NON-NATURAL NUCLEOSIDES BASED ON 1,2,4-TRIAZOLO[1,5-a]PYRIMIDIN-7-ONES

被引:7
作者
Chupakhin, Oleg N. [1 ,2 ]
Shestakova, Tatiana S. [1 ]
Deev, Sergey L. [1 ]
Eltsov, Oleg S. [1 ]
Rusinov, Vladimir L. [1 ]
机构
[1] Ural State Tech Univ, Dept Organ Chem, Ekaterinburg 620002, Russia
[2] Russian Acad Sci, Inst Organ Synth, Ekaterinburg 620002, Russia
关键词
Non-Natural Nucleoside; Nucleoside Analog; 1,2,4-Triazolo[1,5-a]pyrimidin-7-one; Glycosylation; Alkyl Fragment; ANALOGS; GLYCOSYLATION; INHIBITORS; POTENT;
D O I
10.3987/COM-09-S(S)97
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two methods for synthesis of new nucleosides bearing 6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-ones as a base have been developed. The first one includes Vorbruggen glycosylation reaction. The second method, which is effective for synthesis of acyclic nucleosides, is based on the condensation between sodium salts of 6-phenyl-1,2,4-triazolo [1,5-a]pyrimidin-7-ones and 4-bromobuthyl acetate or (Z)-4-bromobut-2-en-1-yl acetate.
引用
收藏
页码:1149 / 1163
页数:15
相关论文
共 33 条
[1]  
[Anonymous], RUSS J ORG CHEM
[2]   Bicyclic pyrimidine nucleoside analogues (BCNAs) as highly selective and potent inhibitors of varicella-zoster virus replication [J].
Balzarini, J ;
McGuigan, C .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2002, 50 (01) :5-9
[3]   Pyrrolo-dC and pyrrolo-C:: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides [J].
Berry, DA ;
Jung, KY ;
Wise, DS ;
Sercel, AD ;
Pearson, WH ;
Mackie, H ;
Randolph, JB ;
Somers, RL .
TETRAHEDRON LETTERS, 2004, 45 (11) :2457-2461
[4]   SYNTHESIS OF NOVEL POLYCYCLIC NUCLEOSIDE ANALOGS, INCORPORATION INTO OLIGODEOXYNUCLEOTIDES, AND INTERACTION WITH COMPLEMENTARY SEQUENCES [J].
BISCHOFBERGER, N ;
MATTEUCCI, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :3041-3046
[5]   POTENTIAL INHIBITORS OF S-ADENOSYLMETHIONINE-DEPENDENT METHYLTRANSFERASES .11. MOLECULAR DISSECTIONS OF NEPLANOCIN-A AS POTENTIAL INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE [J].
BORCHERDING, DR ;
NARAYANAN, S ;
HASOBE, M ;
MCKEE, JG ;
KELLER, BT ;
BORCHARDT, RT .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1729-1738
[6]   CHEMISTRY AND ANTIVIRAL ACTIVITIES OF ACYCLONUCLEOSIDES [J].
CHU, CK ;
CUTLER, SJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) :289-319
[7]  
De Clercq E, 2001, J PHARMACOL EXP THER, V297, P1
[8]   Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections [J].
De Clercq, E .
CLINICAL MICROBIOLOGY REVIEWS, 2001, 14 (02) :382-+
[9]   Non-natural nucleosides based on 1,2,4-triazolo[5,1-c][1,2,4]triazin-4(6H)-ones [J].
Deev, Sergey L. ;
Shestakova, Tatiana S. ;
Rusinov, Vladimir L. ;
Chupakhin, Oleg N. ;
Shashkov, Alexander S. .
ARKIVOC, 2009, :196-207
[10]   7-ethoxycarbonylmethyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine [J].
Fettouhi, M ;
Boukhari, A ;
ElOtmani, B ;
Essassi, E .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1996, 52 :1031-1032