Rapid synthesis of F-18 and H-2 dual-labeled altanserin, a metabolically resistant PET ligand for 5-HT2a receptors

Autor:	Ping-Zhong Tan, Ronald M. Baldwin, Dennis S. Charney, Robert B. Innis, Tao Fu
Rok vydání:	1999
Předmět:	Bicyclic molecule Stereochemistry Organic Chemistry Biochemistry Medicinal chemistry Chemical synthesis Analytical Chemistry chemistry.chemical_compound Hydrolysis chemistry Drug Discovery Altanserin Nitro Lactam Radiology Nuclear Medicine and imaging Acid hydrolysis Piperidine Spectroscopy
Zdroj:	Journal of Labelled Compounds and Radiopharmaceuticals. 42:457-467
ISSN:	1099-1344 0362-4803
DOI:	10.1002/(sici)1099-1344(199905)42:5<457::aid-jlcr206>3.0.co;2-0
Popis:	F-18 and H-2 dual-labeled altanserin (3, [18F]d-ALT), a novel PET tracer for 5-HT2A receptors with metabolically resistant properties, was synthesized by [18F]fluoride displacement of the corresponding deuterated nitro precursor in 32% yield (EOB) in 108 min with radiochemical purity 95% and specific activity >1000 mCi/μmol (EOS). The key intermediate ethyl N-(2-chloroethyl-2,2-d2)carbamate (7) was obtained by LiA1D4 reduction of a glycine ester (93%), chlorination and carbamoylation (79%). 4-(4-Nitro-benzoyl)piperidine (13) was synthesized (60%) by improving the published coupling reaction of p-nitrophenyltrimethylstannane (10), obtained from p-iodonitrobenzene and (CH3)6Sn2 (94%), with 1-benzoylisonipecotic acid chloride (11) followed by acid hydrolysis. 13 was alkylated with 7 (82%), hydrolyzed and condensed with methyl o-isothiocyanatobenzoyate to provide with the precursor deuteronitroaltanserin (4, 75%). Copyright © 1999 John Wiley & Sons, Ltd.
Databáze:	OpenAIRE
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