Fluoro norcholesterol analogues. Synthesis of 6 beta-(2'-fluoro) ethyl-19-norcholest-5(10)-en-3 beta-ol
Journal Article
·
· Steroids; (United States)
A synthetic route for labelling 6 beta-(2'-fluoro)ethyl-19-norcholest-5(10)-en-3 beta-ol (VII) with fluorine-18 was developed to evaluate the potential utility of VII as an adrenal imaging agent. 6 beta-p-Toluene-sulphonyloxymethyl-19-norcholest-5(10)-en-3 beta-ol acetate (I) was converted to the 6 beta-(2'-hydroxy)ethyl (VI) in a five-step process. The treatment of VI with N-N-diethyl (2-chloro-1,1,2,-trifluoroethyl)amine in methylene chloride and subsequent hydrolysis with base gave the required VII. Iodination of VI with triphenoxymethylphosphonium iodide followed by alkaline hydrolysis gave the 6 beta-(2'-iodo)ethyl (IX) which, on treatment with silver fluoride in acetonitrile, furnished the 6 beta-(2'-fluoro)ethyl (VII). Excellent conversion of the 6-beta-(2'-p-toluenesulphonyloxy)-ethyl (X) into VII was also achieved by heating with potassium fluoride for 2 hr in diethylene glycol in 76% yield, which is a readily applicable method for labelling with fluorine-18.
- Research Organization:
- Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
- OSTI ID:
- 6376329
- Journal Information:
- Steroids; (United States), Journal Name: Steroids; (United States) Vol. 39:5; ISSN STEDA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ADRENAL GLANDS
ALKALINE HYDROLYSIS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BIOCHEMISTRY
BODY
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHEMISTRY
COUNTING TECHNIQUES
DECOMPOSITION
DIAGNOSTIC TECHNIQUES
DRUGS
ENDOCRINE GLANDS
ENERGY LEVELS
FLUORINE 18
FLUORINE ISOTOPES
GLANDS
HOURS LIVING RADIOISOTOPES
HYDROLYSIS
IMAGES
ISOBARIC ANALOGS
ISOTOPE APPLICATIONS
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
LYSIS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANS
RADIOISOTOPE SCANNING
RADIOISOTOPES
RADIOPHARMACEUTICALS
SCINTISCANNING
SOLVOLYSIS
STEROIDS
SYNTHESIS
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ADRENAL GLANDS
ALKALINE HYDROLYSIS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BIOCHEMISTRY
BODY
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHEMISTRY
COUNTING TECHNIQUES
DECOMPOSITION
DIAGNOSTIC TECHNIQUES
DRUGS
ENDOCRINE GLANDS
ENERGY LEVELS
FLUORINE 18
FLUORINE ISOTOPES
GLANDS
HOURS LIVING RADIOISOTOPES
HYDROLYSIS
IMAGES
ISOBARIC ANALOGS
ISOTOPE APPLICATIONS
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
LYSIS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANS
RADIOISOTOPE SCANNING
RADIOISOTOPES
RADIOPHARMACEUTICALS
SCINTISCANNING
SOLVOLYSIS
STEROIDS
SYNTHESIS