191794-20-4

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole-2-methanol,4-methyl-(9CI) is utilized as a pharmaceutical intermediate for the synthesis of various drugs and medicinal compounds. Its unique structure and functional groups contribute to the development of new therapeutic agents with potential applications in treating different diseases and conditions.
Used in Chemical Industry:
In the chemical industry, 1H-Benzimidazole-2-methanol,4-methyl-(9CI) serves as a key building block for the synthesis of various organic compounds and materials. Its presence in the benzimidazole family allows for the creation of novel chemical entities with diverse properties and potential applications in areas such as materials science, agrochemicals, and specialty chemicals.

InChI:InChI=1/C9H10N2O/c1-6-3-2-4-7-9(6)11-8(5-12)10-7/h2-4,12H,5H2,1H3,(H,10,11)

Upstream product

• 79-14-1 glycolic Acid 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 56-40-6 glycine 

Downstream Products

• 673487-32-6 4-methyl-1H-benzo[d]imidazole-2-carboxylic acid 
• 1357162-27-6 C₂₁H₂₀N₂O₃ 
• 1357162-36-7 C₂₁H₂₀N₂O₃ 
• 199594-63-3 1-(2,6-difluorobenzyl)-2-t-butyldimethylsiloxymethyl-4-methylbenzimidazole 
• 199594-81-5 1-(2,6-difluorobenzyl)-2-hydroxymethyl-4-methylbenzoimidazole 
• 199594-82-6 1-(2,6-difluorobenzyl)-4-methylbenzoimidazole 

Relevant academic research and scientific papers

Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity

A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4- methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 μM has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 μM has a strong inhibitory effect on the growth of MCF-7 cancer cells.

HETEROCYCLIC COMPOUNDS

Certain thienopyrrolyl and furanopyrrolyl compounds are disclosed as useful to treat or prevent disorders and conditions mediated by the histamine H4 receptor, including allergic rhinitis.

Substituted benzimidazoles, and methods of use thereof, for the inhibition of HIV reverse transcription and for the treatment of HIV infection

The present invention provides compositions and methods for the treatment of HIV infection. In particular, the present invention provides non-nucleoside inhibitors of reverse transcriptase (RT), as well as methods to treat HIV infection using these non-nucleoside inhibitors of RT. In preferred embodiments, the present invention provides a novel class of substituted benzimidazoles, effective in the inhibition of human immunodeficiency virus (HIV) RT.

Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Aryl-substituted benzimidazoles

The development of new nonnucleoside inhibitors of human immunodeficiency virus type-1 (HIV-1) reverse transcriptase (RT) active against the drug-induced mutations in RT continues to be a very important goal of AIDS research. We used a known inhibitor of HIV-1 RT, 1-(2,6- difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole (TZB), as the lead structure for drug design with the objective of making more potent inhibitors against both wild-type (WT) and variant RTs. A series of structurally related 1,2-substituted benzimidazoles was synthesized and evaluated for their ability to inhibit in vitro polymerization by HIV-1 WT RT. A structure- activity study was carried out for the series of compounds to determine the optimum groups for substitution of the benzimidazole ring at the N1 and C2 positions. The best inhibitor, 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)- 4-methylbenzimidazole (35), has an IC50 = 200 nM against HIV-1 WT RT in an in vitro enzyme assay. Cytoprotection assays utilizing HIV-infected MT-4 cells revealed that 35 had strong antiviral activity (EC50 = 440 nM) against wild-type virus while retaining broad activity against many clinically observed HIV-1 strains resistant to nonnucleoside inhibitors. Overall, the activity of 35 against wild-type and resistant strains with amino acid substitution in RT is 4-fold or greater than that of TZB and is comparable to that of other nonnucleoside inhibitors currently undergoing clinical trials, most of which do not have the capacity to inhibit the variant forms of the enzyme.

Ambident heterocyclic reactivity: Intramolecular alkylations of 2,4-disubstituted benzimidazoles

Alkali induced intramolecular cyclizations of 2-(3-chloropropyl)- and 2-(4-chlorobutyl)-4-substituted benzimidazoles bearing 4-nitro-, 4-amino-, and 4-methyl groups show enhanced N3/N1 regioselectivity compared to the corresponding intermolecular alkylations with 1-chlorobutane. The observed N1:N3 cyclization ratios vary from 94:6 to 10:90, with the largest preference for reaction at the 'congested' N3-site occurring in the 5-membered ring formation. In contrast, related base induced reactions of (2-benzimidazolyl)methyl chloroacetate and 3-(2-benzimidazolyl)propyl chloroacetate give excellent yields of macrocyclic dimeric systems. These results are interpreted as involving interplay between electrostatic field, through-bond electronic, and steric approach control factors within variable geometry S(N)2 transition state structures. Calculations (AMI and molecular mechanics) on these systems and conformational analysis of the expected transition states for the intramolecular cyclizations do not support any appreciable use of out-of-plane approach trajectories for these heterocyclic N- alkylation reactions.