402948-33-8

Basic information

• Product Name: 1H-Benzimidazole-2-acetic acid, 5-(4-morpholinyl)-, ethyl ester
• CAS NO: 402948-33-8
• Molecular Formula: C15H19N3O3
• Molecular Weight: 289.334
• Mol File: 402948-33-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Benzimidazole-2-acetic acid, 5-(4-morpholinyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-2-acetic acid, 5-(4-morpholinyl)-, ethyl ester(402948-33-8)
• EPA Substance Registry System: 1H-Benzimidazole-2-acetic acid, 5-(4-morpholinyl)-, ethyl ester(402948-33-8)

Safety Data

• Hazardous Substances Data: 402948-33-8(Hazardous Substances Data)

Usage

Chemical structure

A heterocyclic compound with a benzene ring fused to an imidazole ring, an ethyl ester group at the 2-position, and a morpholinyl group at the 5-position.

Molecular weight

Approximately 260.29 g/mol

Functional groups

Ester, benzimidazole, and morpholine

Potential pharmaceutical uses

Due to its structure and properties, this compound may have potential as a substrate or modulator for enzymes or receptors, making it a target for further research and development in the pharmaceutical industry.

Biological activity

The addition of a morpholinyl group to the 5 position of the benzimidazole ring enhances the compound's potential for biological activity.

Solubility

The compound may have varying solubility in different solvents, depending on the polarity and hydrogen bonding capabilities of the solvent.

Stability

The stability of the compound may be influenced by factors such as temperature, pH, and exposure to light or air.

Synthesis

The compound can be synthesized through various chemical reactions, involving the formation of the benzimidazole core, introduction of the ethyl ester group, and attachment of the morpholinyl group at the 5-position.

Analytical techniques

Techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared (IR) spectroscopy can be used to analyze and confirm the structure of the compound.

Purity

The purity of the compound can be assessed using techniques like high-performance liquid chromatography (HPLC) or gas chromatography (GC).

Safety and handling

As with any chemical compound, appropriate safety measures should be taken when handling 1H-Benzimidazole-2-acetic acid, 5-(4-morpholinyl)-, ethyl ester, including the use of personal protective equipment (PPE) and following proper disposal procedures.

Upstream product

• 2318-25-4 ethyl 3-ethoxy-3-iminopropanoate hydrochloride 
• 119421-28-2 4-morpholinobenzene-1,2-diamine 
• 54998-00-4 5-morpholino-2-nitroaniline 
• 1336-21-6 ammonium hydroxide 

Downstream Products

• 405171-01-9 4-hydroxy-3-(5-morpholin-4-ylbenzimidazol-2-yl)-1-benzylhydroquinolin-2-one 

Relevant articles and documents

Design, structure-activity relationships and in vivo characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: Novel class of receptor tyrosine kinase inhibitors

The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino- 3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TKI258), are reversible ATP- competitive inhibitors of VEGFR-2, FGFR-1, and PDGFRβ with IC50 values 0.1 μM. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.

Inhibition of FGFR3 and treatment of multiple myeloma

Methods of inhibiting fibroblast growth factor receptor 3 and treating various conditions mediated by fibroblast growth factor receptor 3 are provided that include administering to a subject a compound of Structure I, a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer. Compounds having the Structure I have the following structure where and have the variables described herein. Such compounds may be used to prepare medicaments for use in inhibiting fibroblast growth factor receptor 3 and for use in treating conditions mediated by fibroblast growth factor receptor 3 such as multiple myeloma.

Quinolinone derivatives

Organic compounds having the formulas I and II are provided where the variables have the values described herein. Pharmaceutical formulations include the organic compounds or pharmaceutically acceptable salts thereof and a pharmaceutically acceptable carrier and may be prepared by mixing the organic compounds or pharmaceutically acceptable salts of the organic compounds with a carrier and water. A method of treating a patient includes administering a pharmaceutical formulation according to the invention to a patient in need thereof.