Design and synthesis of heterocyclic carboxamides as natural nucleic acid base mimics

被引：24

作者：

Bergstrom, DE ^{[1
]}

Zhang, PM ^{[1
]}

Johnson, WT ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT MED CHEM & PHARMACOGNOSY,W LAFAYETTE,IN 47907

来源：

NUCLEOSIDES & NUCLEOTIDES | 1996年 / 15卷 / 1-3期

关键词：

D O I：

10.1080/07328319608002370

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of heterocyclic carboxamides have been designed as mimics for the natural nucleic acid bases. The nucleosides 1-(2'-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide (1), 1-(2'-deoxy-beta-D-ribofuranosyl)pyrazole-3-carboxamide (2), and 1-(2'-deoxy-beta-D-ribofuranosy])pyrrole-3-carboxamide (3) were synthesized and their structures confirmed by spectroscopic and analytical means.

引用

页码：59 / 68

页数：10

共 20 条

[1]

ANDREWS PD, UNPUB

[2] SYNTHESIS OF 2'-DEOXY-BETA-D-RIBOFURANOSYL IMIDAZOLE AND THIAZOLE C-NUCLEOSIDES [J].

BERGSTROM, DE ;

ZHANG, PM ;

ZHOU, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (20) :3029-3034

[3] AN EFFICIENT ROUTE TO C-4 LINKED IMIDAZOLE NUCLEOSIDES - SYNTHESIS OF 2-CARBAMOYL-4-(2'-DEOXY-BETA-D-RIBOFURANOSYL)IMIDAZOLE [J].

BERGSTROM, DE ;

ZHANG, PM .

TETRAHEDRON LETTERS, 1991, 32 (45) :6485-6488

[4]

Bhat C.C., 1968, SYNTHETIC PROCEDURES, P521

[5] INOSINE.ADENINE BASE-PAIRS IN A B-DNA DUPLEX [J].

CORFIELD, PWR ;

HUNTER, WN ;

BROWN, T ;

ROBINSON, P ;

KENNARD, O .

NUCLEIC ACIDS RESEARCH, 1987, 15 (19) :7935-7949

[6] REFINED CRYSTAL-STRUCTURE OF AN OCTANUCLEOTIDE DUPLEX WITH IT MISMATCHED BASE-PAIRS [J].

CRUSE, WBT ;

AYMANI, J ;

KENNARD, O ;

BROWN, T ;

JACK, AGC ;

LEONARD, GA .

NUCLEIC ACIDS RESEARCH, 1989, 17 (01) :55-72

[7] NEW SYNTHESIS OF 2-NITROIMIDAZOLES [J].

DAVIS, DP ;

KIRK, KL ;

COHEN, LA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) :253-256

[8] PYRAZOLOPYRIMIDINE NUCLEOSIDES .3. SYNTHESIS OF 1-(BETA-D-RIBOFURANOSYL)PYRAZOLO[3,4-D]PYRIMIDINES) AND 2-(BETA-D-RIBOFURANOSYL)PYRAZOLO[3,4-D]PYRIMIDINES FROM PYRAZOLE NUCLEOSIDE DERIVATIVES [J].

EARL, RA ;

TOWNSEND, LB ;

PANZICA, RP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (21) :2672-&

[9] STUDIES ON NUCLEIC-ACID INTERACTIONS .1. STABILITIES OF MINI-DUPLEXES (DG2A4XA4G2.DC2T4YT4C2) AND SELF-COMPLEMENTARY D(GGGAAXYTTCCC) CONTAINING DEOXYINOSINE AND OTHER MISMATCHED BASES [J].

KAWASE, Y ;

IWAI, S ;

INOUE, H ;

MIURA, K ;

OHTSUKA, E .

NUCLEIC ACIDS RESEARCH, 1986, 14 (19) :7727-7736

[10] SYNTHESIS OF 2'-DEOXYTUBERCIDIN, 2'-DEOXYADENOSINE, AND RELATED 2'-DEOXYNUCLEOSIDES VIA A NOVEL DIRECT STEREOSPECIFIC SODIUM-SALT GLYCOSYLATION PROCEDURE [J].

KAZIMIERCZUK, Z ;

COTTAM, HB ;

REVANKAR, GR ;

ROBINS, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (21) :6379-6382

← 1 2 →