135352-52-2Relevant academic research and scientific papers
SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF
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Paragraph 0041;0042, (2015/05/26)
The present invention relates to methods of inhibiting shikimate pathway, comprising administering to a subject a pharmaceutically acceptable composition comprising a compound having a formula: or pharmaceutically acceptable salts thereof. The present invention also provides a synergistic antibacterial composition containing compound
Diethyl 2,4-Dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons Reagents for the Mild and Efficient Preparation of C-5 Unsaturated Hydantoin Derivatives
Meanwell, Nicholas A.,Roth, Herbert R.,Smith, Edward C. R.,Wedding, Donald L.,Wright, J. J. Kim
, p. 6897 - 6904 (2007/10/02)
The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite.The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield.The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate.The isomeric configuration of the products was determined from analysis of NMR spectral data.Long-range (13)C-(1)H coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry.Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and α-dicarbonyl compounds to afford the corresponding olefinic products.C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to α-amino acid derivatives, pyruvates, and the imidazoquinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
