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AZ20

Product Name
AZ20
CAS No.
1233339-22-4
Chemical Name
AZ20
Synonyms
AZ20;CS-1335;AZ20 ，S7050;AZ-20; AZ 20;;AZ20 USP/EP/BP;AZ20, 10 mM in DMSO;1H-Indole, 4-[4-[(3R)-3-methyl-4-morpholinyl]-6-[1-(methylsulfonyl)cyclopropyl]-2-pyr;(3R)-4-[2-(3H-indol-4-yl)-6-(1-methylsulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine;(R)-4-(2-(1H-Indol-4-yl)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine;4-[4-(1-Methanesulfonylcyclopropyl)-6-[(3R)-3-methylmorpholin-4-yl]pyrimidin-2-yl]-1H-indole
CBNumber
CB32655393
Molecular Formula
C21H24N4O3S
Formula Weight
412.51
MOL File
1233339-22-4.mol
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AZ20 Property

Boiling point:
634.6±55.0 °C(Predicted)
Density 
1.42±0.1 g/cm3(Predicted)
storage temp. 
-20°
solubility 
Soluble in DMSO (up to 20 mg/ml).
form 
solid
pka
15.65±0.30(Predicted)
color 
Off-white
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChIKey
SCGCBAAYLFTIJU-CQSZACIVSA-N
SMILES
N1C2=C(C(C3=NC(C4(S(C)(=O)=O)CC4)=CC(N4CCOC[C@H]4C)=N3)=CC=C2)C=C1
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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

Cayman Chemical
Product number
17589
Product name
AZ 20
Purity
≥98%
Packaging
1mg
Price
$26
Updated
2024/03/01
Cayman Chemical
Product number
17589
Product name
AZ 20
Purity
≥98%
Packaging
5mg
Price
$58
Updated
2024/03/01
Cayman Chemical
Product number
17589
Product name
AZ 20
Purity
≥98%
Packaging
10mg
Price
$102
Updated
2024/03/01
Cayman Chemical
Product number
17589
Product name
AZ 20
Purity
≥98%
Packaging
25mg
Price
$625
Updated
2023/06/20
Tocris
Product number
5198
Product name
AZ20
Purity
≥98%(HPLC)
Packaging
50
Price
$1217
Updated
2021/12/16
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AZ20 Chemical Properties,Usage,Production

Description

AZ20 (1233339-22-4) is a potent and highly selective inhibitor of Ataxia telangiectasia mutated and RAD3-related (ATR) kinase (IC50?= 5 nM in vitro; IC50?= 50 nM in HT29 colorectal adenocarcinoma cells).1?Combination therapy with AZ20 and gemcitabine resulted in synergistic inhibition of tumor cell growth and cell death initiation in pancreatic cancer cell lines.2

Uses

AZ20 is a potent and selective inhibitor of ATR (ATM-Rad3-related) kinase with in vivo antitumor activity.

Definition

ChEBI: (3R)-4-[2-(1H-indol-4-yl)-6-(1-methylsulfonylcyclopropyl)-4-pyrimidinyl]-3-methylmorpholine is a member of indoles.

Synthesis

1233339-68-8

220465-43-0

1233339-22-4

The general steps for the synthesis of (R)-4-(2-(1H-indol-4-yl)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine from the compound (CAS:1233339-68-8) and 4-indolylboronic acid were as follows: 1. suspend bis(triphenylphosphine)palladium chloride (1.692 g, 2.41 mmol), (R)-4-(2-chloro-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine (8.00 g, 24.11 mmol), 1H-indol-4-ylboronic acid (4.27 g 26.52 mmol) and 2M aqueous sodium carbonate (36.2 mL, 72.33 mmol) were heated to 90 °C for overnight reaction. 2. After the reaction was completed, the DME was removed and the reaction mixture was diluted with EtOAc (100 mL). 3. The mixture was washed with water (2 x 100 mL), the organic phase was separated, filtered through a diatomaceous earth pad and concentrated in vacuum to give the crude product. 4. Purify the crude product by silica gel column chromatography with an elution gradient of 0 to 10% EtOAc in DCM solution. The grades containing the target product were combined and the solvent was evaporated. 5. The residue was purified again by silica gel column chromatography with an elution gradient of 0 to 25% EtOAc in DCM solution. The fractions containing the target product were combined and the solvent was evaporated. 6. The residue is dissolved and purified by reversed-phase C18 silica gel column (415g HP C18 column) using a mixture of water (containing 1% NH3) and MeCN as the eluent with decreasing polarity. The grades containing the target product were combined and the solvent was evaporated. 7. The residue was dissolved in anhydrous MeOH, dried over MgSO4, filtered and the solvent evaporated to give a gel. 8. The colloid was dissolved in DCM (500 mL), filtered and the solvent was removed under reduced pressure. 9. The residue was dissolved in MeOH (50 mL), stirred overnight at room temperature, and the resulting precipitate was collected by filtration to afford the target product (R)-4-(2-(1H-indol-4-yl)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine (5.10 g, 51% yield). Product characterization: 1H NMR (400 MHz, DMSO-d6) δ 1.29 (3H, d), 1.57-1.64 (2H, m), 1.68-1.78 (2H, m), 3.24-3.31 (1H, td), 3.29 (3H, s), 3.51 (1H, td), 3.67 (1H, dd), 3.80 (1H, d). d), 3.93-4.06 (1H, dd), 4.21 (1H, d), 4.61 (1H, bs), 6.85 (1H, s), 7.21 (1H, t), 7.32 (1H, t), 7.46 (1H, t), 7.56 (1H, d), 8.06 (1H, dd), 11.25 (1H, s); m/z (ESI+ ) MH+, 413.12. Chiral HPLC analysis (HPI 100 system on a 4,5 μm Chiralpak AS-H (250 mm × 4.6 mm) column, elution conditions: isohexane/EtOH/TEA 60/40/0.1) showed an Rf value of 8.815 and a purity of >99%.

