418795-27-4

Basic information

• Product Name: 1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridine
• CAS NO: 418795-27-4
• Molecular Weight: 176.218
• Mol File: 418795-27-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridine(418795-27-4)
• EPA Substance Registry System: 1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridine(418795-27-4)

Safety Data

• Hazardous Substances Data: 418795-27-4(Hazardous Substances Data)

Usage

General Description

1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridine is a chemical compound with a molecular formula C11H14N2O. It is a heterocyclic compound with a pyrrolo-pyridine structure. This chemical can be used in various applications, including but not limited to pharmaceuticals, agrochemicals, and material science. It may also have potential biological activities and may act as a building block in organic synthesis. The presence of the methoxyethyl group in the compound suggests that it is likely to have solubility in organic solvents. Further research and experimentation may be required to fully understand the potential uses and properties of this chemical compound.

Upstream product

• 271-63-6 7-Azaindole 
• 6482-24-2 2-Bromoethyl methyl ether 
• 109-86-4 2-methoxy-ethanol 
• 143141-23-5 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Synthesis, antitumor activity and CDK1 inhibiton of new thiazole nortopsentin analogues

A new series of thiazole nortopsentin analogues was conveniently synthesized with fair overall yields. The antiproliferative activity of the new derivatives was tested against different human tumor cell lines of the NCI full panel. Four of them showed good antitumor activity with GI50 values from micro to nanomolar level. The mechanism of the antiproliferative effect of these derivatives, was pro-apoptotic, being associated with externalization of plasma membrane phosphatidylserine and DNA fragmentation. The most active and selective of the new thiazoles confined viable cells in G2/M phase and markedly inhibited in vitro CDK1 activity.

Characterization of maleimide-based glycogen synthase kinase-3 (GSK-3) inhibitors as stimulators of steroidogenesis

Inhibition of GSK-3β has been well documented to account for the behavioral actions of the mood stabilizer lithium in various animal models of mood disorders. Recent studies have showed that genetic or pharmacological inhibition of GSK-3β resulted in anxiolytic-like and pro-social behavior. In our ongoing efforts to develop GSK-3β inhibitors for the treatment of mood disorders, SAR studies on maleimide-based compounds were undertaken. We present herein for the first time that some of these GSK-3β inhibitors, in particular analogues 1 and 9, were able to stimulate progesterone production in the MA-10 mouse tumor Leydig cell model of steroidogenesis without any significant toxicity. These two compounds were tested in the SmartCube behavioral assay and showed anxiolytic-like signatures following daily dose administration (50 mg/kg, ip) for 13 days. Taken together, these results support the hypothesis that GSK-3β inhibition could influence neuroactive steroid production thereby mediating the modulation of anxiety-like behavior in vivo.

Potent platelet-derived growth factor-β receptor (PDGF-βR) inhibitors: Synthesis and structure-activity relationships of 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl} quinoxalin-2(1H)-one derivatives

We found previously that 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H- pyrrolo[2,3-b]pyridin-3-yl}quinoxalin-2(1H)-one (7d-6) has considerable potency as a PDGF inhibitor. This compound showed potent inhibitory activity in a PDGF-induced CPA (Cell Proliferation Assay) and APA (Auto-Phosphorylation Assay) (IC50=0.05 μmol/l in CPA, 0.03 μmol/l in APA). Therefore, we tried to develop a novel and effective PDGF-βR inhibitor by optimizing a series of its derivatives. We found that trifluoroacetic acid (TFA)-catalyzed coupling of pyrrolo[2,3-b]pyridines with quinoxalin-2-ones proceeded efficiently under mild oxidation condition with manganese(IV) oxide (MnO2) in situ, so this method was applied to prepare a series of derivatives. Results of in vitro screening of newly synthesized derivatives identified compound 7d-9 as having potent (IC50=0.014 μmol/l in CPA, 0.007 μmol/l in APA) and selective [IC50 values against vascular endothelial growth factor receptor 2 (VEGFR2, kinase domain region, KDR), epidermal growth factor receptor (EGFR), c-Met (hepatocyte growth factor receptor) and insulin growth factor I receptor (IGF-IR)/IC50 against PDGFR were each >1000] inhibitory activity. Moreover, in this series of derivatives, 7b-2 showed potent inhibitory activity toward both PDGF- and VEGF-induced signaling (PDGFR: IC50=0.004 μmol/l in CPA, 0.0008 μmol/l in APA, KDR: IC 50=0.008 μmol/l in APA). Herein we report a new and convenient synthetic method for this series of derivatives and its SAR study.