N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide

Base Information

• Chemical Name: N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide
• CAS No.: 832115-62-5
• Molecular Formula: C₁₁H₁₀N₂O₂S
• Molecular Weight: 234.279
• ChEMBL ID: CHEMBL1222381
• DSSTox Substance ID: DTXSID50880071
• Nikkaji Number: J3.551.730H
• Wikidata: Q27166781
• Mol file: 832115-62-5.mol

Synonyms:isoxazole-9;Isx-9 compound;N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide;N-cyclopropyl-TIC;T63 compound

Chemical Property of N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide

Chemical Property:

• Boiling Point: 468.1±35.0 °C(Predicted)
• PKA: 13.60±0.20(Predicted)
• PSA: 86.86000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 2.87010
• Storage Temp.: -20°
• Solubility.: Soluble in DMSO (up to 60 mg/ml) or in Ethanol (up to 16 mg/ml).
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 234.04629874
• Heavy Atom Count: 16
• Complexity: 283

Purity/Quality:

97% ^*data from raw suppliers

ISX 9 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1NC(=O)C2=NOC(=C2)C3=CC=CS3
• Description: ISX9 (832115-62-5) promotes neurogenesis in vivo enhancing the proliferation and differentiation of hippocampal subgranular zone neuroblasts and enhances memory.1?Induces robust neuronal differentiation in adult neural stem cells.2?Increases insulin production by pancreatic β cells.3?ISX9 blocks malignant astrocyte proliferation, downregulates their astrocyte character, induces reentry into the cell cycle and upregulates neuronal gene expression.4 Induces sensory neurons from neuroepithelial stem cells.5 Potentiates cell proliferation and neuronal commitment in the rat dentate gyrus.6
• Uses: N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide was shown to exhibit regulatory effects towards the expression of pH sensing G protein-coupled receptor-68 and is now a new drug target for ischemic heart disease.

Technology Process of N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide

There total 2 articles about N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

2-ethynyl-thiophene (4298-52-6) + 2-amino-N-cyclopropylacetamide hydrochloride (670253-51-7) → N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide (832115-62-5)

Guidance literature:

With tert.-butylnitrite; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; zinc dibromide; In tert-butyl methyl ether; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c02281

Reference yield: 64.0%

ethyl 5-(2-thiophenyl)-isoxazole-3-carboxylate (90924-54-2) + Cyclopropylamine (765-30-0) → N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide (832115-62-5)

Guidance literature:

In ethanol; at 80 ℃; for 24h;

upstream raw materials:

ethyl 5-(2-thiophenyl)-isoxazole-3-carboxylate

Cyclopropylamine

2-ethynyl-thiophene

2-amino-N-cyclopropylacetamide hydrochloride