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SU 6668

Product Name
SU 6668
CAS No.
210644-62-5
Chemical Name
SU 6668
Synonyms
SU 6668;(Z)-SU6668;(Z)-TSU-68;(Z)-Orantinib;(Z)-Orantinib/SU6668/TSU-68);PDGFR Tyrosine Kinase Inhibitor VI, SU6668;PDGFR Tyrosine Kinase Inhibitor VI, SU6668 - CAS 210644-62-5 - Calbiochem;3-[2,4-dimethyl-5-[(Z)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoicacid;3-(2,4-Dimethyl-5-{[(3Z)-2-oxo-1H-indol-3-ylidene]methyl}-1H-pyrrol-3-yl)propanoic acid;3-(2,4-Dimethyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl)-propionic acid
CBNumber
CB91312244
Molecular Formula
C18H18N2O3
Formula Weight
310.35
MOL File
210644-62-5.mol
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SU 6668 Property

storage temp. 
+2C to +8C
solubility 
DMSO : 50 mg/mL (161.11 mM; Need ultrasonic)
form 
Dark yellow solid
color 
Orange to red
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
CDS023028
Product name
2,4-Dimethyl-5-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-pyrrole-3-propanoic acid
Packaging
100MG
Price
$308
Updated
2023/01/07
Tocris
Product number
3335
Product name
SU6668
Purity
≥99%(HPLC)
Packaging
10
Price
$208
Updated
2021/12/16
TRC
Product number
D457088
Product name
(Z)​-​3-​(2,​4-​Dimethyl-​5-​((2-​oxoindolin-​3-​ylidene)​methyl)​-​1H-​pyrrol-​3-​yl)​propanoicacid(SU-6668)
Packaging
5mg
Price
$90
Updated
2021/12/16
Usbiological
Product number
256776
Product name
SU 6668
Packaging
10mg
Price
$466
Updated
2021/12/16
Matrix Scientific
Product number
132613
Product name
(Z)-3-(2,4-Dimethyl-5-((2-oxoindolin-3-ylidene)-methyl)-1H-pyrrol-3-yl)propanoicacid
Purity
97%
Packaging
250mg
Price
$537
Updated
2021/12/16
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SU 6668 Chemical Properties,Usage,Production

Uses

PDGFR Tyrosine Kinase Inhibitor VI, SU6668 is a potent ATP-competitive inhibitor against tyrosine kinases.

General Description

A cell-permeable indolinone compound that acts as a potent ATP-competitive inhibitor against RTKs (receptor tyrosine kinases) Kit, PDGFRβ, VEGFR2 (Flk-1/KDR), FGFR1 activity in vitro (IC50 = 0.01, 0.1, 3.9, and 3.8 μM, respectively) and PDGF/VEGF/bFGF-mediated angiogenesis and tumor development in vivo. Although initially characterized as an RTK inhibitor, SU6668 is now also known to target ser/thr kinases Aurora A, Aurora B, TBK1 (NAK/T2K), and AMPK (IC50 = 0.85, 0.047, 1.4, and 1.8 μM, respectively), as well as non-receptor TKs Lyn and Yes (IC50 = 4.3 and 5.8 μM, respectively).

Synthesis

59-48-3

1133-96-6

210644-62-5

A mixture of 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propionic acid (10 g, 51 mmol), 2-indolone (6.5 g, 49 mmol) and sodium hydroxide (40 g, 58 mmol) was dissolved in 50 ml of water and the reaction was stirred for 4 hr at 50 °C. After completion of the reaction, the mixture was cooled to room temperature, filtered and the filtrate was acidified with 12N hydrochloric acid to pH 3. The precipitated solid was collected by vacuum filtration, washed with 10 ml of water and dried under vacuum overnight. The crude product was washed twice with hot ethanol, then the solid was collected by vacuum filtration, washed with 10 ml of ethanol and dried under vacuum to give 13.8 g (91% yield) of (Z)-3-(2,4-dimethyl-5-((2-oxoindolin-3-ylidene)methyl)-1H-pyrrol-3-yl)propionic acid.1HNMR (360 MHz, DMSO-d6) data were as follows: δ 13.38 (s, br, 1H, NH-1'), 12.05 (s, br, 1H, COOH), 10.70 (s, br, 1H, NH-1), 7.69 (d, J=7.39 Hz, 1H, H-4), 7.53 (s, 1H, H-vinyl), 7.06 (t, J=7.39 Hz, 1H, H-6), and 6.95 (t, J=7.39Hz, 1H, H-5), 6.85 (d, J=7.39Hz, 1H, H-7), 2.63 (t, J=7.45Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.45Hz, 2H, CH2CH2COOH), 2.28 (s, 3H, CH3), 2.24 ( s, 3H, CH3). Mass spectral data: MS m/z 311 ([M+1]+, 100).

