Conformational analysis of the tropane analogue of pethidine and related compounds by 1H NMR spectroscopy

Wiley - Tập 6 Số 8 - Trang 441-444 - 1974
A. F. Casy1, James E. Coates2
1School of Pharmacy, Liverpool Polytechnic, Byrom Street, Liverpool L3 3AF, England
2Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada

Tóm tắt

AbstractThe preferred solute conformation of ethyl 3α‐phenyltropane‐3β‐carboxylate hydrochloride, the tropane analogue of pethidine, is shown to be a piperidine chair with an axial 3‐phenyl substituent by analysis of its 1H NMR characteristics and spectral comparisons with model compounds. Conformational studies of synthetic intermediates are also reported and favoured boat forms identified for 3α‐diphenylhydroxymethyl‐3β‐tropanol and 3α‐phenyl‐3β‐tropanyl phenyl ketone. In the hot‐plate test for analgesia performed on mice, ethyl 3α‐phenyltropane‐3β‐carboxylate is about 1·5 times as effective as pethidine.

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Thông tin
Thông tin xuất bản

Wiley

Tập 6 Số 8

441-444

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