2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

Bezeichnung:2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

CAS-Nr128607-22-7

Englisch Name:2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

CBNumberCB01335273

SummenformelC24H23ClO2

Molgewicht378.89

MOL-Datei128607-22-7.mol

2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol physikalisch-chemischer Eigenschaften

Siedepunkt	544.6±50.0 °C(Predicted)
Dichte	1.166±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
Löslichkeit	DMSO: soluble20mg/mL, clear
Aggregatzustand	powder
pka	14.26±0.10(Predicted)
Farbe	white to beige
InChIKey	LUMKNAVTFCDUIE-VHXPQNKSSA-N
CAS Datenbank	128607-22-7

Sicherheit

Kennzeichnung gefährlicher	N
R-Sätze:	50/53
S-Sätze:	60-61
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
HS Code	2909.49.1500
Giftige Stoffe Daten	128607-22-7(Hazardous Substances Data)

Gefahreninformationscode (GHS)

2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
In February 2013, the US FDA approved ospemifene (also referred to as FC1271a), for the treatment ofmoderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy (VVA), due tomenopause. It is estimated that there are 150 million postmenopausal women worldwide with 40–70% suffering from VVA. Ospemifene is a selective estrogen receptor (ER) modulator (SERM) and the first nonhormonal, nonestrogen for the treatment of moderate to severe dyspareunia in women with menopausal VVA. It binds to ERα (IC₅₀～800 nM) and ERβ (IC₅₀～1600 nM) with tissue-specific estrogenic agonist/antagonist effects. Treatment with ospemifene increases the thickness of the vaginal tissue thereby decreasing fragility of the tissue and reducing potential for pain during sexual intercourse.
Originator
Tess Diagnostics and Pharmaceuticals/Hormos Medical/QuatRx (Finland)
Verwenden
Treatment of vaginal atrophy, osteoporosis, and vasomotor symptoms.
Definition
ChEBI: An organochlorine compound that is a selective estrogen receptor modulator; used for treatment of dyspareunia.
Trademarks
Osphena
Clinical Use
Ospemifene is a SERM that is currently in Phase II/III clinical trials for the treatment of postmenopausal osteoporosis and urogenital atrophy. It is a known metabolite of toremifene, a triphenylethylene derivative used to treat breast cancer.Ospemifene has been shown to have beneficial effects on the bone without significant estrogen-related side effects. The beneficial effect observed on bone stems from this agent's ability to increase osteoblast proliferation and, as a result, to enhance bone mineralization as well as bone formation. Unlike tamoxifen, ospemifene does not induce osteocyte apoptosis.
Synthese
The drug can be synthesized succinctly in two steps. First, alkylation of commercially available 4-hydroxybenzophenone (130) with ethylene carbonate and catalytic sodium iodide in refluxing toluene provided benzophenone 131 in 94% yield. This was followed by a McMurry coupling involving benzophenone 131 with chloropropiophenone 132 in the presence of zinc powder and titanium tetrachloride in 2-methyltetrahydrofuran. This reaction gave rise to a mixture of triphenylethylenes directly as a 5.5:1 ratio of Z to E isomers which could be separated by crystallization in aqueous methanol to give a mixture of olefins, 98% of which was comprised of the desired Z-isomer corresponding to ospemifene (XVII). The product purity was further improved by recrystallization to give 99.9% of the Z-isomer in 46% yield from 131. Thus, ospemifene was synthesized in two steps and 43% overall yield.

2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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