2-(3-methoxyphenyl)-N-[2-(5-methyl-1H-benzimidazol-2-yl)phenyl]acetamide
[CAS# 1251678-63-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: 2-(3-methoxyphenyl)-N-[2-(5-methyl-1H-benzimidazol-2-yl)phenyl]acetamide
• Molecular Formula: C₂₇H₂₄N₄O₂
• Molecular Weight: 436.51
• CAS Registry Number: 1251678-63-3
• SMILES: CC1=CC=C(C=C1)CNC(=O)C2=CC3=C4C(=CN=C3C=C2)C(=O)N(N4)C5=CC(=C(C=C5)C)C

Discovory and Applicatios

2-(3-Methoxyphenyl)-N-\[2-(5-methyl-1H-benzimidazol-2-yl)phenyl]acetamide is a synthetic organic compound of interest in the field of medicinal chemistry, particularly for its relevance in structure–activity relationship studies of benzimidazole derivatives. Compounds bearing the benzimidazole scaffold are widely recognized for their biological activities, and modifications of this core structure have yielded promising candidates for pharmacological development in areas such as cancer, inflammation, and microbial infections.

The molecule consists of a substituted benzimidazole ring system connected via a phenyl linker to an acetamide group bearing a 3-methoxyphenyl substituent. The benzimidazole moiety includes a methyl group at the 5-position, which may influence its electronic properties and steric interactions with biological targets. The phenyl group connecting the two core regions plays a pivotal role in maintaining the molecular rigidity and positioning required for specific receptor binding. The 3-methoxyphenyl ring contributes additional electronic characteristics and increases lipophilicity, potentially enhancing membrane permeability or influencing binding affinity.

The discovery of this compound is tied to efforts to optimize the therapeutic profiles of benzimidazole derivatives. Benzimidazoles have long been explored as bioisosteres of purine bases, allowing them to interact with nucleotide-binding proteins, including enzymes and receptors. In this compound, the substitution pattern and linker length have been tailored to maximize specific interactions, such as hydrogen bonding and π-stacking, within target protein sites.

Although detailed pharmacological data on 2-(3-methoxyphenyl)-N-\[2-(5-methyl-1H-benzimidazol-2-yl)phenyl]acetamide is limited in public literature, structurally similar molecules have been reported to act as kinase inhibitors, tubulin polymerization disruptors, or DNA-intercalating agents. The presence of an amide bond suggests potential for hydrogen bonding interactions, commonly involved in molecular recognition by biological targets. The methoxy group on the aromatic ring is also a known modulator of electron density and can affect the compound's metabolic stability or binding dynamics.

In synthetic terms, this molecule can be assembled through conventional multi-step organic synthesis. The benzimidazole ring is typically formed via condensation of o-phenylenediamine with a carboxylic acid derivative or aldehyde, often under acidic conditions. The acetamide linkage can be constructed by activating the corresponding acid (or its derivative) and coupling it to the amine. Introduction of the 3-methoxyphenyl unit can be achieved through standard substitution reactions, often involving an aryl halide or boronic acid and transition-metal-catalyzed cross-coupling strategies, depending on the synthetic route.

Applications of such benzimidazole-derived compounds are being investigated across a spectrum of therapeutic areas. Structural analogues of the title compound have demonstrated anti-proliferative activity in cancer cell lines and have been explored for their potential as receptor antagonists or modulators of cellular signaling pathways. The precise arrangement of aromatic systems, hydrogen bond donors and acceptors, and hydrophobic groups in this molecule supports its candidacy for further evaluation in drug discovery pipelines.

The structure–activity relationship of this class of compounds underscores the importance of substitution patterns on the benzimidazole and phenylacetamide moieties. Small structural variations often result in significant differences in biological response, emphasizing the value of such molecules as probes in medicinal chemistry and chemical biology. Continued research may uncover specific biological targets and confirm the potential of 2-(3-methoxyphenyl)-N-\[2-(5-methyl-1H-benzimidazol-2-yl)phenyl]acetamide or its derivatives as lead structures in therapeutic development.