1261433-14-0

Basic information

• Product Name: 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester
• Synonyms: 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester;Ethyl 1H-pyrrolo[3,2-b]pyridine-5-carboxylate
• CAS NO: 1261433-14-0
• Molecular Formula: C10H10N2O2
• Molecular Weight: 190.1986
• Mol File: 1261433-14-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester(1261433-14-0)
• EPA Substance Registry System: 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester(1261433-14-0)

Safety Data

• Hazardous Substances Data: 1261433-14-0(Hazardous Substances Data)

Usage

General Description

1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester is a chemical compound with the molecular formula C11H11NO2. It is a pyrrole derivative with a pyridine ring fused to it, and a carboxylic acid group at the 5-position. The ethyl ester group is also attached to the carboxylic acid moiety. 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, ethyl ester is often used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It may also have potential applications in the field of medicinal chemistry, particularly in the development of new drugs. However, it is important to handle this compound with care, as it may pose hazards if not used properly.

Upstream product

• 1346569-66-1 ethyl 5-acetamido-6-[2-(trimethylsilyl)ethynyl]pyridine-2-carboxylate 
• 1346569-65-0 ethyl 5-amino-6-iodopyridine-2-carboxylate 
• 1346569-64-9 ethyl 5-amino-6-((trimethylsilyl)ethynyl)picolinate 

Downstream Products

• 1346569-67-2 1H-pyrrolo[3,2-b]pyridin-5-ylmethanol 

Relevant articles and documents

Design, Synthesis, and Pharmacological Evaluation of 5,6-Disubstituted Pyridin-2(1H)-one Derivatives as Phosphodiesterase 10A (PDE10A) Antagonists

We report the design and synthesis of novel 5,6-diarylated pyridin-2(1H)-one derivatives as pharmacophoric PDE10A inhibitors. This highly potent molecular scaffold was developed from an inactive diarylpyridine-2-amine derivative 3b by extensive and systematic analogue synthesis and SAR analysis. Further optimization of the scaffold resulted in identification of pyridin-2(1H)-one 18b as a lead compound with good potency (IC50 = 1.6 nM) and selectivity (>6000-fold) over other related PDEs but with a poor pharmacokinetic profile. Careful metabolite profiling of 18b revealed that poor systemic exposure in rats (Cmax = 44 ng/mL; AUC0-t = 359 ng·h/mL) at 10 mg/kg was due to the formation of O-glucuronide conjugate by phase 2 metabolism. The structure of the glucuronide metabolite was confirmed by retention time and LC-MS/MS fragmentation matching with the synthetic glucuronide 26. The problem of low exposure of 18b was effectively addressed by its conversion to an acetate prodrug 25b, which upon oral dosing resulted in an improved pharmacokinetic profile (Cmax = 359 ng.h/mL; AUC0-t = 2436 ng.h/mL) and a desirable brain to plasma ratio of 1.2. The prodrug 25b showed good efficacy in selected rodent models of psychosis.