1-Substituted 2'-deoxyinosine analogues

被引：30

作者：

DeNapoli, L ^{[1
]}

Messere, A ^{[1
]}

Montesarchio, D ^{[1
]}

Piccialli, G ^{[1
]}

Varra, M ^{[1
]}

机构：

[1] UNIV NAPLES FEDERICO II,DIPARTIMENTO CHIM ORGAN & BIOL,I-80134 NAPLES,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 14期

关键词：

D O I：

10.1039/a700987i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base 2-carbon of 2',3'-di-O-acetyl-2'-deoxyinosine is strongly activated towards nucleophillic attack when either the 4-nitrophenyl or 2,4-dinitrophenyl group is attached to its N-1 position (product 1 or 2), 1-(omega-Aminoalkyl)- and 1-(omega-hydroxyalkyl)-2'-deoxyinosine derivatives 5, 8-10 have been efficiently synthesized by a rearrangement of the purine ring upon treatment of compound 1 or 2 with the appropriate alpha,omega-diamine or alpha,omega-hydroxyamine. Moreover 1-amino-2'-deoxyinosine 11 and 1-hydroxy-2'-deoxyinosine 13 have been easily prepared in high yields by reaction of substrate 1 or 2, respectively with hydrazine or hydroxylamine.

引用

页码：2079 / 2082

页数：4

共 18 条

[1]

BETBEDER D, 1990, NUCLEOS NUCLEOT, V90, P569

[2] PURINE NUCLEOSIDES .23. DIRECT AMINATION OF PURINE NUCLEOSIDES [J].

BROOM, AD ;

ROBINS, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :1025-&

[3] REACTION OF 3',5'-DI-O-ACETYL-2'-DEOXYINOSINE WITH THE CHLORINATING AGENT P(PH)3-CCL4 - SYNTHESIS OF THE 6-CHLORODERIVATIVE AND OF A NEW BASE LINKED DIMER, USEFUL INTERMEDIATE TO N-15-1-LABELED 2'-DEOXYINOSINE [J].

DENAPOLI, L ;

MESSERE, A ;

MONTESARCHIO, D ;

PICCIALLI, G ;

SANTACROCE, C ;

VARRA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :923-925

[4]

DENAPOLI L, 1995, J ORG CHEM, V60, P2251

[5]

FUJII T, 1986, CHEM PHARM BULL, V34, P1094

[6] STUDIES ON CHEMICAL ALTERATIONS OF NUCLEIC-ACIDS AND THEIR COMPONENTS .9. SYNTHESIS AND REACTION OF 1-AMINOADENOSINE AND RELATED COMPOUNDS [J].

HUANG, GF ;

MAEDA, M ;

OKAMOTO, T ;

KAWAZOE, Y .

TETRAHEDRON, 1975, 31 (11-1) :1363-1367

[7]

KATRITZKY AR, 1971, CHEM HETEROCYCLIC N

[8]

Minakawa N, 1996, CHEM PHARM BULL, V44, P288

[9] 1-GLYCOSYL DERIVATIVES OF 5-AMINOIMIDAZOLE-4-CARBOXAMIDE [J].

MONTGOMERY, JA ;

THOMAS, HJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (12) :1334-+

[10] DIRECTIVE INFLUENCES IN PREPARATION OF PURINE NUCLEOSIDES [J].

MONTGOMERY, JA ;

THOMAS, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (09) :2304-&

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