22128-99-0

Usage

Category

Benzimidazole derivative

Substitution

Methoxy group at the 2-position of the benzimidazole ring

Usage

Building block in the synthesis of pharmaceuticals and fine chemicals

Reactivity

High reactivity, can participate in a range of organic reactions

Value

Valuable for the production of diverse compounds

Biological activities

Studied for potential therapeutic applications

Upstream product

• 1850-14-2 tetramethoxymethane 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 89843-42-5 2-methoxy-5(6)-nitrobenzimidazole 
• 1542704-23-3 N-benzyl-5-(2-methoxy-1H-benzo[d]imidazol-1-yl)thiazolo[5,4-d]pyrimidin-7-amine 
• 1542709-50-1 N-benzyl-2-(2-methoxy-1H-benzo[d]imidazol-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine 
• 1542704-70-0 N-benzyl-2-(2-methoxy-1H-benzo[d]imidazol-1-yl)-8-(2-methoxyethoxy)quinazolin-4-amine 
• 1542704-16-4 N-benzyl-8-methoxy-2-(2-methoxy-1H-benzo[d]imidazol-1-yl)quinazolin-4-amine 

Relevant academic research and scientific papers

Deprotection of N-benzylbenzimidazoles and N-benzylimidazoles with triethylsilane and Pd/C

The benzyl group is a protecting group for benzimidazoles and imidazoles that can survive acidic, basic, oxidizing, and reducing conditions. Deprotection, however, can require vigorous and potentially non-chemoselective methods. The triethylsilane–Pd/C reduction system is an exceptionally mild, convenient, and efficient method for deprotecting N-benzylbenzimidazoles that are unsubstituted at the 2- and 4-positions as well as suitably substituted N-benzylimidazoles.

SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted benzimidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

Pharmacophore Identification and Scaffold Exploration to Discover Novel, Potent, and Chemically Stable Inhibitors of Acid Ceramidase in Melanoma Cells

Acid ceramidase (AC) hydrolyzes ceramides, which are central lipid messengers for metabolism and signaling of sphingolipids. A growing body of evidence links deregulation of sphingolipids to several diseases, including cancer. Indeed, AC expression is abn

Discovery of a First-in-Class, Potent, Selective, and Orally Bioavailable Inhibitor of the p97 AAA ATPase (CB-5083)

The AAA-ATPase p97 plays vital roles in mechanisms of protein homeostasis, including ubiquitin-proteasome system (UPS) mediated protein degradation, endoplasmic reticulum-associated degradation (ERAD), and autophagy. Herein we describe our lead optimization efforts focused on in vitro potency, ADME, and pharmaceutical properties that led to the discovery of a potent, ATP-competitive, D2-selective, and orally bioavailable p97 inhibitor 71, CB-5083. Treatment of tumor cells with 71 leads to significant accumulation of markers associated with inhibition of UPS and ERAD functions, which induces irresolvable proteotoxic stress and cell death. In tumor bearing mice, oral administration of 71 causes rapid accumulation of markers of the unfolded protein response (UPR) and subsequently induces apoptosis leading to sustained antitumor activity in in vivo xenograft models of both solid and hematological tumors. 71 has been taken into phase 1 clinical trials in patients with multiple myeloma and solid tumors.