ChemicalBook > CAS DataBase List > N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide

N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide

Product Name
N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide
CAS No.
487020-03-1
Chemical Name
N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide
Synonyms
HI-TOPK-32;HI-TOPK-032;HI-TOPK-032 (HI TOPK 032;HITOPK032,inhibit,HI TOPK 032,TOPK,Inhibitor;N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide;N-(12-Cyanoindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxamide;2-Thiophenecarboxamide, N-(12-cyanoindolizino[2,3-b]quinoxalin-2-yl)-
CBNumber
CB42695998
Molecular Formula
C20H11N5OS
Formula Weight
369.4
MOL File
487020-03-1.mol
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N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide Property

Boiling point:
415.3±45.0 °C(Predicted)
Density 
1.50±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble3mg/mL, clear (warmed)
pka
9.32±0.46(Predicted)
form 
powder
color 
orange-brown
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
HS Code 
2922500090
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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
SML0796
Product name
HI-TOPK-032
Purity
≥98% (HPLC)
Packaging
5mg
Price
$123
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0796
Product name
HI-TOPK-032
Purity
≥98% (HPLC)
Packaging
25mg
Price
$482
Updated
2024/03/01
Sigma-Aldrich
Product number
614849
Product name
TOPK/PBK Inhibitor, HI-TOPK-032 - CAS 487020-03-1 - Calbiochem
Purity
A cell-permeable, selective, ATP competitive, reversible inhibitor of T-LAK-cell-originated protein kinase (IC?? = 2 μM).
Packaging
5MG
Price
$201
Updated
2023/06/20
Cayman Chemical
Product number
19815
Product name
HI TOPK 032
Purity
≥95%
Packaging
1mg
Price
$34
Updated
2024/03/01
Cayman Chemical
Product number
19815
Product name
HI TOPK 032
Purity
≥95%
Packaging
5mg
Price
$92
Updated
2024/03/01
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N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide Chemical Properties,Usage,Production

Description

HI TOPK 032 is an inhibitor of lymphokine-activated killer T cell-originated protein kinase (TOPK), blocking phosphorylation of the substrate histone H2AX with an IC50 value of ~2 μM and providing complete inhibition at 5 μM. It also inhibits checkpoint kinase 1 (Chk1; IC50 = 9.6 μM). In addition, HI TOPK 032 inhibits MEK1, achieving 40% inhibition at 5 μM, but it does not alter the activities of ERK1, JNK1, or p38 MAPK at 2 μM. HI TOPK 032 decreases the growth of colon cancer and glioma initiating cells in vitro and suppresses tumor growth in vivo.

Uses

HI-TOPK-032 has been used as a PDZ binding-kinase (PBK) inhibitor.

Uses

N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxamide is a novel TOPK inhibitor that was shown to effectively suppress colon cancer growth.

Biological Activity

HI-TOPK-032 is a potent and specific inhibitor of TOPK. HI-TOPK-032 also reduces ERK-RSK phosphorylation, modulates the abundance of p53, cleaved caspase-7, and cleaved PARP, and induces apoptosis in cancer cells.

Biochem/physiol Actions

HI-TOPK-032 is a specific TOPK (T-LAK cell–originated protein kinase) inhibitor both in vitro and in vivo. HI-TOPK-032 suppressed tumor growth in a colon cancer xenograft model.

in vitro

HI-TOPK-032 strongly suppresses TOPK kinase activity but has little effect on extracellular signal-regulated kinase 1 (ERK1), c-jun-NH2-kinase 1, or p38 kinase activities. HI-TOPK-032 occupies the ATP-binding site of TOPK and fits the binding site very well. The compound forms hydrogen bonds with GLY83 and ASP151 and has a hydrophobic interaction with LYS30. However, HI-TOPK-032 at the highest concentration (5 μM) also inhibits MEK1 activity by 40%. HI-TOPK-032 also inhibits anchorage-dependent and -independent colon cancer cell growth by reducing ERK-RSK phosphorylation as well as increasing colon cancer cell apoptosis through regulation of the abundance of p53, cleaved caspase-7, and cleaved PARP.

in vivo

Treatment of mice with 1 or 10 mg/kg of HI-TOPK-032 significantly inhibits HCT-116 tumor growth by more than 60% relative to the vehicle-treated group. Mice are well tolerated with HI-TOPK-032 treatment. The expression of p53 is strongly induced, and phosphorylation of ERK and RSK, a direct downstream protein of ERK, is markedly inhibited in the HI-TOPK-032-treated group.

N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide Preparation Products And Raw materials

Raw materials

Preparation Products

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N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide Suppliers

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487020-03-1, N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMideRelated Search:


  • N-(12-Cyanindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxaMide
  • HI-TOPK-032
  • HI-TOPK-32
  • N-(12-Cyanoindolizino[2,3-b]quinoxalin-2-yl)-2-thiophenecarboxamide
  • HI-TOPK-032 (HI TOPK 032
  • 2-Thiophenecarboxamide, N-(12-cyanoindolizino[2,3-b]quinoxalin-2-yl)-
  • HITOPK032,inhibit,HI TOPK 032,TOPK,Inhibitor
  • 487020-03-1
  • C20H11N5OS
  • Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds