1203680-76-5

Basic information

• Product Name: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide
• Synonyms: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide;AS 1949490;3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]- 2-thiophenecarboxamide
• CAS NO: 1203680-76-5
• Molecular Formula: C20H18ClNO2S
• Molecular Weight: 371.88042
• Mol File: 1203680-76-5.mol

Chemical Properties

• Appearance: white to beige/
• Storage Temp.: Store at RT
• Solubility: DMSO: soluble20mg/mL, clear
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 month.
• CAS DataBase Reference: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide(1203680-76-5)
• EPA Substance Registry System: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide(1203680-76-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 1203680-76-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide is used as a potent and selective SHIP2 phosphatase inhibitor for the treatment of diabetes. It activates insulin signaling pathways in the liver, which helps in lowering glucose levels in diabetic mice. 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide has demonstrated its effectiveness in enhancing the expression of brain-derived neurotrophic factor (BDNF) in cultured cortical neurons, which could potentially contribute to the development of treatments for neurological disorders.
Used in Research Applications:
In the field of scientific research, 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide serves as a valuable tool for studying the role of SHIP2 phosphatase in various cellular processes. Its selective inhibition of SHIP2 allows researchers to investigate the specific functions and pathways regulated by this enzyme, contributing to a better understanding of its role in health and disease.
Used in Drug Development:
The compound's ability to activate insulin signaling via the Akt pathway in the liver and its potential to ameliorate reactive oxygen species (ROS) generation make it a promising candidate for the development of new drugs targeting diabetes and other related metabolic disorders. Additionally, its impact on apoptosis in CD2AP-deficient mouse podocytes could be explored for the development of therapeutic strategies for kidney diseases.

References

Suwa et al. (2009), Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2; Br. J Pharmacol., 158 879 Suwa et al. (2010), Glucose metabolism activation by SHIP2 inhibitors via up-regulation of GLUT1 gene in L6 myotubes; Eur. J. Pharmacol., 642 177 Tsuneki et al. (2019), AS1949490, an inhibitor of 5’-lipid phosphatase SHIP2, promotes protein kinase C-dependent stabilization of brain-derived neurotrophic factor mRNA in cultured neurons; Eur. J. Pharmacol., 851 69 Saurus et al. (2017), Inhibition of SHIP2 in CD2AP-deficient podocytes ameliorates reactive oxygen species generation but aggravates apoptosis; Sci. Rep., 7 10731