ChemInform Abstract: Syntheses of New Compounds with Localanesthetic Activity. Part 10. Synthesis of 14C‐Fomocaine

Oelschlaeger, H.; Ewald, H.

doi:10.1002/chin.198629209

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1995

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“…3-(4-Bromophenyl)-l-propanoI was prepared from 4-bromocinnamic acid according to the literature procedure. 32 In our hands the product was contaminated with up to 10% 3-phenyl-l-propanol. The alcohol was converted in two steps to the fluoride.…”

Section: Methodsmentioning

confidence: 72%

Syntheses and Biological Properties of Chiral Fluoroalkyl Quinuclidinyl Benzilates

Kiesewetter¹,

Silverton²,

Eckelman³

1995

J. Med. Chem.

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Previously, (R)-quinuclidinyl (R)-4-iodobenzilate ((R,R)-IQNB), a muscarinic receptor antagonist, has been labeled with 123I and 125I for use in in vitro and in vivo studies in animals and humans. We have prepared fluoroalkyl analogs of QNB, which are amenable to labeling with 18F, for potential imaging applications with positron emission tomography. The enantiomers of (fluoroalkyl)benzilic acids were prepared via an enantioselective Grignard addition reaction. Subsequent coupling of the enantiomeric (fluoroalkyl)benzilic acid with a selected enantiomer of quinuclidinol provides fluorinated analogs of QNB with known stereochemistry at each of the stereogenic centers. These compounds exhibit different affinities for the muscarinic receptor tissue subtypes in vitro. (R,R)-4-(Fluoromethyl)-QNB, and (R,R)-IQNB, and (R,R)-4-(fluoroethyl)-QNB exhibit selectivity for the M1 subtype, and (R,S)-4-(fluoromethyl)-QNB exhibits selectivity for the M2 subtype.

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Section: Methodsmentioning

confidence: 72%