Synthesis of 5-Alkynyl Isoxazolidinyl Nucleosides

被引：22

作者：

Romeo, Roberto ^{[1
]}

Giofre, Salvatore Vincenzo ^{[1
]}

Iaria, Daniela ^{[1
]}

Sciortino, Maria Teresa ^{[2
]}

Ronsisvalle, Simone ^{[3
]}

Chiacchio, Maria Assunta ^{[3
]}

Scala, Angela ^{[1
]}

机构：

[1] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

[2] Univ Messina, Dipartimento Sci Microbiol Genet & Mol, I-98168 Messina, Italy

[3] Univ Catania, Dipartimento Sci Farmaceut, I-95125 Catania, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 28期

关键词：

Nucleosides; Cycloaddition; Cross-coupling; Antitumor agents; ANALOGS; ANTIMETABOLITES; CYCLOADDITIONS; PSEUDOURIDINE; CYTOTOXICITY; NITRONE; DNA;

D O I：

10.1002/ejoc.201100767

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting with 5-iodo N,O-nucleosides, prepared by 1,3-dipolar cycloaddition of nitrones with vinyliodouracil, or vinyl acetate followed by coupling with silylated iodouracil, a series of 5-alkynyl N,O-nucleosides were synthesized via a palladium-catalyzed (Sonogashira) coupling reaction. The cytotoxic activity of modified nucleosides against HEp-2 cell lines was determined in vitro. The 5-ethynyl N,O-nucleoside, the only compound in the series containing a terminal acetylene unit, was found to be the most active compound.

引用

页码：5690 / 5695

页数：6

共 24 条

[1] Understanding ribonucleotide reductase inactivation by gemcitabine
Cerqueira, Nuno M. F. S. A.
Fernandes, Pedro A.
Ramos, Maria L.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (30) : 8507 - 8515
[2] CHEN X, 1994, CURR MED CHEM, V1, P105
[3] Zinc(II) triflate-controlled 1,3-dipolar cycloadditions of C-(2-thiazolyl)nitrones: Application to the synthesis of a novel isoxazolidinyl analogue of tiazofurin
Chiacchio, U
Rescifina, A
Saita, MG
Iannazzo, D
Romeo, G
Mates, JA
Tejero, T
Merino, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) : 8991 - 9001
[4] Synthesis of phosphonated carbocyclic 2′-oxa-3′-aza-nucleosides:: Novel inhibitors of reverse transcriptase
Chiacchio, U
Balestrieri, E
Macchi, B
Iannazzo, D
Piperno, A
Rescifina, A
Romeo, R
Saglimbeni, M
Sciortino, MT
Valveri, V
Mastino, A
Romeo, G
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (05) : 1389 - 1394
[5] Isoxazolidine analogues of pseudouridine: a new class of modified nucleosides
Chiacchio, U
Corsaro, A
Mates, J
Merino, P
Piperno, A
Rescifina, A
Romeo, G
Romeo, R
Tejero, T
[J]. TETRAHEDRON, 2003, 59 (26) : 4733 - 4738
[6] Enantioselective syntheses and cytotoxicity of N,O-nucleosides
Chiacchio, U
Corsaro, A
Iannazzo, D
Piperno, A
Pistarà, V
Rescifina, A
Romeo, R
Valveri, V
Mastino, A
Romeo, G
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (17) : 3696 - 3702
[7] Dalpozzo R, 2002, SYNTHESIS-STUTTGART, P172
[8] NITRONE CYCLO-ADDITIONS - AN EFFICIENT METHOD FOR THE HOMOLOGATION OF ALDEHYDES TO ALPHA,BETA-UNSATURATED ALDEHYDES
DESHONG, P
LEGINUS, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (18) : 3421 - 3423
[9] Ribose-modified mizoribine analogues: Synthesis and biological evaluation
Franchetti, P
Pasqualini, M
Cappellacci, L
Petrelli, R
Vita, P
Grifantini, M
Jayaram, HN
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2005, 24 (10-12) : 2023 - 2027
[10] Role of antimetabolites of purine and pyrimidine nucleotide metabolism in tumor cell differentiation
Hatse, S
De Clercq, E
Balzarini, J
[J]. BIOCHEMICAL PHARMACOLOGY, 1999, 58 (04) : 539 - 555

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