1229583-70-3

Basic information

• Product Name: 5-bromo-3-(1H-indol-5-yl)-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine
• Synonyms: 5-bromo-3-(1H-indol-5-yl)-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine
• CAS NO: 1229583-70-3
• Molecular Weight: 466.358
• Mol File: 1229583-70-3.mol

Chemical Properties

• CAS DataBase Reference: 5-bromo-3-(1H-indol-5-yl)-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-3-(1H-indol-5-yl)-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine(1229583-70-3)
• EPA Substance Registry System: 5-bromo-3-(1H-indol-5-yl)-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine(1229583-70-3)

Safety Data

• Hazardous Substances Data: 1229583-70-3(Hazardous Substances Data)

Upstream product

• 875639-15-9 5-bromo-3-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 144104-59-6 1H-indole-5-boronic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 757978-18-0 3-iodo-5-bromo-1H-pyrrolo[2,3-b]-pyridine 
• 269410-24-4 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 10075-50-0 5-bromo-1H-indole 

Downstream Products

• 1229583-71-4 5-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine 
• 1229583-69-0 C₃₁H₂₇N₃O₅S 
• 1229583-72-5 4-(3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzaldehyde 
• 1229583-46-3 {4-[3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone 
• 1229583-41-8 1-(4-{4-[3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzyl}-piperazin-1-yl)-ethanone 
• 1229583-73-6 3-(1H-indol-5-yl)-5-(3-methoxy-4-(2-(piperazin-1-yl)ethoxy)phenyl)-1H-pyrrolo[2,3-b]pyridine 
• 1229582-00-6 3-(1H-indol-5-yl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrrolo-[2,3-b]pyridine 
• 1229582-35-7 3-(1H-indol-5-yl)-5-(3-methoxy-4-(2-(piperazin-1-yl)ethoxy)phenyl)-1H-pyrrolo[2,3-b]pyridine 
• 1361323-76-3 C₄₀H₃₇N₅O₂S 
• 1361323-63-8 C₃₄H₃₀F₂N₄O₂S 
• 1361323-57-0 C₃₃H₃₀N₄O₃S 
• 1351478-08-4 4-[3-(1H-indol-5-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-trifluoromethyl-benzaldehyde 
• 1351476-79-3 5-(4-((1H-imidazol-1-yl)methyl)phenyl)-3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1351477-91-2 C₃₆H₃₅N₅O₄S 

Relevant articles and documents

Structural Optimization and Pharmacological Evaluation of Inhibitors Targeting Dual-Specificity Tyrosine Phosphorylation-Regulated Kinases (DYRK) and CDC-like kinases (CLK) in Glioblastoma

The DYRK family contains kinases that are up-regulated in malignancy and control several cancer hallmarks. To assess the anticancer potential of inhibitors targeting DYRK kinases, we developed a series of novel DYRK inhibitors based on the 7-azaindole scaffold. All compounds were tested for their ability to inhibit DYRK1A, DYRK1B, DYRK2, and the structurally related CLK1. The library was screened for anticancer efficacy in established and stem cell-like glioblastoma cell lines. The most potent inhibitors (IC50 ≤ 50 nM) significantly decreased viability, clonogenic survival, migration, and invasion of glioblastoma cells. Target engagement was confirmed with genetic knockdown and the cellular thermal shift assay. We demonstrate that DYRK1A’s thermal stability in cells is increased upon compound treatment, confirming binding in cells. In summary, we present synthesis, structure-activity relationship, and efficacy in glioblastoma-relevant models for a library of novel 7-azaindoles.

Compounds used as JAK inhibitor, and use of compounds

The invention provides compounds used as a JAK inhibitor, and a use of the compounds, and concretely provides compounds (represented by formula (I)) with JAK inhibition activity or a stereoisomer, a geometric isomer, a tautomer, a racemate, a nitrogen oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, and a medicinal composition including the compounds. The invention also discloses a use of the compounds or the medicinal composition thereof in the preparation of medicines used for treating autoimmune diseases or proliferative diseases.

HETEROARYL COMPOUNDS AND PHARMACEUTICAL APPLICATIONS THEREOF

The present invention provides herein is a heteroaryl compound or a stereoisomer, a geometric isomer, a tautomer, a racemate, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, as well as a pharmaceutical composition containing the compound disclosed herein. The present invention also provides herein is use of the compound or the pharmaceutical composition thereof disclosed herein in the manufacture of a medicine for treating autoimmune diseases or proliferative diseases.

MIXED LINEAGE KINASE INHIBITORS FOR HIV/AIDS THERAPIES

Disclosed are methods for treating an individual infected with a retrovirus that comprise administering to the individual effective amounts of a mixed lineage kinase inhibitor and antiretroviral drug. In further aspects, disclosed are methods for treating an individual infected with a retrovirus that comprises administering an antiretroviral drug formulated into a crystalline nanoparticle comprising a surfactant, and a MLK inhibitor. Still further disclosed are methods for treating an individual infected with a retrovirus that comprises administering a composition comprising both an antiretroviral and MLK inhibitor formulated into a crystalline nanoparticle, which comprises a surfactant. Still further disclosed are compositions that comprise an antiretroviral drug, a MLK inhibitor, and a surfactant, wherein the composition is a crystalline nanoparticle. Compostions comprising MLK inhibitors with other drugs in nanoparticulate form, and methods of there use, are also disclosed.

Discovery, synthesis, and characterization of an orally bioavailable, brain penetrant inhibitor of mixed lineage kinase 3

Inhibition of mixed lineage kinase 3 (MLK3) is a potential strategy for treatment of Parkinson's disease and HIV-1 associated neurocognitive disorders (HAND), requiring an inhibitor that can achieve significant brain concentration levels. We report here URMC-099 (1) an orally bioavailable (F = 41%), potent (IC50 = 14 nM) MLK3 inhibitor with excellent brain exposure in mouse PK models and minimal interference with key human CYP450 enzymes or hERG channels. The compound inhibits LPS-induced TNFα release in microglial cells, HIV-1 Tat-induced release of cytokines in human monocytes and up-regulation of phospho-JNK in Tat-injected brains of mice. Compound 1 likely functions in HAND preclinical models by inhibiting multiple kinase pathways, including MLK3 and LRRK2 (IC50 = 11 nM). We compare the kinase specificity and BBB penetration of 1 with CEP-1347 (2). Compound 1 is well tolerated, with excellent in vivo activity in HAND models, and is under investigation for further development.

BICYCLIC HETEROARYL KINASE INHIBITORS AND METHODS OF USE

Provided are compounds having an inhibitory effect on kinases including Mixed Lineage Kinases. Also provided are pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions that are affected by Mixed Lineage Kinase inhibition. Also provided are methods of treatment of neuropsychiatric disorders that comprise the inhibition of Mixed Lineage Kinases.

MLK INHIBITORS AND METHODS OF USE

Provided are compounds having an inhibitory effect on Mixed Lineage Kinases. Also provided are pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by Mixed Lineage Kinase inhibition. Also provided are methods of treatment of neuropsychiatric disorders which comprise the inhibition of Mixed Lineage Kinases.