112185-26-9Relevant academic research and scientific papers
Synthesis of a tetronic acid library focused on inhibitors of tyrosine and dual-specificity protein phosphatases and its evaluation regarding VHR and Cdc25B inhibition
Sodeoka,Sampe,Kojima,Baba,Usui,Ueda,Osada
, p. 3216 - 3222 (2007/10/03)
Selective inhibitors of protein tyrosine phosphatases (PTPs) and dual-specificity phosphatases (DSPs) are expected to be useful tools for clarifying the biological functions of the PTPs themselves and also to be candidates for novel therapeutics. We planned a library approach for the identification of PTP/DSP inhibitors in which 3-acyltetronic acid is used as a "core" phosphate mimic. A series of novel tetronic acid derivatives were synthesized and evaluated as inhibitors of the dual-specificity protein phosphatases VHR and cdc25B. Several compounds are found to be potent inhibitors of cdc25B, which is a key enzyme for cell-cycle progression. The promising results described herein strongly indicated that this tetronic acid library is potent as a library focused on the PTP/DSP-selective inhibitor.
Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities
Sodeoka, Mikiko,Sampe, Ruriko,Kagamizono, Terumi,Osada, Hiroyuki
, p. 8775 - 8778 (2007/10/03)
We report an asymmetric synthesis of a potent tyrosine phosphatase inhibitor, RK-682 and its analogs. The absolute stereochemistry of RK-682 was determined to be (R). The inhibitory activities of RK-682 and its analogs, (R)-1a, (S)-1a, (R)-1b and (R)-1c toward various protein phosphatases (VHR, cdc25A, cdc25B, and PPI) are also reported.
Further Reactions of t-Butyl 3-Oxobutanthioate and t-Butyl 4-Diethylphosphono-3-oxobutanthioate: Carbonyl Coupling Reactions, Amination, Use in The Preparation of 3-Acyltetramic Acids and Application to The Total Synthesis of Fuligorubin A.
Ley, Steven V.,Smith, Stephen C.,Woodward, Peter R.
, p. 1145 - 1174 (2007/10/02)
Key words: Acyltetramic acid; Phosphonate; Wadsworth-Emmons; Dieckmann cyclisation; Fuligorubin A. Abstract: The use of t-butyl-3-oxobutanthioate (1) and t-butyl 4-diethylphosphono-3-oxobuthanthioate (2) for the preparation of homologated derivatives suitable for amination in the presence of silver(I) trifluoroacetate to afford the corresponding β-ketoamides is discussed.In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products.Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckman cyclisation with tetra-n-butyl ammonium fluoride as the cyclising base.These new reactions were applied to the total synthesis of the polyene 3-acyltetramic acid fuligorubin A.
PREPARATION OF t-BUTYL 4-DIETHYLPHOSPHONO-3-OXOBUTANETHIOATE AND USE IN THE SYNTHESIS OF (E)-4-ALKENYL-3-OXOESTERS AND MACROLIDES
Ley, Steven V.,Woodward, Peter R.
, p. 345 - 346 (2007/10/02)
The preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate (1) and Wadsworth- Emmons reaction with aldehydes and ketones is reported.Some of the products of these reactions were converted to unsaturated 3-oxomacrolides or 3-oxodiolides by transester
