinase inhibitory activity. Compounds 1a-1m, which all possessed the (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold, were synthesized using a tandem reaction consisting of an isoxazolone ring formation and a Knoevenagel condensation, and three starting materials, Et benzoylacetate, hydroxylamine and benzaldehydes. Some of the compounds showed inhibitory activity against mushroom tyrosinase as potent as compounds containing the “(E)”-β-phenyl-α, β-unsaturated carbonyl scaffold. Compounds 1c and 1m showed greater inhibitory activity than kojic acid: IC₅₀ = 32.08 ± 2.25 μM for 1c; IC₅₀ = 14.62 ± 1.38 μM for 1m; and IC₅₀ = 37.86 ± 2.21 μM for kojic acid. A kinetic study indicated that 1m inhibited tyrosinase in a competitive manner and that it probably binds to the enzyme’s active site. In silico docking simulation supported binding of 1m (-7.6 kcal/mol) to the active site of tyrosinase with stronger affinity than kojic acid (-5.7 kcal/mol). Similar results were obtained using cell-based assays, and in B16F10 cells, compound 1m dose-dependently inhibited tyrosinase activity and melanogenesis. These results indicate the anti-melanogenic effect of compound 1m is due to the inhibition of tyrosinase and (Z)-isomer of the β-phenyl-α, β-unsaturated carbonyl scaffold can, like its congener the (E)-isomer, act as an excellent scaffold for tyrosinase inhibition.

Bioorganic & Medicinal Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, Related Products of isoxazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Liang, Hong-Wen published the artcileAtom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones, SDS of cas: 1076-59-1, the publication is Angewandte Chemie, International Edition (2018), 57(20), 5720-5724, database is CAplus and MEDLINE.

An unprecedented silver-catalyzed difunctionalization of the isocyano group with cyclic oximes is described. This method allows efficient and atom-economic assembly of a vast array of structurally novel and interesting pyrimidinediones, and tolerates a range of functionalities. The resulting products can be easily converted into some useful compounds Furthermore, the method can also be applied for the late-stage modification of a few biol. active mols.

Angewandte Chemie, International Edition published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, SDS of cas: 1076-59-1.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Shen, Yao-Bin published the artcileHexafluoroisopropanol-Mediated Redox-Neutral α-C(sp³)-H Functionalization of Cyclic Amines via Hydride Transfer, SDS of cas: 1076-59-1, the publication is Journal of Organic Chemistry (2020), 85(4), 1915-1926, database is CAplus and MEDLINE.

Hexafluoroisopropanol has been demonstrated as the versatile promoter for redox-neutral α-C(sp³)-H functionalization of cyclic amines via the cascade [1,5]-hydride transfer/cyclization strategy. A wide range of cyclic amines are functionalized into bioactive tetrahydroquinolines, quinazolines, benzoxazines, and benzotriazepines in moderate to excellent yields. This protocol features additive-free conditions, operational simplicity, and wide substrate scope.

Journal of Organic Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C14H14, SDS of cas: 1076-59-1.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Too, Pei-Chui published the artcileRhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes, COA of Formula: C9H7NO2, the publication is Organic Letters (2010), 12(24), 5688-5691, database is CAplus and MEDLINE.

A synthetic method of isoquinolines, e.g., I from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp^*RhCl₂]₂-NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C-H vinylation via ortho-rhodation and C-N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

Organic Letters published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C14H26O2, COA of Formula: C9H7NO2.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Lang, Jian published the artcileDifunctionalization of the Isocyano Group: Atom-Economic Synthesis of Pyrimidinediones, Recommanded Product: 3-Phenylisoxazol-5(2H)-one, the publication is Synlett (2019), 30(3), 252-256, database is CAplus.

The exploration of synthetic methods involving the formation of new chem. bonds at both the nitrogen and carbons atoms of the isocyano group would largely enrich the structural diversity of compounds Herein, we disclosed a silver-catalyzed difunctionalization of the isocyano group with cyclic oximes. This method can generate a great array of structurally novel and interesting pyrimidinediones and features excellent atom economy, good functional group compatibility, and amenability to late-stage modifications.

Synlett published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, Recommanded Product: 3-Phenylisoxazol-5(2H)-one.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Sukanya, S. H. published the artcileAn efficient p-TSA catalyzed synthesis of some new substituted-(5-hydroxy-3-phenylisoxazol-4-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-dione/3,3-dimethyl-2H-xanthen-1(9H)-one scaffolds and evaluation of their pharmacological and computational investigations, Related Products of isoxazole, the publication is Journal of Molecular Structure (2022), 133587, database is CAplus.

