ChemicalBook > CAS DataBase List > N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea

N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea

Product Name
N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea
CAS No.
1020172-07-9
Chemical Name
N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea
Synonyms
CS-1867;Rebastinib;DCC2036;DCC 2036;Rebastinib Tosylate;Rebastinib(DCC-2036);DCC-2036 (Rebastinib);Rebastinib, 10 mM in DMSO;Rebastinib (DCC-2036) ，S2634;DCC2036; DCC-2036; DCC 2036; REBASTINIB.;4-(4-(3-(3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)-N-methylpic
CBNumber
CB52547102
Molecular Formula
C30H28FN7O3
Formula Weight
553.59
MOL File
1020172-07-9.mol
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N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea Property

Melting point:
>181°C (dec.)
Boiling point:
666.8±55.0 °C(Predicted)
Density 
1.32
storage temp. 
-20°C Freezer
solubility 
Methanol (Slightly)
pka
12.25±0.70(Predicted)
form 
Solid
color 
Off-White
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
21465
Product name
Rebastinib
Purity
≥98%
Packaging
1mg
Price
$47
Updated
2024/03/01
Cayman Chemical
Product number
21465
Product name
Rebastinib
Purity
≥98%
Packaging
5mg
Price
$206
Updated
2024/03/01
Cayman Chemical
Product number
21465
Product name
Rebastinib
Purity
≥98%
Packaging
10mg
Price
$360
Updated
2024/03/01
Cayman Chemical
Product number
21465
Product name
Rebastinib
Purity
≥98%
Packaging
25mg
Price
$788
Updated
2024/03/01
TRC
Product number
R139300
Product name
Rebastinib
Packaging
10mg
Price
$450
Updated
2021/12/16
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N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea Chemical Properties,Usage,Production

Description

Rebastinib is an orally bioavailable tyrosine kinase inhibitor that inhibits Abl1 (IC50 = 0.8 nM) as well as the gatekeeper mutant Abl1T315I (IC50 = 4 nM) and the activation loop mutant Abl1H396P. It also inhibits the Src family kinases Src, Lyn, Fgr, and Hck and the tyrosine kinases KDR, FLT3, and Tie2 at nanomolar concentrations. Rebastinib inhibits mutant Abl1T315I signaling and prolongs survival in a mouse Ba/F3 cell allograft model. Rebastinib also exhibits in vivo antineoplastic activity against cells with the T674I point mutation of FIP1-like-1-platelet-derived growth factor receptor α.

Uses

A conformational control inhibitor of Abl1 and Abl1-T315I with IC50s of 0.8 nM and 4 nM, respectively.

Uses

Rebastinib shows the selectivity for growth inhibition of Bcr-Abl-positive cells by its marked inhibition of CML cell lines compared to non-CML leukemia lines. Rebastinib (DCC-2036) is a conformational control Bcr-Abl inhibitor for Abl1(WT) and Abl1(T315I) with IC50 of 0.8 nM and 4 nM, also inhibits SRC, LYN, FGR, HCK, KDR, FLT3, and Tie-2, and low activity to seen towards c-Kit. Phase 1. It is a COVID19-related research product.

Definition

ChEBI: DCC-2036 is a member of the class of ureas that is urea in which one of the nitrogens bears a 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl substituent, while the other bears a 2-fluoro-4-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}phenyl substituent. It has a role as a tyrosine kinase inhibitor. It is a member of quinolines, a pyridinecarboxamide, a member of pyrazoles, an organofluorine compound and a member of phenylureas.

