188106-94-7

Basic information

• Product Name: 1H-Benzimidazole-4-carboxylicacid,2-methyl-(9CI)
• Synonyms: 1H-Benzimidazole-4-carboxylicacid,2-methyl-(9CI);2-Methylbenzimidazole-4-carboxylic acid;2-Methyl-1H-benzimidazole-4-carboxylic acid;2-Methyl-1H-1,3-benzodiazole-7-carboxylic acid;2-methyl-1H-benzo[d]imidazole-7-carboxylic acid;2-Methyl-3H-benzimidazole-4-carboxylic acid
• CAS NO: 188106-94-7
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.174
• Product Categories: BENZIMIDAZOLE
• Mol File: 188106-94-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Benzimidazole-4-carboxylicacid,2-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-4-carboxylicacid,2-methyl-(9CI)(188106-94-7)
• EPA Substance Registry System: 1H-Benzimidazole-4-carboxylicacid,2-methyl-(9CI)(188106-94-7)

Safety Data

• Hazardous Substances Data: 188106-94-7(Hazardous Substances Data)

Usage

General Description

1H-Benzimidazole-4-carboxylicacid,2-methyl-(9CI) is a chemical compound that falls under the class of Benzimidazoles, which are organic compounds containing an imidazole ring fused to a benzene ring. This specific compound is characterized by a 2-methyl group and a carboxylic acid group at the fourth position of the benzimidazole ring. Due to the properties of its benzimidazole group, it may exhibit biological activities such as antifungal, antiviral, or anticancer properties. However, detailed information about its usage, biological activity and potential toxicity is not widely available in the literature and it is not commonly used in the pharmaceutical industry.

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Relevant articles and documents

OXADIAZOLE DERIVATIVES AND PHARMACEUTICAL USES THEREOF

PROBLEM TO BE SOLVED: To provide therapeutic or preventive agents for various diseases or symptoms associated with a serotonin 4 receptor (particularly, neuropsychiatric diseases such as Alzheimer-type dementia). SOLUTION: The present invention provides a compound represented by formula (1) or a pharmaceutically acceptable salt thereof. In the formula (1), Het represents formula (Het-1) or the like, A represents formula (A-1) or the like, B represents (B-1) or the like, R1A represents a hydrogen atom, an alkyl group or the like, R2A, R5, R6 and R7 represent a hydrogen atom, a halogen atom, an alkyl group or the like, R8 and R9 represent a hydrogen atom, an alkyl group or the like, and l represents an integer of 0-4. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

A facile one-pot synthesis of benzimidazoles from 2-nitroanilines by reductive cyclization

A facile one-pot process to prepare benzimidazole derivatives is described. Reductive cyclization of a serial of 2-nitroanilines with orthoesters in the presence of Pd/C in methanol at room temperature, which is promoted by a catalytic amount of acetic acid, affords the corresponding benzimidazole derivatives in high yields.

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).