NUCLEOSIDES AND NUCLEOTIDES .130. THE SYNTHESIS OF IMIDAZO[4,5-E][1,4]DIAZEPINE NUCLEOSIDES FROM N-1-SUBSTITUTED INOSINES

被引：6

作者：

AOYAGI, M ^{[1
]}

MINAKAWA, N ^{[1
]}

MATSUDA, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA KU,SAPPORO 060,JAPAN

来源：

NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 6-7期

关键词：

D O I：

10.1080/15257779408012169

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：

New synthetic methods for pyrimidine ring-expanded xanthosine, guanosine, and inosine analogues containing imidazo[4,5-e][1,4]diazepine nucleus are described. Treatment of N-1-substituted inosine derivatives 5, 12, 19 with aqueous NaOH gave 5-amino-4-(N-substituted carbamoyl)imidazole derivatives, followed by appropriate manipulations to cyclize these to constitute imidazo[4,5-e][1,4]diazepine nucleosides 11, 17, 22.

引用

页码：1535 / 1549

页数：15

共 21 条

[11] NUCLEOSIDES AND NUCLEOTIDES .117. A TRANSITION-STATE ANALOG IN PURINE NUCLEOTIDE BIOSYNTHESIS - THE DESIGN AND SYNTHESIS OF AN IMIDAZO[4,5-C]AZEPINE NUCLEOSIDE [J].

MINAKAWA, N ;

SASAKI, T ;

MATSUDA, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (02) :183-186

[12] A CONVENIENT PREPARATION OF 5-AMINO-4-IMIDAZOLECARBOXAMIDE RIBOSIDE - RING OPENING OF N1-PARA-TOLUENESULFONYL-INOSINE [J].

SHAW, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (22) :6021-6022

[13] 5-AMINO-4-IMIDAZOLECARBOXAMIDE RIBOSIDE FROM INOSINE - RING-OPENING REACTIONS OF PURINE NUCLEOSIDES [J].

SHAW, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (15) :3899-3902

[14] SYNTHESIS OF ISOCOFORMYCIN, AN ADENOSINE-DEAMINASE INHIBITOR OF SYNTHETIC ORIGIN [J].

SHIMAZAKI, M ;

KONDO, S ;

MAEDA, K ;

OHNO, M ;

UMEZAWA, H .

JOURNAL OF ANTIBIOTICS, 1979, 32 (05) :537-538

[15] ADENOSINE-DEAMINASE INHIBITORS - SYNTHESIS AND BIOLOGICAL EVALUATION OF (+/-)-3,6,7,8-TETRAHYDRO-3-[(2-HYDROXYETHOXY)METHYL]IMIDAZO[4,5-D][1,3]DIAZEPIN-8-OL AND SOME SELECTED C-5 HOMOLOGS OF PENTOSTATIN [J].

SHOWALTER, HDH ;

PUTT, SR ;

BORONDY, PE ;

SHILLIS, JL .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (10) :1478-1482

[16]

SHUTO S, IN PRESS BIOMED CHEM

[17] 2'-CHLOROPENTOSTATIN - DISCOVERY, FERMENTATION AND BIOLOGICAL-ACTIVITY [J].

TUNAC, JB ;

UNDERHILL, M .

JOURNAL OF ANTIBIOTICS, 1985, 38 (10) :1344-1349

[18]

UMEZAWA H, 1967, J ANTIBIOT, V20, P308

[19]

WEILERFEILCHENF.H, 1975, CHEM ABSTR 159350Z, V83

[20] ATOMIC-STRUCTURE OF ADENOSINE-DEAMINASE COMPLEXED WITH A TRANSITION-STATE ANALOG - UNDERSTANDING CATALYSIS AND IMMUNODEFICIENCY MUTATIONS [J].

WILSON, DK ;

RUDOLPH, FB ;

QUIOCHO, FA .

SCIENCE, 1991, 252 (5010) :1278-1284

← 1 2 3 →