ChemicalBook > CAS DataBase List > 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide

3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide

Product Name: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide
CAS No.: 1203680-76-5
Chemical Name: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide
Synonyms: AS194949;AS 1949490;AS-1949490 (AS 1949490;AS1949490, 10 mM in DMSO;(S)-3-((4-Chlorobenzyl)oxy)-N-(1-phenylethyl)thiophene-2-carboxamide;3-[(4-chlorobenzyl)oxy]-n-[(1s)-1-phenylethyl]-2-thiophenecarboxa Mide;3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide;3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]- 2-thiophenecarboxamide;2-Thiophenecarboxamide, 3-[(4-chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]-;inhibit,Protein kinase B,glucose uptake,AS 1949490,diabetes,insulin signalling pathway,Akt,AS1949490,glucose consumption,Inhibitor,Phosphatase,PKB,L6 myotubes,AS-1949490
CBNumber: CB92518678
Molecular Formula: C20H18ClNO2S
Formula Weight: 371.88
MOL File: 1203680-76-5.mol

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3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide Property

Melting point:: 89 - 91°C
storage temp.: Store at RT
solubility: DMSO: soluble20mg/mL, clear
form: powder
color: white to beige
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.

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1022
Product name: AS1949490
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $121
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML1022
Product name: AS1949490
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $332
Updated: 2025/07/31

Cayman Chemical

Product number: 17627
Product name: AS-1949490
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 17627
Product name: AS-1949490
Purity: ≥98%
Packaging: 5mg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 17627
Product name: AS-1949490
Purity: ≥98%
Packaging: 10mg
Price: $160
Updated: 2024/03/01

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3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide Chemical Properties,Usage,Production

Description

AS-1949490 (1203680-76-5) is a? potent and selective inhibitor of the intracellular phosphatase SHIP2 (SH2 domain-containing inositol 5′-phosphatase 2), IC50 = 0.62 μM.1 Displays ca. 30-fold selectivity for SHIP2 over SHIP1. Activates insulin signaling via the Akt pathway in liver and lowers glucose levels in diabetic mice.1,2 Enhances BDNF expression in cultured cortical neurons.3 Ameliorates ROS generation but aggravates apoptosis in CD2AP-deficient mouse podocytes.4

Uses

AS1949490 is a potent, selective SHIP2 phosphatase inhibitor. It activates insulin signaling pathways in liver and lowers glucose levels in diabetic mice.

in vivo

AS1949490 (300 mg/kg; p.o.; twice daily, for 7 or 10 d) decreases plasma glucose and activates intracellular insulin signalling in diabetic mice^[1].? AS1949490 (300 mg/kg; p.o.; once, for 8 h; male ICR mice) suppresses gluconeogenesis and the expression of related genes^[1].

Animal Model:	Male C57BL/KsJ Jcl-dbm mice and db/+db mice^[1]
Dosage:	300 mg/kg
Administration:	Oral administration; twice daily, for 7 or 10 days
Result:	Decreased plasma glucose (23% reduction, relative to vehicle). Reduced fasting blood glucose (37% reduction, relative to vehicle) and the area under the blood glucose concentration time curve (AUC). Increased the phosphorylation of GSK3β in the liver without changing the overall levels of GSK3β protein.

Animal Model:	Male ICR mice (6 weeks of age)^[1]
Dosage:	300 mg/kg
Administration:	Oral administration; once, for 8 hours
Result:	Reduced an approximately 50% of both PEPCK and G6Pase mRNA levels.

storage

Store at RT

References

[1] A SUWA. Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2[J]. British Journal of Pharmacology, 2009, 158 3: 879-887. DOI:10.1111/j.1476-5381.2009.00358.x
[2] AKIRA SUWA. Glucose metabolism activation by SHIP2 inhibitors via up-regulation of GLUT1 gene in L6 myotubes[J]. European journal of pharmacology, 2010, 642 1: Pages 177-182. DOI:10.1016/j.ejphar.2010.06.002
[3] HIROSHI TSUNEKI . AS1949490, an inhibitor of 5′-lipid phosphatase SHIP2, promotes protein kinase C-dependent stabilization of brain-derived neurotrophic factor mRNA in cultured cortical neurons[J]. European journal of pharmacology, 2019, 851: Pages 69-79. DOI:10.1016/j.ejphar.2019.02.003
[4] PAULIINA SAURUS. Inhibition of SHIP2 in CD2AP-deficient podocytes ameliorates reactive oxygen species generation but aggravates apoptosis.[J]. Scientific Reports, 2017: 10731. DOI:10.1038/s41598-017-10512-w

3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide Preparation Products And Raw materials

Raw materials

Preparation Products

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1203680-76-5, 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamideRelated Search:

Fruquintinib PF-01367338 N-(3-Chlorophenyl)-N'-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-2-thiazolyl]urea methanesulfonate (1:1) AZ20

3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide

AS 1949490

3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]- 2-thiophenecarboxamide

AS-1949490 (AS 1949490

3-[(4-chlorobenzyl)oxy]-n-[(1s)-1-phenylethyl]-2-thiophenecarboxa Mide

2-Thiophenecarboxamide, 3-[(4-chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]-

(S)-3-((4-Chlorobenzyl)oxy)-N-(1-phenylethyl)thiophene-2-carboxamide

inhibit,Protein kinase B,glucose uptake,AS 1949490,diabetes,insulin signalling pathway,Akt,AS1949490,glucose consumption,Inhibitor,Phosphatase,PKB,L6 myotubes,AS-1949490

AS1949490, 10 mM in DMSO

AS194949

1203680-76-5