Month: October 2022

Lipshutz, Bruce H.’s team published research in Tetrahedron Letters in 1988 | CAS: 29278-09-9

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.COA of Formula: C12H12N2O3

In 1988,Tetrahedron Letters included an article by Lipshutz, Bruce H.; Reuter, Deborah C.. COA of Formula: C12H12N2O3. The article was titled 《Cyclopeptide alkaloid model studies. A two-step conversion of 5-aminoisoxazoles to amino acid bis-amides》. The information in the text is summarized as follows:

Thermolyses of substituted 5-aminoisoxazoles I (R = CH2SPh, CH2OCH2Ph, CH2OMe, Me, H, Ph, CH2 Ph, Pr), readily available from common starting materials, lead to azirines II in good yields. Subsequent hydration affords bisamide derivatives of amino acids, e.g. B2NHCHRCON(CH2Ph)2.Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9COA of Formula: C12H12N2O3) was used in this study.

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.COA of Formula: C12H12N2O3

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Ponticelli, Fabio’s team published research in Gazzetta Chimica Italiana in 1983 | CAS: 29278-09-9

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Synthetic Route of C12H12N2O3

In 1983,Gazzetta Chimica Italiana included an article by Ponticelli, Fabio; Tedeschi, Piero. Synthetic Route of C12H12N2O3. The article was titled 《Ethyl 5-imino-2-methyl-2,5-dihydroisoxazole-3- and 4-carboxylates: synthesis and alkaline ring opening》. The information in the text is summarized as follows:

Methylation of I (R = Me, Ph, R1 = CO2Et, R2 = H, Me; R = CO2Et, R1 = Me, Ph, R2 = H; R = Me, Ph, R1 = CO2H, R2 = H) by FSO3Me gave II which (R = Me, Ph, R1 = CO2Et, R2 = H) were heated with alc. NaOH to give III (R1 = CN) which were hydrolyzed to give IV (R3 = Me, Ph). Treatment of the latter with SOCl2 gave MeN(OH)C(:NH)CH2CO2Et.HCl; catalytic hydrogenation gave MeNHC(:NH)CH2COR3.HCl. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9Synthetic Route of C12H12N2O3)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Synthetic Route of C12H12N2O3

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Li, Zhiqiang’s team published research in Journal of Medicinal Chemistry in 2020 | CAS: 1202769-66-1

2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol(cas: 1202769-66-1) belongs to isoxazoles. Isoxazoles is an oxygen-containing azole derivative found in some natural products such as amantine, as well as in several drugs, including COX-2 inhibitors and furoxan oxide (a nitric oxide donor). body). Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-olIsoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.

《Discovery of a Potent and Selective NF-κB-Inducing Kinase (NIK) Inhibitor That Has Anti-inflammatory Effects in Vitro and in Vivo》 was written by Li, Zhiqiang; Li, Xinzhi; Su, Ming-Bo; Gao, Li-Xin; Zhou, Yu-Bo; Yuan, Bingchuan; Lyu, Xilin; Yan, Ziqin; Hu, Chujiao; Zhang, Hao; Luo, Cheng; Chen, Zheng; Li, Jia; Zhao, Yujun. Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol And the article was included in Journal of Medicinal Chemistry on April 23 ,2020. The article conveys some information:

The overexpression of NIK plays a critical role in liver inflammatory diseases. Treatment of such diseases with small-mol. NIK inhibitors is a reasonable but underexplored approach. In this paper, we reported the discovery of a potent and selective NIK inhibitor I (XT2). The compound I inhibited the NIK kinase with an IC50 value of 9.1 nM in vitro, and it also potently suppressed NIK activities in intact cells. In isogenic primary hepatocytes, treatment with I efficiently suppressed the expressions of NIK-induced genes. The compound I was orally bioavailable in mice with moderate systemic exposure. In a NIK-associated mouse liver inflammation model, the compound I suppressed CCl4-induced upregulation of ALT, a key biomarker of acute liver injury, and also decreased immune cell infiltration into the injured liver tissue. Overall, these studies provide examples that an NIK inhibitor is able to suppress toxin-induced liver inflammations, which indicates its therapeutic potentials for the treatment of liver inflammatory diseases. In addition to this study using 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol, there are many other studies that have used 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol(cas: 1202769-66-1Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol) was used in this study.

