Month: November 2022

Barnes, David M. published the artcileDevelopment of a catalytic, asymmetric Michael addition in the synthesis of endothelin antagonist ABT-546, Recommanded Product: (3aS,3a’S,8aR,8a’R)-2,2′-(Cyclobutane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole), the publication is ACS Symposium Series (2002), 45-59, database is CAplus.

The selective endothelin A antagonist ABT-546 I is prepared enantioselectively on large (13 mol) scale using the catalytic addition of ketoester II to nitrostyrene III in the presence of bisoxazoline IV and magnesium triflate as the key step. E.g., magnesium triflate is hydrated in chloroform; ligand IV is added and the mixture stirred for about 1 h to generate the active catalyst. E.g., II and III are added with mol. sieves to give a 0.2 M solution; N-methylmorpholine is added as an amine cocatalyst when the mixture is dry and the reaction is stirred to give intermediate V in 83% yield and 88% ee on 13 mol scale. The Michael addition reaction was extensively optimized. No other bisoxazoline ligand tested was as effective as IV. Other magnesium salts with coordinating anions are less effective as catalysts. An amine cocatalyst is necessary for high stereoselectivity in the Michael addition Chloroform is the best solvent for the Michael addition, although toluene also is effective. The presence of water during the generation of the active catalyst is necessary for high yields, but the presence of water during the reaction inhibits the reaction and decreases selectivity; the use of mol. sieves is necessary to obtain product in high yields. The purity of the substrates in the enantioselective Michael addition is important for good rates and selectivities. The scope of the asym. Michael addition reaction of ketoesters to nitroolefins to give nitroketoesters is extended to other ketoester and malonate nucleophiles such as di-Et malonate, and to other nitroolefins such as β-nitrostyrene and 1-nitro-1-heptene.

ACS Symposium Series published new progress about 182122-10-7. 182122-10-7 belongs to isoxazole, auxiliary class BOX or PyBox,BOX or PyBox, name is (3aS,3a’S,8aR,8a’R)-2,2′-(Cyclobutane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole), and the molecular formula is C24H22N2O2, Recommanded Product: (3aS,3a’S,8aR,8a’R)-2,2′-(Cyclobutane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole).

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

Wang, Lei published the artcileSite-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes, Category: isoxazole, the publication is Synthesis (2016), 48(5), 737-750, database is CAplus.

A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes was responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system was able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chem.

Synthesis published new progress about 57103-14-7. 57103-14-7 belongs to isoxazole, auxiliary class Fused Tricycles,Carbazoles, name is 9-(4-Fluorophenyl)-9H-carbazole, and the molecular formula is C8H6ClF, Category: isoxazole.

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

Esmaeilpour, Mohsen published the artcileFacile synthesis of 1- and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe₃O₄@SiO₂ nanoparticles, Recommanded Product: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, the publication is Journal of Molecular Catalysis A: Chemical (2014), 18-29, database is CAplus.

A new method for preparing functionalized superparamagnetic Fe₃O₄@SiO₂ possessing high saturation magnetization was reported. Magnetite particles were prepared by simple co-precipitation method in aqueous medium, and then Fe₃O₄@SiO₂ nanosphere was synthesized by using nano Fe₃O₄ as the core, TEOS as the silica source and polyethylene glycol (PEG 1000) as the surfactant. Then, the silica-coated Fe₃O₄ nanoparticles were covered with ligand complex of Cu(II). The functionalized magnetic core-shell nanoparticles (MNPs) were investigated by Fourier transform IR spectroscopy, transmission electron microscopy, SEM, X-ray diffraction, thermogravimetric anal., dynamic light scattering and N₂ adsorption/desorption. Also, its Cu content was determined by inductively coupled plasma (ICP) analyzer. Then, the immobilized copper complex was used as an efficient catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines in good to excellent yields. The results show that the supported catalyst could be conveniently recovered through the use of an external magnetic field and reused for subsequent reactions for at least 6 times with less deterioration in catalytic activity.

Journal of Molecular Catalysis A: Chemical published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Recommanded Product: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole.

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

Lavanya, M. published the artcileSynthesis, crystal structure, DNA binding and antitumor studies of β-diketonate complexes of divalent copper, zinc and palladium, Related Products of isoxazole, the publication is Inorganica Chimica Acta (2018), 76-86, database is CAplus.

