Synthesis and properties of a novel nucleoside derivative possessing a 2,3,5,6-tetraazabenzo[cd]azulene skeleton

被引：8
|
作者：
Hirama, Yasuyuki [3 ]
Abe, Hiroshi [2 ]
Minakawa, Noriaki [1 ]
Matsuda, Akira [3 ]
机构：
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
[2] RIKEN Adv Sci Inst, Nano Med Engn Lab, Wako, Saitama 3510198, Japan
[3] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
来源：
TETRAHEDRON | 2010年 / 66卷 / 43期
关键词：
Nucleoside; Nucleobase; Tetraazabenzo[cd]azulene; IMIDAZOPYRIDOPYRIMIDINENAPHTHYRIDINE BASE-PAIRS; 4; HYDROGEN-BONDS; OLIGODEOXYNUCLEOTIDES; NAPHTHYRIDINE; STABILITY; SYSTEMS; MOTIFS;
D O I：
10.1016/j.tet.2010.08.063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe herein the synthesis and properties of the novel nucleoside derivative, 4,7-diamino-2-(2-deoxy-beta-D-erythro-pentofuranosyl)-2,6-dihydro-7H-2,3,5,6-tetraazabenzo[cd]azulene (1). The palladium catalyzed cross-coupling reaction of 2,4-diamino-5-iodo-7-(2-deoxy-beta-D-erythro-pentofuranosyl) pyrrolo[2,3-d]pyrimidine (9) with acrylonitrile afforded 2,4-diamino-5-[(E)-1-cyano-2-ethenyl]-7-(2-deoxy-beta-D-erythro-pentofuranosyl)pyrrolo[2,3-d]pyrimidine (10) in 77% yield, which was treated with NaOMe in MeOH in the presence of NaSPh to give the desired 1 in 64% yield. Whereas 1 was stable in concentrated ammonia at room temperature, it was gradually hydrolyzed in water to give 4-amino-2-(2deoxy-beta-D-erythro-pentofuranosyl)-2,6-dihydro-7H-2,3,5,6-tetraazabenzo[cd]azulen-7-one (12). Density functional calculations indicated that 12 was 20 kcal/mol more thermodynamically stable than 1 in a model study. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8402 / 8406
页数：5
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