91444-18-7

Basic information

• Product Name: 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE
• Synonyms: 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE
• CAS NO: 91444-18-7
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.32
• Mol File: 91444-18-7.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE(91444-18-7)
• EPA Substance Registry System: 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE(91444-18-7)

Safety Data

• Hazardous Substances Data: 91444-18-7(Hazardous Substances Data)

Usage

Description

2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE, also known as 5-Methoxy-2-(p-methoxyphenyl)skatole, is an organic compound that serves as a reactant in the synthesis of a metabolite of Bazedoxifene (B129250), a nonsteroidal selective estrogen receptor modulator (SERM). It is characterized by its indole structure with methoxy and methyl substituents, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE is used as a reactant in the synthesis of Bazedoxifene metabolites for the development of pharmaceuticals.
It plays a crucial role in the production of Bazedoxifene Acetate, which is used as an antiosteoporotic agent, helping to prevent bone loss and maintain bone density in patients suffering from osteoporosis.

Upstream product

• 156785-63-6 5-methoxy-2-<(4-methoxybenzoyl)amino>acetophenone 
• 104-94-9 4-methoxy-aniline 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 91444-54-1 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol 
• 74-88-4 methyl iodide 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 121-97-1 4-Methoxypropiophenone 
• 156785-62-5 1-(5-methoxy-2-nitrophenyl)ethanol 
• 23042-77-5 1-(2-amino-5-methoxy-phenyl)-ethanone 
• 42887-67-2 1-(5-methoxy-2-nitrophenyl)ethanone 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 
• 42454-06-8 2-nitro-5-hydroxybenzaldehyde 
• 21086-33-9 2-bromo-1-(4-methoxyphenyl)-1-propanone 

Downstream Products

• 115119-04-5 1-(4-bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole 
• 91444-35-8 1-Isopropyl-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole 
• 115119-08-9 1-(4-Bromomethyl-benzyl)-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole 
• 115119-05-6 1-(5-Bromo-pentyl)-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole 
• 115084-37-2 1-(6-bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methylindole 
• 104598-98-3 5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-1-phenyl-1H-indole 
• 91444-36-9 1-Butyl-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole 
• 127451-67-6 1-(8-bromooctyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole 
• 91466-48-7 5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-1-pentyl-1H-indole 
• 132751-73-6 1-(6-cyanohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methylindole 
• 130628-32-9 Ethyl 6-<5-methoxy-2-(4-methoxyphenyl)-3-methylindol-1-yl>hexanoate 
• 104598-93-8 5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-1-(3-methyl-benzyl)-1H-indole 
• 129423-38-7 6-[5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-indol-1-yl]-hexanoic acid benzylamide 
• 104598-95-0 1-(2-Chloro-benzyl)-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole 

Relevant articles and documents

ESTROGEN RECEPTOR TARGETING ANTAGONISTS

The present disclosure relates to compounds that act as antagonists via binding to the ER ligand binding domain non-covalently or covalently, or act as both antagonists and ER protein degraders, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for proliferative diseases, including cancer, particularly breast cancer, and especially ER+ breast cancer.

Oxygenophilic Lewis Acid Promoted Synthesis of 2-Arylindoles from Anilines and Cyanoepoxides in Alcohol

A convenient synthetic method to indoles from anilines and cyanoepoxides was developed under the catalysis of BF3·OEt2 or AlCl3 in alcohols. The reaction involves a tandem reaction of the regiospecific ring-opening of cyanoepoxides with anilines, elimination of cyanide, intramolecular aromatic electrophilic substitution, and water elimination. The Lewis acid generated protic acid is an efficient catalyst. The method features readily accessible starting materials, wide substrate scope, transition-metal-free environment, and regiospecificity in the ring-opening of cyanoepoxides.

Synthesis, antiproliferative and pro-apoptotic activity of 2-phenylindoles

Breast cancer is the second most common cancer worldwide after lung cancer with the vast majority of early stage breast cancers being hormone-dependent. One of the major therapeutic advances in the clinical treatment of breast cancer has been the introduction of selective estrogen receptor modulators (SERMs). We describe the design and synthesis of novel SERM type ligands based on the 2-arylindole scaffold to selectively target the estrogen receptor in hormone dependent breast cancers. Some of these novel compounds are designed as bisindole type structures, while others are conjugated to a cytotoxic agent based on combretastatin A4 (CA4) which is a potent inhibitor of tubulin polymerisation. The indole compounds synthesised within this project such as 31 and 86 demonstrate estrogen receptor (ER) binding and strong antiproliferative activity in the ER positive MCF-7 breast cancer cell line with IC50values of 2.71?μM and 1.86?μM respectively. These active compounds induce apoptotic activity in MCF-7 cells with minimal effects on normal peripheral blood cells. Their strong anti-cancer effect is likely mediated by the presence of two ER binding ligands for 31 and an ER binding ligand combined with a cytotoxic agent for 86.