10-MEMBERED NEOCARZINOSTATIN CHROMOPHORE ANALOGS LEADING TO SIGMA,SIGMA-BIRADICAL VIA A CUMULENE INTERMEDIATE

被引：18

作者：

KAWATA, S ^{[1
]}

OISHI, T ^{[1
]}

HIRAMA, M ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(00)60739-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New neocarzinostatin chromophore analogs of 10-membered ring are synthesized. Generation of sigma,sigma-biradical via a cumulene intermediate has been demonstrated. The DNA-cleaving activity of the hybrid 5 is found to be 50-fold more potent than 1.

引用

页码：4595 / 4598

页数：4

共 26 条

[1] THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM [J].

EDO, K ;

MIZUGAKI, M ;

KOIDE, Y ;

SETO, H ;

FURIHATA, K ;

OTAKE, N ;

ISHIDA, N .

TETRAHEDRON LETTERS, 1985, 26 (03) :331-334

[2] ENYNE[3]CUMULENE - SYNTHESIS AND MODE OF AROMATIZATION [J].

FUJIWARA, K ;

SAKAI, H ;

HIRAMA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1688-1689

[3] MOLECULAR-MODELS OF NEOCARZINOSTATIN DAMAGE OF DNA - ANALYSIS OF SEQUENCE DEPENDENCE IN 5'-GAGCG-5'CGCTC [J].

GALAT, A ;

GOLDBERG, IH .

NUCLEIC ACIDS RESEARCH, 1990, 18 (08) :2093-2099

[4]

GOLDBERG IH, 1991, ACCOUNTS CHEM RES, V24, P1914

[5]

HIRAMA M, 1991, SYNLETT, P651

[6] DESIGN AND SYNTHESIS OF NEOCARZINOSTATIN ANALOGS [J].

HIRAMA, M .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1991, 49 (11) :1032-1042

[7] SYNTHESIS AND DNA-CLEAVING ABILITIES OF FUNCTIONAL NEOCARZINOSTATIN CHROMOPHORE ANALOGS - BASE DISCRIMINATION BY A SIMPLE ALCOHOL [J].

HIRAMA, M ;

GOMIBUCHI, T ;

FUJIWARA, K ;

SUGIURA, Y ;

UESUGI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9851-9853

[8]

HIRAMA M, 1993, RECENT PROGR CHEM SY, V2, P293

[9]

ISHIDA N, 1965, J ANTIBIOT, V18, P68

[10] THEORY OF PROTON COUPLING CONSTANTS IN UNSATURATED MOLECULES [J].

KARPLUS, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (16) :4431-4432

← 1 2 3 →