945016-63-7

Basic information

• Product Name: 3-(2-chloropyriMidin-4-yl)-1H-indole
• Synonyms: 3-(2-chloropyriMidin-4-yl)-1H-indole;3-(2-Chloro-4-pyrimidinyl)-1H-indole
• CAS NO: 945016-63-7
• Molecular Formula: C₁₂H₈ClN₃
• Molecular Weight: 229.66502
• Mol File: 945016-63-7.mol
• Article Data: 27

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-(2-chloropyriMidin-4-yl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-chloropyriMidin-4-yl)-1H-indole(945016-63-7)
• EPA Substance Registry System: 3-(2-chloropyriMidin-4-yl)-1H-indole(945016-63-7)

Safety Data

• Hazardous Substances Data: 945016-63-7(Hazardous Substances Data)

Usage

General Description

3-(2-chloropyrimidin-4-yl)-1H-indole is a chemical compound with the molecular formula C12H8N3Cl. It is a heterocyclic compound that consists of an indole ring and a chloropyrimidine group. 3-(2-chloropyrimidin-4-yl)-1H-indole has potential applications in medicinal chemistry, specifically in the development of pharmaceuticals and agrochemicals. It may also be used as a research tool in the study of biological processes and interactions. The specific properties and potential uses of 3-(2-chloropyrimidin-4-yl)-1H-indole may vary depending on its structural characteristics and the specific reactions it is subjected to.

Upstream product

• 120-72-9 indole 
• 3934-20-1 2,6-Dichloropyrimidine 
• 586-96-9 Nitrosobenzene 
• 37968-69-7 2-chloro-4-ethynylpyrimidine 
• 129271-98-3 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid 
• 882562-58-5 3-(2-chloropyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole 

Downstream Products

• 289628-76-8 4-(1H-indol-3-yl)pyrimidin-2-amine 
• 1638281-44-3 N-(2-{2-di(D₃-methyl)aminoethyl-methylamino}-4-methoxy-5-{[4-(1-(D₃-methyl)indol-3-yl)pyrimidin-2-yl]amino}phenyl)-2-acrylamide 
• 1032452-86-0 2-chloro-4-(1'-methyl-1H-indol-3-yl)pyrimidine 
• 1421373-74-1 C₂₈H₃₁N₇O₂ 
• 1421373-71-8 EB₁₀₄ 
• 1421373-68-3 C₂₉H₃₃N₇O₂ 
• 1421373-66-1 N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate 
• 1421373-65-0 [N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide] 
• 1421373-52-5 N-(5-(4-(1H-indol-3-yl)pyrimidin-2-ylamino)-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl)acrylamide 
• 1421373-36-5 3-chloro-N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propanamide 
• 1421373-35-4 tert-butyl (2-((5-methoxy-4-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)-2-nitrophenyl)(methyl)amino)ethyl)(methyl)carbamate 
• 1421373-34-3 tert-butyl (2-((2-amino-5-methoxy-4-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)(methyl)amino)ethyl)(methyl)carbamate 
• 1421373-33-2 tert-butyl N-[2-[[5-methoxy-4-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-2-(prop-2-enoylamino)phenyl](methyl)amino]ethyl]-N-methylcarbamate 
• 1421373-32-1 N₁-(4-(1H-indol-3-yl)pyrimidin-2-yl)-N₄-(2-(dimethylamino)ethyl)-2-methoxy-N₄-methyl-5-nitrobenzene-1,4-diamine 

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.

Structural modifications on indole and pyrimidine rings of osimertinib lead to high selectivity towards L858R/T790M double mutant enzyme and potent antitumor activity

EGFR inhibitors represent a significant milestone for treatment of non-small cell lung cancer, however, they suffer from the acquired drug resistance. Utilizing osimertinib as the lead compound, this work has explored the structural modifications on the indole and pyrimidine rings of osimertinib to generate novel osimertinib derivatives. The in vitro enzymatic and cellular studies showed that the derivatives possessed high selectivity towards double mutant EGFR and potent antitumor activity. Particularly, compound 6b-1, the most active compound, exhibited excellent inhibitory activity against double mutant EGFR (IC50 = 0.18 nM) and wild-type EGFR (IC50 = 2.89 nM) as well as H1975 cells (IC50 = 1.44 nM). Western blot analysis showed that 6b-1 completely inhibited double mutant EGFR and Erk phosphorylation. In vivo test using xenograft model indicated that compound 6b-1 had better antitumor efficacy than osimertinib. More importantly, 6b-1 displayed many advantages in the pharmacokinetic study, including better oral bioavailability and metabolism character.

Preparation method of 4-(1-cyclopropyl-1H-indole-3-yl)-N-phenylpyrimidine-2-amine derivative

The invention relates to a preparation method of a 4-(1-cyclopropyl-1H-indole-3-yl)-N-phenylpyrimidine-2-amine derivative. The structural formula of the derivative is shown in the descriptions of theinvention. Specifically, the invention relates to a preparation method of a 4-(1-cyclopropyl-1H-indole-3-yl)-N-phenylpyrimidine-2-amine derivative with a compound structure as shown in a general formula (IV). According to the method, defects in the prior art are overcome, cost is greatly reduced, an obtained product is good in purity, high in yield and strong in process operability, and process safety is also greatly improved. Therefore, the preparation method and the application thereof are suitable for industrial application.