1,2-annulated adamantane heterocyclic derivatives as anti-influenza Α virus agents
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 adamant...
| Permalink: | http://skupni.nsk.hr/Record/nsk.NSK01001074264/Details |
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| Matična publikacija: |
Croatica chemica acta (Online) 92 (2019), 2 ; str. 211-228 |
| Glavni autori: | Pardali, Vasiliki (Author), Giannakopoulou, Erofili, Konstantinidi, Athina, Kolocouris, Antonios, Zoidis, Grigoris |
| Vrsta građe: | e-članak |
| Jezik: | eng |
| Predmet: | |
| Online pristup: |
https://doi.org/10.5562/cca3540 Hrčak |
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| 008 | 200916s2019 ci a |o |0|| ||eng | ||
| 024 | 7 | |2 doi |a 10.5562/cca3540 | |
| 035 | |a (HR-ZaNSK)001074264 | ||
| 040 | |a HR-ZaNSK |b hrv |c HR-ZaNSK |e ppiak | ||
| 041 | 0 | |a eng |b eng | |
| 042 | |a croatica | ||
| 044 | |a ci |c hr | ||
| 080 | 1 | |a 577 |2 2011 | |
| 080 | 1 | |a 615 |2 2011 | |
| 100 | 1 | |a Pardali, Vasiliki |4 aut |9 HR-ZaNSK | |
| 245 | 1 | 0 | |a 1,2-annulated adamantane heterocyclic derivatives as anti-influenza Α virus agents |h [Elektronička građa] / |c Vasiliki Pardali, Erofili Giannakopoulou, Athina Konstantinidi, Antonios Kolocouris, Grigoris Zoidis. |
| 246 | 3 | |a One, two-annulated adamantane | |
| 300 | |b Ilustr. | ||
| 504 | |a Bibliografija: 87 jed. | ||
| 504 | |a Abstract. | ||
| 520 | |a 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. | ||
| 653 | 0 | |a Heterociklički spojevi |a Adamantan |a Derivati |a Antivirusne tvari |a Protuvirusni lijekovi |a Influenca A |a Virus gripe A |a Virus H1N1 | |
| 700 | 1 | |a Giannakopoulou, Erofili |4 aut |9 HR-ZaNSK | |
| 700 | 1 | |a Konstantinidi, Athina |4 aut |9 HR-ZaNSK | |
| 700 | 1 | |a Kolocouris, Antonios |4 aut |9 HR-ZaNSK | |
| 700 | 1 | |a Zoidis, Grigoris |4 aut |9 HR-ZaNSK | |
| 773 | 0 | |t Croatica chemica acta (Online) |x 1334-417X |g 92 (2019), 2 ; str. 211-228 |w nsk.(HR-ZaNSK)000255036 | |
| 981 | |b Be2019 |b B05/19 | ||
| 998 | |b tino2011 | ||
| 856 | 4 | 0 | |u https://doi.org/10.5562/cca3540 |
| 856 | 4 | 0 | |u https://hrcak.srce.hr/227081 |y Hrčak |
| 856 | 4 | 1 | |y Digitalna.nsk.hr |