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General Description

The chemical compound 2-(4-HYDROXY-3-METHOXY-PHENYL)-1H-BENZOIMIDAZOLE-4-CARBOXYLIC ACID, also known as BHPI, is a benzimidazole derivative that consists of a benzimidazole core with a carboxylic acid group and a phenolic hydroxyl group. It is often used in medicinal chemistry as a potential therapeutic agent due to its ability to exhibit anti-inflammatory, anti-tumor, and anti-oxidant properties. BHPI has been studied for its potential anti-cancer effects and ability to inhibit the growth of various cancer cell lines. Additionally, it has shown potential as an anti-inflammatory agent by reducing the production of inflammatory cytokines and modulating immune responses. Its ability to scavenge free radicals and protect against oxidative stress also makes it a promising candidate for further research and development in the pharmaceutical industry.

InChI:InChI=1/C15H12N2O4/c1-21-12-7-8(5-6-11(12)18)14-16-10-4-2-3-9(15(19)20)13(10)17-14/h2-7,18H,1H3,(H,16,17)(H,19,20)

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Relevant academic research and scientific papers

Resistance-modifying agents. 9. Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase

The nuclear enzyme poly(ADP-ribose) polymerase (PARP) facilitates the repair of DNA strand breaks and is implicated in the resistance of cancer cells to certain DNA-damaging agents. Inhibitors of PARP have clinical potential as resistance-modifying agents capable of potentiating radiotherapy and the cytotoxicity of some forms of cancer chemotherapy. The preclinical development of 2-aryl-1H-benzimidazole-4-carboxamides as resistance-modifying agents in cancer chemotherapy is described. 1H-Benzimidazole-4-carboxamides, particularly 2-aryl derivatives, are identified as a class of potent PARP inhibitors. Derivatives of 2-phenyl-1H-benzimidazole-4-carboxamide (23, K(i) = 15 nM), in which the phenyl ring contains substituents, have been synthesized. Many of these derivatives exhibit K(i) values for PARP inhibition 10 nM, with 2-(4-hydroxymethylphenyl)-1H-benzimidazole-4-carboxamide (78, K(i) = 1.6 nM) being one of the most potent. Insight into structure-activity relationships (SAR) for 2-aryl-1H-benzimidazole-4-carboxamides has been enhanced by studying the complex formed between 2-(3-methoxyphenyl)-1H-benzimidazole-4-carboxamide (44, K(i) = 6 nM) and the catalytic domain of chicken PARP. Important hydrogen-bonding and hydrophobic interactions with the protein have been identified for this inhibitor. 2-(4-Hydroxyphenyl)-1H-benzimidazole-4-carboxamide (45, K(i) = 6 nM) potentiates the cytotoxicity of both temozolomide and topotecan against A2780 cells in vitro (by 2.8- and 2.9-fold, respectively).