30030-91-2

Basic information

• Product Name: 2-CHLORO-1-(5-METHOXY-1H-INDOL-3-YL)-ETHANONE
• Synonyms: 2-CHLORO-1-(5-METHOXY-1H-INDOL-3-YL)-ETHANONE
• CAS NO: 30030-91-2
• Molecular Formula: C₁₁H₁₀ClNO₂
• Molecular Weight: 223.66
• Mol File: 30030-91-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-CHLORO-1-(5-METHOXY-1H-INDOL-3-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1-(5-METHOXY-1H-INDOL-3-YL)-ETHANONE(30030-91-2)
• EPA Substance Registry System: 2-CHLORO-1-(5-METHOXY-1H-INDOL-3-YL)-ETHANONE(30030-91-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 30030-91-2(Hazardous Substances Data)

Upstream product

• 1006-94-6 5-methoxylindole 
• 79-04-9 chloroacetyl chloride 
• 2675-89-0 2-chloro-N,N-dimethylacetamide 

Downstream Products

• 123310-20-3 N-Benzyl-N'-[4-(5-methoxy-1H-indol-3-yl)-thiazol-2-yl]-guanidine 
• 396101-55-6 C₂₃H₂₆N₂O₂ 
• 1134099-82-3 2-(4-benzylpiperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone 
• 1347685-38-4 2-(4-benzylpiperazin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone 
• 1549940-48-8 2-(4-(4-fluorobenzyl)piperidin-1-yl)-1-(5-methoxy-1H-indol-3-yl)ethanone 
• 36246-11-4 4-(5-methoxy-1H-indol-3-yl)thiazol-2-amine 

Relevant articles and documents

From NMDA receptor antagonists to discovery of selective σ2 receptor ligands

Following previous studies focused on the search for new molecules targeting GluN2B-containing NMDA, a small series of 1-(1H-indol-3-yl)-2-(4- phenylpiperidin-1-yl)ethanone derivatives has been synthesized by using Microwave Assisted Organic Synthesis (MAOS). Given that GluN2B ligands frequently exert off-target effects we also tested their affinity towards sigma receptors. Binding assay revealed that only the 1-(5-hydroxy-1H-indol-3-yl)-2- (4-phenylpiperidin-1-yl)ethanone (7a) retained GluN2B affinity. Interestingly, the 5-methoxyindoles 5a and 6a were efficient and selective ligands toward σ2 receptor (Ki values of 10 nM and 20 nM, respectively). Thus, in this case the discovery of new σ2 receptor selective ligands was an unexpected result emerging from the screening of cross-activity against other CNS receptors.

Structure-guided design of new indoles as negative allosteric modulators (NAMs) of N-methyl-d-aspartate receptor (NMDAR) containing GluN2B subunit

Negative allosteric modulators (NAMs) of GluN2B-containing NMDARs provide pharmacological tools for the treatment of chronic neurodegenerative diseases. Novel NAMs have been designed on the basis of computational studies focused on the 'hit compound' 3. This series of indoles has been tested in competition assay. Compounds 16 and 17 were the most active ligands (IC50 values of 83 nM and 71 nM, respectively) and they showed a potency close to that of reference compounds ifenprodil (1, IC50 = 47 nM) and 3 (IC50 = 25 nM). Furthermore, docking studies have been performed for active ligand 16 and the results were in a good agreement with biological data.

Synthesis and biological characterization of 3-substituted-1h-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors

As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-1-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [3H]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the σ2 receptor.