Synthesis

757251-39-1

1011464-72-4

1020172-07-9

Example 1: 4-(4-amino-3-fluorophenoxy)-N-methylpyridine-2-carboxamide (7.0 g, 15.8 mmol), compound (CAS:1011464-72-4, 4.14 g, 15.8 mmol) and N,N-diisopropylethylamine (DIEA, 4.5 g, 34.9 mmol) were dissolved in dimethyl sulfoxide (DMSO 70 ml). The reaction mixture was heated in an oil bath at 70°C for 8 hours. After completion of the reaction, the mixture was poured into water (500 ml), stirred overnight and the solid was collected by filtration. The crude product was purified by successive crystallization from toluene and acetone to afford 1-(3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenyl)urea as a white crystalline solid (4.06 g, 46% yield). The product was characterized by 1H NMR (DMSO-d6) and mass spectrometry (ESI): 1H NMR δ 8.90 (m, 2H), 8.79 (m, 1H), 8.52 (m, 2H), 8.2 (m, 3H), 7.96 (dd, J = 9,2 Hz, 1H), 7.63 (dd, J = 8,4 Hz, 1H), 7.40 (br s, 1H) 7.30 (dd, J = 3,12 Hz, 1H), 7.17 (m, 1H), 7.05 (d, J = 9 Hz, 1H), 6.50 (s, 1H), 2.80 (d, J = 5Hz), 1.32 (s, 9H); MS (ESI) m/z: 554 (M + H+).

in vivo

A single dose of Rebastinib (DCC-2036; oral; 100 mg/kg) affords circulating plasma levels that exceeds 12 μM for up to 24 hours, and effectively inhibits BCR-ABL1 signaling for up to 8 hours in Ba/F3-BCR-ABL1T315I leukemia cells isolated from BM and spleen of tumor-bearing mice[1].
Treatment of mice bearing Ba/F3-BCR-ABL1T315I leukemia cells with Rebastinib at 100 mg/kg once daily by oral gavage significantly prolonged their survival, while STI571 at 100 mg/kg twice daily is ineffective[1].
In this aggressive allograft model, Rebastinib is as effective for treatment of BCR-ABLT315I leukemia as STI571 at 100 mg/kg twice daily in BCR-ABL1native leukemia, and reduces the leukemia cell burden in the spleens of treated mice[1].

References

[1] chan w w, wise s c, kaufman m d, et al. conformational control inhibition of the bcr-abl1 tyrosine kinase, including the gatekeeper t315i mutant, by the switch-control inhibitor dcc-2036. cancer cell, 2011, 19(4): 556-568.

N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea Preparation Products And Raw materials

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Preparation Products

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N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea Suppliers

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View Lastest Price from N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea manufacturers

Career Henan Chemical Co
Product
4-(4-(3-(3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)-N-methylpicolinamide 1020172-07-9
Price
US $1.00/KG
Min. Order
1KG
Purity
95%
Supply Ability
500KG
Release date
2018-08-19

1020172-07-9, N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]ureaRelated Search:

Tazemetostat 2-Bromo-2-methylpropane Roxadustat Saracatinib Dabrafenib AVP-AEW541 AZD-9291

  • CS-1867
  • DCC2036;DCC 2036
  • Rebastinib
  • DCC-2036 (Rebastinib)
  • N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(MethylcarbaMoyl)pyridin-4-yl)
  • 1-(3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenyl)urea
  • N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea DCC-2036 (Rebastinib)
  • Rebastinib(DCC-2036)
  • N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea
  • Rebastinib Tosylate
  • 4-(4-(3-(3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)-N-methylpic
  • 4-[4-[(5-tert-butyl-2-quinolin-6-ylpyrazol-3-yl)carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide
  • 4-(4-(3-(3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)-N-methylpicolinamide
  • DCC2036; DCC-2036; DCC 2036; REBASTINIB.
  • 2-Pyridinecarboxamide, 4-[4-[[[[3-(1,1-dimethylethyl)-1-(6-quinolinyl)-1H-pyrazol-5-yl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-
  • N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea USP/EP/BP
  • Rebastinib, 10 mM in DMSO
  • CD135,Apoptosis,inhibit,Rebastinib,Bcr-Abl,Fms like tyrosine kinase 3,Inhibitor,FLT3,Src,Cluster of differentiation antigen 135
  • Rebastinib (DCC-2036) ，S2634
  • 1020172-07-9
  • C30H28FN7O3
  • Inhibitors