alkyne cyclization
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We present the application of a Glaser-Hay diyne coupling for the synthesis of conformationally constrained Nα-amino acid amides with different diyne ring sizes. Twelve-membered rings were the smallest rings that could be prepared by this approach. We observed the formation of triethylammonium adducts in the cases of smaller (10- and 11-membered) rings. Calculation of the conformational barriers for the cyclization reactions of various ring sizes demonstrated that the formation of amino acid-derived smaller rings by this reaction is thermodynamically unfavorable.
- MeSH
- alkyny chemie MeSH
- amidy chemická syntéza MeSH
- aminokyseliny chemie MeSH
- aminy chemie MeSH
- cyklizace MeSH
- diyny chemie MeSH
- katalýza MeSH
- molekulární konformace MeSH
- molekulární modely MeSH
- techniky syntézy na pevné fázi metody MeSH
- termodynamika MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
An efficient and high-yielding solid phase synthesis of a small library of imidazolidin-2-ones and imidazol-2-ones was carried out employing a high chemo- and regioselective gold-catalyzed cycloisomerization as a key step. Polymer-supported amino acids derivatized with several alkyne functionalities combined with tosyl- and phenylureas have been subjected to gold-catalysis exhibiting exclusively C-N bond formation. The present work proves the potential of solid phase synthesis and homogeneous gold catalysis as an efficient and powerful synthetic tool for the generation of drug-like heterocycles.
A simple, versatile, protein-repulsive, substrate-independent biomimetic surface modification is presented that is based on the creation of a PEO brush on a polydopamine anchoring layer and its capacity for selective follow-up modifications with various ligands using a copper-catalyzed alkyne-azide cycloaddition reaction. The desired surface concentration of peptide biomimetic ligands can be controlled by adjusting the peptide concentration in the reaction mixture, then measuring the activity of (125)I-radiolabeled peptides that are immobilized on the substrates. The performance of the prepared substrates is tested in cell cultures with MEF cells and a human ECC line.
- MeSH
- biomimetika * MeSH
- cyklizace MeSH
- kultivované buňky MeSH
- lidé MeSH
- povrchové vlastnosti MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
To identify novel estrogen receptor ligands a series of substituted 17alpha-arylestradiols were synthesized using the catalytic [2 + 2 + 2]cyclotrimerization of 17alpha-ethynylestradiol with various 1,7-diynes in the presence of Wilkinson's catalysts [Rh(PPh(3))(3)Cl]. The compounds were subjected to competitive binding assays, cell-based luciferase reporter assays, and proliferation assays. These experiments confirmed their estrogenic character and revealed some interesting properties like mixed partial/full agonism for ERalpha/ERbeta and different selectivity as a result of differing potencies for either ER.
- MeSH
- aktivace transkripce MeSH
- alfa receptor estrogenů agonisté genetika MeSH
- alkyny chemie MeSH
- beta receptor estrogenů agonisté genetika MeSH
- buněčné linie MeSH
- cyklizace MeSH
- estradiol analogy a deriváty chemická syntéza farmakologie MeSH
- fluorescenční polarizace MeSH
- kompetitivní vazba MeSH
- lidé MeSH
- ligandy MeSH
- luciferasy genetika MeSH
- nádorové buněčné linie MeSH
- parciální agonismus léků MeSH
- proliferace buněk účinky léků MeSH
- reportérové geny MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
