ISX-9 , CAS No.832115-62-5

CAS: 832115-62-5 Cat. No.: I1372002-GMP Molecular Weight: 234.27 EC Number: 993-123-2

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Overview

ISX-9 (Isoxazole 9) (GMP) is a GMP grade ISX-9. GMP grade small molecules can be used as auxiliary reagents in cell therapy. ISX-9 is a small molecule with antioxidant, pro survival, and regenerative properties.

Biological activity:

ISX-9 (Isoxazole 9) is a potent inducer of adult neural stem cell differentiation. ISX-9 activates Ca2+ influx through both voltage-gated Ca2+ channels and NMDA receptors and increases neuroD expression. ISX-9 also induces cardiomyogenic differentiation of Notch-activated epicardium-derived cells (NECs). In Vitro: ISX-9 promotes neurogenesis in vivo, enhancing the proliferation and differentiation of hippocampal subgranular zone (SGZ) neuroblasts, and the dendritic arborization of adult-generated dentate gyrus neurons. At 2.5-20 μM, ISX-9 has been shown to dose-dependently trigger neurogenesis and block gliogenesis in adult rat hippocampal stem cells through a calcium-activated signaling pathway dependent on myocyte-enhancer factor 2-dependent gene expression.

Molecular exploration of ISX-9-induced regulation of neurogenesis (via FACS and microarray of SGZ stem and progenitor cells) suggested the involvement of the myocyte-enhancer family of proteins (Mef2). In Vivo: ISX-9 (20 mg/kg; for 12 days; mice) treatment improves hippocampal function. ISX-9 enhances spatial memory ability in the Morris water maze test. ISX-9 enhances hippocampal neurogenesis and memory in vivo, and its effects are reliant on Mef2.

Specifications

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Names and Identifiers

• Canonical Smiles: C1CC1NC(=O)C2=NOC(=C2)C3=CC=CS3
• IUPAC Name: N-cyclopropyl-5-thiophen-2-yl-1,2-oxazole-3-carboxamide
• InChIKey: SYENTKHGMVKGAQ-UHFFFAOYSA-N
• INCHI: 1S/C11H10N2O2S/c14-11(12-7-3-4-7)8-6-9(15-13-8)10-2-1-5-16-10/h1-2,5-7H,3-4H2,(H,12,14)
• Isomeric SMILES: C1CC1NC(=O)C2=NOC(=C2)C3=CC=CS3
• Molecular Weight: 234.27
• Reaxy-Rn: 18935384
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=18935384&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives
        • Level5 Carboxylic acid amides
          • Level6 2-heteroaryl carboxamides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Carboxylic acid derivatives
• Intermediate Tree Nodes: Carboxylic acid amides
• Direct Parent: 2-heteroaryl carboxamides
• Alternative Parents: Thiophenes Isoxazoles Heteroaromatic compounds Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-heteroaryl carboxamide - Azole - Isoxazole - Thiophene - Heteroaromatic compound - Secondary carboxylic acid amide - Organoheterocyclic compound - Oxacycle - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 2-heteroaryl carboxamides. These are compounds containing a heteroaromatic ring that carries a carboxamide group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y