SEMISYNTHESES, X-RAY CRYSTAL-STRUCTURES AND TUBULIN-BINDING PROPERTIES OF 7-OXODEACETAMIDOCOLCHICINE AND 7-OXODEACETAMIDOISOCOLCHICINE

被引：15

作者：

BANWELL, MG

PETERS, SC

GREENWOOD, RJ

MACKAY, MF

HAMEL, E

LIN, CM

机构：

[1] LA TROBE UNIV,DEPT CHEM,BUNDOORA,VIC 3083,AUSTRALIA

[2] NCI,DCT,DTP,MOLEC PHARMACOL LAB,BETHESDA,MD 20892

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1992年 / 45卷 / 10期

关键词：

D O I：

10.1071/CH9921577

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Commercially available (-)-colchicine (1) has been converted, via deacetylcolchiceine (4), into a mixture of 7-oxodeacetamidocolchicine (2) and 7-oxodeacetamidoisocolchicine (3). The X-ray structures and tubulin-binding properties of these title ketones are described.

引用

收藏

页码：1577 / 1588

页数：12

相关论文

共 32 条

[1] NEW NATURAL COLCHICINOIDS - INDICATIONS OF 2 POSSIBLE CATABOLIC ROUTES FOR THE COLCHICINE ALKALOIDS [J].

ALTEL, TH ;

ABUZARGA, MH ;

SABRI, SS ;

FREYER, AJ ;

SHAMMA, M .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (03) :623-629

[2] THE ROLE OF THE B-RING OF COLCHICINE IN THE STABILITY OF THE COLCHICINE-TUBULIN COMPLEX [J].

BANERJEE, A ;

BARNES, LD ;

LUDUENA, RF .

BIOCHIMICA ET BIOPHYSICA ACTA, 1987, 913 (02) :138-144

[3] THE DEVELOPMENT OF A FULLY REGIOCONTROLLED SYNTHESIS OF (+/-)-12A,12B-MONOSECOCOLCHICINE USING A SYNTHETIC EQUIVALENT FOR THE 7-METHOXY-3-TROPONYL ANION [J].

BANWELL, MG ;

GRAVATT, GL ;

BUCKLETON, JS ;

CLARK, GR ;

RICKARD, CEF .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :865-867

[4] SYNTHESIS, X-RAY CRYSTAL-STRUCTURE, AND ANTIMITOTIC PROPERTIES OF 6-CHLORO-2-METHOXY-5-(2',3',4'-TRIMETHOXYPHENYL)CYCLOHEPTA-2,4,6-TRIEN-1-ONE, A BICYCLIC ANALOG OF COLCHICINE [J].

BANWELL, MG ;

HERBERT, KA ;

BUCKLETON, JR ;

CLARK, GR ;

RICKARD, CEF ;

LIN, CM ;

HAMEL, E .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4945-4952

[5] AN EFFICIENT SYNTHESIS OF 5-BROMO-2-HYDROXYCYCLO-HEPTA-2,4,6-TRIEN-1-ONE AND ITS METHYL-ETHER [J].

BANWELL, MG ;

LAMBERT, JN ;

REUM, ME ;

ONRUST, R .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1988, 20 (04) :393-399

[6] FULLY REGIOCONTROLLED SYNTHESIS OF DEACETAMIDOISOCOLCHICINE - FORMAL TOTAL SYNTHESIS OF COLCHICINE [J].

BANWELL, MG ;

LAMBERT, JN ;

CORBETT, M ;

GREENWOOD, RJ ;

GULBIS, JM ;

MACKAY, MF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11) :1415-1426

[7] THE PALLADIUM-MEDIATED CROSS COUPLING OF BROMOTROPOLONES WITH ORGANOSTANNANES OR ARYLBORONIC ACIDS - APPLICATIONS TO THE SYNTHESIS OF NATURAL-PRODUCTS AND NATURAL PRODUCT ANALOGS [J].

BANWELL, MG ;

CAMERON, JM ;

COLLIS, MP ;

CRISP, GT ;

GABLE, RW ;

HAMEL, E ;

LAMBERT, JN ;

MACKAY, MF ;

REUM, ME ;

SCOBLE, JA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (05) :705-728

[8] EFFICIENT SYNTHESES OF CIS-6-BROMO-2,2-DIMETHYL-3A,4,5,7A-TETRAHYDRO-1,3-BENZODIOXOLE AND CIS-7-BROMO-2,2-DIMETHYL-3A,4,5,7A-TETRAHYDRO-1,3-BENZODIOXOLE [J].

BANWELL, MG ;

LAMBERT, JN ;

RICHARDS, SL .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (07) :939-950

[9] A BIOMIMETIC AND FULLY REGIOCONTROLLED TOTAL SYNTHESIS OF (+/-)-COLCHICINE [J].

BANWELL, MG ;

LAMBERT, JN ;

MACKAY, MF ;

GREENWOOD, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) :974-975

[10] B-RING REGULATION OF COLCHICINE BINDING-KINETICS AND FLUORESCENCE [J].

BHATTACHARYYA, B ;

HOWARD, R ;

MAITY, SN ;

BROSSI, A ;

SHARMA, PN ;

WOLFF, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (07) :2052-2055

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