Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a “Cage” Residue.

Romański, Jarosław; Mlostoń, Grzegorz; Linden, Anthony; Heimgartner, Heinz

doi:10.1002/chin.200547110

Cited by 2 publications

(2 citation statements)

References 15 publications

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“…Pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane is a particularly good synthetic precursor for multi-functional inhibitors, as the diketone can be easily converted to a diol, hydroxyl amine, or hydroxyl ketone 21. Our recent high resolution X-ray crystal structure of A/M2 revealed two layers of well-organized water molecules positioned above the proton-accepting H37 residues 18.…”

Section: Sar Of the Polar Headgroupmentioning

confidence: 99%

Exploring the Requirements for the Hydrophobic Scaffold and Polar Amine in Inhibitors of M2 from Influenza A Virus

Wang

Ma²,

Balannik³

et al. 2011

ACS Med. Chem. Lett.

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Inhibitors targeting the influenza A virus M2 (A/M2) proton channel, have lost their effectiveness due to widespread resistance. As a first step in the development of new inhibitors that address this problem, we have screened several focused collections of small molecules using two electrode voltage patch clamp assays (TEVC) on Xenopus laevis Oocyte. Diverse head groups and scaffolds of A/M2 inhibitors have been explored. It has been found that not only amine, but also hydroxyl, aminooxyl, guanidine and amidine compounds are active against the A/M2 proton channel. Moreover, the channel is able to accommodate a wide range of structural variation in the apolar scaffold. This study offers information to guide the next generation of A/M2 proton channel inhibitor design.

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Section: Sar Of the Polar Headgroupmentioning

confidence: 99%

Exploring the Requirements for the Hydrophobic Scaffold and Polar Amine in Inhibitors of M2 from Influenza A Virus

Wang

Ma²,

Balannik³

et al. 2011

ACS Med. Chem. Lett.

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“…Firstly, the addition of 7 to the thioketones 1a and 1b occurs selectively in a carbophilic fashion. Secondly, the nucleophilic attack of 7 onto the C=S group of 1b proceeds, as expected [11,12], from the exo side.…”

Section: Methodsmentioning

confidence: 63%

Reactions of polycyclic thioketones with a phosphonylated carbanion

Mlostoń

Obijalska

Urbaniak

et al. 2008

Heteroatom Chemistry

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Polycyclic, nonenolizable cycloaliphatic thioketones 1a and 1b react smoothly with the lithium salt of diethyl methylphosphonate 7 in THF solution at −40°C to afford products of the carbophilic attack exclusively. Quenching of the obtained lithium thiolates with alkyl iodides yields sulfanes of type 9 or 11, respectively, in good yields. 1‐Fluoro‐2,4‐dinitrobenzene was shown to act as an arylating agent. In the case of the “cage” thioketone 1b, the carbanion of salt 7 approaches the CS bond from the exo‐side exclusively. In contrast to the parent carbonyl compounds, thioketones 1 show no tendency to undergo the conversion analogous to the Horner–Wadsworth–Emmons reaction, which would result in the formation of an olefinic product. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:182–187, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20390

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Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a “Cage” Residue.

Cited by 2 publications

References 15 publications

Exploring the Requirements for the Hydrophobic Scaffold and Polar Amine in Inhibitors of M2 from Influenza A Virus

Exploring the Requirements for the Hydrophobic Scaffold and Polar Amine in Inhibitors of M2 from Influenza A Virus

Reactions of polycyclic thioketones with a phosphonylated carbanion

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