301836-35-1

Usage

Uses

Used in Medicinal Chemistry:
4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid is used as a building block in the design of new pharmaceutical agents due to its complex chemical structure and the potential for diverse biological activities.
Used in Drug Discovery Research:
In the field of drug discovery, 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid serves as a starting point for the development of novel therapeutics, leveraging its unique structural elements to target specific biological pathways or receptors.
Used in Organic Synthesis:
4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid is utilized as a key intermediate in organic synthesis processes, where its structural components can be modified to create a variety of new compounds with potential applications in various industries.
Used in Drug Development:
In the pharmaceutical industry, 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid is used as a precursor in the synthesis of new drug candidates, taking advantage of its chemical properties to explore its efficacy and safety in treating various diseases.

Synthetic route

4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzonitrile (301836-34-0) → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
With hydrogenchloride for 36h; Heating;

2-hydroxyimino-2-(2-pyridyl)-(2,3-methylenedioxy)-acetophenone → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NH4OAc / acetic acid / 36 h / Heating 2: P(OEt)3 / dimethylformamide / 1 h / 110 °C 3: conc. HCl / 36 h / Heating View Scheme

2-(4-cyanophenyl)-4-(3,4-methylenedioxyphenyl)-N-1-hydroxy-5-(2-pyridyl)-imidazole (301836-33-9) → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: P(OEt)3 / dimethylformamide / 1 h / 110 °C 2: conc. HCl / 36 h / Heating View Scheme

4-cyanobenzaldehyde (105-07-7) + resin-bound phenylboronic acid → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NH4OAc / acetic acid / 36 h / Heating 2: P(OEt)3 / dimethylformamide / 1 h / 110 °C 3: conc. HCl / 36 h / Heating View Scheme

oxalyl dichloride (79-37-8) + 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1) → 4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzoyl chloride

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide

oxalyl dichloride (79-37-8) + 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1) → 4-[4-(3,4-methylenedioxyphenyl)-5-(2-pyridyl)-1H-imidazol-2-yl]benzoyl chloride hydrochloride

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide

4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1) → SB-431542

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane; N,N-dimethyl-formamide 2: ammonium hydroxide / tetrahydrofuran View Scheme

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 301836-33-9 2-(4-cyanophenyl)-4-(3,4-methylenedioxyphenyl)-N-1-hydroxy-5-(2-pyridyl)-imidazole 
• 301836-34-0 4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzonitrile 

Relevant academic research and scientific papers

Identification of novel inhibitors of the transforming growth factor β1 (TGF-β1) type 1 receptor (ALK5)

Screening of our internal compound collection for inhibitors of the transforming growth factor β1 (TGF-β1) type I receptor (ALK5) identified several hits. Optimization of the dihydropyrroloimidazole hit 2 by introduction of a 2-pyridine and 3,4-methylenedioxyphenyl group gave 7, a selective ALK5 inhibitor. With this information, optimization of the triarylimidazole hit 8 gave the selective inhibitor 14, which inhibits TGF-β1-induced fibronectin mRNA formation while displaying no measurable cytotoxicity in the 48 h XTT assay.

Triarylimidazoles

Compounds of formula (I) or a pharmaceutically acceptable salt thereof: wherein R1, R2and R3are various substituent groups; and one of X1and X2is N or CR′, and the other is NR′ or CHR′ wherein R′ is hydrogen, OH, C1-6alkyl, or C3-7cycloalkyl; or when one of X1and X2is N or CR′ then the other may be S or O; and their use as pharmaceuticals.