A novel and facile reaction to N6-alkylated adenosine via benzotriazole as a synthetic auxiliary

被引：3

作者：

Afify, HMNM

Pedersen, EB ^{[1
]}

Zahran, MA

机构：

[1] Odense Univ, Univ So Denmark, Dept Chem, DK-5230 Odense M, Denmark

[2] Menoufia Univ, Fac Sci, Dept Chem, Shebin El Koam, Egypt

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2000年 / 37卷 / 02期

关键词：

D O I：

10.1002/jhet.5570370218

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of benzotriazole with aliphatic, aromatic or heteroaromatic aldehyde and adenosine leads to a benzotriazole adduct which is reduced with sodium borohydride to the corresponding N-6-alkylated adenosine derivatives. This procedure is also utilized in a new route to N-6-(3-iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA) which is considered an important adenosine agonist at A(3) adenosine receptors.

引用

收藏

页码：339 / 341

页数：3

相关论文

共 23 条

[1]

DALY JW, 1995, ADENOSINE AND ADENINE NUCLEOTIDES: FROM MOLECULAR BIOLOGY TO INTEGRATIVE PHYSIOLOGY, P157

[2] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF SOME N6-(NITROBENZYL)ADENOSINES AND N6-(AMINOBENZYL)ADENOSINES [J].

DUTTA, SP ;

TRITSCH, GL ;

COX, C ;

CHHEDA, GB .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (08) :780-783

[3] A novel route to N6-alkylated 2′-deoxyadenosine using benzotriazole as a synthetic auxiliary [J].

El-Kafrawy, SA ;

Zahran, MA ;

Pedersen, EB .

ACTA CHEMICA SCANDINAVICA, 1999, 53 (04) :280-283

[4]

FREDHOLM BB, 1994, PHARMACOL REV, V46, P143

[5] STRUCTURE-ACTIVITY-RELATIONSHIPS OF N-6-BENZYLADENOSINE-5'-URONAMIDES AS A(3)-SELECTIVE ADENOSINE AGONISTS [J].

GALLORODRIGUEZ, C ;

JI, XD ;

MELMAN, N ;

SIEGMAN, BD ;

SANDERS, LH ;

ORLINA, J ;

FISCHER, B ;

PU, QL ;

OLAH, ME ;

VANGALEN, PJM ;

STILES, GL ;

JACOBSON, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (05) :636-646

[6] An improved approach to the synthesis of adenosine-5'-N-ethyluronamides of interest as adenosine receptor agonists [J].

Ha, SB ;

Nair, V .

TETRAHEDRON LETTERS, 1996, 37 (10) :1567-1570

[7]

HILL JA, 1994, DRUG DEVELOP RES, V31, P278

[8] ADENOSINE RECEPTORS - PHARMACOLOGY, STRUCTURE-ACTIVITY-RELATIONSHIPS, AND THERAPEUTIC POTENTIAL [J].

JACOBSON, KA ;

VANGALEN, PJM ;

WILLIAMS, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (03) :407-422

[9] THE CHEMISTRY OF BENZOTRIAZOLE .3. THE AMINOALKYLATION OF BENZOTRIAZOLE [J].

KATRITZKY, AR ;

RACHWAL, S ;

RACHWAL, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (04) :799-804

[10] 2-SUBSTITUTION OF N-6-BENZYLADENOSINE-5'-URONAMIDES ENHANCES SELECTIVITY FOR A-3 ADENOSINE RECEPTORS [J].

KIM, HO ;

JI, XD ;

SIDDIQI, SM ;

OLAH, ME ;

STILES, GL ;

JACOBSON, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (21) :3614-3621