124845-04-1

Basic information

• Product Name: 5-CYCLOPROPYLISOXAZOLE-4-CARBOXYLIC ACI&
• Synonyms: 4-Isoxazolecarboxylicacid,5-cyclopropyl-(9CI);5-cyclopropyl-1,2-oxazole-4-carboxylic acid;5-CYCLOPROPYLISOXAZOLE-4-CARBOXYLIC ACI&
• CAS NO: 124845-04-1
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.136
• Product Categories: CARBOXYLICACID;OXAZOLE;Building Blocks;Heterocyclic Building Blocks;Isoxazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;carboxylic acid
• Mol File: 124845-04-1.mol

Chemical Properties

• Melting Point: 161-165 °C(lit.)
• Boiling Point: 317.6°C at 760 mmHg
• Flash Point: 145.9°C
• Appearance: /
• Density: 1.445g/cm³
• Vapor Pressure: 0.000159mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 5-CYCLOPROPYLISOXAZOLE-4-CARBOXYLIC ACI&(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CYCLOPROPYLISOXAZOLE-4-CARBOXYLIC ACI&(124845-04-1)
• EPA Substance Registry System: 5-CYCLOPROPYLISOXAZOLE-4-CARBOXYLIC ACI&(124845-04-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 124845-04-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Cyclopropylisoxazole-4-carboxylic acid is used as a building block for the synthesis of various pharmaceutical compounds, leveraging its unique chemical structure to create novel drugs with potential therapeutic benefits.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 5-Cyclopropylisoxazole-4-carboxylic acid is utilized as an antimicrobial agent, exhibiting properties that can combat bacterial infections, thereby contributing to the development of new antibiotics.
Used in Antifungal Applications:
5-Cyclopropylisoxazole-4-carboxylic acid is employed as an antifungal agent, demonstrating its potential to treat fungal infections, which is crucial in addressing the growing concern of antifungal resistance.
Used in Neurodegenerative Disorder Treatment:
5-Cyclopropylisoxazole-4-carboxylic acid is used as a modulator of the central nervous system, specifically for the treatment of neurodegenerative disorders. Its potential to influence neurological pathways makes it a candidate for drug discovery in this area.
Used in Drug Discovery and Development:
Overall, 5-Cyclopropylisoxazole-4-carboxylic acid is a valuable compound in drug discovery and development, with its diverse applications ranging from infectious disease treatment to neurological conditions, highlighting its versatility and importance in the pharmaceutical sector.

InChI:InChI=1/C7H7NO3/c9-7(10)5-3-8-11-6(5)4-1-2-4/h3-4H,1-2H2,(H,9,10)

Upstream product

• 32249-35-7 methyl 3-cyclopropyl-3-oxopropanoate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 124844-97-9 5-cyclopropyl-N-(4-(trifluoromethyl)phenyl)isoxazole-4-carboxamide 

Relevant articles and documents

Design, Synthesis, and Herbicidal Activity of N-Benzyl-5-cyclopropyl-isoxazole-4-carboxamides

Based on the structures of isoxaflutole (IFT) and N-isobutyl-N-(4-chloro-benzyl)-4-chloro-2-pentenamide, a series of N-benzyl-5-cyclopropyl-isoxazole-4-carboxamides was designed by connecting their pharmacophores (i.e., a multitarget drug design strategy). A total of 27 N-benzyl-5-cyclopropyl-isoxazole-4-carboxamides were prepared from 5-cyclopropylisoxazole-4-carboxylic acid and substituted benzylamines, and their structures were confirmed by NMR and MS. Laboratory bioassays indicated that I-26 showed 100% inhibition against Portulaca oleracea and Abutilon theophrasti at a concentration of 10 mg/L, better than the positive control butachlor (50% inhibition for both weeds). A strong growth inhibition was observed, but a typical bleaching phenomenon of IFT could not be observed in the Petri dish assay. I-05 displayed excellent postemergence herbicidal activity against Echinochloa crusgalli and A. theophrasti at a rate of 150 g/ha, and bleaching symptoms were observed in the leaves of treated weeds. The bleaching effect of Chlamydomonas reinhardtii treated by I-05 could be reversed by adding homogentisate. Enzymatic bioassays indicated that I-05 could not inhibit 4-hydroxyphenylpyruvate dioxygenase (HPPD) activity, but II-05, an isoxazole ring-opening product of I-05, could inhibit HPPD activity with an EC50 value of 1.05 μM, similar to that of mesotrione (with an EC50 value of 1.35 μM). Detailed discussion about observed herbicidal symptoms is provided in the Results and Discussion section. This investigation provided a proof-of-concept foundation that a multitarget drug design strategy could be applied in agrochemical research.

Design, synthesis and herbicidal activity of 5-cyclopropyl-N-phenylisoxazole-4-carboxamides

4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a type of important herbicides, and they cause bleaching symptoms by indirectly inhibiting the biosynthesis of carotenoids. In this study, thirty isoxazolamide compounds were designed based on the structure of Isoxaflutole, a commercial HPPD herbicide. Starting from 1,1-dimethoxy-N,N-dimethyl-methanamine and methyl 3-cyclopropyl-3-oxo-propanoate, the title compounds were readily prepared and their structures were determined by MS and NMR analysis. In Petri dish tests, most of the title compounds showed strong inhibitory effect on the root and stem growth of both monocotyledon and dicotyledon weeds, and it was clearly different from the symptoms caused by HPPD inhibitors. However, several of them, especially I-17, showed characteristic bleaching symptoms of HPPD herbicides and good post-emergence herbicidal activity on tested weeds in glasshouse assay. These compounds are prodrugs, and compounds undergo conversion to the active entity diketonitrile (DKN) in plant and soil. The result of molecular docking analysis revealed that the DKN moiety of I-17 excellently binds to the active sites of HPPD. The 1,3-diketone can form bidentate interaction with FeII, and the benzene ring can form π-π interaction with Phe 360 and Phe 403. These results indicated that the title compounds bears other herbicidal mechanism except for HPPD inhibitor. Therefore, a lead compound for the discovery of novel multi-target herbicides is provided.

SUBSTITUTED AZOLE AROMATIC HETEROCYCLES AS INHIBITORS OF 11BETA-HSD-1

Compounds of formula I and IV are described and have therapeutic utility, particularly in the treatment of diabetes, obesity and related conditions and disorder: wherein the variables A-B, R1, R2, m, and Q are described herein.

Antiarthritic isoxazole-4-carboxamides

Disclosed herein are isoxazole-4-carboxamides having the formula STR1 wherein R1 is C3-6 cycloalkyl and R2 is selected from the group consisting of C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, C3-6 cycloalkyl, phenyl, and phenyl substituted with at least one group selected from C1-5 alkyl, C1-5 alkoxy, C1-5 alkylthio, and halo-substituted C1-5 alkyl; with the proviso that when R1 is cyclopropyl, R2 is not methyl, ethyl, or cyclobutyl; or R1 is C1-5 alkyl and R2 is phenylmethyl wherein the ring portion is opt. substituted with a halo-substituted C1-5 alkyl group. These compounds have antiinflammatory and antiarthritic activities and are also useful as intermediates in the preparation of β-ketonitriles.

Antiarthritic β-cycloalkyl-β-oxopropionitriles

Disclosed herein are novel β-cycloalkyl-β-oxopropionitriles which exhibit anti-inflammatory/antiarthritic activities.