1214264-48-8

Basic information

• Product Name: 3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole
• Synonyms: 3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole
• CAS NO: 1214264-48-8
• Molecular Formula: C12H7ClN4O2
• Molecular Weight: 274.66258
• Mol File: 1214264-48-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 205 °C
• Boiling Point: 597.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.548±0.06 g/cm3(Predicted)
• PKA: 11.97±0.30(Predicted)
• CAS DataBase Reference: 3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole(1214264-48-8)
• EPA Substance Registry System: 3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole(1214264-48-8)

Safety Data

• Hazardous Substances Data: 1214264-48-8(Hazardous Substances Data)

Usage

General Description

3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole is a chemical compound with a molecular formula C15H8ClN5O2. It is a fused heterocyclic compound containing both indole and pyrimidine rings. 3-(2-chloropyrimidin-4-yl)-7-nitro-1H-indole is known for its diverse range of biological activities, including being a potent inhibitor of the enzyme cyclic GMP-specific phosphodiesterase (PDE5), which makes it a potential candidate for the treatment of erectile dysfunction. Additionally, it has been studied for its potential as an anti-tumor and anti-cancer agent. The presence of a nitro group in the molecule also makes it a versatile precursor for the synthesis of other organic compounds.

Upstream product

• 37968-69-7 2-chloro-4-ethynylpyrimidine 
• 612-29-3 o-nitronitrosobenzene 
• 1446428-14-3 1-[(4-methylphenyl)sulfonyl]-7-nitro-1H-indole 
• 6960-42-5 7-nitro-1H-indole 
• 2091135-02-1 3-bromo-1-[(4-methylphenyl)sulfonyl]-7-nitro-1H-indole 
• 3934-20-1 2,6-Dichloropyrimidine 

Downstream Products

• 2091134-68-6 (2R)-N-(3-{2-[(3-methoxy-1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-1H-indol-7-yl)-2-(4-methylpiperazin-1-yl)propanamide 

Relevant articles and documents

Structure-Based design of Marine-derived Meridianin C derivatives as glycogen synthase kinase 3β inhibitors with improved oral bioavailability: From aminopyrimidyl-indoles to the sulfonyl analogues

Glycogen synthase kinase 3β (GSK-3β) has become an attractive target for the treatment of diabetes. Compound I is an indole-based GSK-3β inhibitor designed from the Meridianin C, a marine natural product (MNP) isolated from Aplidium meridianum. However, this compound has a moderate inhibitory activity toward GSK-3β (IC50 = 24.4 μM), moderate glucose uptake (38%), and especially, a low oral bioavailability (F = 11.4%). In the present study, applying the structure-based design strategy, a series of derivatives modified on the indole moiety were synthesized based on the lead compound I, followed by evaluating their cytotoxic activity, antihyperglycemic activity, and kinase inhibitory activity. Among this series, compound 6x with a sulfonyl group displayed the highest glucose uptake (83.5%) in muscle L6 cells, showing much higher inhibitory activity against GSK-3β (IC50 = 5.25 μM). Molecular docking indicated that compound 6x was properly inserted into the ATP-binding binding pocket of GSK-3β with a higher docking score (-8.145 kcal/mol) compared with that of compound I (-6.950 kcal/mol), interpreting the higher kinase inhibitory activity toward GSK-3β. Remarkably, compound 6x showed favorable drug-like properties, including significantly better oral bioavailability (F = 47.4%) and no two-week acute toxicity at a dose of 1 g/kg. Our findings suggest that these MNP-derived sulfonyl indole derivatives could be used as lead compounds for the development of anti-hyperglycemic drugs.

COMPOUNDS AND METHODS FOR INHIBITING JAK

Disclosed are compounds of formula (I), pharmaceutical compositions comprising such compounds and methods/uses of using the same, for example, for treating a JAK-related disorder, such as cancer, cancer cachexia or an immune disorder: (I) wherein R1 is methyl or ethyl; R2 is selected from methyl, ethyl, methoxy and ethoxy; R3 is selected from hydrogen, chlorine, fluorine, bromine and methyl; R4 is selected from methyl, ethyl and -CH2OCH3; R5 and R6 are each individually methyl or hydrogen; and R7 is selected from methyl, ethyl, -(CH2)2OH and –(CH2)2OCH3, or a pharmaceutically acceptable salt thereof.