7781-10-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is used as a key intermediate in the preparation of indoline derivatives, which are known as PERK (Protein Kinase R-like Endoplasmic Reticulum Kinase) inhibitors. These inhibitors play a crucial role in the development of therapeutic agents targeting various diseases, including neurodegenerative disorders and cancer, by modulating the unfolded protein response and cellular stress pathways.

Upstream product

• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 74-88-4 methyl iodide 
• 3680-71-5 7-deazahypoxanthine 

Downstream Products

• 7752-54-7 4-Amino-7-methyl-7H-pyrrolo<2,3-d>pyrimidin 
• 1041703-69-8 C₁₅H₁₃N₇ 
• 875340-66-2 lithium 4-chloro-7-methyl-7H-pyrrolo[2,3-c]pyrimidine-6-carboxylate 
• 1337530-96-7 7-methyl-5-[1-(phenylacetyl)-2,3-dihydro-1H-indol-5-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337532-51-0 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1398560-46-7 4-((7-methyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl)oxy)aniline 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 4-(pyrrolo[2,3-d]pyrimidine-4-yloxy)benzamide derivatives as potential antitumor agents

Cancer is a major cause of death worldwide. Small molecule inhibitors have become a major therapeutic treatment for cancer. In this study, a series of novel 4-(pyrrolo[2,3-d]pyrimidine-4-yloxy)benzamide derivatives were designed, synthesized and evaluated

Diversification of Heteroaryl-Aryl Ether via Ligand-Free, Copper-Catalyzed O-Arylation Under Microwave Heating

Diverse O-arylated pyrrolo[2,3-d]pyrimidine and pyrrolo[2,3-b]pyridine were obtained using relatively low amounts of Cu catalyst with ligand-free conditions under microwave heating. The O-arylation reaction could be applied to less oxidative heteroaryl-chlorides. The microwave-assisted Cu-catalyzed O-aryaltion would be useful for preparing potent bioactive compounds for drug discovery while reducing waste, time, and saving energy.

PHENYL-2-HYDROXY-ACETYLAMINO-2-METHYL-PHENYL COMPOUNDS

The present invention provides phenyl-2-hydroxy-acetylamino-2-methyl-phenyl compounds, to pharmaceutical compositions comprising the compounds, to methods of using the compounds to treat physiological disorders such as cancer.

NEW (HETERO)ARYL-SUBSTITUTED-PIPERIDINYL DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I):wherein R1, R2, J, K, L, n and W are as defined in the description. Medicaments.

IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS OF PERK

The invention is directed to substituted imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y1, Y2 and Z are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes, as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt-Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

NEW PIPERIDINYL DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I) wherein R1, R2, R3, n and W are as defined in the description. Medicaments.

A critical evaluation of pyrrolo[2,3-d]pyrimidine-4-amines as Plasmodium falciparum apical membrane antigen 1 (AMA1) inhibitors

We have determined that a previously reported class of pyrrolo[2,3-d]pyrimidine-4-amines exhibit low binding to apical membrane antigen 1 (AMA1) and suffer from unattractive qualities, such as aggregation. We attempted to remove these traits by generating

Discovery of 7-methyl-5-(1-{[3-(trifluoromethyl)phenyl]acetyl}-2,3-dihydro- 1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (GSK2606414), a potent and selective first-in-class inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK)

Protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK) is activated in response to a variety of endoplasmic reticulum stresses implicated in numerous disease states. Evidence that PERK is implicated in tumori-genesis and cancer cell survival stim

Identification and synthesis of substituted pyrrolo[2,3-d]pyrimidines as novel firefly luciferase inhibitors

A novel firefly luciferase inhibitor (3a) with a pyrrolo[2,3-d]pyrimidine core was identified in a cell-based NF-κB luciferase reporter gene assay. It potently inhibited the firefly luciferase derived from Photinus pyralis with an IC50 value of 0.36 ± 0.05 μM. Kinetic analysis of 3a inhibition showed that it is predominantly competitive with respect to d-luciferin and uncompetitive with respect to ATP. Therefore, several pyrrolo[2,3-d]pyrimidine analogues were prepared to further investigate the structure-activity relationship (SAR) for luciferase inhibition. The most potent inhibitor of this series was 4c, which showed an IC50 value of 0.06 ± 0.01 μM. In addition, molecular docking studies suggested that both 3a and 4c could be accommodated in the d-luciferin binding pocket, which is expected for a predominantly competitive inhibitor with respect to d-luciferin.

CHEMICAL COMPOUNDS

The invention is directed to substituted indoline derivatives. Specifically, the invention is directed to compounds according to Formula I wherein R1, R2 and R3 are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, ocular diseases, and diseases associated with activated unfolded protein response pathways, such as Alzheimer?s disease, stroke, Type 1 diabetes Parkinson disease, Huntington?s disease, amyotrophic lateral sclerosis, myocardial infarction, cardiovascular disease, atherosclerosis, and arrhythmias, and more specifically cancers of the breast, colon, pancreatic, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.