in vivo

SU6668 (4-200 mg/kg/day; p.o. for 21 d) induces dose-dependent inhibition of A431 tumor growth in athymic mice[1].
SU6668 (75 mg/kg/day; i.p. for 22 d) significantly suppresses tumor angiogenesis and vascularization in mice[1].
SU6668 (200 mg/kg/day; p.o. for 11-27 d) induces striking regression of large established A431 xenografts in athymic mice[1].

Animal Model:Female athymic mice (BALB/c, nu/nu) were implanted A431 tumor cells[1]
Dosage:4, 40, 75, 200 mg/kg
Administration:P.o. daily for 21 days
Result:Induced 97% growth inhibition against A431 tumor at the dose of 97%.
No mortality was observed in any treatment group.

IC 50

Flk-1/KDR: 2.1 μM (IC50); PDGFRβ: 0.008 μM (IC50); FGFR1: 1.2 μM (IC50)

References

[1] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 215
[2] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 215
[3] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 1, p. 181 - 185
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 25, p. 5120 - 5130
[5] Patent: US6395734, 2002, B1

SU 6668 Preparation Products And Raw materials

Raw materials

Preparation Products

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SU 6668 Suppliers

China 51 India 1 United States 8 Global 60
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
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BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
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United States
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12952
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65
Nanjing JinruiJiuAn Biotechnology Co., Ltd.
Tel
025-58196018 800028039
Fax
025-83453306
Email
sales@fartop.net
Country
China
ProdList
2229
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Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51395
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SPIRO PHARMA
Tel
Fax
-
Email
eric_feng1954@126.com
Country
China
ProdList
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Nanjing River Chemical Co., Ltd.
Tel
13951936332 18305166317
Fax
-
Email
info@serpharm.com
Country
China
ProdList
493
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55
Shanghai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847; 18021002903
Fax
QQ:3008007432
Email
3008007409@qq.com
Country
China
ProdList
71826
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Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
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sales@amadischem.com
Country
China
ProdList
131957
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Shanghai Biopharmaleader Co., Ltd.
Tel
+86 18721201413
Fax
+86 (21) 5775-8967
Email
sales@biopharmaleader.com
Country
China
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Henan Alfachem Co.,Ltd.
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0371-55051623 18137891487
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QQ：2853979817
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2853979817@qq.com
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China
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  • SU 6668
  • 3-(2,4-Dimethyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl)-propionic acid
  • 1H-Pyrrole-3-propanoic acid, 5-((Z)-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-
  • 5-((Z)-1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-propanoic acid
  • PDGFR Tyrosine Kinase Inhibitor VI, SU6668
  • 3-[2,4-dimethyl-5-[(Z)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoicacid
  • PDGFR Tyrosine Kinase Inhibitor VI, SU6668 - CAS 210644-62-5 - Calbiochem
  • 3-(2,4-Dimethyl-5-{[(3Z)-2-oxo-1H-indol-3-ylidene]methyl}-1H-pyrrol-3-yl)propanoic acid
  • (Z)?-?3-?(2,?4-?Dimethyl-?5-?((2-?oxoindolin-?3-?ylidene)?methyl)?-?1H-?pyrrol-?3-?yl)?propanoic acid (SU-6668)
  • (Z)-Orantinib
  • (Z)-SU6668
  • (Z)-TSU-68
  • 5-(Z)-(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl-2,4-dimethyl-1H-pyrrol-3-propanoic acid
  • (Z)-Orantinib/SU6668/TSU-68)
  • 2,4-Dimethyl-5-[(1,2-dihydro-2-oxo-3<i>H</i>-indol-3-ylidene)methyl]-pyrrole-3-propanoic acid
  • 210644-62-5