SYNTHESIS OF 2-METHYL-(Z)-4-(PHENYLIMINO)NAPHTH[2,3-D]OXAZOL-9-ONE, A MONOIMINE QUINONE WITH SELECTIVE CYTOTOXICITY TOWARD CANCER-CELLS

被引：30

作者：

BENEDETTIDOCTOROVICH, V

BURGESS, EM

LAMBROPOULOS, J

LEDNICER, D

VANDERVEER, D

ZALKOW, LH

机构：

[1] GEORGIA INST TECHNOL,SCH CHEM & BIOCHEM,ATLANTA,GA 30332

[2] NCI,PHARMACEUT RESOURCES BRANCH,BETHESDA,MD 20892

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1994年 / 37卷 / 05期

关键词：

D O I：

10.1021/jm00031a023

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A regio and stereospecific synthesis of 2-methyl-(Z)-4-(phenylimino)naphth[2,3-d]oxazol-9-one (1) was achieved by using titanium tetrachloride in methylene chloride in the preparation of the imine. The regiochemistry was assigned by single-crystal X-ray analysis. In vitro tests showed that this diastereomer is selectively active for some solid cancer tumors.

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页码：710 / 712

页数：3

相关论文

共 12 条

[1]

Boyd M.K., 1989, CANCER PRINCIPLES PR, V3, P1

[2] REACTION OF METHYLTITANIUM TRICHLORIDE WITH SOME UNIDENTATE AND BIDENTATE LIGANDS [J].

FOWLES, GWA ;

RICE, DA ;

WILKINS, JD .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1971, (11) :1920-&

[3] New information on dichlorine-2.3-naphthoquinone-1.4. [J].

Fries, K ;

Ochwat, P .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1923, 56 :1291-1304

[4] NRCVAX - AN INTERACTIVE PROGRAM SYSTEM FOR STRUCTURE-ANALYSIS [J].

GABE, EJ ;

LEPAGE, Y ;

CHARLAND, JP ;

LEE, FL ;

WHITE, PS .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 :384-387

[5] REACTION OF ACID-AMIDES WITH 2,3-DICHLORO-1,4-NAPHTHOQUINONE, A NOVEL ROUTE TO NAPHTH[2,3-D]OXAZOLE-4,9-DIONES [J].

HAMMAM, AS ;

OSMAN, AM .

JOURNAL FUR PRAKTISCHE CHEMIE, 1977, 319 (02) :254-258

[6]

LEDNICKER D, COMMUNICATION

[7] FEASIBILITY OF A HIGH-FLUX ANTICANCER DRUG SCREEN USING A DIVERSE PANEL OF CULTURED HUMAN TUMOR-CELL LINES [J].

MONKS, A ;

SCUDIERO, D ;

SKEHAN, P ;

SHOEMAKER, R ;

PAULL, K ;

VISTICA, D ;

HOSE, C ;

LANGLEY, J ;

CRONISE, P ;

VAIGROWOLFF, A ;

GRAYGOODRICH, M ;

CAMPBELL, H ;

MAYO, J ;

BOYD, M .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1991, 83 (11) :757-766

[8] DISPLAY AND ANALYSIS OF PATTERNS OF DIFFERENTIAL ACTIVITY OF DRUGS AGAINST HUMAN-TUMOR CELL-LINES - DEVELOPMENT OF MEAN GRAPH AND COMPARE ALGORITHM [J].

PAULL, KD ;

SHOEMAKER, RH ;

HODES, L ;

MONKS, A ;

SCUDIERO, DA ;

RUBINSTEIN, L ;

PLOWMAN, J ;

BOYD, MR .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1989, 81 (14) :1088-1092

[9]

STEWART JJP, QCPE560 IND U

[10] KETIMINE SYNTHESES . USE OF TITANIUM TETRACHLORIDE IN A NEW PROCEDURE FOR THEIR PREPARATION [J].

WEINGARTEN, H ;

CHUPP, JP ;

WHITE, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :3246-+