SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 5-THIOABBEYMYCIN - LIMITATIONS OF THE IMINOTHIOETHER APPROACH TO CARBINOLAMINE-CONTAINING PYRROLOBENZODIAZEPINES

被引：14

作者：

KAMAL, A ^{[1
]}

REDDY, BSP ^{[1
]}

THURSTON, DE ^{[1
]}

机构：

[1] UNIV PORTSMOUTH,SCH PHARM & BIOMED SCI,DIV MED CHEM,PORTSMOUTH PO1 2DZ,ENGLAND

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 04期

关键词：

D O I：

10.1016/S0960-894X(01)81266-X

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of 5-thioabbeymycin (7) by a modified iminothioether route is described. This analog of abbeymycin exhibits potent antimicrobial activity. Attempts to synthesize the natural product abbeymycin (8) by reduction of 2(S)-hydroxy-11-S-methylpyrrolobenzodiazepine 4b with Al-Hg amalgam gave the over-reduction product (6) as the only isolable product.

引用

页码：743 / 746

页数：4

共 15 条

[1] DESIGN AND SYNTHESIS OF POTENTIAL DNA CROSS-LINKING REAGENTS BASED ON THE ANTHRAMYCIN CLASS OF MINOR GROOVE BINDING-COMPOUNDS [J].

CONFALONE, PN ;

HUIE, EM ;

KO, SS ;

COLE, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :482-487

[2] DESIGN OF SEQUENCE-SPECIFIC DNA-BINDING MOLECULES [J].

DERVAN, PB .

SCIENCE, 1986, 232 (4749) :464-471

[3] ABBEYMYCIN, A NEW ANTHRAMYCIN-TYPE ANTIBIOTIC PRODUCED BY A STREPTOMYCETE [J].

HOCHLOWSKI, JE ;

ANDRES, WW ;

THERIAULT, RJ ;

JACKSON, M ;

MCALPINE, JB .

JOURNAL OF ANTIBIOTICS, 1987, 40 (02) :145-148

[4] DNA AS A TARGET FOR DRUG-ACTION [J].

HURLEY, LH ;

BOYD, FL .

TRENDS IN PHARMACOLOGICAL SCIENCES, 1988, 9 (11) :402-407

[5] PYRROLO[1,4]BENZODIAZEPINE ANTITUMOR ANTIBIOTICS - RELATIONSHIP OF DNA ALKYLATION AND SEQUENCE SPECIFICITY TO THE BIOLOGICAL-ACTIVITY OF NATURAL AND SYNTHETIC COMPOUNDS [J].

HURLEY, LH ;

RECK, T ;

THURSTON, DE ;

LANGLEY, DR ;

HOLDEN, KG ;

HERTZBERG, RP ;

HOOVER, JRE ;

GALLAGHER, G ;

FAUCETTE, LF ;

MONG, SM ;

JOHNSON, RK .

CHEMICAL RESEARCH IN TOXICOLOGY, 1988, 1 (05) :258-268

[6] ENZYMATIC REGIOSPECIFIC OXIDATIVE CONVERSION OF 5-THIO TO 5-OXO BY BAKERS-YEAST IN 5,11-DITHIOPYRROLO[1,4]BENZODIAZEPINE ANTIBIOTICS [J].

KAMAL, A ;

REDDY, BSP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (03) :159-160

[7] REACTION OF PYRROLO[2,1-C][1,4]BENZODIAZEPINE-2,5,11-TRIONES WITH PHOSPHORUS OXYCHLORIDE [J].

KAMAL, A ;

THURSTON, DE .

TETRAHEDRON LETTERS, 1989, 30 (45) :6221-6222

[8] A NEW AND MILD METHOD FOR THE REDUCTION OF SECONDARY AMIDES TO CARBINOLAMINE ETHERS AND IMINES - A CONVERSION OF OXOTOMAYMYCIN TO TOMAYMYCIN [J].

KANEKO, T ;

WONG, H ;

DOYLE, TW .

TETRAHEDRON LETTERS, 1983, 24 (47) :5165-5168

[9]

KANEKO T, 1984, J ANTIBIOT, V37, P300, DOI 10.7164/antibiotics.37.300

[10] BICYCLIC AND TRICYCLIC ANALOGS OF ANTHRAMYCIN [J].

KANEKO, T ;

WONG, H ;

DOYLE, TW ;

ROSE, WC ;

BRADNER, WT .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (03) :388-392

← 1 2 →