2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol(cas: 1202769-66-1) belongs to isoxazoles. Isoxazoles is an oxygen-containing azole derivative found in some natural products such as amantine, as well as in several drugs, including COX-2 inhibitors and furoxan oxide (a nitric oxide donor). body). Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-olIsoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Beccalli, Egle M.’s team published research in Journal of Organic Chemistry in 1985 | CAS: 29278-09-9

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Formula: C12H12N2O3

Beccalli, Egle M.; Manfredi, Amadea; Marchesini, Alessandro published an article in Journal of Organic Chemistry. The title of the article was 《Alkynes from 5-aminoisoxazoles》.Formula: C12H12N2O3 The author mentioned the following in the article:

Diazotization of 5-aminoisoxazoles I [R = Ph, H, CO2Et, Me; R1 = CONH2, CO2Et, p-O2NC6H4, 4-pyridyl, etc. (≥1 of R and R1 is an electron-withdrawing group)] by reaction with NaNO2 in AcOH-H2O afforded the corresponding RCCR1. A reaction path involving an intermediate isoxazol-5-yl radical is proposed. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9Formula: C12H12N2O3)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Formula: C12H12N2O3

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Smalley, R K’s team published research in Science of Synthesis in 2002 | 21725-69-9

Science of Synthesis published new progress about Aromatization. 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Electric Literature of 21725-69-9.

Smalley, R. K. published the artcile< Product class 10: 1,2-benzisoxazoles and related compounds>, Electric Literature of 21725-69-9, the main research area is review benzisoxazole preparation.

A review presents various methods of ring-closure reaction and substituent modification for the synthesis of 1,2-benzisoxazoles and related compounds

Science of Synthesis published new progress about Aromatization. 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Electric Literature of 21725-69-9.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Urban, Frank J’s team published research in Tetrahedron: Asymmetry in 1995-02-28 | 21725-69-9

Tetrahedron: Asymmetry published new progress about 21725-69-9. 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Recommanded Product: Benzo[d]isoxazol-3-ol.

Urban, Frank J.; Breitenbach, Ralph; Murtiashaw, Charles W.; Vanderplas, Brian C. published the artcile< Synthesis of an optically active octahydro-2H-pyrido[1,2-a]pyrazine based CNS agent>, Recommanded Product: Benzo[d]isoxazol-3-ol, the main research area is pyridopyrazine octahydro optically active.

A synthesis of an optically active octahydro-2H-pyrido[1,2-a]pyrazine (I) is presented. The key sequence involved the equilibration of an optically active cis-aldehyde to give the thermodn. trans-aldehyde that was trapped by nitromethane anion.

Tetrahedron: Asymmetry published new progress about 21725-69-9. 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Recommanded Product: Benzo[d]isoxazol-3-ol.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Ueda, Mitsuru’s team published research in Journal of Polymer Science, Polymer Chemistry Edition in 1981-05-31 | 21725-69-9

Journal of Polymer Science, Polymer Chemistry Edition published new progress about Aminolysis. 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, COA of Formula: C7H5NO2.

Ueda, Mitsuru; Harada, Toshiaki; Aoyama, Shigeto; Imai, Yoshio published the artcile< Synthesis of polyamides from active diacyl derivatives of 3-hydroxy-1,2-benzisoxazole and diamines under mild conditions>, COA of Formula: C7H5NO2, the main research area is benzisoxazole ester amide polymer; polyamide benzisoxazole; aminolysis benzoisoxazole ester amide.

New active diesters and diamides derived by O- or N-acylation of 3-hydroxy-1,2-benzisoxazole [21725-69-9] were prepared for use in polyamide synthesis. The active esters and amides reacted readily with amines to give quant. yields of amides. The high reactivity of these active esters and amides was discussed in relation to the electron-withdrawing effect of the leaving group and intramol. general-base catalysis. Solution polycondensation of the new diesters and diamides with aliphatic and aromatic diamines proceeded slowly under mild conditions to produce polyamides with inherent viscosities up to 1.5.

Journal of Polymer Science, Polymer Chemistry Edition published new progress about Aminolysis. 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, COA of Formula: C7H5NO2.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Deering, Robert W’s team published research in Journal of Antibiotics in 2021-06-30 | 21725-69-9

Journal of Antibiotics published new progress about 16S rRNA Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Electric Literature of 21725-69-9.

Deering, Robert W.; Whalen, Kristen E.; Alvarez, Ivan; Daffinee, Kathryn; Beganovic, Maya; LaPlante, Kerry L.; Kishore, Shreya; Zhao, Sijing; Cezairliyan, Brent; Yu, Shen; Rosario, Margaret; Mincer, Tracy J.; Rowley, David C. published the artcile< Identification of a bacteria-produced benzisoxazole with antibiotic activity against multi-drug resistant Acinetobacter baumannii>, Electric Literature of 21725-69-9, the main research area is Acinetobacter benzisoxazole antibiotic activity.

