4-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile
Grundinformationen
- CAS
154992-24-2- Standard-SMILES
CC1(C)C(=O)N(c2ccc(C#N)c(C(F)(F)F)c2)C(=O)N1CCCCO- InChIKey
ARBYGDBJECGMGA-UHFFFAOYSA-N- Summenformel
- C17H18F3N3O3
- Durchschnittliche Molmasse
- 369,34 g/mol
- Monoisotopische Masse
- 369,1300261
Überblick
a topically active non-steroidal antiandrogen; structure given in first source
Namen und Bezeichner
- Bevorzugter Name
- 4-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile
- IUPAC
- 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
- Englischer Name
- RU 58841
- Summenformel
- C17H18F3N3O3
- Molmasse
- 369.34
Namen und Synonyme
154992-24-2RU 58841RU-58841RU588410D8FJQ0ADW4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrileBenzonitrile, 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)-DTXSID20165781Benzonitrile, 4-(3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)-4-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrileRefChem:912121DTXCID8088272
Weitere Namen anzeigen
PSK-3841HMR-3841CS-637RU 5884RU 58884154RU 58841Ru58841 CASRU 58841(RU-58841)
4-(3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrileCHEMBL9337MFCD00925776PSK-3841; HMR-38414-(4,4-Dimethyl-2,5-dioxo-3-(4-hydroxybutyl)-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrileUNII-0D8FJQ0ADW
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 84,6 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 611
Physikochemische Eigenschaften
- Siedepunkt
- 493.6 · 493.6±55.0 °C(Predicted)
- Dichte
- 1.39 · 1.39
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- 33 mg/ml; · DMF: 33 mg/ml; DMSO: 25 mg/ml; Ethanol: 33 mg/ml; Ethanol:PBS(pH 7.2) (1:5): 0.16 mg/ml
- Aggregatzustand
- Powder
- pka
- 15.09 · 15.09±0.10(Predicted)
- Farbe
- White to off-white
- InChI
- InChI=1S/C17H18F3N3O3/c1-16(2)14(25)23(15(26)22(16)7-3-4-8-24)12-6-5-11(10-21)13(9-12)17(18,19)20/h5-6,9,24H,3-4,7-8H2,1-2H3
- InChIKey
- ARBYGDBJECGMGA-UHFFFAOYSA-N
- SMILES
- C(#N)C1=CC=C(N2C(=O)N(CCCCO)C(C)(C)C2=O)C=C1C(F)(F)F
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Alarmwort
- Achtung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H290
Chemie und Industrie
Anwendungen
BeschreibungRU-58841 is a non-steroidal antiandrogen that binds to the androgen receptor (Kd = 1.8, 1.1, 5.6, 1.3, and 1.4 nM for human, rat, mouse, hamster prostate, and hamster flank organ receptors, respectively). In vivo, topical administration of RU-58841 (1-100 μg per animal) reduces size of the flank organ without affecting sex organs in a dose-dependent manner in hamsters. It has no effect on sex organ weight in intact rats when administered percutaneously, subcutaneously, or orally at doses up to 1 mg per animal. RU-58841 (5% v/v) also induces hair regrowth in the bald frontal scalps of postpubertal stumptailed macaques, a model for male pattern baldness.
VerwendenRU 58841, is a specific androgen receptor antagonist or anti-androgen, that has shown to have effect on hair growth.
Darstellung
synthetischeRU58841 is active against baldness and is commercially available. The previously reported synthesis uses phosgene, three discrete inert atmosphere steps and three steps that require flash chromatography. Our synthesis uses no phosgene, only one inert atmosphere step and does not require flash chromatography. Alternative synthesis of the anti-baldness compound RU58841
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