Synthesis and analgesic activity of N-aryl/arylalkyl-N-[2-(1-pyrrolidinyl)cyclohexyl]propanamides.
The synthesis and in vivo analgesic activity (hot-plate test) of N-benzyl, N-(2-phenylethyl) and N-(3-phenylpropyl) derivatives of trans-(+/-)-N-[2-(1-pyrrolidinyl)cyclohexyl]propanamide (5-7, respectively) are discussed. Attempts to synthesize the N-phenyl derivative 4 are also discussed. The lack of significant analgesic activity of 5-7 indicated the stringent structural requirement for the N-methyl-N-arylacetamido group of the chi-selective opioid trans-(+/-)-2-(3,4-dichlorophenyl)- N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide (U50488) (1).
Essawi
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MY
Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Egypt.
D019900:3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer / Q000494:pharmacology; D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D051379:Mice; D010147:Pain Measurement / Q000187:drug effects; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
D018712:Analgesics, Non-Narcotic; D011759:Pyrrolidines; D019900:3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer