5991-01-5Relevant articles and documents
Synthesis of 7-Deaza-cyclic Adenosine-5′-diphosphate-carbocyclic-ribose and Its 7-Bromo Derivative as Intracellular Ca2+-Mobilizing Agents
Takano, Satoshi,Tsuzuki, Takayoshi,Murayama, Takashi,Sakurai, Takashi,Fukuda, Hayato,Arisawa, Mitsuhiro,Shuto, Satoshi
, p. 6619 - 6627 (2015)
Cyclic ADP-carbocyclic-ribose (cADPcR, 3) is a biologically and chemically stable equivalent of cyclic ADP-ribose (cADPR, 1), a Ca2+-mobilizing second messenger. We became interested in the biological activity of the 7-deaza analogues of cADPcR, i.e., 7-deaza-cADPcR (7) and its 7-bromo derivative, i.e., 7-deaza-7-Br-cADPcR (8), because 7-deazaadenosine is an efficient bioisostere of adenosine. The synthesis of 7 and 8 required us to construct the key N1-carbocyclic-ribosyl-7-deazaadenosine structure. Therefore, we developed a general method for preparing N1-substituted 7-deazaadenosines by condensing a 2,3-disubstituted pyrrole nucleoside with amines. Using this method, we prepared the N1-carbocyclic ribosyl 7-deazaadenosine derivative 10a, from which we then synthesized the target 7-deaza-cADPcR (7) via an Ag+-promoted intramolecular condensation to construct the 18-membered pyrophosphate ring structure. The corresponding 7-bromo derivative 8, which was the first analogue of cADPR with a substitution at the 7-position, was similarly synthesized. Biological evaluation for Ca2+-mobilizing activity in the sea urchin egg homogenate system indicated that 7-deaza-cADPcR (7) and 7-deaza-7-Br-cADPcR (8) acted as a full agonist and a partial agonist, respectively.
Novel synthesis method of nicotinamide ribose
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Paragraph 0022; 0046-0047; 0048-0049; 0050-0051, (2020/11/22)
The invention discloses a novel synthesis method of nicotinamide ribose. According to the method, 2,3,4,5-tetrabenzoyloxy ribose is added into an alcoholic solution; acetyl chloride is dropwise added;chlorination reaction is performed; a chlorination product and nicotinamide are condensed; benzoyl is removed from a condensation product in sodium methoxide; stirring and purification are performedthrough an organic solvent; and crystallization is performed to obtain a finished product. The novel synthesis method has the advantages that the 2,3,4,5-tetrabenzoyloxy ribose is used as a starting material; ribose 2-benzoyl is selectively chloridized by the acetyl chloride; a product with beta-nicotinamide riboside as a main ingredient is generated; a catalyst is common and easy to obtain; the cost can be effectively reduced; the reaction design ingredients are simple; post treatment is simple; after deprotection, a protective agent and alpha impurities are removed by the organic solvent; and the high-purity finished product can be obtained through recrystallization.
A One-Pot Synthesis of Highly Functionalized Purines
Zelli, Renaud,Zeinyeh, Wa?l,Haudecoeur, Romain,Alliot, Julien,Boucherle, Benjamin,Callebaut, Isabelle,Décout, Jean-Luc
supporting information, p. 6360 - 6363 (2017/12/08)
Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.
Synthesis of novel 6-substituted thymine ribonucleosides and their 3′-fluorinated analogues
Bozhok, Tatyana S.,Sivets, Grigorii G.,Baranovsky, Alexander V.,Kalinichenko, Elena N.
, p. 6518 - 6527 (2016/09/23)
Nine novel 6-fluorothymine nucleoside analogues of both N(1)-α/β and N(3)-β-ribo series were prepared by the Vorbrüggen method starting from persilylated 6-fluorothymine and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-D-ribofuranose or 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose and its α-anomer. Protected N(3)-β-D-ribofuranosides were prepared as sole products in high yields at room temperature. A mixture of benzoylated N(1)-β- and α-anomeric ribonucleosides was obtained at lower temperatures. Yields of β-anomers and stereoselectivities (β:α=2.2/4.5:1) of the condensation reactions depended on reaction conditions and the structure of the glycosylating agent. Debenzoylation of 6-fluorothymine N(1)- or N(3)-β-D-ribofuranosides and their 3′-fluorodeoxy analogues by LiOH monohydrate in MeCN/H2O resulted in the corresponding fluorinated nucleosides in good yields, whereas the deprotection of N(1)-α-ribofuranosides under the same conditions unexpectedly yielded 6,2′-O-α-D-anhydronucleosides. 6-Substituted (OMe, NH2) thymine β-ribonucleosides were prepared by the treatment of protected N(1)-β-D-ribosides with nucleophilic agents.
Synthesis of new pyrazoline-nucleoside analogue derivatives
Azouz,Lammara,Benallia,Guenane
, p. 294 - 305 (2013/08/26)
In this work, a synthesis of pyrazoline nucleosides analogues is presented, using the stereospecific sodium salt glycosylation procedure. In the first step, chalcones were prepared using Claisen Schmidt reaction by reacting benzaldehyde with enolizable ketones in ethanolic NaOH solutions. Next, these chalcones were immediately reacted with hydrazine hydrochloridein the presence of dry methanol to obtain the corresponding 2-pyrazolines. Finally, the coupling of the pyrazolines with 1-chloro-arabinofuranose leads to different β-nucleosides as the major product (13-17) in good yields. The structures of these derivatives were characterized by infrared and 1HNMR spectroscopy and mass spectrometry.
ENZYME DETECTION/ASSAY METHOD AND SUBSTRATES
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, (2008/06/13)
The invention relates to a method of detecting and/or assaying nucleoside hydrolases or nucleoside phosphorylases using a chromogenic substrate. Preferred chromogenic substrates have formula (I) where X is OH, or H, and Y is the residue of Y—OH where Y—OH is a chromophore or a compound readily converted to a chromophore and the substrates are hydrolysed by the nucleoside hydrolase to yield ribose or 2-deoxyribose plus Y—OH. Alternatively those substrates may be phosphorylysed by nucleoside phosphorylase to yield ribose-1-phosphate plus Y—OH. The methods may be used to detect and/or assay parasites in biological samples.
Facile synthesis of glycofuranosyl isothiocyanates
Marino, Carla,Varela, Oscar,De Lederkremer, Rosa M.
, p. 257 - 260 (2007/10/03)
Peracylated glycofuranosyl isothiocyanates are obtained under smooth conditions starting from the corresponding glycosyl chloride by reaction with potassium thiocyanate in anhydrous acetone at room temperature, classical conditions for the synthesis of gl
SOME 1-β-D-RIBOFURANOSYL-5-PHENYLCYTOSINES AND -5-(2-CHLOROPHENYL)-2-THIOCYTOSINE
Budesinsky, Zdenek,Smejkal, Frantisek,Budesinsky, Milos
, p. 2145 - 2149 (2007/10/02)
5-Phenylcytidine (XI), 5-(4-nitrophenyl)cytidine (XII) and 5-(2-chlorophenyl)-2-thiocytidine (XIII) were prepared from corresponding trimethylsilyl derivatives V-VII.Nitro derivative XII was converted to amino derivative XIV by catalytic reduction.Cytidines XI-XIV and the starting cytosines I-IV do not display any in vitro inhibitory effect against the influenza virus AWS, virus NDV, vaccinia, herpes simplex and WEE, or in vivo effect on mice infected with the herpes simplex virus type 2 (HSV-2) either.
