ChemicalBook > CAS DataBase List > 2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester

2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester

Product Name
2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester
CAS No.
305834-79-1
Chemical Name
2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester
Synonyms
SC79;SC97;CS-2177;SC79;SC 79;Akt Activator II;Akt Activator II, SC79;SC79;SC 79;AKT ACTIVATOR II;Akt Activator II, SC79 - CAS 305834-79-1 - Calbiochem;SC79,inhibit,Akt,Protein kinase B,Inhibitor,SC-79,PKB;Ethyl-2-amino-6-chloro-4-(1-cyano-2-ethoxy-2-oxoethyl)-4Hchromene-3-carboxylat
CBNumber
CB82708757
Molecular Formula
C17H17ClN2O5
Formula Weight
364.78
MOL File
305834-79-1.mol
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2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester Property

Boiling point:
524.8±50.0 °C(Predicted)
Density 
1.340±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: soluble20mg/mL, clear
form 
powder
pka
3.03±0.40(Predicted)
color 
white to beige
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
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Safety

WGK Germany 
3
HS Code 
2932990090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0749
Product name
SC79
Purity
≥97% (NMR)
Packaging
5mg
Price
$119
Updated
2024/03/01
Sigma-Aldrich
Product number
123871
Product name
Akt Activator II, SC79
Packaging
25mg
Price
$225
Updated
2024/03/01
Cayman Chemical
Product number
14972
Product name
SC-79
Purity
≥95%
Packaging
5mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
14972
Product name
SC-79
Purity
≥95%
Packaging
10mg
Price
$107
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0749
Product name
SC79
Purity
≥97% (NMR)
Packaging
25mg
Price
$289.2
Updated
2024/03/01
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2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester Chemical Properties,Usage,Production

Description

SC-79 is an activator of Akt that blocks its membrane translocation while allowing its phosphorylation, in the cytosol, by upstream kinases. For example, both Thr308 and Ser473 on Akt are phosphorylated in serum starved HeLa cells treated for 1 hour with insulin growth factor and SC-79 (4 μg/ml). SC-79 permits phosphorylation and activation of all isoforms of Akt, it is active in multiple cell types, and works in both receptor tyrosine kinase- and G protein-coupled receptor-mediated signaling. SC-79 has been used to elucidate the role of Akt signaling in neuronal survival, glucose-mediated apoptosis in podocytes, and miR-221-regulated cancer cell proliferation.

Uses

2-Amino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester is a useful synthetic intermediate.

Uses

SC79 has been used in western blot analysis as a positive control to measure the extent of phosphorylation of Akt and also to activate Akt that has been suppressed by nitidine chloride, a natural bioactive alkaloid.

General Description

A cell-permeable and blood-brain barrier permeant bromo-to-chloro substituted HA14-1 (Cat. No. 371971) analog that renders Akt in a conformation susceptible to phosphorylation by upstream kinases via specific interaction with Akt pleckstrin homology (PH) domain PtdIns(3,4,5)P3- (PIP3) binding pocket. Shown to enhance both basal and receptor-mediated Akt phosphorylation (Thr308 and Ser473) in a time- and dose-dependent manner (2 to 4 μg/ml) with concomitant inhibition Akt membrane translocation in various cell cultures. Efficiently reduces glutamate-induced neurotoxicity both in primary neuron cultures (EC50 = 4 μg/ml) in vitro and in a murine MCAO (middle cerebral artery occlusion) model (40 mg/kg, i.p.) in vivo.

Biochem/physiol Actions

Cell permeable: yes

in vitro

sc79 was identified by a cell-based high-throughput chemical genetic screening, and inhibits akt membrane translocation. however, akt was paradoxically activated by sc79in the cytosol, specifically binding to the ph domain of akt. the conformation of sc79-bound akt is favorable for phosphorylation by upstream protein kinases. in a mouse model and a hippocampal neuronal culture system for ischemic stroke, the result of augmented neuronal survival is attained, based on the cytosolic activation of akt by sc79, which is sufficient to recapitulate the primary cellular function of akt signaling. thus, sc79, a unique specific akt activator, may be applied to enhance akt activity in various physiological and pathological conditions.

in vivo

in aqueous environment, sc79 is relatively unstable. intriguingly, however, the sustained level of phosphorylated akt was observed both in cell culture and in vivo after the removal of sc79, indicating that sc79 may act irreversibly. the chemical moieties of sc79 (i.e., nitrile group) could be modified and/or reacts with amino acids. nevertheless, sc79, a relatively safe drug, was revealed by following fact. assignment of sc79 treatment much high dose (0.4 mg/g of body weight) did not accelerate any detectable changes in body weight (survival rate, appearance, and behavior) in mice. achievement of neuronal protective effect by i.p. injection suggests that sc79 also has a good penetration of blood–brain barrier. sc79 can be applied as a chemical platform to develop novel drugs for neurological and other complications

storage

Store at -20°C

References

1) Jo?et al. (2012),?Small-molecule-induced cytosolic activation of protein kinase Akt rescues ischemia-elicited neuronal death; Proc. Natl. Acad. Sci. USA,?109?10581 2) Yang?et al.?(2016),?MiR-221 Promotes Capan-2 Pancreatic Ductal Adenocarcinoma Cells Proliferation by Targeting PTEN-Akt; Cell. Physiol. Biochem.?38?2366 3) Chen?et al.?(2017),?Novel Akt activator SC-79 is a potential treatment for alcohol-induced osteonecrosis of the femoral head; Oncotarget,?8?31065

2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester manufacturers

Henan Fengda Chemical Co., Ltd
Product
2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester 305834-79-1
Price
US $8.00-2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-24
Career Henan Chemical Co
Product
2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester 305834-79-1
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-23

305834-79-1, 2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl EsterRelated Search:

Astemizole U-74389G GF109203X BCTC 2-chloro-5-cyanopyridine 4-ThiazolecarboxaMide, N-(6-benzoyl-1H-benziMidazol-2-yl)-2-(1-thieno[3,2-d]pyriMidin-4-yl-4-piperidinyl)- SC-514 SC 57461A SC 66 α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile

  • SC79
  • 2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester
  • 2-Amino-6-chloro-alpha-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic acid ethyl ester
  • Akt Activator II, SC79
  • Akt Activator II
  • SC79;SC 79;AKT ACTIVATOR II
  • 4H-1-Benzopyran-4-acetic acid, 2-amino-6-chloro-α-cyano-3-(ethoxycarbonyl)-, ethyl ester
  • SC79;SC 79
  • Akt Activator II, SC79 - CAS 305834-79-1 - Calbiochem
  • CS-2177
  • Ethyl-2-amino-6-chloro-4-(1-cyano-2-ethoxy-2-oxoethyl)-4Hchromene-3-carboxylat
  • SC97
  • 2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester
  • Ethyl 2-amino-6-chloro-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
  • SC79,inhibit,Akt,Protein kinase B,Inhibitor,SC-79,PKB
  • 305834-79-1
  • Inhibitors