Synthesis of Purine Nucleosides Built on a 3-Oxabicyclo[3.2.0]heptane Scaffold

被引：27
作者：
Flores, Ramon [1 ]
Rustullet, Albert [1 ]
Alibes, Ramon [1 ]
Alvarez-Larena, Angel [2 ]
de March, Pedro [1 ]
Figueredo, Marta [1 ]
Font, Josep [1 ]
机构：
[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain
[2] Univ Autonoma Barcelona, Unitat Crystal Lografia, Bellaterra 08193, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 13期
关键词：
VIRUS TYPE-1 INFECTION; ANTI-HIV ACTIVITY; ANTIVIRAL ACTIVITY; DIASTEREOSELECTIVE SYNTHESIS; FLUORINATED NUCLEOSIDES; 2+2 PHOTOCYCLOADDITION; ACID; 2(5H)-FURANONES; CYCLOBUTANE; ADENINE;
D O I：
10.1021/jo200775x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated.
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收藏
页码：5369 / 5383
页数：15
相关论文
共 57 条
[1]   Synthesis and conformational analysis of new cyclobutane-fused nucleosides [J].
Alibés, R ;
Alvárez-Larena, A ;
de March, P ;
Figueredo, M ;
Font, J ;
Parella, T ;
Rustullet, A .
ORGANIC LETTERS, 2006, 8 (03) :491-494
[2]   Photocycloaddition of (Z)-1,2-dichloroethylene to enantiopure 2(5H)-furanones:: an efficient strategy for the diastereoselective synthesis of cyclobutane and cyclobutene derivatives [J].
Alibés, R ;
de March, P ;
Figueredo, M ;
Font, J ;
Racamonde, M ;
Rustullet, A ;
Alvarez-Larena, A ;
Piniella, JF ;
Parella, T .
TETRAHEDRON LETTERS, 2003, 44 (01) :69-71
[3]   Photochemical [2+2] cycloaddition of acetylene to chiral 2(5H)-furanones [J].
Alibés, R ;
de March, P ;
Figueredo, M ;
Font, J ;
Fu, XL ;
Racamonde, M ;
Alvarez-Larena, A ;
Piniella, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1283-1289
[4]   STEREOSELECTIVE (2+2) PHOTOCYCLOADDITION OF CHIRAL 2(5H)-FURANONES TO ALKENES [J].
ALIBES, R ;
BOURDELANDE, JL ;
FONT, J .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1391-1402
[5]   [2+2] Photocycloaddition of homochiral 2(5H)-furanones to alkenes. First step for an efficient and diastereoselective synthesis of (+)- and (-)-grandisol [J].
Alibes, R ;
Bourdelande, JL ;
Font, J ;
Gregori, A ;
Parella, T .
TETRAHEDRON, 1996, 52 (04) :1267-1278
[6]   DETERMINATION OF THE RELATIVE RATES OF FORMATION, FATES, AND STRUCTURES OF TRIPLET 1,4-BIRADICALS GENERATED IN THE PHOTOCHEMICAL CYCLOADDITION REACTIONS OF 2-CYCLOPENTENONES WITH 2-METHYLPROPENE [J].
ANDREW, D ;
WEEDON, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5647-5663
[7]   The anti-HIV activity of ADS-J1 targets the HIV-1 gp120 [J].
Armand-Ugón, M ;
Clotet-Codina, I ;
Tintori, C ;
Manetti, F ;
Clotet, B ;
Botta, M ;
Esté, JA .
VIROLOGY, 2005, 343 (01) :141-149
[8]   5-CHLORO-SUBSTITUTED DERIVATIVES OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYURIDINE, 3'-FLUORO-2',3'-DIDEOXYURIDINE AND 3'-AZIDO-2',3'-DIDEOXYURIDINE AS ANTI-HIV AGENTS [J].
BALZARINI, J ;
VANAERSCHOT, A ;
HERDEWIJN, P ;
DECLERCQ, E .
BIOCHEMICAL PHARMACOLOGY, 1989, 38 (06) :869-874
[9]  
Bauslaugh P.G., 1970, SYNTHESIS, P287
[10]   Inhibition of human immunodeficiency virus type 1 infection in macrophages by an alpha-v integrin blocking antibody [J].
Bosch, B ;
Clotet-Codina, I ;
Blanco, J ;
Pauls, E ;
Coma, G ;
Cedeño, S ;
Mitjans, F ;
Llano, A ;
Bofill, M ;
Clotet, B ;
Piulats, J ;
Esté, JA .
ANTIVIRAL RESEARCH, 2006, 69 (03) :173-180
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