Day: November 21, 2022

Murugesan, Natesan published the artcileBiphenylsulfonamide endothelin receptor antagonists: discovery of 4′-oxazolyl biphenylsulfonamides as a new class of potent, highly selective ET_A antagonists, Computed Properties of 72571-06-3, the publication is Journal of Medicinal Chemistry (2000), 43(16), 3111-3117, database is CAplus and MEDLINE.

The synthesis and structure-activity relationship (SAR) studies of a series of 4′-oxazolyl-N-(3,4-dimethyl-5-isoxazolyl)[1,1′-biphenyl]-2-sulfonamide derivatives as endothelin-A (ET_A) receptor antagonists are described. The data reveal a remarkable improvement in potency and metabolic stability when the 4′-position of the biphenylsulfonamide is substituted with an oxazole ring. Addnl. 2′-substitution of an acylaminomethyl group further increased the binding activity and provided one of the first subnanomolar ET_A-selective antagonists in the biphenylsulfonamide series (ET_A K_i = 0.2 nM). Among the compounds described, (N-(3,4-dimethyl-5-isoxazolyl)-4′-(2-oxazolyl)[1,1′-biphenyl]-2-sulfonamide; BMS-193884) had the optimum pharmacol. profile and was therefore selected as a clin. candidate for studies in congestive heart failure.

Journal of Medicinal Chemistry published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Computed Properties of 72571-06-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Bredereck, Hellmut published the artcileRing cleavage of oxazoles with 2,4-dinitrophenylhydrazine, Synthetic Route of 20662-83-3, the publication is Chemische Berichte (1960), 2010-15, database is CAplus.

The ring cleavage of oxazoles with 2,4-(O₂N)₂C₆H₃NHNH₂ (I) to the osazones of glyoxal derivatives is described. BzCHBrMe (63 g.), 96 g. HCO₂NH₄, 390 g. HOC₂H, and 45 cc. Ac₂O refluxed 5 hrs. and distilled gave 24 g. 5-methyl-4-phenyloxazole (II), b₁₁ 122°, m. 1°, n²⁰_D 1.5723. BzCH(OH)Ph (53 g.), 225 g. HCONH₂, and 49 g. concentrated H₂SO₄ heated 1 hr. at 100-20° and 2 hrs. at 150° yielded 33.5 g. 4,5-diphenyloxazole (IIa), b_0.002 115°, m. 44°. BzCH₂Br (100 g.) and 50 g. AcNH₂ heated 2 hrs. at 120-40° gave 35 g. 2-methyl-4-phenyloxazole (III), b₁₁ 116°, m. 42.5°. The appropriate oxazole (about 1 g.) in 10 cc. MeOH and 600 cc. reagent solution (cold-saturated solution of I in 2N HCl) kept at room temperature and filtered, and the residue washed with 2N HCl and H₂O, dried, and recrystallized from HCONMe₂ gave the corresponding cleavage product. III gave (during 2 weeks) phenylglyoxal 2,4-dinitrophenylosazone (IV), m. 299-300°, and benzoylcarbinol 2,4-dinitrophenylosazone (V), m. 234-5°. 4-Phenyloxazole (VI) gave (during 6 weeks) IV and V. 2-Methyl-4-carbethoxyoxazole (VII) gave (during 2 days) Et α-acetamido-α-formylacetate 2,4-dinitrophenylhydrazone (VIII), m. 185-6° (EtOAc), and (during 12 days) VIII and [2,4-(O₂N)₂C₆H₃NHN: CH]₂ (IX), m. 328-30°. The appropriate oxazole (about 1 g.) refluxed with 400 cc. reagent solution (1% I in 2N HCl) and worked up in the usual manner gave the derivative of the cleavage product(s) in 75-95% yield. IIa gave [2,4-(O₂N)₂C₆H₃NHN:CPh]₂, m. 310-11° (decomposition), which was also obtained by refluxing 2 g. Bz₂, 5 g. I, and 400 cc. 6N HCl 10 hrs., and boiling the precipitate with 300 cc. EtOAc and recrystallizing it from HCONMe₂. 4,5-Dimethyloxazole, b₇₆₀ 128°, n²⁰_D 1.4281, and 2,4,5-trimethyloxazole, b₁₁ 43°, n²⁰_D 1.4270, yielded similarly [2,4-(O₂N)₂C₆H₃NHN:-CMe]₂, m. 330-3° (decomposition). II, 5-methyl-4-phenyloxazole, and 2,5-dimethyl-4-phenyloxazole gave methylphenylglyoxal 2,4-dinitrophenylosazone, m. 259°. VII gave IX, m. 328-30° (decomposition). III and VI yielded IV, m. 299-300°. 5-Ethyl-4-phenyloxazole and 2-methyl-5-ethyl-4-phenyloxazole yielded ethylphenylglyoxal 2,4-dinitrophenylosazone, m. 226°. 5-Propyl-4-phenyloxazole gave propylphenylglyoxal 2,4-dinitrophenylosazone, m. 244°. 4-Methyl-5-benzyl-, 2,4-dimethyl-5-benzyl-, and 2,5-dimethyl-4-benzyloxazole yielded methylbenzylglyoxal 2,4-dinitrophenylosazone, m. 264°. 4,5-Diethyloxazole, 2-methyl-4,5-diethyloxazole, b₃₀ 76°, n²⁰_D 1.4423, and 2,4,5-triethyloxazole, b₃₀ 85°, n²⁰_D 1.4494, gave [2,4-(O₂N)₂C₆H₃NHN:CEt]₂, m. 290-1°.

Chemische Berichte published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, Synthetic Route of 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Bredereck, H. published the artcileA new synthesis of β-oxocarboxylic acid amides and substituted quinolines, Recommanded Product: 4,5-Dimethyloxazole, the publication is Angewandte Chemie (1959), 32, database is CAplus.

Molar amounts of POCl₃ produce a self-condensation of N,N-dimethylcarboxamides to β-oxo-N,N-dimethylcarboxamides which then react with aromatic amines and POCl₃ to yield substituted 2-dimethylaminoquinolines. Thus, from acetic, propionic, and butyric acid dimethylamides are obtained the corresponding α-acyl-N,N-dimethylcarboxamides. The acetylacetic acid dimethylamide and aniline give a moderate yield of 2-dimethylamino-4-methylquinoline, obtained in better yield starting from β-dimethylaminocrotonic acid N,N-dimethylamide.

Angewandte Chemie published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, Recommanded Product: 4,5-Dimethyloxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Brown, Desmond J. published the artcileSpectra, ionization, and deuteration of oxazoles and related compounds, HPLC of Formula: 20662-83-3, the publication is Journal of the Chemical Society [Section] B: Physical Organic (1969), 270-6, database is CAplus.

The 1H N.M.R. spectra of oxazole, its derivatives and some related compounds in nonpolar, polar, and protonating media are discussed. The pKa values for oxazole (0.8, measured by the chem. shifts of H-2 in acidic media) and its derivatives show that the nucleus is far less basic than previously supposed, primarily owing to the powerful inductive effect of the O atom. The uv spectra of 2,5- and 2,4-diphenyloxazole indicate through-conjugation only in the former. This fact and other data suggest that oxazoles should be considered more as conjugated dienes than as fully aromatic compounds The rates for the 2-deuteration of simple oxazoles increase with the alkalinity; oxazole also undergoes 5- but not 4-deuteration under extreme conditions. On these grounds, the electron-distribution of the 3 C atoms of oxazole is clearly in the order 4 > 5 > 2. This is confirmed by the chem. shifts of the resp. protons and the pKa values of 2-, 4-, and 5-carboxyoxazole. Isoxazole (pKa – 2.03) is a much weaker base than previously reported.

