188106-81-2

Basic information

• Product Name: 1H-Benzimidazole-4-carboxamide(9CI)
• Synonyms: 1H-Benzimidazole-4-carboxamide(9CI);1H-Benzo[d]imidazole-4-carboxamide
• CAS NO: 188106-81-2
• Molecular Formula: C8H7N3O
• Molecular Weight: 161.16
• Product Categories: AMIDE;BENZIMIDAZOLE
• Mol File: 188106-81-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Benzimidazole-4-carboxamide(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-4-carboxamide(9CI)(188106-81-2)
• EPA Substance Registry System: 1H-Benzimidazole-4-carboxamide(9CI)(188106-81-2)

Safety Data

• Hazardous Substances Data: 188106-81-2(Hazardous Substances Data)

Usage

Core structure

Benzimidazole

Functional group

Carboxamide attached at the 4-position

Use as a building block

Synthesis of pharmaceuticals and agrochemicals

Bioactivity potential

Anti-cancer, anti-inflammatory, and antiviral properties

Therapeutic potential

Treatment of various diseases

Enzyme inhibition potential

Inhibition of certain enzymes and biological processes

Value in medicinal chemistry

Further research and development for new drug discovery.

Upstream product

• 780804-82-2 1H-benzimidazole-4-carbonyl chloride 
• 606-18-8 3-nitroanthranilic acid 
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• 603-81-6 2,3-diaminobenzoic acid 
• 77326-45-5 2-carbamoyl-3-nitrobenzoic acid 

Relevant articles and documents

HETERO COMPOUND

[Problems] To provide a useful compound as an active ingredient for a preventing and/or treating agent for rejection in the transplantation of an organ, bone marrow, or a tissue, an autoimmune disease, or the like, which has an excellent S1P1 a

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).

Benzimidazole compounds

Benzimidazole-4-carboxamide compounds (I) which can act as potent inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase or PARP enzyme (EC 2.4.2.30), and which thereby can provide useful therapeutic compounds for use in conjunction with DNA-damaging cytotoxic drugs or radiotherapy to potentiate the effects of the latter. In formula (I), R and R' may each be selected independently from hydrogen, alkyl, hydroxyalkyl (e.g. CH2CH2OH), acyl (e.g. acetyl or benzoyl) or an optionally substituted aryl (e.g. phenyl) or aralkyl (e.g. benzyl or carboxybenzyl) group. R is generally a substituted phenyl group in the most preferred compounds. The compounds may also be used in the form of pharmaceutically acceptable salts or pro-drugs.