Synthesis of 1,2-annulated adamantane heterocycles: structural determination studies of a bioactive cyclic sulfite

Zoidis, Grigoris; Benaki, Dimitra; Myrianthopoulos, Vassilios; Naesens, Lieve; Clercq, Erik De; Mikros, Emmanuel; Kolocouris, Nicolas

doi:10.1016/j.tetlet.2009.03.132

Cited by 11 publications

(14 citation statements)

References 33 publications

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“…The antiviral effects of the synthesized 1,2 annulated adamantane analogues 19, 20, 21, 27, 29, 31, 33, 34, 42, 45, 47, 50, 51, 52, 60, 62, 63, 67 and 69 were determined in vitro against influenza A/Hong Kong/7/87 (H3N2) strain [63,64,69] and were compared to the activity of amantadine, rimantadine and ribavirin ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Synthetic procedures for the preparation of the 1,2-annulated adamantanopiperidines 60, 62 and 63, [64,65] and the 1,2-annulated adamantane heterocycles 50, 51 and 52. [69] Croat. Chem.…”

Section: Synthesis Of 12-annulated Adamantanopiperidinesmentioning

confidence: 99%

“…Acta 2019, 92 (2), 211-228 DOI: 10.5562/cca3540 described using the freshly prepared triphenyldibromophosphorane in one pot procedure. [69] The adamantane halide 54 was heated with sodium cyanide at high temperature to provide the dinitrile 55. [64,65] The procedure applied for the synthesis of the cyclic amines 67 and 69 [64] is illustrated in Scheme 9.…”

Section: Synthesis Of 12-annulated Adamantanopiperidinesmentioning

confidence: 99%

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

Pardali

Giannakopoulou

Konstantinidi

et al. 2019

Croat. chem. acta (Online)

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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.

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Section: Resultsmentioning

confidence: 99%

“…Synthetic procedures for the preparation of the 1,2-annulated adamantanopiperidines 60, 62 and 63, [64,65] and the 1,2-annulated adamantane heterocycles 50, 51 and 52. [69] Croat. Chem.…”

Section: Synthesis Of 12-annulated Adamantanopiperidinesmentioning

confidence: 99%

Section: Synthesis Of 12-annulated Adamantanopiperidinesmentioning

confidence: 99%

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

Pardali

Giannakopoulou

Konstantinidi

et al. 2019

Croat. chem. acta (Online)

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“…The introduction of this kind of bulky carbocyclic ring increases lipophilicity and biological membrane crossings [11]. Hence, the chemistry of adamantane continues to attract research interest due to the significant pharmacological activity of its derivatives [12][13][14][15].…”

Section: Chemistrymentioning

confidence: 99%

“…Herein we report the synthesis and biological evaluation of two new 5-HT1A inhibitors bearing the 2-MeO-Ph-piperazine moiety linked via a three carbon atom linker to cage-like structures of 1-adamantanamine and memantine. The introduction of this kind of bulky carbocyclic ring increases lipophilicity and biological membrane crossings [11] Hence, the chemistry of adamantane continues to attract research interest due to the significant pharmacological activity of its derivatives [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine

Zoidis

Loza

Catto

2022

Molbank

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Based on previously highlighted structural features, the development of highly selective 5-HT1A receptor inhibitors is closely linked to the incorporation of a 4-alkyl-1-arylpiperazine scaffold on them. In this paper, we present the synthesis of two new compounds bearing the 2-MeO-Ph-piperazine moiety linked via a three carbon atom linker to the amine group of 1-adamantanamine and memantine, respectively. Both were tested for their binding affinity against 5-HT1A receptor. N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine fumarate (8) and N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine fumarate (10) proved to be highly selective ligands towards 5-HT1A receptor with a binding constant of 1.2 nM and 21.3 nM, respectively, while 5-carboxamidotriptamine (5-CT) (2) was used as an internal standard for this assay with a measured Ki = 0.5 nM.

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Photopolymerization of 1‐adamantyl acrylate pohotoinitiated by free radical photoinitiators

Wang

Cui

et al. 2011

J of Applied Polymer Sci

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1-Adamantyl acrylate was synthesized by reacting of 1-adamantanol with acryloyl chloride in the presence of tertiary amine. The structure of monomer was characterized by FTIR and 1 H NMR spectroscopy. The influence of photoinitiator and monomer types on the photopolymerization kinetics of this monomer was investigated by real-time infrared spectroscopy (RTIR). In the UV curing system, the introduction of 1-adamantyl acrylate could significantly reduce the polymerization shrinkage.Thermogravimetric analysis of 1-adamantyl acrylate indicated that 1-adamantyl acrylate polymer has higher thermal stability than that of general commercial products. The results indicated that the synthesized monomer has good curing performance.

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Synthesis of 1,2-annulated adamantane heterocycles: structural determination studies of a bioactive cyclic sulfite

Cited by 11 publications

References 33 publications

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

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

Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine

Photopolymerization of 1‐adamantyl acrylate pohotoinitiated by free radical photoinitiators

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