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Keywords = spiroannulations

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16 pages, 7923 KB  
Article
3-[N,N-Bis(sulfonyl)amino]isoxazolines with Spiro-Annulated or 1,2-Annulated Cyclooctane Rings Inhibit Reproduction of Tick-Borne Encephalitis, Yellow Fever, and West Nile Viruses
by Kseniya N. Sedenkova, Artem S. Sazonov, Dmitry A. Vasilenko, Kristian S. Andriasov, Marina G. Eremenko, Yuri K. Grishin, Evgeny V. Khvatov, Alexander S. Goryashchenko, Victoria I. Uvarova, Dmitry I. Osolodkin, Aydar A. Ishmukhametov and Elena B. Averina
Int. J. Mol. Sci. 2023, 24(13), 10758; https://doi.org/10.3390/ijms241310758 - 28 Jun 2023
Cited by 6 | Viewed by 2926
Abstract
Spirocyclic compounds containing heterocyclic moieties represent promising 3D scaffolds for modern drug design. In the search for novel anti-flaviviral agents, we have obtained a series of 3-[N,N-bis(sulfonyl)amino]isoxazolines containing spiro-annulated cyclooctane rings and assessed their antiviral activity against tick-borne encephalitis (TBEV), yellow [...] Read more.
Spirocyclic compounds containing heterocyclic moieties represent promising 3D scaffolds for modern drug design. In the search for novel anti-flaviviral agents, we have obtained a series of 3-[N,N-bis(sulfonyl)amino]isoxazolines containing spiro-annulated cyclooctane rings and assessed their antiviral activity against tick-borne encephalitis (TBEV), yellow fever (YFV), and West Nile (WNV) viruses. The structural analogs of spirocyclic compounds with a single sulfonyl group or 1,2-annulated cyclooctane ring were also investigated. Almost all the studied 3-[N,N-bis(sulfonyl)amino]isoxazolines revealed antiviral activity against TBEV and WNV. The most active against TBEV was spiro-isoxazoline derivative containing p-nitrophenyl groups in the sulfonyl part (EC50 2.0 ± 0.5 μM), while the highest potency against WNV was found for the compounds with lipophilic substituents in sulfonyl moiety, naphtyl being the most favorable one (EC50 1.3 ± 0.5 μM). In summary, two novel scaffolds of anti-flaviviral agents based on N,N-bis(sulfonyl)amino]isoxazoline were proposed, and the compounds of this type demonstrated activity against TBEV and WNV. Full article
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11 pages, 310 KB  
Article
The Tandem Ring Opening/Ring Closing Metathesis Route to Oxaspirocycles: An Approach to Phelligridin G
by Harold D. Cooper and Dennis L. Wright
Molecules 2013, 18(2), 2438-2448; https://doi.org/10.3390/molecules18022438 - 21 Feb 2013
Cited by 11 | Viewed by 6980
Abstract
Phelligridin G is an unusual natural product that contains an embedded spiro-fused furanone core. We have investigated two furan-based synthetic approaches towards the spirocyclic core structure of this natural product from readily available 2-phenylfurans. Although initial studies involving an oxidative cyclization were unsuccessful, [...] Read more.
Phelligridin G is an unusual natural product that contains an embedded spiro-fused furanone core. We have investigated two furan-based synthetic approaches towards the spirocyclic core structure of this natural product from readily available 2-phenylfurans. Although initial studies involving an oxidative cyclization were unsuccessful, we were ultimately able to access this key system through a sequential intermolecular furan Diels-Alder reaction followed by a metathesis-based reorganization. A related approach led to an expanded C ring to form spiro-fused pyran spirocycles. Full article
(This article belongs to the Special Issue Spiro Compounds)
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4 pages, 143 KB  
Short Note
Synthesis of N-(2,8-Dioxo-1-oxaspiro[4.5]deca-6,9-dien-7-yl) Acetamide and Benzamide
by Guy L. Plourde and Randy R. Spaetzel
Molbank 2009, 2009(2), M599; https://doi.org/10.3390/M599 - 7 Apr 2009
Cited by 3 | Viewed by 6139
Abstract
The syntheses of two new spirolactones are described. Each compound was obtained as an off-white solid in 66% yields from 4-hydroxy-3-nitrobenzaldehyde. Full article
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4 pages, 306 KB  
Short Note
Determination of the Absolute Configurations of (+)-N-((3S)-3- {[(4-methylphenyl)sulfonyl]amino}-1-oxaspiro[4.5]deca-6,9- dien-2,8-dion-7-yl) Acetamide and Benzamide
by Guy L. Plourde, Lyndia M. Susag and David G. Dick
Molbank 2008, 2008(3), M579; https://doi.org/10.3390/M579 - 7 Nov 2008
Cited by 3 | Viewed by 5370
Abstract
We recently reported the asymmetric synthesis of the two title compounds without the configurational assignments of the newly formed chiral spirocarbons. We now wish to report that both compounds have a (R)-configuration at the spirocarbon based on 1D and 2D nuclear Overhauser enhancement [...] Read more.
