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Original scientific paper
https://doi.org/10.5562/cca3540

1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents

Vasiliki Pardali ; School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, GR-15771 Athens, Greece
Erofili Giannakopoulou ; School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, GR-15771 Athens, Greece
Athina Konstantinidi ; School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, GR-15771 Athens, Greece
Antonios Kolocouris ; School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, GR-15771 Athens, Greece
Grigoris Zoidis   ORCID icon orcid.org/0000-0002-9442-5186 ; School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, GR-15771 Athens, Greece

Fulltext: english, pdf (16 MB) pages 211-228 downloads: 228* cite
APA 6th Edition
Pardali, V., Giannakopoulou, E., Konstantinidi, A., Kolocouris, A. & Zoidis, G. (2019). 1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents. Croatica Chemica Acta, 92 (2), 211-228. https://doi.org/10.5562/cca3540
MLA 8th Edition
Pardali, Vasiliki, et al. "1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents." Croatica Chemica Acta, vol. 92, no. 2, 2019, pp. 211-228. https://doi.org/10.5562/cca3540. Accessed 11 Apr. 2021.
Chicago 17th Edition
Pardali, Vasiliki, Erofili Giannakopoulou, Athina Konstantinidi, Antonios Kolocouris and Grigoris Zoidis. "1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents." Croatica Chemica Acta 92, no. 2 (2019): 211-228. https://doi.org/10.5562/cca3540
Harvard
Pardali, V., et al. (2019). '1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents', Croatica Chemica Acta, 92(2), pp. 211-228. https://doi.org/10.5562/cca3540
Vancouver
Pardali V, Giannakopoulou E, Konstantinidi A, Kolocouris A, Zoidis G. 1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents. Croatica Chemica Acta [Internet]. 2019 [cited 2021 April 11];92(2):211-228. https://doi.org/10.5562/cca3540
IEEE
V. Pardali, E. Giannakopoulou, A. Konstantinidi, A. Kolocouris and G. Zoidis, "1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents", Croatica Chemica Acta, vol.92, no. 2, pp. 211-228, 2019. [Online]. https://doi.org/10.5562/cca3540

Abstracts
In this report we review our results on the development of 1,2-annulated adamantane heterocyclic derivatives and we discuss the structure-activity relationships obtained from their biological evaluation against influenza A virus. We have designed and synthesized numerous potent 1,2-annulated adamantane analogues of amantadine and rimantadine against influenza A targeting M2 protein the last 20 years. For their synthesis we utilized the key intermediates 2-(2-oxoadamantan-1-yl)acetic acid and 3-(2-oxoadamantan-1-yl)propanoic acid, which were obtained by a simple, fast and efficient synthetic protocol. The latter involved the treatment of protoadamantanone with different electrophiles and a carbon-skeleton rearrangement. These ketoesters offered a new pathway to the synthesis of 1,2-disubstituted adamantanes, which constitute starting materials for many molecules with pharmacological potential, such as the 1,2-annulated adamantane heterocyclic derivatives. To obtain additional insight for their binding to M2 protein three structurally similar 1,2-annulated adamantane piperidines, differing in nitrogen position, were studied using molecular dynamics (MD) simulations in palmitoyl-oleoyl-phosphatidyl-choline (POPC) hydrated bilayers.

Creative Commons License This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords
1,2-Annulated adamantane derivatives; Anti-influenza A virus agents; H3N2; H1N1; Rimantadine; Amantadine; SAR; M2 protein; POPC hydrated bilayers

Hrčak ID: 227081

URI
https://hrcak.srce.hr/227081

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