in vivo

AZ20 (25, 50 mg/kg, p.o.) has high permeability combined with good stability to rat hepatocytes and, despite the lack of progress in achieving markedly higher solubility, has respectable bioavailability in a low dose rat PK study. AZ20 (25, 50 mg/kg, p.o.) leads to significant tumor growth inhibition in female nude mice bearing LoVo tumors[1].

IC 50

ATR: 5 nM (IC50); mTOR: 38 nM (IC50); PI3Kα: 13000 nM (IC50)

storage

Store at -20°C

References

[1] KEVIN M. FOOTE*. Discovery of 4-{4-[(3R)-3-Methylmorpholin-4-yl]-6-[1-(methylsulfonyl)cyclopropyl]pyrimidin-2-yl}-1H-indole (AZ20): A Potent and Selective Inhibitor of ATR Protein Kinase with Monotherapy in Vivo Antitumor Activity[J]. Journal of Medicinal Chemistry, 2013, 56 5: 2125-2138. DOI:10.1021/jm301859s
[2] SHUANG LIU. Inhibition of ATR potentiates the cytotoxic effect of gemcitabine on pancreatic cancer cells through enhancement of DNA damage and abrogation of ribonucleotide reductase induction by gemcitabine.[J]. Oncology reports, 2017: 3377-3386. DOI:10.3892/or.2017.5580

AZ20 Preparation Products And Raw materials

Raw materials

Preparation Products

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AZ20 Suppliers

China 124 France 1 India 2 The Netherlands 1 United Kingdom 3 United States 18 Global 149
Shanghai Star Pharmaceutical Chemical Technology Co., Ltd.
Tel
021-58521787 17701827760
Email
starpharmsh@gmail.com
Country
China
ProdList
292
Advantage
58
Wuhan Augda Biotechnology Co., Ltd
Tel
15071299552
Fax
QQ:262933239
Email
262933239@qq.com
Country
China
ProdList
7048
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6003
Advantage
61
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
12952
Advantage
65
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4747
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 13167063860
Fax
021-50323701
Email
anhua.mao@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
Jinan Mingya Medical Technology Co., Ltd.
Tel
0531-85828981
Fax
+86-531-85806006
Email
864598798@qq.com
Country
China
ProdList
588
Advantage
58
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View Lastest Price from AZ20 manufacturers

Career Henan Chemical Co
Product
AZ20 1233339-22-4
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-23

1233339-22-4, AZ20Related Search:

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  • AZ-20; AZ 20;
  • CS-1335
  • AZ20
  • 1H-Indole, 4-[4-[(3R)-3-methyl-4-morpholinyl]-6-[1-(methylsulfonyl)cyclopropyl]-2-pyrimidinyl]-
  • 4-[4-[(3R)-3-Methyl-4-morpholinyl]-6-[1-(methylsulfonyl)cyclopropyl]-2-pyrimidinyl]-1H-indole AZ20
  • AZ20 4-[4-[(3R)-3-Methyl-4-morpholinyl]-6-[1-(methylsulfonyl)cyclopropyl]-2-pyrimidinyl]-1H-indole
  • 4-[4-[(3R)-3-Methyl-4-morpholinyl]-6-[1-(methylsulfonyl)cyclopropyl]-2-pyrimidinyl]-1H-indole
  • (3R)-4-[2-(3H-indol-4-yl)-6-(1-methylsulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine
  • 4-[4-(1-Methanesulfonylcyclopropyl)-6-[(3R)-3-methylmorpholin-4-yl]pyrimidin-2-yl]-1H-indole
  • AZ20 USP/EP/BP
  • (R)-4-(2-(1H-Indol-4-yl)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine
  • 1H-Indole, 4-[4-[(3R)-3-methyl-4-morpholinyl]-6-[1-(methylsulfonyl)cyclopropyl]-2-pyr
  • AZ20, 10 mM in DMSO
  • AZ20 ，S7050
  • 1233339-22-4
  • Inhibitors