An easy and efficient protocol for the synthesis of a series of some novel substituted-(5-hydroxy-3-phenylisoxazol-4-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-diones, I [R = H, 5-methoxy, 7-nitro, etc.] /3,3-dimethyl-2H-xanthen-1(9H)-one derivatives II [R¹ = H, 5-methoxy, 7-nitro, etc.] via p-TSA catalyzed reaction of 1,3-dimethylbarbituric acid/dimedone, substituted salicylaldehyde/2-hydroxy-naphthaldehyde and 3-phenyl-5-isoxazolone was administered in refluxed temperature in the presence of aqueous ethanol was reported. All the obtained compounds I and II were evaluated for their therapeutic effect using pharmacol. and computational investigations, and structures were confirmed using anal. and spectroscopic techniques. Absorption spectra were recorded in six different solvents such as polar protic, polar aprotic, and nonpolar solvents, λ_max of all the compounds I and II appeared at bathochromic shift towards the longer wavelength due to the π-π* & n-π* transitions. The results of pharmacol. investigations revealed that the compounds I [R = C₄H₄, 7-bromo] and II [R¹ = C₄H₄] possessed excellent cytotoxicity efficacy, and compounds I [R = C₄H₄, 7-nitro] andII [R¹ = C₄H₄, 7-nitro] showed better anti-TB efficiency. The SAR study shows the importance of the electron-withdrawing group and addnl. Ph nucleus enhancing the biol. potency of the compounds The results of the in silico mol. docking studies revealed that the compounds I [R = C₄H₄] and II [R¹ = C₄H₄] effectively interacted with P38 MAP kinase (-10.9 kcal/mol) and InhA-Enoyl-Acyl Carrier Protein Reductase (-11.0 kcal/mol), resp. Further, the mol. dynamics (MD) simulation studies revealed that the compounds I [R = C₄H₄] and II [R¹ = C₄H₄] stabilized the macromol. structures in terms of RMSD, RMSF, the Radius of gyration, and SASA compared to their unbound and standard compound bound structures. DFT study suggested that the compounds are chem. and biol. more reactive due to less energy gap.

Journal of Molecular Structure published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C11H8O3, Related Products of isoxazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Sukanya, S. H. published the artcileFacile TiO₂ NPs catalysed synthesis of substituted-4-Hydroxy/methoxy benzylidene derivatives as potent antioxidant and anti-tubercular agents, Name: 3-Phenylisoxazol-5(2H)-one, the publication is Chemical Data Collections (2021), 100713, database is CAplus.

In this work, a facile synthesis of a series of substituted-4-hydroxy/methoxy benzylidene derivatives e.g., I via Knoevenagel condensation reaction of different active methylene compounds e.g., II with 4-hydroxy/methoxy benzaldehyde under reflux condition in aqueous EtOH using catalytic amount of TiO₂ NPs was reported. The structures of all the obtained compounds were confirmed by anal. and spectroscopic methods and screened for their antioxidant and anti-tubercular activities. Antioxidant activity results revealed that, the compound I with IC₅₀ value 105.48μg/mL showed very effective DPPH scavenging activity and compound III with IC₅₀ value 129.72μg/mL exhibited most effective nitric oxide radical scavenging activity compared to the reference standard BHT and ascorbic acid resp. From the results of anti-TB activity, compound IV displayed a more sensitivity at 25μg/mL. Furthermore, synthesized compounds were assessed for mol. docking studies on the target enzymes Human peroxiredoxin 5 and enoyl-ACP reductase and they were emerged has an active antioxidant and anti-TB agents with least binding energy -5.8 and -8.0 kJ mol^-1 resp.

Chemical Data Collections published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C44H28ClFeN4, Name: 3-Phenylisoxazol-5(2H)-one.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Arora, Komal published the artcileSynthesis, configurational analysis and antimicrobial activity of imidazolidinone, thiazolidinone and isoxazolone derivatives of 9,10-phenanthrenequinone, Category: isoxazole, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2011), 50B(1), 83-88, database is CAplus.

Knoevenagel-type condensations of phenanthrenequinone with imidazolidinones, thiazolidinones, and isoxazolone were described. The newly synthesized products were characterized by spectral data. The exclusive formation of anti-configuration of the mono-condensation product was explained on the basis of AM1 calculations Some of the products were screened for antimicrobial activity.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, Category: isoxazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Terent’ev, Alexander O. published the artcileSelective Oxidative Coupling of 3H-Pyrazol-3-ones, Isoxazol-5(2H)-ones, Pyrazolidine-3,5-diones, and Barbituric Acids with Malonyl Peroxides: An Effective C-O Functionalization, Application of 3-Phenylisoxazol-5(2H)-one, the publication is ChemistrySelect (2017), 2(11), 3334-3341, database is CAplus.

Oxidative functionalization of 3H-pyrazol-3-ones, isoxazol-5(2H)-ones, pyrazolidine-3,5-diones, and barbituric acids by malonyl peroxides results exclusively in C-O coupling products. Traditional hydroxylation, formation of carbonyl groups, or oxidative destruction of the heterocyclic ring are not observed Under optimized reactions conditions – fluorinated alcs. as activating medium and at room temperature (20 – 25°) – the selective C-O coupling proceeds in high yields (up to 94 %). The oxidative insertion into the enolizable C-H bond of the substrate is mechanistically viewed as a nucleophilic attack by the heterocycle onto the electrophilically activated malonyl peroxides. For heterocyclic substrates with an active methylene group – 3H-pyrazol-3-ones, isoxazol-5(2H)-ones, and barbituric acids – both C-H bonds are oxidized to afford double oxidative C-O coupling products in good yields (up to 72 %).

ChemistrySelect published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H9NO6S, Application of 3-Phenylisoxazol-5(2H)-one.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Toran, Ricardo published the artcileOrganocatalytic Enantioselective 1,6-aza-Michael Addition of Isoxazolin-5-ones to p-Quinone Methides, Quality Control of 1076-59-1, the publication is European Journal of Organic Chemistry (2020), 2020(5), 627-630, database is CAplus.

A thiourea-Bronsted base bifunctional catalyst allowed the enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides to give isoxazolin-5-ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses. To the best of our knowledge this reaction represents the first example of enantioselective N-alkylation of isoxazolin-5-ones as well as the first example of enantioselective 1,6-aza-Michael reaction involving p-quinone methides.

European Journal of Organic Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C20H40O2, Quality Control of 1076-59-1.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem