A-85380-[18F]-F, [18F]-F-A-85380
Chemical Name: 3-[Azetidin-2(S)-ylmethoxy]-2-(18-fluoro)pyridine
CAS No. 205594-65-6
项目整合开发状态: Phase I
项目研究机构: Commissariat a l'Energie Atomique (Originator)
合成路线:In a related procedure,2-fluoro-3-hydroxypyridine (IX) was treated with dimethylamine to provide (dimethylamino)pyridine (X).This was coupled to alcohol (III) to give ether (XI).Alternatively,(XI) was prepared by coupling fluoropyridine (IX) with alcohol (III) and subsequently treated with dimethylamine.Quaternization by means of methyl trifluoromethanesulfonate produced trimethylammonium derivative (XIII).Further displacement in (XIII) using [18F]KF-Kryptofix K222 complex provided radiolabeled fluoropyridine (VI),which was finally deprotected as above.
📌 参考资料/链接：
参考文献标题:Synthesis and nicotinic acetylcholine receptor in vivo binding properties of 2-fluoro-3-[2(S)-2azetidinylmethoxylpyridine: A new positron emission tomography ligand for nicotinic receptors
文献作者:Doll,F.; Dolci,L.; Valette,H.; Hinnen,F.; Vaufrey,F.; Guenther,I.; Fuseau,C.; Coulon,C.; Bottlaender,M.; Crouzel,C.
参考来源:J Med Chem 1999,42(12),2251
📄 详细内容
合成路线:Title radiolabeled compound has been obtained by several related procedures.Protection of (S)-2-azetidinecarboxylic acid (I) with tert-butyl dicarbonate provided carbamate (II),which was reduced to alcohol (III) using borane-dimethyl sulfide in THF at -78 C (1,3).Subsequent coupling of (III) with 3-hydroxy-2-nitropyridine (IV) under Mitsunobu conditions gave ether (V).Introduction of the 18F in (IV) was performed by means of [18F]KF-Kryptofix K222 complex in DMSO,either by conventional heating at 150 C or by microwave activation yielding (VI).The resulting radiolabeled fluoropyridine (VI) was finally deprotected with trifluoroacetic acid in CH2Cl2.
参考文献标题:Synthesis of 2-[18F]fluoro-3-[2(s)-azetidnylmethoxy]pyridine,a higly potent radioligand for in vivo imaging central nicotinic acetylcholine receptors
文献作者:Dolle,F.; et al.
参考来源:J Label Compd Radiopharm 1998,41451-463
合成路线:In an alternative procedure,Mitsunobu coupling of alcohol (III) with 3-hydroxy-2-iodopyridine (VII) provided ether (VIII).The iodo atom of (III) was then displaced using [18F]KF-Kryptofix K222 complex in DMSO to provide radiolabeled precursor (VI),which was finally deprotected with trifluoroacetic acid.
参考文献标题:Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: 2-[18F]fluoro-3-(2(S)-azetidinylmethoxy)pyridine (2-[18F]A85380)
文献作者:Hrti,A.; et al.
参考来源:J Label Compd Radiopharm 1998,41309-318
产品链接: CAS No. 205594-65-6››