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dc.creatorJevtić, Ivana
dc.creatorSavić Vujović, Katarina
dc.creatorSrebro, Dragana
dc.creatorVučković, Sonja
dc.creatorIvanović, Milovan D.
dc.creatorKostić Rajačić, Slađana
dc.date.accessioned2020-07-14T18:44:18Z
dc.date.available2020-07-14T18:44:18Z
dc.date.issued2020
dc.identifier.issn1734-1140
dc.identifier.urihttps://cer.ihtm.bg.ac.rs/handle/123456789/3591
dc.description.abstractBackground 4-Anilidopiperidine class of synthetic opioid analgesics, with it’s representative fentanyl, are by far the most potent and clinically significant for the treatment of the severe chronic and surgical pain. However, side effects of μ-opioids are often quite serious. In order to improve the pharmacological profile of this class of opioid analgesics, a novel fentanyl analogs were designed, synthesized and evaluated in vivo for their antinociceptive activity. Methods The title compounds were prepared using known synthetic transformations, including N-bromoacetamide mediated Hofmann rearrangement, highly selective carbamate cleavage with trimethylsilyl iodide and dehydration of carboxamide group to nitrile in the presence of SOCl2. The antinociceptive activity of the synthesized compounds was determined by tail-immersion and formalin test. Results The scalable synthetic route towards novel fentanyl analogs bearing nitrogen groups in position C3 of piperidine ring is designed. In addition, Hofmann rearrangement was substantially improved for the more efficient synthesis of previously published 3-substituted fentanyl analogs. The series of ten fentanyl analogs was tested in vivo for their antinociceptive activity. The most potent compound of the series was found to be cis-4, based on the determined ED50 values in tail-immersion test. Conclusion Of ten compounds tested for their antinociceptive activity, compound cis-4 is characterized by high potency, rapid beginning and short duration of action and due to this might be incorporated in different pharmaceutical forms.en
dc.language.isoensr
dc.publisherSpringer Naturesr
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200026/RS//sr
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200110/RS//sr
dc.rightsrestrictedAccesssr
dc.sourcePharmacological Reportssr
dc.subjectOpioidsr
dc.subjectFentanylsr
dc.subjectAntinociceptivesr
dc.subjectAnilidopiperidinesr
dc.titleSynthesis and pharmacological evaluation of novel cis and trans 3‑substituted anilidopiperidinesen
dc.typearticlesr
dc.rights.licenseARRsr
dcterms.abstractКостић-Рајачић, Слађана; Јевтић, Ивана; Сребро, Драгана; Савић Вујовић, Катарина; Ивановић, Милован; Вучковић, Соња;
dc.citation.volume72
dc.citation.issue4
dc.citation.spage1069
dc.citation.epage1075
dc.citation.rankM22~
dc.description.otherThe peer-reviewed version: [http://cer.ihtm.bg.ac.rs/handle/123456789/3592]
dc.identifier.pmid32613543
dc.identifier.doi10.1007/s43440-020-00121-2
dc.identifier.scopus2-s2.0-85087288966
dc.identifier.wos000547634000001
dc.type.versionpublishedVersionsr


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