Synthesis and adrenergic activity of ring-fluorinated phenylephrines

…, O Olubajo, K Buchhold, GA Lewandowski…

Index: Kirk, Kenneth L.; Olubajo, Olarangbe; Buchhold, Konstantin; Lewandowski, Gail A.; Gusovsky, Fabian; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 1982 - 1988

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Citation Number: 37

Abstract

2-Fluoro-, 4-fluoro-, and 6-fluorophenylephrine (6-FPE) were synthesized from the corresponding fluorinated 3-hydroxybenzaldehydes. New routes to 2-fluoro-and 6-fluoro-3- hydroxybenzaldehydes were developed based on regioselective lithiation of 2-and 4- [(dimethyl-tert-butylsilyl) oxy] fluorobenzene ortho to fluorine. As with norepinephrine and isoproterenol analogues, the adrenergic properties of phenylephrine were markedly ...