Recent advances in the synthesis of confortnationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets

被引:33
作者
Choi, Y [1 ]
Moon, HR [1 ]
Yoshimura, V [1 ]
Marquez, VE [1 ]
机构
[1] NCI, Med Chem Lab, Ctr Canc Res, NIH,HHS, Frederick, MD 21702 USA
关键词
bicyclo[3.1.0]hexane and bicyclo[3.1.0]hexene; conformationally locked carbocyclic nucleosides; pseudorotational analysis; D4T and carbovir analogues; intramolecular cyclopropanation; lipase-catalyzed resolution;
D O I
10.1081/NCN-120021954
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The present work describes some recent approaches to the syntheses of three classes of locked-North nucleosides: beta-D-ribo-, beta-D-deoxyribo-, and beta-D-dideoxy-ribonucleosides. The method developed for the latter class permitted access to a novel bicyclo[3.1.0]hexene-type nucleosides structurally similar to D4T and carbovir. A structural analysis and biological activities are discussed.
引用
收藏
页码:547 / 557
页数:11
相关论文
共 17 条
  • [1] 2-chloro N6-methyl-(N)-methanocarba-2′-deoxyadenosine-3′,5′-bisphosphate is a selective high affinity P2Y1 receptor antagonist
    Boyer, JL
    Adams, M
    Ravi, RG
    Jacobson, KA
    Harden, TK
    [J]. BRITISH JOURNAL OF PHARMACOLOGY, 2002, 135 (08) : 2004 - 2010
  • [2] Cohen N., 1985, ORG SYNTH, V63, P127
  • [3] (1S,2R)-[(benzyloxy)methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4',1'a-methano- and 1',1'a-methanocarbocyclic nucleosides
    Ezzitouni, A
    Russ, P
    Marquez, VE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4870 - 4873
  • [4] HIV-1 reverse transcriptase can discriminate between two conformationally locked carbocyclic AZT triphosphate analogues
    Marquez, VE
    Ezzitouni, A
    Russ, P
    Siddiqui, MA
    Ford, H
    Feldman, RJ
    Mitsuya, H
    George, C
    Barchi, JJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) : 2780 - 2789
  • [5] Marquez VE, 1999, HELV CHIM ACTA, V82, P2119
  • [6] Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides?
    Marquez, VE
    Siddiqui, MA
    Ezzitouni, A
    Russ, P
    Wang, JY
    Wagner, RW
    Matteucci, MD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) : 3739 - 3747
  • [7] A remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides
    Moon, HR
    Ford, H
    Marquez, VE
    [J]. ORGANIC LETTERS, 2000, 2 (24) : 3793 - 3796
  • [8] Synthesis of cyclopropyl-fused carbocyclic nucleosides via the regioselective opening of cyclic sulfites
    Moon, HR
    Kim, HO
    Chun, MW
    Jeong, LS
    Marquez, VE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) : 4733 - 4741
  • [9] Noy R, 2002, MOL CANCER THER, V1, P585
  • [10] Stereoselective transformations leading to pentono-1,4-lactones
    Rao, BV
    Lahiri, S
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (08) : 975 - 984