139297-55-5

Basic information

• Product Name: 3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI)
• Synonyms: 3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI);Methyl 5-(hydroxymethyl)isoxazole-3-carboxylate;methyl 5-(hydroxymethyl)-1,2-oxazole-3-carboxylate
• CAS NO: 139297-55-5
• Molecular Formula: C6H7NO4
• Molecular Weight: 157.12408
• Product Categories: OXAZOLE;ALDEHYDE
• Mol File: 139297-55-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI)(139297-55-5)
• EPA Substance Registry System: 3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI)(139297-55-5)

Safety Data

• Hazardous Substances Data: 139297-55-5(Hazardous Substances Data)

Usage

General Description

3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI) is a chemical compound with the formula C7H7NO3. It is a derivative of isoxazole and is commonly used in organic synthesis and pharmaceutical research. 3-Isoxazolecarboxylic acid, 5-(hydroxymethyl)-, methyl ester (9CI) is also known for its potential biological and pharmacological activities, including antimicrobial and antifungal properties. The methyl ester group makes it a versatile building block for the synthesis of a wide range of compounds. It is commonly used in the development of new drug candidates and in the study of various biological processes.

Upstream product

• 37428-55-0 (E)-3-bromoprop-2-en-1-ol 
• 2483-57-0 methyl 2-nitroacetate 
• 252769-66-7 methyl 5-(tetrahydro-2H-pyran-2-yloxymethyl)isoxazole-3-carboxylate 
• 30673-27-9 methyl chlorooximidoacetate 
• 107-19-7 propargyl alcohol 

Downstream Products

• 22667-21-6 methyl 5-formylisoxazole-3-carboxylate 
• 139297-56-6 5-(hydroxymethyl)-1,2-oxazole-3-carboxylic acid 

Relevant articles and documents

Structure-activity relationship studies of novel heteroretinoids: Induction of apoptosis in the HL-60 cell line by a novel isoxazole-containing heteroretinoid

In a search for retinoic acid receptor (RAR and RXR)-selective ligands, a series of isoxazole retinoids was synthesized and evaluated in vitro in transcriptional activation and competition binding assays for RARs and RXRs. In addition, these compounds were evaluated for their differentiating, cytotoxic, and apoptotic activities. In general, these derivatives showed scarcely any binding affinity and were not active in the transcriptional assay. However, among these isoxazole derivatives, the cis-isomer 14b was identified as a potent inducer of apoptosis, and its activity was found to be 6.5 and 4 times superior than that of 13-cis- and 9-cis-retinoic acids, respectively. On the other hand, compound 13b, which has the trans stereochemistry at the double bond, was found not to be active in the apoptotic assay, but it was endowed with appreciable differentiating activity. Therefore, it seems that the different stereochemistry of the double bond may be associated with a different biological activity: potent apoptotic activity for the cis-isomer but differentiating activity for the trans structure. This biological behavior was found, at least in part, for the 9-cis- and 13-cis-retinoic acids with respect to the all-trans-retinoic acid. Thus, structure 14b could offer an interesting model for the design of new compounds endowed with apoptotic activity.

Substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as hypoglycemic agents

A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.