37699-03-9Relevant articles and documents
Design, synthesis, and biological evaluation of unconventional aminopyrimidine, aminopurine, and amino-1,3,5-triazine methyloxynucleosides
Fernndez-Cureses, Gloria,De Castro, Sonia,Jimeno, Mara-Luisa,Balzarini, Jan,Camarasa, Mara-Jos
, p. 321 - 335 (2015)
Herein we describe a class of unconventional nucleosides (methyloxynucleosides) that combine unconventional nucleobases such as substituted aminopyrimidines, aminopurines, or aminotriazines with unusual sugars in their structures. The allitollyl or altritollyl derivatives were pursued as ribonucleoside mimics, whereas the tetrahydrofuran analogues were pursued as their dideoxynucleoside analogues. The compounds showed poor, if any, activity against a broad range of RNA and DNA viruses, including human immunodeficiency virus (HIV). This inactivity may be due to lack of an efficient metabolic conversion into their corresponding 5′-triphosphates and poor affinity for their target enzymes (DNA/RNA polymerases). Several compounds showed cytostatic activity against proliferating human CD4+ T-lymphocyte CEM cells and against several other tumor cell lines, including murine leukemia L1210 and human prostate PC3, kidney CAKI-1, and cervical carcinoma HeLa cells. A few compounds were inhibitory to Moloney murine sarcoma virus (MSV) in C3H/3T3 cell cultures, with the 2,6-diaminotri-O-benzyl-D-allitolyl- and -D-altritolyl pyrimidine analogues being the most potent among them. This series of unconventional nucleosides may represent a novel family of potential antiproliferative agents.
Synthesis of Fluorinated Homo-C-Nucleoside Analogues from New Carbohydrate-Derived Acylsilanes
Chanteau, Frédéric,Plantier-Royon, Richard,Portella, Charles
, p. 512 - 516 (2007/10/03)
Abstract: The stereocontrolled synthesis of new carbohydrate-derived acylsilanes with the silylcarbonyl moiety linked to the anomeric carbon via a methylene group is described. Reaction of these acylsilanes with perfluoroorganometallic reagents followed by treatment with hydrazines or amidines led to new polyfluorinated homo-C-nucleoside analogues, in a one-pot or two-step transformation, respectively.
Three-component biginelli cyclocondensation reaction using C-glycosylated substrates. Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues
Dondoni, Alessandro,Massi, Alessandro,Sabbatini, Simona,Bertolasi, Valerio
, p. 6979 - 6994 (2007/10/03)
The aldehyde-ketoester-urea cyclocondensation reaction has been revisited using C-glycosylated reagents with the aim of exploring a potential entry to a library of dihydropyrimidinone glycoconjugates. A collection of 13 mono- and bis-C-glycosylated dihydropyrimidinones has been prepared by a parallel synthesis approach using the three-component promoter CuCl/AcOH/BF3· Et2O. The sugar residues have been installed at either N1, C4, or C6 in the monoglycosylated derivatives and at both the C4 and C6 in the bisglycosylated products. The mono- and bisglycosylated products at C4 and C6 were obtained as mixtures of diastereoisomers with good to excellent selectivities due to the asymmetric induction by the sugar residue in the formation of the C4 stereocenter of the dihydropyrimidinone ring. Individual stereoisomers were isolated as pure compounds and their structures assigned with the aid of X-ray crystallography and chiroptical properties. As a demonstration of this new concept in the Biginelli reaction, the synthesis of two C4 epimer monastrol analogues bearing the ribofuranosyl moiety at C6 has been described.
Selectivity in the SmI2-induced deoxygenation of thiazolylketoses for formyl C-glycoside synthesis and revised structure of C-ribofuranosides
Dondoni, Alessandro,Formaglio, Paolo,Marra, Alberto,Massi, Alessandro
, p. 7719 - 7727 (2007/10/03)
Deoxygenation of thiazolylketose acetates using SmI2-(CH2OH)2 or TMSOTf-Et3SiH affords thiazolyl C-glycosides with opposite α/β ratios. Examination of the thiazolyl α- and β-C-ribofuranoside pair by NOE experime
Alkynylation of Mixed Acetals with Organotin Acetylides
Zhai, Dongguan,Zhai, Weixu,Williams, Robert M.
, p. 2501 - 2505 (2007/10/02)
Reaction of halo acetals containing O, N, or S heteroatoms with tri-n-butyltin acetylides in the presence of ZnCl2 in CCl4 leads to the formation of α-alkynyl ethers, amines, and sulfides in good yields.The methodology is exemplified with the synthesis of amino acids and C-glycosides.
