FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2019473313> ?p ?o ?g. }

• W2019473313 endingPage "3625" @default.
• W2019473313 startingPage "3617" @default.
• W2019473313 abstract "To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Witting reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a-->6b-->6c-->6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. alpha-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs 1a-d were prepared and showed moderately high affinities (18-55 nM). However analogs 1a-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in 1a-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vivo activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles. It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed." @default.
• W2019473313 created "2016-06-24" @default.
• W2019473313 creator A5008994767 @default.
• W2019473313 creator A5028297061 @default.
• W2019473313 creator A5029862342 @default.
• W2019473313 creator A5030031258 @default.
• W2019473313 creator A5077728218 @default.
• W2019473313 date "1997-10-01" @default.
• W2019473313 modified "2023-10-08" @default.
• W2019473313 title "Potent Anandamide Analogs: The Effect of Changing the Length and Branching of the End Pentyl Chain" @default.
• W2019473313 cites W1970112727 @default.
• W2019473313 cites W1970242856 @default.
• W2019473313 cites W1975161769 @default.
• W2019473313 cites W1976216957 @default.
• W2019473313 cites W1984563050 @default.
• W2019473313 cites W1989073099 @default.
• W2019473313 cites W2009051797 @default.
• W2019473313 cites W2012322257 @default.
• W2019473313 cites W2029255415 @default.
• W2019473313 cites W2031888213 @default.
• W2019473313 cites W2046945092 @default.
• W2019473313 cites W2057054987 @default.
• W2019473313 cites W2065241852 @default.
• W2019473313 cites W2073042925 @default.
• W2019473313 cites W2074504109 @default.
• W2019473313 cites W2085408989 @default.
• W2019473313 cites W2950826308 @default.
• W2019473313 doi "https://doi.org/10.1021/jm970212f" @default.
• W2019473313 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/9357528" @default.
• W2019473313 hasPublicationYear "1997" @default.
• W2019473313 type Work @default.
• W2019473313 sameAs 2019473313 @default.
• W2019473313 citedByCount "61" @default.
• W2019473313 countsByYear W20194733132013 @default.
• W2019473313 countsByYear W20194733132014 @default.
• W2019473313 countsByYear W20194733132018 @default.
• W2019473313 crossrefType "journal-article" @default.
• W2019473313 hasAuthorship W2019473313A5008994767 @default.
• W2019473313 hasAuthorship W2019473313A5028297061 @default.
• W2019473313 hasAuthorship W2019473313A5029862342 @default.
• W2019473313 hasAuthorship W2019473313A5030031258 @default.
• W2019473313 hasAuthorship W2019473313A5077728218 @default.
• W2019473313 hasConcept C114373084 @default.
• W2019473313 hasConcept C116073593 @default.
• W2019473313 hasConcept C161790260 @default.
• W2019473313 hasConcept C164361826 @default.
• W2019473313 hasConcept C178790620 @default.
• W2019473313 hasConcept C185592680 @default.
• W2019473313 hasConcept C193557335 @default.
• W2019473313 hasConcept C202751555 @default.
• W2019473313 hasConcept C2779167645 @default.
• W2019473313 hasConcept C2779825165 @default.
• W2019473313 hasConcept C2780263894 @default.
• W2019473313 hasConcept C2780707935 @default.
• W2019473313 hasConcept C55493867 @default.
• W2019473313 hasConcept C71240020 @default.
• W2019473313 hasConcept C94412978 @default.
• W2019473313 hasConceptScore W2019473313C114373084 @default.
• W2019473313 hasConceptScore W2019473313C116073593 @default.
• W2019473313 hasConceptScore W2019473313C161790260 @default.
• W2019473313 hasConceptScore W2019473313C164361826 @default.
• W2019473313 hasConceptScore W2019473313C178790620 @default.
• W2019473313 hasConceptScore W2019473313C185592680 @default.
• W2019473313 hasConceptScore W2019473313C193557335 @default.
• W2019473313 hasConceptScore W2019473313C202751555 @default.
• W2019473313 hasConceptScore W2019473313C2779167645 @default.
• W2019473313 hasConceptScore W2019473313C2779825165 @default.
• W2019473313 hasConceptScore W2019473313C2780263894 @default.
• W2019473313 hasConceptScore W2019473313C2780707935 @default.
• W2019473313 hasConceptScore W2019473313C55493867 @default.
• W2019473313 hasConceptScore W2019473313C71240020 @default.
• W2019473313 hasConceptScore W2019473313C94412978 @default.
• W2019473313 hasIssue "22" @default.
• W2019473313 hasLocation W20194733131 @default.
• W2019473313 hasLocation W20194733132 @default.
• W2019473313 hasOpenAccess W2019473313 @default.
• W2019473313 hasPrimaryLocation W20194733131 @default.
• W2019473313 hasRelatedWork W2018675170 @default.
• W2019473313 hasRelatedWork W2024190341 @default.
• W2019473313 hasRelatedWork W2086256002 @default.
• W2019473313 hasRelatedWork W2419170290 @default.
• W2019473313 hasRelatedWork W2770244260 @default.
• W2019473313 hasRelatedWork W3023383587 @default.
• W2019473313 hasRelatedWork W3210120534 @default.
• W2019473313 hasRelatedWork W4318219069 @default.
• W2019473313 hasRelatedWork W588494818 @default.
• W2019473313 hasRelatedWork W2766458129 @default.
• W2019473313 hasVolume "40" @default.
• W2019473313 isParatext "false" @default.
• W2019473313 isRetracted "false" @default.
• W2019473313 magId "2019473313" @default.
• W2019473313 workType "article" @default.