Journal of the Chemical Society [Section] B: Physical Organic published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, HPLC of Formula: 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Wen, Shu′an published the artcileComparison of the in vitro activity of linezolid, tedizolid, sutezolid, and delpazolid against rapidly growing mycobacteria isolated in Beijing, China, Computed Properties of 1219707-39-7, the publication is International Journal of Infectious Diseases (2021), 253-260, database is CAplus and MEDLINE.

The natural resistance of rapidly growing mycobacteria (RGM) to multiple antibiotics renders the treatment of the infections caused less successful. The objective of this study was to evaluate the in vitro susceptibilities of four oxazolidinones against different RGM species. The microplate alamarBlue assay was performed to identify the min. inhibitory concentrations (MICs) of four oxazolidinones as delpazolid, sutezolid, tedizolid, and linezolid for 32 reference strains and 115 clin. strains of different RGM species. The MIC breakpoint concentration was defined as 16 μg/mL for linezolid. Next, the gene fragments associated with oxazolidinone resistance were amplified and sequenced, and mutations were defined in contrast with the sequences of the reference strains. Tedizolid showed the strongest inhibitory activity against the Mycobacterium abscessus isolates. Delpazolid exhibited better antimicrobial activity against the Mycobacterium fortuitum isolates when compared to linezolid, with 4-fold lower MIC values. The protein alignment and structure-based anal. showed that there might be no correlation between oxazolidinone resistance and mutations in the rplC, rplD, and 23S rRNA genes in the tested RGM. Tedizolid had the strongest inhibitory activity against M. abscessus in vitro, while delpazolid presented the best inhibitory activity against M. fortuitum. This provides important insights into the potential clin. application of oxazolidinones to treat RGM infections.

International Journal of Infectious Diseases published new progress about 1219707-39-7. 1219707-39-7 belongs to oxazolidine, auxiliary class Other Aliphatic Heterocyclic,Oxazolidine,Chiral,Fluoride,Benzene,Amide,Alcohol,Anti-infection, name is (R)-3-(3-Fluoro-4-(1-methyl-5,6-dihydro-1,2,4-triazin-4(1H)-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one, and the molecular formula is C8H14O4, Computed Properties of 1219707-39-7.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Yonezawa, Yasushi published the artcileDesymmetrization of meso-methylenecyclopropanes by a palladium-catalyzed asymmetric ring-opening bis(alkoxycarbonylation) reaction, Name: (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Tetrahedron: Asymmetry (2014), 25(12), 936-943, database is CAplus.

Desymmetrization of various meso-(methylene)cyclopropane derivatives was accomplished by a palladium-catalyzed asym. ring-opening bis(alkoxycarbonylation) reaction using a chiral bis[oxazole] ligand. The reaction proceeded smoothly in the presence of copper(I) triflate under carbon monoxide and oxygen at ambient pressure to give the corresponding optically active α-(methylene)glutarate derivatives with up to 60% ee. Desymmetrization of protected meso-(3-methylenecyclopropane-1,2-diyl)dimethanol derivatives was also carried out to give enantioenriched highly oxygen-functionalized α-(methylene)glutaric acid esters. Under optimized conditions the synthesis of the target compounds was achieved using palladium chloride (PdCl₂) and , (4S,4′S)-4,4′,5,5′-tetrahydro-4,4′-bis(phenylmethyl)-2,2′-bioxazole as catalyst and ligand combination. Starting materials included 7-(methylene)bicyclo[4.1.0]heptane, (1R,8S)-rel-9-(methylene)bicyclo[6.1.0]nonane, rel-1,1′-[[(1R,2S)-3-methylene-1,2-cyclopropanediyl]bis(methyleneoxymethylene)]bis[benzene].

Tetrahedron: Asymmetry published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H10O4S2, Name: (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Qin, Xurong published the artcileCopper(II)-catalyzed dehydrogenative cross-coupling between two azoles, COA of Formula: C9H6BrNO, the publication is Journal of Organic Chemistry (2012), 77(17), 7677-7683, database is CAplus and MEDLINE.

