180915-78-0

Basic information

• Product Name: rac-Lasofoxifene
• Synonyms: rac-Lasofoxifene;(5R,6S)-rel-5,6,7,8-Tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-2-naphthalenol;cis-5,6,7,8-Tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-2-naphthalenol
• CAS NO: 180915-78-0
• Molecular Formula: C28H31NO2
• Molecular Weight: 413.55124
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 180915-78-0.mol
• Article Data: 35

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: rac-Lasofoxifene(CAS DataBase Reference)
• NIST Chemistry Reference: rac-Lasofoxifene(180915-78-0)
• EPA Substance Registry System: rac-Lasofoxifene(180915-78-0)

Safety Data

• Hazardous Substances Data: 180915-78-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

rac-Lasofoxifene is a non-steroidal selective estrogen receptor modulator, used to treat osteoporosis.

Upstream product

• 180915-95-1 1-{2-[4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yl)phenoxy] ethyl}pyrrolidine 
• 497-19-8 sodium carbonate 
• 98-80-6 phenylboronic acid 
• 5879-98-1 1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine 
• 1081-73-8 1-[2-(4-bromophenoxy)ethyl]pyrrolidine 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 5879-91-4 4-(cis-6-methoxy-2-phenyltetralin-1-yl)phenol 
• 1729-38-0 1-(p-hydroxyphenyl)-6-methoxy-2-phenyl-3,4-dihydronaphthalene 
• 1845-11-0 nafoxidine 

Downstream Products

• 190791-29-8 Lasofoxifene tartrate 

Relevant articles and documents

Enzyme-catalyzed asymmetric deacylation for the preparation of Lasofoxifene (CP-336156), a selective estrogen receptor modulator

(Matrix presented) A potent and selective estrogen receptor modulator (SERM), Lasofoxifene (CP-336156), was prepared by an enzyme-catalyzed asymmetric deacylation with high optical purity and excellent yield even though the hydrolytic site is remote from

LASOFOXIFENE MODULATION OF MEMBRANE-INITIATED ESTROGEN SIGNALS AND METHODS FOR TUMOR TREATMENT

The present invention found that lasofoxifene is an antagonist of ER-α36. It not only inhibits the growth of ER-α36 positive lung, colon and gastric cancers, and also it can inhibit the growth of acquired or de novo tamoxifen-resistant MCF-7 cells. Our finding also provides methods and compositions for treating cancer comprising lasofoxifene alone or in combination with at least one other agent selected from the group consisting of gefitinib and/or trastuzumab or functional equivalent thereof, and an inhibitor in hormonal or epidermal growth factor signal transduction pathways.

An ortho-quinodimethane route to Lasofoxifene and U23469

Lasofoxifene, a third-generation selective estrogen receptor modulator, could be synthesized via regio-and stereoselective [4 + 2] cycloaddition between an ortho-quinodimethane and a borylalkene. This protocol was also applicable to the synthesis of antie

METHOD FOR THE PREPARATION OF LASOFOXIFENE

A method of preparing (?)-cis-(5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol D-tartrate-lasofoxifene of formula 1, comprising the following steps a) Preparation of cis-1-{2-[4-(2-phenyl-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-phenoxy]ethyl}pyrrolidine of formula (3) by alkylation of cis-1-(4-hydroxyphenyl)-2-phenyl-6-methoxy-1,2,3,4-tetrahydronaphthalene with 1-(2-chloroethyl)pyrrolidine base or its salt, b) Deprotection of the hydroxyl group in the substance of formula (3) by the effect of hydrobromic acid generating cis-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol hydrobromide of formula (2a), c) Conversion of the substance of formula (2a) into cis-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol of formula (2b), d) Preparation of lasofoxifene of formula (1) by conversion into the corresponding diasteroisomer by reaction with D-tartaric acid and crystallization.