Matches in SemOpenAlex for { <https://semopenalex.org/work/W72058801> ?p ?o ?g. }
Showing items 1 to 80 of
80
with 100 items per page.
- W72058801 abstract "Investigating the methylation of amides 1 (Scheme 1) which were derived from �-aminobutyric acid we observed the interesting chemical behaviour of these substances. When heated in the presence of sodium hydride the truncated esters 2 were formed, which led us to the assumption that N-acylpyrrolidin -2-ones 5 might be involved as intermediates. Another interesting fact is that N-acylpyrrolidin -2-ones 5 can easily be prepared by means of oxalyl chloride and acids 3. The formed acyl chlorides 4 seem to be very reactive as slight heating in the presence of diisopropyl ethyl amine for de protonation gives N-acylpyrrolidin -2-ones 5 in moderate to good yields. Once the amide nitrogen in compounds 1 or 4 gets deprotonated (Scheme 2) its nucleophilicity seems to be high and the formed five -membered ring is energetically favoured. As the chlorine in acyl chlorides 4 represents a good leaving group the reaction demands conditions only slightly above room temperature. Instead the amides 1, deprotonated by sodium hydride, require higher temperatures fo r further reaction as the ethylate function is a rather weak leaving group. Thus, the intermediatly released ethylate might attack the forme d N-acylpyrrolidin -2-ones 5 to yield the finally observed esters 2. As this step imitates the acylation of an active site serine r esidue in serine proteases or esterases [2,3] we synthesized compounds 5a -d for evaluation as inhibitors of chymotrypsin and human leukocyte elastase (HLE)." @default.
- W72058801 created "2016-06-24" @default.
- W72058801 creator A5076429935 @default.
- W72058801 date "2002-01-01" @default.
- W72058801 modified "2023-09-23" @default.
- W72058801 title "N-Acylpyrrolidin -2-ones: Potential inhibitors of serine proteases and esterases" @default.
- W72058801 cites W1984075743 @default.
- W72058801 cites W1989562681 @default.
- W72058801 cites W2012276488 @default.
- W72058801 hasPublicationYear "2002" @default.
- W72058801 type Work @default.
- W72058801 sameAs 72058801 @default.
- W72058801 citedByCount "1" @default.
- W72058801 crossrefType "journal-article" @default.
- W72058801 hasAuthorship W72058801A5076429935 @default.
- W72058801 hasConcept C118629725 @default.
- W72058801 hasConcept C145148216 @default.
- W72058801 hasConcept C155647269 @default.
- W72058801 hasConcept C160964918 @default.
- W72058801 hasConcept C161790260 @default.
- W72058801 hasConcept C164361826 @default.
- W72058801 hasConcept C178790620 @default.
- W72058801 hasConcept C178907741 @default.
- W72058801 hasConcept C181199279 @default.
- W72058801 hasConcept C182220744 @default.
- W72058801 hasConcept C185592680 @default.
- W72058801 hasConcept C193557335 @default.
- W72058801 hasConcept C2776378156 @default.
- W72058801 hasConcept C2776414213 @default.
- W72058801 hasConcept C2776643749 @default.
- W72058801 hasConcept C2778439535 @default.
- W72058801 hasConcept C2778607336 @default.
- W72058801 hasConcept C30095370 @default.
- W72058801 hasConcept C71240020 @default.
- W72058801 hasConceptScore W72058801C118629725 @default.
- W72058801 hasConceptScore W72058801C145148216 @default.
- W72058801 hasConceptScore W72058801C155647269 @default.
- W72058801 hasConceptScore W72058801C160964918 @default.
- W72058801 hasConceptScore W72058801C161790260 @default.
- W72058801 hasConceptScore W72058801C164361826 @default.
- W72058801 hasConceptScore W72058801C178790620 @default.
- W72058801 hasConceptScore W72058801C178907741 @default.
- W72058801 hasConceptScore W72058801C181199279 @default.
- W72058801 hasConceptScore W72058801C182220744 @default.
- W72058801 hasConceptScore W72058801C185592680 @default.
- W72058801 hasConceptScore W72058801C193557335 @default.
- W72058801 hasConceptScore W72058801C2776378156 @default.
- W72058801 hasConceptScore W72058801C2776414213 @default.
- W72058801 hasConceptScore W72058801C2776643749 @default.
- W72058801 hasConceptScore W72058801C2778439535 @default.
- W72058801 hasConceptScore W72058801C2778607336 @default.
- W72058801 hasConceptScore W72058801C30095370 @default.
- W72058801 hasConceptScore W72058801C71240020 @default.
- W72058801 hasLocation W720588011 @default.
- W72058801 hasOpenAccess W72058801 @default.
- W72058801 hasPrimaryLocation W720588011 @default.
- W72058801 hasRelatedWork W1485027271 @default.
- W72058801 hasRelatedWork W1515716819 @default.
- W72058801 hasRelatedWork W1966353073 @default.
- W72058801 hasRelatedWork W1977749190 @default.
- W72058801 hasRelatedWork W1985628088 @default.
- W72058801 hasRelatedWork W199748819 @default.
- W72058801 hasRelatedWork W2012196150 @default.
- W72058801 hasRelatedWork W2018071745 @default.
- W72058801 hasRelatedWork W2020820449 @default.
- W72058801 hasRelatedWork W2023267471 @default.
- W72058801 hasRelatedWork W2026918667 @default.
- W72058801 hasRelatedWork W2037363477 @default.
- W72058801 hasRelatedWork W2039068762 @default.
- W72058801 hasRelatedWork W2078791545 @default.
- W72058801 hasRelatedWork W2082639742 @default.
- W72058801 hasRelatedWork W2230717221 @default.
- W72058801 hasRelatedWork W2475029411 @default.
- W72058801 hasRelatedWork W2982440624 @default.
- W72058801 hasRelatedWork W313397817 @default.
- W72058801 hasRelatedWork W3207458419 @default.
- W72058801 isParatext "false" @default.
- W72058801 isRetracted "false" @default.
- W72058801 magId "72058801" @default.
- W72058801 workType "article" @default.