Abstract: The emergence of multi-drug resistant pathogenic bacteria represents a serious and growing threat to national healthcare systems. Most pressing is an immediate need for the development of novel antibacterial agents to treat Gram-neg. multi-drug resistant infections, including the opportunistic, hospital-derived pathogen, Acinetobacter baumannii. Herein we report a naturally occurring 1,2-benzisoxazole with min. inhibitory concentrations as low as 6.25μg ml-1 against clin. strains of multi-drug resistant A. baumannii and investigate its possible mechanisms of action. This mol. represents a new chemotype for antibacterial agents against A. baumannii and is easily accessed in two steps via de novo synthesis. In vitro testing of structural analogs suggest that the natural compound may already be optimized for activity against this pathogen. Our results demonstrate that supplementation of 4-hydroxybenzoate in minimal media was able to reverse 1,2-benzisoxazoles antibacterial effects in A. baumannii. A search of metabolic pathways involving 4-hydroxybenzoate coupled with mol. modeling studies implicates two enzymes, chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyltransferase, as promising leads for the target of 3,6-dihydroxy-1,2-benzisoxazole.

Journal of Antibiotics published new progress about 16S rRNA Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Electric Literature of 21725-69-9.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Csakai, Adam’s team published research in Journal of Medicinal Chemistry in 2014-06-26 | 21725-69-9

Journal of Medicinal Chemistry published new progress about Animal gene Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (Cebpb, modified gene consistent with modulation of STAT1 signaling). 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Product Details of C7H5NO2.

Csakai, Adam; Smith, Christina; Davis, Emily; Martinko, Alexander; Coulup, Sara; Yin, Hang published the artcile< Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation>, Product Details of C7H5NO2, the main research area is saccharin derivative suppressant interferon mediated inflammation SAR.

A series of novel, saccharin-based antagonists have been identified for the interferon signaling pathway. Through in vitro high-throughput screening with the Colorado Center for Drug Discovery (C2D2) Pilot Library, we identified isothiazolone 1,1-dioxides as the basis for extensive structure-activity relationship studies. Our efforts produced a lead anti-inflammatory compound, tert-Bu N-(furan-2-ylmethyl)-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ6,2-benzisothiazol-2-yl)methyl]benzoyl}carbamate CU-CPD103 (I), as a potent inhibitor using an established nitric oxide (NO) signaling assay. With further studies of its inhibitory mechanisms, we demonstrated that I carries out this inhibition through the JAK/STAT1 pathway, providing a drug-like small mol. inflammation suppressant for possible therapeutic uses.

Journal of Medicinal Chemistry published new progress about Animal gene Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (Cebpb, modified gene consistent with modulation of STAT1 signaling). 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Product Details of C7H5NO2.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Anand, Mohanam’s team published research in Korean Journal of Chemical Engineering in 2014-04-30 | 21725-69-9

Korean Journal of Chemical Engineering published new progress about Allylic halides Role: RCT (Reactant), RACT (Reactant or Reagent) (bromides, chlorides). 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Recommanded Product: Benzo[d]isoxazol-3-ol.

Anand, Mohanam; Selvaraj, Vaithialingam; Alagar, Muthukaruppan published the artcile< Synthesis, characterization and evaluation of antioxidant and anticancer activities of novel benzisoxazole-substituted-allyl derivatives>, Recommanded Product: Benzo[d]isoxazol-3-ol, the main research area is allylbenzisoxazolone preparation antioxidant anticancer activity human green chem; benzoisoxazolone allyl bromide chloride cesium carbonate catalyst.

A novel series of various 2-allylbenzo[d]isoxazol-3(2H)-ones I [R = allyl, cinnamyl, benzyl, etc.] were synthesized using benzo[d]isoxazol-3(2H)-one treated with different allyl bromides/chlorides in the presence of water-mediated cesium carbonate as a new catalyst. The structures of the allylated benzisoxazolones I were characterized by spectroscopic methods and mass spectrometry. These synthesized compounds I were evaluated for their in vitro antioxidant and anticancer activity. Compounds I [R = 2-pentynyl, 3-methyl-2-butenyl, benzyl, 4-phenyl-2-butynyl] were identified as the best hit against HT-29 Human colon cancer cells, and showed significant antioxidant activity compared to the standard drug butylated hydroxy toluene (BHT).

Korean Journal of Chemical Engineering published new progress about Allylic halides Role: RCT (Reactant), RACT (Reactant or Reagent) (bromides, chlorides). 21725-69-9 belongs to class isoxazole, and the molecular formula is C7H5NO2, Recommanded Product: Benzo[d]isoxazol-3-ol.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem