1619-37-0

Basic information

• Product Name: (5-PHENYLISOXAZOL-3-YL)METHANOL
• Synonyms: SALOR-INT L482692-1EA;AKOS PAO-1437;(5-PHENYL-3-ISOXAZOLYL)METHANOL;(5-PHENYLISOXAZOL-3-YL)METHANOL;3-Isoxazolemethanol, 5-phenyl-;(5-phenyl-3-isoxazolyl)methanol(SALTDATA: FREE);3-Hydroxymethyl-5-phenylisoxazole;(5-phenyl-1,2-oxazol-3-yl)methanol
• CAS NO: 1619-37-0
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: 604-604-1
• Mol File: 1619-37-0.mol

Chemical Properties

• Melting Point: 98-100°
• Boiling Point: 362.8°Cat760mmHg
• Flash Point: 173.2°C
• Appearance: /
• Density: 1.211
• Vapor Pressure: 6.73E-06mmHg at 25°C
• Refractive Index: 1.573
• Solubility: soluble in Methanol
• PKA: 13.04±0.10(Predicted)
• CAS DataBase Reference: (5-PHENYLISOXAZOL-3-YL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (5-PHENYLISOXAZOL-3-YL)METHANOL(1619-37-0)
• EPA Substance Registry System: (5-PHENYLISOXAZOL-3-YL)METHANOL(1619-37-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1619-37-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5-Phenylisoxazol-3-yl)methanol is used as a building block for the synthesis of various organic compounds, particularly in the development of new pharmaceuticals. Its unique structure and properties make it suitable for use in medicinal chemistry, where it can be utilized to create biologically active molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, (5-Phenylisoxazol-3-yl)methanol serves as a starting material for the preparation of biologically active molecules with potential applications in crop protection and pest control. Its versatility as a building block allows for the development of novel compounds with improved efficacy and selectivity in agricultural settings.
Used in Medicinal Chemistry Research:
(5-Phenylisoxazol-3-yl)methanol is used as a research tool in medicinal chemistry to explore its potential as a precursor for the synthesis of new biologically active molecules. Its unique structure and properties make it an attractive candidate for the development of innovative therapeutic agents and drug candidates.

InChI:InChI=1/C10H9NO2/c12-7-9-6-10(13-11-9)8-4-2-1-3-5-8/h1-6,12H,7H2

Upstream product

• 25741-97-3 3-amino-5-methylisoxazole 
• 50-00-0 formaldehyd 
• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 
• 98-85-1 1-Phenylethanol 
• 51677-09-9 methyl 5-phenylisoxazole-3-carboxylate 
• 90770-96-0 3-hydroxyiminomethyl-5-phenylisoxazole 
• 59985-82-9 5-phenylisoxazole-3-carbaldehyde 
• 98-86-2 acetophenone 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 

Downstream Products

• 59985-82-9 5-phenylisoxazole-3-carbaldehyde 
• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 
• 81282-11-3 3-(tetrahydropyran-2-yloxymethyl)-5-phenylisoxazole 
• 94815-37-9 2-buten-1-one-3-amino-4-hydroxy-1-phenyl 
• 154016-50-9 3-(bromomethyl)-5-phenylisoxazole 
• 76422-50-9 4,5-diphenyl-3-hydroxymethylisoxazole 
• 76422-52-1 3-chloromethyl-4,5-diphenylisoxazole 
• 76422-51-0 4,5-diphenylisoxazole-3-carboxylic acid 
• 5198-63-0 5-phenylfuran-3(2H)-one 
• 14731-10-3 3-(chloromethyl)-5-phenylisoxazole 
• 866641-27-2 ethyl (5-phenyl-1,2-oxazol-3-yl)methyl methanesulfonate 
• 1039434-22-4 3-((tert-butyldimethylsilyloxy)methyl)-5-phenylisoxazole 
• 1045792-79-7 methyl 5-(5-phenyl-3-isoxazolylmethoxy)pentanoate 
• 1030829-11-8 5-(4-((5-phenylisoxazol-3-yl)methoxy)phenyl)isoxazol-3-yl pivalate 

Relevant articles and documents

Novel N-Substituted oseltamivir derivatives as potent influenza neuraminidase inhibitors: Design, synthesis, biological evaluation, ADME prediction and molecular docking studies

The discovery of novel potent neuraminidase (NA) inhibitors remains an attractive approach for treating infectious diseases caused by influenza. In this study, we describe the design and synthesis of novel N-substituted oseltamivir derivatives for probing the 150-cavity which is nascent to the activity site of NA. NA inhibitory studies showed that new derivatives demonstrated the inhibitory activity with IC50 values at nM level against NA of a clinical influenza virus strain. Moreover, the in silico ADME predictions showed that the selected compounds had comparable properties with oseltamivir carboxylate, which demonstrated the druggablity of these derivatives. Furthermore, molecular docking studies showed that the most potent compound 6f and 10i could adopt different modes of binding interaction with NA, which may provide novel solutions for treating oseltamivir-resistant influenza. Based on the research results, we consider that compounds 6f and 10i have the potential for further studies as novel antiviral agents.

Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators

Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.

Substituted 1-(isoxazol-3-yl)methyl-1H-1,2,3-triazoles: Synthesis, palladium(II) complexes, and high-turnover catalysis in aqueous media

New substituted 3-((1H-1,2,3-triazol-1-yl)methyl)-5-arylisoxazoles (aryl = Ph, p-Tol) and 2-(5-phenylisoxazol-3-yl)-5-(2-(1-((5-(p-tolyl)isoxazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)ethyl)-1,3,4-oxadiazole were synthesized by means of click-chemistry proce

PYRADAZINONE DERIVATIVES AND THE COMPOSITIONS AND METHODS OF TREATMENT REGARDING THE SAME

The present disclosure is directed to pyridazin-3(2H)-one compounds of formula (I), pharmaceutical compositions thereof and methods for modulating or activating a Parkin ligase The present disclosure is also directed to methods of treating and/or reducing the incidence of diseases or conditions related to the activation of Parkin ligase, R21, R22, R23, R24 and R25 are as defined herein.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.

Design, synthesis and biological evaluation of stilbene derivatives as novel inhibitors of protein tyrosine phosphatase 1B

By imitating the scaffold of lithocholic acid (LCA), a natural steroidal compound displaying Protein Tyrosine Phosphatase 1B (PTP1B) inhibitory activity, a series of stilbene derivatives containing phenyl-substituted isoxazoles were designed and synthesized. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Activities of the title compounds were evaluated on PTP1B and the homologous enzyme TCPTP by using a colorimetric assay. Most of the target compounds had good activities against PTP1B. Among them, compound 29 (IC50 = 0.91 ± 0.33 μM), characterized by a 5-(2,3-dichlorophenyl) isoxazole moiety, exhibited an activity about 14-fold higher than the lead compound LCA and a 4.2-fold selectivity over TCPTP. Compound 29 was identified as a competitive inhibitor of PTP1B with a Ki value of 0.78 μM in enzyme kinetic studies.

Synthesis of functionally substituted isoxazole and isothiazole derivatives

Acylation of benzene and toluene with 5-phenyl- and 5-(p-tolyl)isoxazole-3- carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH 3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.

2-Amino-3-cyano-4-(5-arylisoxazol-3-yl)-4H-chromenes: Synthesis and in vitro cytotoxic activity

A new series of 4-aryl-4H-chromenes bearing a 5-arylisoxazol-3-yl moiety at the C-4 position were prepared as potential anticancer agents. The in vitro cytotoxic activity of the synthesized compounds was investigated against a panel of tumor cell lines in

NOVEL PHENYL-ISOXAZOL-3-OL DERIVATIVE

The present invention relates to a compound represented by formula (I), which has a GPR120 agonist action and thus is useful for treatment of diabetes mellitus or hyperlipidemia, or a pharmaceutically acceptable salt thereof. In the formula, (AA) represents a phenyl or the like, which may be substituted with a lower alkoxy group or the like; (BB) represents a divalent group or the like, derived by removal of two hydrogen atoms from a benzene which may be substituted with a halogen atom or the like; X represents a spacer having a main chain composed of 1-8 carbon atoms wherein 1-3 carbon atoms in the main chain may be substituted with an oxygen atom or the like; and Y represents a hydrogen atom or the like.

Use of the Nitrile Oxide Cycloaddition (NOC) reaction for molecular probe generation: A new class of enzyme selective histone deacetylase inhibitors (HDACIs) showing picomolar activity at HDAC6

A series of hydroxamate based HDAC inhibitors containing a phenylisoxazole as the CAP group has been synthesized using nitrile oxide cycloaddition chemistry. An HDAC6 selective inhibitor having a potency of ～2 picomolar was identified. Some of the compounds were examined for their ability to block pancreatic cancer cell growth and found to be about 10-fold more potent than SAHA. This research provides valuable, new molecular probes for use in exploring HDAC biology.