1234616-31-9

Usage

Uses

Used in Organic Synthesis:
Ethyl 3-amino-5-bromothieno[2,3-b]pyridine-2-carboxylate is used as a key intermediate in organic synthesis for the development of novel compounds with potential applications in various industries. Its unique molecular structure allows for further functionalization and modification, enabling the creation of new molecules with desired properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, ethyl 3-amino-5-bromothieno[2,3-b]pyridine-2-carboxylate is utilized as a building block for the design and synthesis of new pharmaceuticals. Its specific molecular features, such as the presence of an ethyl ester and a bromine atom, can be exploited to create bioactive molecules with potential therapeutic effects.
Used in Research and Development:
Due to its precise synthesis and structural characteristics, ethyl 3-amino-5-bromothieno[2,3-b]pyridine-2-carboxylate serves as a valuable target for research and development in the field of organic chemistry. It can be used to explore new synthetic routes, investigate its reactivity, and study its potential applications in various chemical processes.
Used in Pharmaceutical Industry:
Ethyl 3-amino-5-bromothieno[2,3-b]pyridine-2-carboxylate is used as a precursor in the pharmaceutical industry for the synthesis of new drug candidates. Its unique molecular structure can be optimized to target specific biological pathways or receptors, potentially leading to the development of innovative therapeutic agents for the treatment of various diseases.

Upstream product

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 405224-22-8 2-hydroxy-3-cyano-5-bromopyridine 
• 20577-27-9 2-hydroxy-3-cyanopyridine 
• 623-51-8 ethyl 2-sulfanylacetate 
• 405224-23-9 5-bromo-2-chloropyridine-3-carbonitrile 

Relevant academic research and scientific papers

TRICYCLIC HETEROCYCLIC COMPOUNDS AS PHOSPHOINOSITIDE 3-KINASE INHIBITORS

The invention relates to a compound of formula I: (I) or a pharmaceutically acceptable salt thereof, wherein each R3 is independently selected from H, halo, fluorinated C1-C10 alkyl, -O-C1-C10 alkyl, -NH-C1-C10 alkyl, -S-C1-C10 alkyl, -O-fluorinated C1-C10 alkyl, -NH-acyl, -NH-C(O)-NH-alkyl, -C-(O)- NH-alkyl, with the proviso that at least one of R3 is not H.

TRICYCLIC HETEROCYCLIC COMPOUNDS AS PHOSPHOINOSITIDE 3-KINASE INHIBITORS

The invention relates to a compound of formula I: (I) or a pharmaceutically acceptable salt thereof and/or stereoisomers thereof. The compounds of the invention are useful in therapy.

Discovery of dual death-associated protein related apoptosis inducing protein kinase 1 and 2 inhibitors by a scaffold hopping approach

DRAK2 emerged as a promising drug target for the treatment of autoimmune diseases and to prevent graft rejection after organ transplantation. Screening of a compound library in a DRAK2 binding assay led to the identification of an isothiazolo[5,4-b]pyridine derivative as a novel ligand for DRAK2, displaying a Kdvalue of 1.6 μM. Subsequent medicinal chemistry work led to the discovery of a thieno[2,3-b]pyridine derivative with strong DRAK2 binding affinity (Kd= 9 nM). Moreover, this compound also behaves as a functional inhibitor of DRAK2 enzymatic activity, displaying an IC50value of 0.82 μM, although lacking selectivity, when tested against DRAK1. This paper describes for the first time functionally active dual DRAK1 and DRAK2 inhibitors that can be used as starting point for the synthesis of chemical tool compounds to study DRAK1 and DRAK2 biology, or they can be considered as hit compounds for hit-to-lead optimization campaigns in drug discovery programs.

Synthesis and structure-activity relationship studies of 2-(1,3,4-oxadiazole-2(3H)-thione)-3-amino-5-arylthieno[2,3-b]pyridines as inhibitors of DRAK2

In recent years, DAPK-related apoptosis-inducing protein kinase 2 (DRAK2) has emerged as a promising target for the treatment of a variety of autoimmune diseases and for the prevention of graft rejection after organ transplantation. However, medicinal chemistry optimization campaigns for the discovery of novel small-molecule inhibitors of DRAK2 have not yet been published. Screening of a proprietary compound library led to the discovery of a benzothiophene analogue that displays an affinity constant (Kd) value of 0.25 μM. Variation of the core scaffold and of the substitution pattern afforded a series of 5-arylthieno[2,3-b]pyridines with strong binding affinity (Kd=0.008 μM for the most potent representative). These compounds also show promising activity in a functional biochemical DRAK2 enzyme assay, with an IC50 value of 0.029 μM for the most potent congener. Selectivity profiling of the most potent compounds revealed that they lack selectivity within the DAPK family of kinases. However, one of the less potent analogues is a selective ligand for DRAK2 and can be used as starting point for the synthesis of selective and potent DRAK2 inhibitors.

Synthesis and Structure-Activity Relationship Studies of 2-(1,3,4-Oxadiazole-2(3H)-thione)-3-amino-5-arylthieno[2,3-b]pyridines as Inhibitors of DRAK2

In recent years, DAPK-related apoptosis-inducing protein kinase 2 (DRAK2) has emerged as a promising target for the treatment of a variety of autoimmune diseases and for the prevention of graft rejection after organ transplantation. However, medicinal chemistry optimization campaigns for the discovery of novel small-molecule inhibitors of DRAK2 have not yet been published. Screening of a proprietary compound library led to the discovery of a benzothiophene analogue that displays an affinity constant (Kd) value of 0.25 μM. Variation of the core scaffold and of the substitution pattern afforded a series of 5-arylthieno[2,3-b]pyridines with strong binding affinity (Kd=0.008 μM for the most potent representative). These compounds also show promising activity in a functional biochemical DRAK2 enzyme assay, with an IC50 value of 0.029 μM for the most potent congener. Selectivity profiling of the most potent compounds revealed that they lack selectivity within the DAPK family of kinases. However, one of the less potent analogues is a selective ligand for DRAK2 and can be used as starting point for the synthesis of selective and potent DRAK2 inhibitors.