151720-06-8

Basic information

• Product Name: 1-chloro-3-(indol-4-yloxy)propane
• Synonyms: 1-chloro-3-(indol-4-yloxy)propane
• CAS NO: 151720-06-8
• Molecular Formula: C₁₁H₁₂ClNO
• Molecular Weight: 210
• Mol File: 151720-06-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 384.8±17.0 °C(Predicted)
• Appearance: /
• Density: 1.231±0.06 g/cm3(Predicted)
• PKA: 17.12±0.30(Predicted)
• CAS DataBase Reference: 1-chloro-3-(indol-4-yloxy)propane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-3-(indol-4-yloxy)propane(151720-06-8)
• EPA Substance Registry System: 1-chloro-3-(indol-4-yloxy)propane(151720-06-8)

Safety Data

• Hazardous Substances Data: 151720-06-8(Hazardous Substances Data)

Usage

Functional groups

Chloro, oxy, and indol-4-yloxy

Structure

Chloroalkyl ether derivative of indole

Bicyclic aromatic compound

Indole is commonly found in plants

Applications

Medicinal chemistry, drug discovery research, agrochemistry, and biological studies

Reactivity

Useful for a variety of chemical transformations and applications

Building block

Used for the synthesis of novel organic molecules with potential pharmaceutical applications

Upstream product

• 180161-01-7 2-(1H-Indol-4-yloxy)-chloroethane 
• 2380-94-1 1H-indol-4-ol 
• 109-70-6 1.3-chlorobromopropane 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 874988-16-6 (4-fluoro-phenyl)-{4-[3-(1H-indol-4-yloxy)-propoxy]-phenyl}-methanone 
• 873696-97-0 ethyl 2-{4-[3-(2-phenyl-7-propyl-1H-indol-6-yloxy)propoxy]indol-1-yl}ethanoate 
• 873696-98-1 ethyl 2-{4-[3-(3-phenyl-7-propylbenzo[b]furan-6-yloxy)propoxy]indol-1-yl}ethanoate 
• 873696-99-2 ethyl 2-{4-[3-(2-phenyl-7-propylbenzo[b]furan-6-yloxy)propoxy]indol-1-yl}ethanoate 
• 873696-92-5 ethyl 2-{4-[3-(3-phenyl-7-propylbenzo[b]isoxazol-6-yloxy)propoxy]indol-1-yl}ethanoate 
• 874988-37-1 {4-[3-(6-benzoyl-1-propyl-naphthalen-2-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester 
• 874988-31-5 (4-{3-[4-(4-fluoro-benzoyl)-2-propyl-phenoxy]-propoxy}-indol-1-yl)-acetic acid methyl ester 
• 874988-34-8 {4-[3-(6-benzoyl-naphthalen-2-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester 
• 874988-28-0 (4-{3-[4-(4-fluoro-benzoyl)-phenoxy]-propoxy}-indol-1-yl)-acetic acid methyl ester 
• 874988-25-7 {6-[3-(1H-indol-4-yloxy)-propoxy]-5-propyl-naphthalen-2-yl}-phenyl-methanone 

Relevant articles and documents

Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity

The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1-n-octyl-1H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-fused ring motif was affirmed by SAR and validated in a mouse model of tuberculosis. As expected for membrane inserting agents, the indolyl azaspiroketal Mannich bases perturbed phospholipid vesicles, permeabilized bacterial cells, and induced the mycobacterial cell envelope stress reporter promoter piniBAC. Surprisingly, their membrane disruptive effects did not appear to be associated with bacterial membrane depolarization. This profile was not uniquely associated with azaspiroketal Mannich bases but was characteristic of indolyl Mannich bases as a class. Whereas resistant mycobacteria could not be isolated for a less potent indolyl Mannich base, the more potent azaspiroketal analog displayed low spontaneous resistance mutation frequency of 10-8/CFU. This may indicate involvement of an additional envelope-related target in its mechanism of action.

Indol-1-yl acetic acids as peroxisome proliferator-activated receptor agonists: Design, synthesis, structural biology, and molecular docking studies

A series of novel indole-based PPAR agonists is described leading to discovery of 10k, a highly potent PPAR pan-agonist. The structural biology and molecular docking studies revealed that the distances between the acidic group and the linker, when a ligan

Novel indole-based peroxisome proliferator-activated receptor agonists: Design, SAR, structural biology, and biological activities

The synthesis and structure-activity relationship studies of novel indole derivatives as peroxisome proliferator-activated receptor (PPAR) agonists are reported. Indole, a druglike scaffold, was studied as a core skeleton for the acidic head part of PPAR