22165-49-7

Basic information

• Product Name: 2-Fluoro-17-ethynylestradiol
• Synonyms: 2-Fluoro-17-ethynylestradiol
• CAS NO: 22165-49-7
• Molecular Formula: C20H23 F O2
• Molecular Weight: 314.39
• Mol File: 22165-49-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 434.9°Cat760mmHg
• Flash Point: 216.8°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 2.46E-08mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 2-Fluoro-17-ethynylestradiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-17-ethynylestradiol(22165-49-7)
• EPA Substance Registry System: 2-Fluoro-17-ethynylestradiol(22165-49-7)

Safety Data

• Hazardous Substances Data: 22165-49-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H23FO2/c1-3-20(23)9-7-16-14-5-4-12-10-18(22)17(21)11-15(12)13(14)6-8-19(16,20)2/h1,10-11,13-14,16,22-23H,4-9H2,2H3/t13-,14+,16-,19-,20-/m0/s1

Upstream product

• 133859-84-4 2-Fluoro-3-(O-tert-butyldimethylsilyl)oestrone 
• 1881-35-2 2-fluoro-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 

Relevant articles and documents

Synthesis of A-Ring Fluorinated Derivatives of (17α,20E/Z)-iodovinylestradiols: Effect on Receptor Binding and Receptor-Mediated Target Tissue Uptake

We have prepared a series of 2- and 4-fluoro derivatives of the isomeric (17α,20E)- and (17α,20Z)iodovinylestradiols (IVE2) and also the analogs substituted with either a 7α-methyl (7α-Me-IVE2) or 11β-methoxy group (11β-OMe-IVE2) and evaluated their in vitro and in vivo properties.Electrophilic substitution of the estrone derivatives with N-fluoropyridinium salt gave the 2- and 4-fluoro analogs which were subsequently converted to the 17α-ethynyl derivatives.The tributylstannyl intermediates were obtained from the corresponding 17α-ethynyl analogs using azobisi sobutyronitrile or triethylborane as catalyst.All 12 products were also prepared as their no-carrier-added iodovinyl analogs via destannylation of the tributylstannyl precursors.Binding affinity for the estrogen receptor (ER) was in general higher for the 4-F derivatives as compared to the 2-F derivatives, while the 20Z isomers of the same compounds showed somewhat higher ER binding affinity as compared to the 20E isomers.The combination of an A-ring fluoro and 7α- or 11β-substituent decreased ER binding affinity.Substitution of a fluoro atom at C-4 on either the 17α-ethynylestradiol or isomeric 17α-IVE2 enhanced the affinity of the parent molecule for the ER.A-ring fluorination of all other analogues tested had no effect or depressed ER binding affinity.Varying incubation conditions showed substantial differences in ER binding kinetics between the 20E and 20Z isomers.Tissue distribution in immature female rats showed that the highest uterus uptake and uterus to blood/nontarget ratios in the IVE2 series were obtained with the 4-F-(17α,20Z)IVE2 isomer.The combination of A-ring fluoro and 7α-or 11β-substitution decreased uterus uptake but had little or no effect on uterus to blood/nontarget ratios.The highest uterus to blood ratios were observed for the 4-F-(17α,20E)11β-OMe-IVE2 (75 at 6h and 125 at 12h pi) reflecting rapid blood clearance and in vivo stability, as confirmed by the low levels of thyroid radioactivity.The lack of correlation between ER binding affinities and uterus uptake, and/or uptake ratios, suggests that other factors, including nonspecific binding and metabolic processes, also are involved in the tissue localization process.Our data suggest that 4-F substitution onto (17α,20Z)IVE2 and (17α,20E)11β-OMe-IVE2 enhances the potential of these compounds to function as SPECT imaging agents of ER-rich tissues.