We recently reported the asymmetric synthesis of the two title compounds without the configurational assignments of the newly formed chiral spirocarbons. We now wish to report that both compounds have a (R)-configuration at the spirocarbon based on 1D and 2D nuclear Overhauser enhancement (nOe) experiments. Full article
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9 pages, 59 KB  
Article
Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1
by Manfred Braun, Anahita Hessamian-Alinejad, Boris Féaux De Lacroix, Birte Hernandez Alvarez and Gunter Fischer
Molecules 2008, 13(4), 995-1003; https://doi.org/10.3390/molecules13040995 - 29 Apr 2008
Cited by 27 | Viewed by 12064
Abstract
The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been madeaccessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclicbenzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 isdescribed. The novel spirocyclic benzofuranones display modest to no inhibition of thehuman peptidyl prolyl [...] Read more.
The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been madeaccessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclicbenzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 isdescribed. The novel spirocyclic benzofuranones display modest to no inhibition of thehuman peptidyl prolyl cis/trans isomerase Pin1. Full article
(This article belongs to the Special Issue Spiro Compounds)
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8 pages, 64 KB  
Article
Diastereoselective Spiroannulation of Phenolic Substrates: Advances Towards the Asymmetric Formation of the Manumycin m-C7N Core Skeleton
by Guy L. Plourde, Randy R. Spaetzel, Jolene S. Kwasnitza and Thomas W. Scully
Molecules 2007, 12(9), 2215-2222; https://doi.org/10.3390/12092215 - 25 Sep 2007
Cited by 6 | Viewed by 9126
Abstract
The asymmetric syntheses of two new spirolactones prepared in optically pure form from L-3-nitrotyrosine are described. The key step, an oxidative spiroannulation, was carried out on the optically active phenols 11a and 11b and afforded the new spirolactones 5a and 5b in 85% [...] Read more.
The asymmetric syntheses of two new spirolactones prepared in optically pure form from L-3-nitrotyrosine are described. The key step, an oxidative spiroannulation, was carried out on the optically active phenols 11a and 11b and afforded the new spirolactones 5a and 5b in 85% and 83% yields, respectively, as mixtures (3:1 dr) of diastereomers. The major diastereomers from these mixtures could be isolated in optically pure form by trituration using acetone-hexanes as the solvent. Thus, the optically active spirolactones (+)-5a (+ 92.8o, c=0.125 acetone) and (+)-5b (+112.0o, c= 0.125 acetone) were obtained after four synthetic steps from L-3-nitrotyrosine in 41% and 43% yield, respectively. Full article
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5 pages, 105 KB  
Article
Diastereoselective Spiroannulation of Phenolic Substrates: Synthesis of (±)-2-tert-Butyl-6-methoxy-1-oxaspiro[4,5]deca-6,9-diene-8-one
by G. Plourde and N. English
Molecules 2005, 10(10), 1335-1339; https://doi.org/10.3390/10101335 - 31 Oct 2005
Cited by 6 | Viewed by 7042
Abstract
The synthesis of a new spiroether is described. The title compound is obtained as a diastereomeric mixture in 45% yield. Full article
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5 pages, 26 KB  
Article
Synthesis of 6-Methoxy-1-oxaspiro[4,5]deca-6,9-diene-8-one
by Guy L. Plourde and Benjamin B. Fisher
Molecules 2002, 7(2), 315-319; https://doi.org/10.3390/70200315 - 28 Feb 2002
Cited by 9 | Viewed by 7830
Abstract
The synthesis of a new spirolactone is described. The title compound is obtained as a white solid in 46% yield from 3-(4-hydroxy-2-methoxyphenyl)propanoic acid using [Bis(trifluoroacetoxy)iodo]benzene (PIFA) as the oxidant. Full article
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