Synthesis of biologically active N2-amine adducts of 2′-deoxyguanosine

被引：26

作者：

Bonala, RR ^{[1
]}

Shishkina, IG ^{[1
]}

Johnson, F ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Pharmacol Sci, Stony Brook, NY 11794 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 38期

基金：

美国国家卫生研究院;

关键词：

2 '-deoxyguanosine; N-2-adducts; Buchwald-Hartwig reaction;

D O I：

10.1016/S0040-4039(00)01196-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several biologically important N-2-adducts of 2'-deoxyguanosine (dG) that previously were difficultly accessible, have been synthesized directly by means of the Buchwald-Hartwig reaction. The reaction employed in each case involves the coupling of 2'-deoxy-2-bromoinosine with the appropriate amine. Deprotection in all cases gave good yields of the desired 2-alkylated or -arylated deoxynucleoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7281 / 7284

页数：4

共 16 条

[1] Synthesis of N2-(2-aminofluoren-3-yl) adducts of 2′-deoxyguanosine
Bonala, RR
Yu, PL
Johnson, F
[J]. TETRAHEDRON LETTERS, 1999, 40 (04) : 597 - 598
[2] SYNTHESIS AND PROPERTIES OF AN OLIGODEOXYNUCLEOTIDE CONTAINING A POLYCYCLIC AROMATIC HYDROCARBON SITE SPECIFICALLY BOUND TO THE N-2 AMINO GROUP OF A 2'-DEOXYGUANOSINE RESIDUE
CASALE, R
MCLAUGHLIN, LW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) : 5264 - 5271
[3] Chemical synthesis of cross-linked purine nucleosides
De Riccardis, F
Johnson, F
[J]. ORGANIC LETTERS, 2000, 2 (03) : 293 - 295
[4] A general method for the synthesis of the N2- and N6- carcinogenic amine adducts of 2′-deoxyguanosine and 2′-deoxyadenosine
De Riccardis, F
Bonala, RR
Johnson, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) : 10453 - 10460
[5] Synthesis of 2-substituted 2'-deoxyguanosines and 6-O-allylguanines via the activation of C-2 by a trifluoromethanesulfonate group
Edwards, C
Boche, G
Steinbrecher, T
Scheer, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12): : 1887 - 1893
[6] NEW STRATEGY FOR THE SYNTHESIS OF OLIGODEOXYNUCLEOTIDES BEARING ADDUCTS AT EXOCYCLIC AMINO SITES OF PURINE NUCLEOSIDES
HARRIS, CM
ZHOU, L
STRAND, EA
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) : 4328 - 4329
[7] Chemical synthesis and preliminary structural characterization of a nitrous acid interstrand cross-linked duplex DNA
Harwood, EA
Sigurdsson, ST
Edfeldt, NBF
Reid, BR
Hopkins, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5081 - 5082
[8] STRUCTURE OF WYE (YT BASE) AND WYOSINE (YT) FROM TORULOPSIS-UTILIS PHENYLALANINE TRANSFER RIBONUCLEIC-ACID
KASAI, H
GOTO, M
IKEDA, K
ZAMA, M
MIZUNO, Y
TAKEMURA, S
MATSUURA, S
SUGIMOTO, T
GOTO, T
[J]. BIOCHEMISTRY, 1976, 15 (04) : 898 - 904
[9] Postsynthetic generation of a major acrolein adduct of 2′-deoxyguanosine in oligomeric DNA
Khullar, S
Varaprasad, CV
Johnson, F
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (06) : 947 - 950
[10] Palladium-catalyzed C-N bond formation:: Facile and general synthesis of N6-Aryl 2′-deoxyadenosine analogues
Lakshman, MK
Keeler, JC
Hilmer, JH
Martin, JQ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) : 6090 - 6091

← 1 2 →