- Synthesis and crystallographic analysis of short pyridine-based oligoamides as DNA-targeting supramolecular binders
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In this study, the synthesis of the pyridine peptides 1-4, formed from amino-picolinic acid, and pyridine peptide 5, made from coupling of a mono-protected pyridine diamine to a mono-protected pyridine dicarboxylic acid and the X-ray crystallographic structures of 1 and 5 are discussed, along with their supramolecular interactions in the solid state. The structure of these compounds showed that they possess concave appearance which can be employed to bind to nucleic acids through multiple hydrogen bonding, which would facilitate the formation of helical-based pyridine oligoamides as novel DNA-binding molecules. This was proven by carrying out DNA denaturation studies and ethidium displacement assay on 5, but, by using MTT assays, 5 was shown to be cytotoxic against drug-resistant chronic myeloid leukaemia K562 cell-line.
- Frimannsson, Daniel O.,McCabe, Thomas,Schmitt, Wolfgang,Lawler, Mark,Gunnlaugsson, Thorfinnur
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scheme or table
p. 483 - 490
(2010/11/18)
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- Deoxygenation of pyridine N-oxides by palladium-catalysed transfer oxidation of trialkylamines
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A convenient and chemoselective method for deoxygenation of pyridine TV-oxide derivatives by transfer oxidation of triethylamine-catalysed by [Pd(OAc)2]/dppf is described.
- Fuentes, José A.,Clarke, Matthew L.
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scheme or table
p. 2579 - 2582
(2009/04/16)
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- Self-assembly of organocatalysts: Fine-tuning organocatalytic reactions
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(Chemical Equation Presented) A cat. with two tales: Hydrogen-bonding interactions between achiral pyridinone additives and unselective chiral proline-derived organocatalysts (see picture) result in highly effective catalysts for the Michael addition of n
- Clarke, Matthew L.,Fuentes, Jose A.
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p. 930 - 933
(2008/02/01)
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- A novel three-component reaction of N-fluoropyridinium salts: A facile approach to imidazo[1,2-a]pyridines
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The reaction of N-fluoropyridinium triflate with isonitriles in acetonitrile and propionitrile in the presence of NaBH(OAc)3 led to the formation of the corresponding imidazo[1,2-a]pyridines in 44-73% yields. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species and apparent reduction of the pyridinium intermediate with NaBH(OAc)3 to yield the targeted heterocycles.
- Kiselyov, Alexander S.
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p. 4487 - 4490
(2007/10/03)
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- Carboxamidation of pyridines by the system of elemental fluorine- carbonitrile-water: A useful alternative to the chichibabin amination
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The title reaction with pyridine, 4-methylpyridine, 3-methylpyridine, 3- bromopyridine, nicotinonitrile, and quinoline yields 2-carboxamido derivatives regioselectively. Isoquinoline is amidated at position 1.
- Kiselyov,Strekowski
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p. 2387 - 2392
(2007/10/02)
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