SYNTHESIS AND CYTOTOXICITY OF ENANTIOMERIC PAIRS OF DUOCARMYCIN-A AND ITS 2-EPIMER

被引：28

作者：

FUKUDA, Y ^{[1
]}

NAKATANI, K ^{[1
]}

TERASHIMA, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR, SAGAMIHARA, KANAGAWA 229, JAPAN

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 07期

关键词：

D O I：

10.1016/S0960-894X(00)80406-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of the four possible diastereomers of duocarmycin A was achieved through optical resolution of a tricyclic synthetic intermediate. The stereochemical configuration of the cyclopropane ring was found to be closely related with their cytotoxicity against P388 murine leukemia.

引用

收藏

页码：755 / 758

页数：4

相关论文

共 11 条

[1]

Boger D. L., 1991, CHEMTRACTS ORG CHEM, V4, P329

[2] DUOCARMYCIN PYRINDAMYCIN DNA ALKYLATION PROPERTIES AND IDENTIFICATION, SYNTHESIS, AND EVALUATION OF AGENTS INCORPORATING THE PHARMACOPHORE OF THE DUOCARMYCIN PYRINDAMYCIN ALKYLATION SUBUNIT - IDENTIFICATION OF THE CC-1065-DUOCARMYCIN COMMON PHARMACOPHORE [J].

BOGER, DL ;

ISHIZAKI, T ;

ZARRINMAYEH, H ;

MUNK, SA ;

KITOS, PA ;

SUNTORNWAT, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :8961-8971

[3] 1ST TOTAL SYNTHESIS OF DL-DUOCARMYCIN-A [J].

FUKUDA, Y ;

NAKATANI, K ;

ITO, Y ;

TERASHIMA, S .

TETRAHEDRON LETTERS, 1990, 31 (46) :6699-6702

[4] SEQUENCE SPECIFICITY OF DNA ALKYLATION BY THE UNNATURAL ENANTIOMER OF CC-1065 AND ITS SYNTHETIC ANALOGS [J].

HURLEY, LH ;

WARPEHOSKI, MA ;

LEE, CS ;

MCGOVREN, JP ;

SCAHILL, TA ;

KELLY, RC ;

MITCHELL, MA ;

WICNIENSKI, NA ;

GEBHARD, I ;

JOHNSON, PD ;

BRADFORD, VS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4633-4649

[5] DC89-A1, A NEW ANTITUMOR ANTIBIOTIC FROM STREPTOMYCES [J].

ICHIMURA, M ;

MUROI, K ;

ASANO, K ;

KAWAMOTO, I ;

TOMITA, F ;

MORIMOTO, M ;

NAKANO, H .

JOURNAL OF ANTIBIOTICS, 1988, 41 (09) :1285-1288

[6] PRELIMINARY TOXICITY STUDIES WITH THE DNA-BINDING ANTIBIOTIC, CC-1065 [J].

MCGOVREN, JP ;

CLARKE, GL ;

PRATT, EA ;

DEKONING, TF .

JOURNAL OF ANTIBIOTICS, 1984, 37 (01) :63-70

[7] NEW ANTITUMOR ANTIBIOTICS, DUOCARMYCIN-B1 AND DUOCARMYCIN-B2 [J].

OGAWA, T ;

ICHIMURA, M ;

KATSUMATA, S ;

MORIMOTO, M ;

TAKAHASHI, K .

JOURNAL OF ANTIBIOTICS, 1989, 42 (08) :1299-1301

[8] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS IN THE PRESENCE OF TERTIARY-AMINES TO CHIRAL ALPHA,BETA-UNSATURATED AMIDO CARBOXYLIC-ACIDS - ADDITION ORDER OF REAGENTS AS AN UNPRECEDENTED FACTOR IN THE DETERMINATION OF THE SENSE OF ASYMMETRIC INDUCTION [J].

SOAI, K ;

OOKAWA, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (05) :759-764

[9] COVALENT ALKYLATION OF DNA WITH DUOCARMYCIN-A - IDENTIFICATION OF ABASIC SITE STRUCTURE [J].

SUGIYAMA, H ;

HOSODA, M ;

SAITO, I ;

ASAI, A ;

SAITO, H .

TETRAHEDRON LETTERS, 1990, 31 (49) :7197-7200

[10] DUOCARMYCIN-A, A NEW ANTITUMOR ANTIBIOTIC FROM STREPTOMYCES [J].

TAKAHASHI, I ;

TAKAHASHI, K ;

ICHIMURA, M ;

MORIMOTO, M ;

ASANO, K ;

KAWAMOTO, I ;

TOMITA, F ;

NAKANO, H .

JOURNAL OF ANTIBIOTICS, 1988, 41 (12) :1915-1917