This paper reports a simple approach for the synthesis of three pairs of novel mononuclear β-diketonate complexes of copper(II), zinc(II) and palladium(II) from monobasic O-O donor ligands 3-phenyl-4-fluorobenzolyl-5-isoxazolone (HL¹) and 3-phenyl-4-toluyl-5-isxoazolone (HL²). The synthesized compounds were characterized by FTIR, ESI/FAB mass, ¹H NMR, UV-visible and thermogravimetric analyses. The free ligand HL¹ and the copper(II) complex, [Cu(L²)₂(CH₃OH)₂] are unambiguously characterized by single crystal x-ray diffraction studies. The free ligand HL¹ has adopted orthorhombic crystal system with P2(1) space group and a 8.1552(3), b 10.1169(4), c 17.0819(6) Å, and α = β = γ 90.°. The crystal structure of the complex, [Cu(L²)₂(CH₃OH)₂] is monoclinic with P2(1)/c space group and a 10.2571(2), b 16.2640(3), c 20.1717(3) Å, and α 90.β 99.56 and γ 90.°. The copper(II) complex has adopted distorted octahedral geometry where the z-axis is occupied by two solvent methanol mols. according to the crystal data. While the EPR spectra of both the Cu(II) complexes display a strong axial signal with g_vbr â‰?2.2 and gbottom â‰?2.0, which obviously suggests the square planar geometry around the copper(II) ion. The interaction of the complexes with calf thymus DNA (CT-DNA) was studied using UV-visible and fluorescence spectroscopic techniques. Anticancer activity of the complexes revealed their potential towards inhibiting the growth of human breast cancer cell lines, MDA-MB-231. The palladium complexes of both the ligands are good in exhibiting apoptosis. Also, the complexes of fluoro-substituted ligand are better antimicrobial agents when compared with those of Me substituted ligand.

Inorganica Chimica Acta 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

Galenko, Ekaterina E. published the artcileSynthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles, Category: isoxazole, the publication is Tetrahedron (2018), 74(43), 6288-6298, database is CAplus.

A novel effective method is reported for the preparation of 1-amino-1H-pyrazole-4-carboxylic acid derivatives by Fe(II)-catalyzed rearrangement of isoxazoles having (2,4-dinitrophenylhydrazono)methyl substituent at C4. The reaction proceeds smoothly for both E and Z isomers of 4-(hydrazonomethyl)isoxazoles, and this means it is not necessary to sep. mixtures of E/Z-isomers of the hydrazones prepared by reaction of 5-methoxy/pirrolidino-4-carbonylisoxazoles and 2,4-dinitrophenylhydrazine. The rearrangement proceeds via the formation of an aziridine intermediate which can be isolated in certain cases. The 2-nitro group in the synthesized 1-[(2,4-dinitrophenyl)amino]-1H-pyrazole-4-carboxylic esters can be selectively reduced in two steps via acylation of the amino group followed by hydrogenation-deacylation using H₂-Pd/C.

Tetrahedron 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

Tang, Dong published the artcileIodine-catalyzed synthesis of sulfonyl isoxazoles from sodium sulfinates and isoxazol-5(4H)-ones, Product Details of C9H7NO2, the publication is Tetrahedron Letters (2021), 152685, database is CAplus.

An efficient I₂-mediated sulfonylation at 4-position of isoxazoles has been developed by employing sodium sulfinate and 3-substituted isoxazol-5(4H)-ones. This metal-free, one-pot strategy provides various sulfonyl isoxazoles under mild reaction conditions. The final product exists in the form of stable organic sodium salt, which can be purified by column chromatog. under air.

Tetrahedron 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 C18H15N3O3, Product Details of C9H7NO2.

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

Long, Hao published the artcileSafety and efficacy of parecoxib sodium in multimode analgesia after osteoarticular surgery, HPLC of Formula: 198470-85-8, the publication is Zhongguo Jiaoxing Waike Zazhi (2014), 22(5), 458-460, database is CAplus.

Objective: To evaluate the safety and efficacy of parecoxib sodium in multimode analgesia after osteoarticular surgery. Methods: 90 patients were divided into group A (parecoxib sodium combined with fentanyl PCIA) and group B (fentanyl PCIA). Group A is further divided into group A 1: venous group (40 mg/time, 1 time/12 h i.v. infusion) and A 2 group: s.c. injection group (40 mg/ time 1 time /12 h). The VAS score, fentanyl dosage and ADR, PCA press number and effective number of each group at 48 h postoperatively were compared. Results: Group A and group B had statistically significant difference in VAS score, fentanyl dosage and ADR, PCA press number and effective (P < 0.05 ). In group A, the venous group and s.c. injection group had no statistically significant difference (P>0.05). Conclusion: The parecoxib sodium combined with PCA multimode analgesia can reduce fentanyl dose and alleviate pain at 48 h postoperatively.

Zhongguo Jiaoxing Waike Zazhi published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C19H17N2NaO4S, HPLC of Formula: 198470-85-8.

