Stereochemical studies on medicinal agents III. Influence of length of N‐aralkyl group on configurational selectivity of receptors toward enantiomeric basic anilide analgesics

Philip S Portoghese, Thomas N. Riley

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3 Citations (Scopus)

Abstract

Enantiomers of N‐[2‐(p‐methylbenzylmethylamino)propyl]propionanilide and of the N‐phenylpropyl analog have been prepared, and the S− (+)‐isomers were found to possess greater analgesic potency. When the number of methylene groups in the N‐aralkyl substituent is increased from one to three, the changes in the enantiomeric potency ratio which occur are considered as being reflective of a diminution in the stereoselectivity of the analgesic receptors. The decrease in stereoselectivity is attributed to differing modes of analgesic‐receptor binding.

Original languageEnglish (US)
Pages (from-to)1831-1833
Number of pages3
JournalJournal of Pharmaceutical Sciences
Volume54
Issue number12
DOIs
StatePublished - Jan 1 1965

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Anilides
Analgesics

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N2 - Enantiomers of N‐[2‐(p‐methylbenzylmethylamino)propyl]propionanilide and of the N‐phenylpropyl analog have been prepared, and the S− (+)‐isomers were found to possess greater analgesic potency. When the number of methylene groups in the N‐aralkyl substituent is increased from one to three, the changes in the enantiomeric potency ratio which occur are considered as being reflective of a diminution in the stereoselectivity of the analgesic receptors. The decrease in stereoselectivity is attributed to differing modes of analgesic‐receptor binding.

AB - Enantiomers of N‐[2‐(p‐methylbenzylmethylamino)propyl]propionanilide and of the N‐phenylpropyl analog have been prepared, and the S− (+)‐isomers were found to possess greater analgesic potency. When the number of methylene groups in the N‐aralkyl substituent is increased from one to three, the changes in the enantiomeric potency ratio which occur are considered as being reflective of a diminution in the stereoselectivity of the analgesic receptors. The decrease in stereoselectivity is attributed to differing modes of analgesic‐receptor binding.

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