91444-54-1

Basic information

• Product Name: 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol
• Synonyms: 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol
• CAS NO: 91444-54-1
• Molecular Weight: 239.274
• Mol File: 91444-54-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 201-204 °C
• Boiling Point: 485.0±40.0 °C(Predicted)
• Density: 1.327±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol(91444-54-1)
• EPA Substance Registry System: 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol(91444-54-1)

Safety Data

• Hazardous Substances Data: 91444-54-1(Hazardous Substances Data)

Usage

Uses

2-(4-Hydroxyphenyl)-3-methyl-1H-indol-5-ol is used as a reagent in the synthesis of tethered indoles as functionalizable ligands for estrogen receptor.

Upstream product

• 91444-18-7 5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole 
• 21086-33-9 2-bromo-1-(4-methoxyphenyl)-1-propanone 
• 104-94-9 4-methoxy-aniline 
• 35081-45-9 1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone 
• 4495-66-3 4-benzyloxypropiophenone 
• 198479-63-9 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole 
• 70-70-2 4-hydroxypropiophenone 
• 54049-23-9 4-hydroxyphenylhydrazine hydrochloride 
• 1610763-22-8 1-(4-(benzyloxy)phenyl)-2-((4-(methoxymethoxy)phenyl)amino)propan-1-one 
• 876-30-2 4-methoxymethyloxyaniline 
• 123-30-8 4-amino-phenol 
• 7107-59-7 4-(N-Benzyloxycarbonylamino)phenol 
• 1610763-24-0 2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-5-ol 

Downstream Products

• 198481-32-2 bazedoxifene 
• 91444-18-7 5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole 
• 91444-55-2 4-(5-acetoxy-3-methyl-1H-indol-2-yl)phenyl acetate 
• 1124291-70-8 C₂₁H₂₅NO₂ 

Relevant articles and documents

METHODS OF PREPARINGBAZEDOXIFENE BY NEW INTERMEDIATES

The present invention relates to a method for manufacturing novel bazedoxifene or a pharmaceutically acceptable salt thereof. A manufacturing method according to the present invention can provide high purity and high yield of bazedoxifene, and is economical in terms of time and cost and eco-friendly due to a relatively simple manufacturing process, thereby being able to be usefully applied to mass production.COPYRIGHT KIPO 2020

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.

In vitro bioactivation of bazedoxifene and 2-(4-hydroxyphenyl)-3-methyl-1H- indol-5-ol in human liver microsomes

Bazedoxifene is a selective estrogen receptor modulator (SERM) that has been developed for use in post-menopausal osteoporosis. However, it contains a potentially toxic 5-hydroxy-3-methylindole moiety. Previous studies on the 5-hydroxyindole and the 3-alkylindole-containing drugs indometacine, zafirlukast and MK-0524 structural analogs have shown that they are bioactivated by cytochrome P450s through a dehydrogenation process to form quinoneimine or 3-methyleneindolenine electrophilic species. In the present study, bazedoxifene was synthesized and then evaluated, together with raloxifene and 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol (13), a 3-methyl-5-hydroxyindole- based structural fragment of bazedoxifene, for its ability to form reactive electrophilic species when incubated with human liver microsomes (HLMs) or recombinant CYP isozymes. We showed that bazedoxifene was bioactivated only in trace amounts with recombinant CYP isozymes. In contrast, the N-dealkylated fragment of bazedoxifene (2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol) was bioactivated in considerable amounts to an electrophilic intermediate, which was trapped with glutathione and identified by LC-MS/MS. This suggests that bazedoxifene would require initial N-dealkylation, which could subsequently lead to the formation of the reactive intermediate. However, such an N-dealkylated metabolite of bazedoxifene was not detected after the incubation of bazedoxifene in HLM or recombinant CYP isozymes.