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

Xu, Shiyang published the artcileRh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide, COA of Formula: C18H12FN, the publication is Organic Letters (2018), 20(18), 5578-5582, database is CAplus and MEDLINE.

A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsym. carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp²/sp³ C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives The practical application to CBP and unsym. TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.

Organic Letters published new progress about 57103-14-7. 57103-14-7 belongs to isoxazole, auxiliary class Fused Tricycles,Carbazoles, name is 9-(4-Fluorophenyl)-9H-carbazole, and the molecular formula is C14H12N2S, COA of Formula: C18H12FN.

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

Li, Li-biao published the artcileComparison of pain thresholds and analgesic effects of parecoxib sodium in surgical patients of different racial and religious backgrounds, Synthetic Route of 198470-85-8, the publication is Zhongguo Yixue Kexueyuan Xuebao (2015), 37(3), 325-330, database is CAplus and MEDLINE.

The aim is to explore the differences of pain thresholds and analgesic effects of parecoxib sodium among patients with different racial and religious backgrounds. A total of 48 male patients aged 18 to 38 years who had undergone elective laparoscopic appendectomy under general anesthesia in our center were enrolled in our study, and then divided into 6 groups(n=8 in each group) based on their racial backgrounds(three levels: Mongoloid, Negroid, and Europoid) and religious backgrounds(two levels: without religion background, with religion background). All subjects received same anesthesia, surgical procedure, and postoperative analgesia with parecoxib sodium. The temperature pain threshold and elec. pain threshold were detected 1 h before and after analgesia. The threshold of pain was higher in Europoids than that in Negroids and Mongoloids before and after treatment. The temperature pain threshold and elec. pain threshold were not significantly different between subjects with or without religious background(before analgesic therapy: F=251.119, P=0.130, F=275.861, P=0.059; after analgesic therapy: F=308.531, P=0.086, F=180.062, P=0.078). Also, there was no interaction between the racial and religious backgrounds in terms of temperature pain threshold and elec. pain threshold(F=13.553, P=0.091, F=22.001, P=0.089; after analgesic therapy: F=4.624, P=0.089, F=15.935, P=0.094). The threshold of pain differed among individuals with different racial background, and it was the highest in Europoids, followed by Negroids and Mongoloids. It showed no obvious difference in people with different religious backgrounds.

Zhongguo Yixue Kexueyuan Xuebao published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C19H17N2NaO4S, Synthetic Route of 198470-85-8.

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

Zhang, Chaofeng published the artcileParacoxib Alleviates Ventilator-Induced Lung Injury Through Functional Modulation of Lung-Recruited CD11bloLy6Chi Monocytes, Formula: C19H17N2NaO4S, the publication is Shock (2021), 55(2), 236-243, database is CAplus and MEDLINE.

Lung-recruited Ly6Chi monocytes had been shown to be involved in ventilator-induced lung injury (VILI). Our present study aimed to investigate whether the cyclooxygenase-2 (COX-2) inhibition modulates the function of lung-recruited Ly6Chi monocytes in a mouse model of VILI. Mice were exposed to lipopolysaccharide (LPS; 20 ng) i.p. prior to injurious mech. ventilation (Vt=30mL/kg, PEEP=0cmH2O). A subgroup of mice was treated with i.v. parecoxib (30mg/kg), a COX-2 inhibitor, 1 h prior to ventilation. Control mice received saline and were not ventilated. At the end of the experiment, blood gas anal. was performed and lung tissue was collected for histol. assessment. Flow cytometry was employed to quantify the different populations of lung monocytes/macrophages and their function. Isolated Ly6Chi cells were used to measure the intracellular concentrations of reactive oxygen species (ROS) and nitric oxide (NO) by fluorescent probes, and cytokine production by cytometric bead array. Exposure to LPS and injurious ventilation was associated with severe lung histol. damage, oxygenation impairment, and pulmonary edema; all of which were largely attenuated following the treatment of parecoxib. Furthermore, flow cytometry anal. revealed that parecoxib caused a reduction in the number of the lung-recruited CD11bloLy6Chi monocytes while there was no effect on tissue-resident CD64+ alveolar macrophages. In addition, the production of oxidative stress products (ROS, NO), MHC-II expression, and inflammatory cytokines in response to LPS and VILI in CD11bloLy6Chi monocytes was ameliorated by parecoxib. Parecoxib-induced alleviation of oxidative stress and inflammation in lung-recruited Ly6Chi monocytes may partly explain the beneficial action of COX-2 inhibition in VILI.

Shock published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C7H6Cl2, Formula: C19H17N2NaO4S.

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