The copper(II)-catalyzed dehydrogenative coupling between two different azoles for the preparation of unsym. biazoles e. g., I has been developed. The current catalytic system can effectively control the chemoselectivity for heterocoupling over homocoupling.

Journal of Organic Chemistry published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, COA of Formula: C9H6BrNO.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Mahadevan, Kritika published the artcileKey Odor Impact Compounds in Three Yeast Extract Pastes, Application In Synthesis of 20662-83-3, the publication is Journal of Agricultural and Food Chemistry (2006), 54(19), 7242-7250, database is CAplus and MEDLINE.

Three types of yeast extract pastes from 2 different suppliers were compared. Compounds responsible for the key odors include 2-methyl-3-furanthiol, 2-methyl-3-methyldithiofuran, methional, 1-octen-3-one, di-Me trisulfide together with a number of pyrazines, thiophenes, and aliphatic compounds The 3 types of yeast extract paste differed in the intensity of their main odors and, in particular, those caused by furans, furanthiols, and heterocyclic sulfur compounds Not only do pastes from different suppliers differ in terms of odor volatiles, but so do different treatments and batches of yeast extract from one supplier. The results suggest that normal variations in the concentrations of precursors and processing conditions may cause variations in the flavor of the end product.

Journal of Agricultural and Food Chemistry published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, Application In Synthesis of 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Bento-Silva, Andreia published the artcileComprehensive two-dimensional gas chromatography as a powerful strategy for the exploration of Broas volatile composition, SDS of cas: 20662-83-3, the publication is Molecules (2022), 27(9), 2728, database is CAplus and MEDLINE.

Broa is a Portuguese maize bread with characteristic sensory attributes that can only be achieved using traditional maize varieties. This study intends to disclose the volatile compounds that are mainly associated with the baking process of broas, which can be important contributors to their aroma. Twelve broas were prepared from twelve maize flours (eleven traditional maize varieties and one com. hybrid). Their volatile compounds were analyzed by GCxGC-ToFMS (two-dimensional gas chromatog. coupled with time-of-flight mass spectrometry) for an untargeted screening of the chem. compounds mainly formed during baking. It was possible to identify 128 volatiles that belonged to the main chem. families formed during this stage. Among these, only 16 had been previously detected in broas. The most abundant were furans, furanones, and pyranones, but the most relevant for the aroma of broas were ascribed to sulfur-containing compounds, in particular di-Me trisulfide and methanethiol. Pyrazines might contribute neg. to the aroma of broas since they were present in higher amounts in the com. broa. This work constitutes the most detailed study of the characterization of broas volatile compounds, particularly those formed during the Maillard reaction. These findings may contribute to the characterization of other maize-based foodstuffs, ultimately improving the production of foods with better sensory features.

Molecules published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, SDS of cas: 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Beatty, Joel W. published the artcileA scalable and operationally simple radical trifluoromethylation, Product Details of C9H6BrNO, the publication is Nature Communications (2015), 7919pp., database is CAplus and MEDLINE.

The large number of reagents that was developed for the synthesis of trifluoromethylated compounds was a testament to the importance of the CF₃ group as well as the associated synthetic challenge. Current state-of-the-art reagents for appending the CF₃ functionality directly were highly effective; however, their use on preparative scale had minimal precedent because they required multistep synthesis for their preparation, and/or were prohibitively expensive for large-scale application. For a scalable trifluoromethylation methodol., trifluoroacetic acid and its anhydride represented an attractive solution in terms of cost and availability; however, because of the exceedingly high oxidation potential of trifluoroacetate, previous endeavours to use this material as a CF₃ source was required the use of highly forcing conditions. A strategy for the use of trifluoroacetic anhydride for a scalable and operationally simple trifluoromethylation reaction using pyridine N-oxide and photoredox catalysis to affect a facile decarboxylation to the CF₃ radical was reported.

Nature Communications published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Product Details of C9H6BrNO.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem