124340-89-2

Basic information

• Product Name: 1H-Benzimidazole-7-carboxylic acid, 2-(3-pyridinyl)-
• Synonyms: 1H-Benzimidazole-7-carboxylic acid, 2-(3-pyridinyl)-;2-(pyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid
• CAS NO: 124340-89-2
• Molecular Formula: C₁₃H₉N₃O₂
• Molecular Weight: 239.23
• Mol File: 124340-89-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Benzimidazole-7-carboxylic acid, 2-(3-pyridinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-7-carboxylic acid, 2-(3-pyridinyl)-(124340-89-2)
• EPA Substance Registry System: 1H-Benzimidazole-7-carboxylic acid, 2-(3-pyridinyl)-(124340-89-2)

Safety Data

• Hazardous Substances Data: 124340-89-2(Hazardous Substances Data)

Usage

Chemical structure

1H-Benzimidazole-7-carboxylic acid, 2-(3-pyridinyl)consists of a benzimidazole ring with a carboxylic acid group at position 7 and a 2-(3-pyridinyl) group attached to the nitrogen at position 2 of the benzimidazole ring.

Usage

Commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals.

Biological activities

Studied for its potential as an inhibitor of protein kinases and as a potential anti-cancer agent.

Versatility

Presence of both a benzimidazole and a pyridinyl moiety makes it a potentially valuable chemical for various applications in medicinal chemistry and pharmacology.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 603-81-6 2,3-diaminobenzoic acid 
• 61063-11-4 2-Amino-3-nitrobenzoic acid,ethyl ester 
• 16533-45-2 ethyl 2-carboxy-3-nitrobenzoate 
• 136285-66-0 3-nitro-phthalic acid-1-ethyl ester-2-chloride 
• 124341-05-5 2-Azidocarbonyl-3-nitro-benzoic acid ethyl ester 
• 641-70-3 3-nitrophthalic acid anhydride 
• 603-11-2 3-nitrophthalic acid 
• 606-18-8 3-nitroanthranilic acid 
• 77326-45-5 2-carbamoyl-3-nitrobenzoic acid 

Downstream Products

• 1309042-22-5 (L)-2-(pyridin-3-yl)-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)-1H-benzimidazole-4-carboxamide 

Relevant articles and documents

Synthesis and biological evaluation of novel benzimidazole derivatives bearing a heterocyclic ring at 4/5 position

A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 (IC50 = 1.08 μg/mL, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.

Inhibitory properties of 2-substituent-1H-benzimidazole-4-carboxamide derivatives against enteroviruses

A series of novel benzimidazole derivatives were designed, synthesized, and evaluated for their activities against four kinds of enteroviruses, that is, Coxsackie virus A16, B3, B6 and Enterovirus 71 in VERO cells. Strong activities against enterovirus replication and low cytotoxicities were observed in these benzimidazoles generally. The most promising compound was (l)-2-(pyridin-2-yl)- N-(2-(4-nitrophenyl)pentan-3-yl)-1H-benzimidazole-4-carboxamide (16), with a high antiviral potency (IC50 = 1.76 μg/mL) and a remarkable selectivity index (328). These compounds were selected for further evaluation as novel enterovirus inhibitors.

Synthesis and antiviral activity against Coxsackie virus B3 of some novel benzimidazole derivatives

Some benzimidazole derivatives were synthesized and the antiviral evaluation against Coxsackie virus B3 is reported. These compounds are proved to be excellent inhibitors of CVB3. Some benzimidazole derivatives were synthesized and evaluated for their antiviral properties. Compounds 20 and 21 showed potent selective activity against Coxsackie virus B3 in VERO cells. Some structure-activity relationships were discussed.

Convenient method for the preparation of 2-aryl-1H-benzimidazole-4- carboxylic acids

The oxidative cyclization of 2,3-diaminobenzoic acid and aromatic aldehydes to give 2-aryl-1H-benzimidazole-4-carboxylic acids is reported. Moreover, three methods were compared in different perspectives from experimental manipulation to yield. Copyright

Benzamide derivatives having a vasopressin antagonistic activity

This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc. and represented by general formula (I): wherein R1is aryl optionally substituted with lower alkoxy, etc., R2is lower alkyl, etc., R3is hydrogen, etc., A is NH, etc., E is etc., X is —CH═CH—, —CH═N—, or S, and Y is a condensed heterocyclic group, etc., and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.

Potential Antitumor Agents. 59. Structure-Activity Relationships for 2-Phenylbenzimidazole-4-carboxamides, a New Class of "Minimal" DNA-Intercalating Agents Which May Not Act via Topoisomerase II

A series of substituted 2-phenylbenzimidazole-4-carboxamides has been synthesized and evaluated for in vitro and in vivo antitumor activity.These compounds represent the logical conclusion to our search for "minimal" DNA-intercalating agents with the lowest possible DNA-binding constants.Such "2-1" tricyclic chromophores, of lower aromaticity than the structurally similar 2-phenylquinolines, have the lowest DNA binding affinity yet seen in the broad series of tricyclic carboxamide intercalating agents.Despite very low in vitro cytotoxicities, several of the compoundshad moderate levels of in vivo antileukemic effects.However, the most interesting aspect of their biological activity was the lack of cross-resistance shown to an amsacrine-resistant P388 cell line, suggesting that these compounds may not express their cytotoxicity via interaction with topoisomerase II.