3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester
[CAS# 211915-84-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Cyanopyridine
• Name: 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester
• Synonyms: Ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate
• Molecular Formula: C₂₇H₂₆N₆O₃
• Molecular Weight: 482.53
• CAS Registry Number: 211915-84-3
• SMILES: CCOC(=O)CCN(C1=CC=CC=N1)C(=O)C2=CC3=C(C=C2)N(C(=N3)CNC4=CC=C(C=C4)C#N)C

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.640, Calc.^*
• Boiling Point: 756.4±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 411.2±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester is a complex organic compound with potential applications in pharmaceutical research. The structure of this compound consists of a benzimidazole ring, a pyridine group, and a cyano-substituted phenyl group, suggesting that it may have diverse biological activity. This combination of functional groups creates a molecule that could be useful in targeting various biological pathways, particularly those related to enzyme inhibition or receptor modulation.

The discovery of 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester emerged from the search for novel compounds with the potential to modulate cellular processes. The benzimidazole scaffold is known for its versatility in medicinal chemistry, often serving as a core structure for drugs targeting a range of diseases, including cancer, infectious diseases, and inflammation. The addition of a pyridine group and a cyano group further enhances the potential reactivity and selectivity of the molecule for certain biological targets.

One of the primary applications of this compound lies in its potential as an enzyme inhibitor. The benzimidazole and pyridine groups in the structure are likely to interact with enzymes or receptors that are involved in cellular signaling, possibly inhibiting key enzymes involved in metabolic processes or gene expression. Such activity could be beneficial in the treatment of diseases such as cancer, where the modulation of specific enzymes or receptors could reduce tumor growth or metastasis. Additionally, the cyano group may contribute to the compound's ability to interact with specific enzymes that require a particular electronic environment for activity.

The ethyl ester group present in the structure also suggests that the compound may have favorable properties for drug formulation. Ester groups are often used to improve the solubility and bioavailability of compounds, and in this case, the ethyl ester of 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid could potentially enhance its pharmacokinetic properties, facilitating better absorption and distribution in the body.

In the context of drug development, this compound may serve as a lead molecule for the design of more potent and selective inhibitors. By optimizing the functional groups within its structure, researchers could enhance its binding affinity to target enzymes or receptors, potentially improving its therapeutic efficacy in treating a range of conditions.

Additionally, the compound’s unique combination of functional groups may offer promise in the development of novel therapies for neurological conditions. The pyridine group and the benzimidazole scaffold are often associated with compounds that modulate neurotransmitter systems, and thus, 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester could be explored further in the context of diseases such as Alzheimer's, Parkinson's, or other neurodegenerative disorders where enzyme inhibition or receptor modulation is beneficial.

In conclusion, 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester is a promising compound in the field of medicinal chemistry. Its complex structure, featuring benzimidazole, pyridine, and cyano groups, provides a foundation for further exploration in enzyme inhibition, receptor modulation, and potentially other therapeutic applications, particularly in the treatment of cancer and neurological diseases.

References

2016. Co-crystallization of a benzimidazole derivative with carboxylic acids. *Research on Chemical Intermediates*, 42(9).
DOI: 10.1007/s11164-016-2666-9

2008. Dabigatran etexilate. *Pharmaceutical Substances*.
URL: KD-04-0169