Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues.
نویسندگان
چکیده
Treatment of the protected (E)-5'-deoxy-5'-[(p-toluenesulfonyl)methylene]uridine and adenosine derivatives with tributyl- or triphenylgermane hydride (AIBN/toluene/Delta) effected radical-mediated germyldesulfonylations to give 5'-(tributyl- or triphenylgermyl)methylene-5'-deoxyuridine and adenosine derivatives as single (E)-isomers. Analogous treatment of 2'-deoxy-2'-[(phenylsulfonyl)methylene]uridine with Ph(3)GeH afforded the corresponding vinyl triphenylgermane product. Stereoselective halodegermylation of the (E)-5'-(tributylgermyl)methylene-5'-deoxy nucleosides with N-iodosuccinimide or N-bromosuccinimide provided the Wittig-type (E)-5'-deoxy-5'-(halomethylene) nucleosides quantitatively, while no halodegermylations was observed with the 5'-deoxy-5'-(triphenylgermyl)methylene counterparts. Treatment of the vinyl trialkylgermanes with aqueous trifluoroacetic acid effected protiodegermylation, while vinyl triarylgermanes were stable under the acidic conditions.
منابع مشابه
TETRA-N-BUTYLAMMONIUM FLUORIDE AS A NOVEL REAGENT FOR THE PREPARATION OF ACYCLO-NUCLEOSIDES. THE SYNTHESIS OF 9- [(2-HYDROXYETHOXY) METHYL] ADENINE, BITAMYCIN.
The synthesis of the title compound, bitamycin, by means of BU4NF is described. This new antiviral drug was found to be one of the most powerful and least toxic substances for antiviral therapy in man. The physical and chemical behavior as well as the antiviral activities and clinical properties of this compound were found to be significantly different from that reported by Schaeffer, et a...
متن کاملOne-pot Synthesis of Amidoalkyl Naphthol Derivatives as Potential Nucleoside Antibiotics and HIV Protease Inhibitors using Nano-SnO2 as an Efficient Catalyst
An efficient three-component one-pot synthesis of 1-amidoalkyl-2-naphthols from 2-naphthol, aldehydes, and acetamide using nano-SnO2as catalyst is described. The reactions were carried out at 80oC under water-solvent media. The structures of the compounds were characterized by IR, 1HNMR, 13C-NMR, and Mass spectra and by elemental analysis. The advantages of the effective meth...
متن کاملDesign, Synthesis and Biological Evaluation of Novel Peptide-Like Analogues as Selective COX-2 Inhibitors
A new series of peptide-like derivatives containing different aromatic amino acids andpossessing pharmacophores of COX-2 inhibitors as SO2Me or N3 attached to the para positionof an end phenyl ring was synthesized for evaluation as selective cyclooxygenase-2 (COX-2)inhibitors. The synthetic reactions were based on the solid phase peptide synthesis methodusing Wang resin. One of the analogues, i...
متن کاملDesign, Synthesis and Biological Evaluation of Novel Peptide-Like Analogues as Selective COX-2 Inhibitors
A new series of peptide-like derivatives containing different aromatic amino acids andpossessing pharmacophores of COX-2 inhibitors as SO2Me or N3 attached to the para positionof an end phenyl ring was synthesized for evaluation as selective cyclooxygenase-2 (COX-2)inhibitors. The synthetic reactions were based on the solid phase peptide synthesis methodusing Wang resin. One of the analogues, i...
متن کاملA Priori Prediction of Tissue: Plasma Partition Coefficients (Log BP) of Drugs to Facilitate the Use of MLR and MLR-GA Methods
It is important to determine whether a candidate molecule is capable of penetrating the plasma-brain barrier indrug discovery and development. The aim of this paper is to establish a predictive model for plasma-brainbarrier penetration using simple descriptors The usefulness of the quantum chemical descriptors, calculated atthe level of the DFT and HE theories using 6-310* basis set for QSAR st...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Nucleosides, nucleotides & nucleic acids
دوره 28 5 شماره
صفحات -
تاریخ انتشار 2009