8-(omega-aminoalkyl)theophyllines and their use in preparing fluorescently labeled derivatives for applications in immunoassay.
Reaction of alkane-1, omega-diamines with 6-chloro-1,3-dimethylpyrimidine-2,4-dione under carefully controlled conditions gives 6-(omega-aminoalkylamino)-1,3-dimethylpyrimidine-2,4-diones, which can be readily separated from traces of products of disubstitution after benzyloxycarbonyl protection. A sequence of nitrosation at the pyrimidine 5-position, thermal cyclization, and deprotection affords 8-(omega-aminoalkyl) derivatives of theophylline, an important drug in the treatment of asthma and related diseases. These 8-(omega-aminoalkyl)theophyllines can be coupled to fluorescein-5-isothiocyanate and to dansyl chloride, giving fluorescent derivatives of theophylline with applications in automated immunoassay of the drug in biofluids using the fluorescence capillary fill device.
Yahioglu
F
F
School of Pharmacy and Pharmacology, University of Bath, Claverton Down, United Kingdom.
Pouton
C W
CW
Threadgill
M D
MD
D005456:Fluorescent Dyes / Q000737:chemistry*; D007118:Immunoassay; D017879:Isothiocyanates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013441:Sulfinic Acids / Q000737:chemistry; D013806:Theophylline / Q000031:analogs & derivatives* / Q000737:chemistry
D005456:Fluorescent Dyes; D017879:Isothiocyanates; D013441:Sulfinic Acids; C044255:sulfonyl chloride; D013806:Theophylline