5381-79-3

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,1-methyl-6-nitro-(9CI) is used as a building block for the synthesis of pharmaceuticals for its unique molecular structure and properties.
Used in Agrochemical Industry:
1H-Benzimidazole,1-methyl-6-nitro-(9CI) is used as a building block for the synthesis of agrochemicals for its potential applications in agriculture.
Used in Materials Science:
1H-Benzimidazole,1-methyl-6-nitro-(9CI) is used as a building block for the synthesis of other organic compounds for its potential applications in materials science.
It is important to handle this chemical with care and follow safety guidelines when working with it due to its potential hazards.

InChI:InChI=1/C8H7N3O2/c1-10-5-9-7-3-2-6(11(12)13)4-8(7)10/h2-5H,1H3

Upstream product

• 64-18-6 formic acid 
• 95576-84-4 N₂-methyl-4-nitrobenzene-1,2-diamine 
• 50-00-0 formaldehyd 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 553-90-2 Dimethyl oxalate 
• 94-52-0 5-nitrobenzimidazole 
• 1632-83-3 1-Methylbenzimidazole 
• 408509-08-0 toluene-4-sulfonic acid-(2-amino-N-methyl-5-nitro-anilide) 
• 857005-56-2 toluene-4-sulfonic acid-(2-chloro-N-methyl-5-nitro-anilide) 
• 74-88-4 methyl iodide 
• 94-52-0 6-nitro-1H-benzo[d]imidazole 
• 51-17-2 benzoimidazole 

Downstream Products

• 5601-10-5 1-methyl-6-nitro-1H-benzo[d]imidazol-2-amine 
• 10394-38-4 1-methyl-1H-benzo[d]imidazol-5-amine 
• 26530-93-8 1-methyl-6-amino-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Fusion of 2-(furan-2-yl)thiazole to 1-methyl-1H-benzimidazole

Methylation of 5(6)-nitro-1H-benzimidazole with methyl iodide in the presence of potassium hydroxide and N-methylpyrrolidin-2-one gave a mixture of isomeric 1-methyl-5-nitro- and 1-methyl-6-nitro-1H-benzimidazoles which were reduced with tin in concentrated aqueous HCl on heating. The resulting amines reacted with furan-2-carbonyl chloride in N-methylpyrrolidin-2-one to give furan-2-carboxamides which were treated with excess P2S5 in pyridine. Oxidation of isomeric furan-2-carbothioamides with K3[Fe(CN)6] in alkaline medium afforded a mixture of intramolecular cyclization products, 2-(furan-2-yl)-6-methyl-6H-imidazo[4,5-g][1,3]benzothiazole and 2-(furan-2-yl)-8-methyl-8H-imidazo[4,5-g][1,3]benzothiazole which were separated by column chromatography and identified.

QUINAZOLINE COMPOUNDS USEFUL AS M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS

The present invention is directed to compounds of Formula (I): (Formula (I)) and pharmaceutically acceptable salts thereof, wherein X, Y, Z, R1, R7, R8, R9, R11, n and p are defined herein. The compounds of Formula (I) are M1 receptor positive allosteric modulators that are useful in the treatment of diseases in which the M1 receptor is involved, including Alzheimer's disease, schizophrenia, pain and sleep disorders. The invention also relates to pharmaceutical compositions comprising a compound of Formula (I) and a pharmaceutically acceptable carrier, and to methods of using the compounds of Formula (I) in the treatment of diseases mediated by the M1 receptor.

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Structure-activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template

In an effort to design inhibitors of human glutaminyl cyclase (QC), we have synthesized a library of N-aryl N-(5-methyl-1H-imidazol-1-yl)propyl thioureas and investigated the contribution of the aryl region of these compounds to their structure-activity relationships as cyclase inhibitors. Our design was guided by the proposed binding mode of the preferred substrate for the cyclase. In this series, compound 52 was identified as the most potent QC inhibitor with an IC50 value of 58 nM, which was two-fold more potent than the previously reported lead 2. Compound 52 is a most promising candidate for future evaluation to monitor its ability to reduce the formation of pGlu-Aβ and Aβ plaques in cells and transgenic animals.

ANTIFUNGAL AGENTS

Compounds of formula (I), and pharmaceutically acceptable salts thereof, may be used in therapy, for example as antifungal agents: (I) wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. Certain compounds of formula (I) are also provided. Compounds of formula (T), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.

The reaction of benzimidazolium derivatives with superoxide

1-Ethoxycarbonyl-3-methylbenzimidazolium salts, which have an electron deficient imidazolium ring and a carbamate moiety, were allowed to react with superoxide to give ring-opened products and 1-methylbenzimidazoles. The products ratio varied on the change of the counter cation species of superoxide. When 1,1',3,3'-tetramethyl-2,2'-bibenzimidazolium salt reacted with KO2, chemiluminescence was observed which did not occur by the use of KOH or H2O2 as a reagent.

FUSED IMIDAZOPHENOTHIAZINES: STUDIES ON THE BERNTHSEN THIONATION OF 1-METHYL-6-(p-TOLYLAMINO)BENZIMIDAZOLE AND 2-METHYL-1-PHENYLBENZIMIDAZOLE

Thionation of 1-methyl-6-(p-tolylamino)benzimidazole (obtained from 1-methyl-6-aminobenzoimidazole and p-tolyllead triacetate) afforded a 7:3 mixture of two isomeric imidazophenothiazines, by inclusion of sulphur into the C7 and C2' or C5 and C2' position

Alkylation with Oxalic Esters. Scope and Mechanism.

Alkyl oxalates are well suited for use as standard synthetic reagents in N-, O-, or S-alkylations and often display an interesting regioselectivity.The mechanism seems to be a direct alkylation of the substrate anion.

A NEW SIMPLE PROCEDURE FOR ALKYLATION OF NITROGEN HETEROCYCLES USING DIALKYL OXALATES AND ALKOXIDES.

A variety of nitrogen heterocycles are N-alkylated in high yields with dialkyl oxalates and potassium alkoxides in refluxing dimethylformamide.