TAXOL STRUCTURE-ACTIVITY-RELATIONSHIPS - SYNTHESIS AND BIOLOGICAL EVALUATION OF 10-DEOXYTAXOL

被引:44
作者
CHEN, SH
FAIRCHILD, C
MAMBER, SW
FARINA, V
机构
[1] Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut 06492-7660
关键词
D O I
10.1021/jo00063a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
10-Deoxytaxol 2 was prepared from taxol (1) in four steps via the intermediate dienone 5b; the key reaction in the sequence is a Yarovenko reagent-mediated dehydration at the C-10 hydroxyl group. Compound 2 was found to possess comparable antitumor activity with respect to taxol. This confirms that the functional group at C-10 in taxol is not involved in receptor binding. © 1993, American Chemical Society. All rights reserved.
引用
收藏
页码:2927 / 2928
页数:2
相关论文
共 8 条
[1]  
CHEN SH, IN PRESS TETRAHEDRON
[2]   THE CHEMISTRY OF TAXOL [J].
KINGSTON, DGI .
PHARMACOLOGY & THERAPEUTICS, 1991, 52 (01) :1-34
[3]   STEROIDS .240. REACTION OF STEROIDAL ALCOHOLS WITH 2-CHLORO-1,1,2-TRIFLUOROTRIETHYLAMINE [J].
KNOX, LH ;
VELARDE, E ;
CROSS, AD ;
BERGER, S ;
CUADRIELLO, D .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (08) :2187-&
[4]   TAXOL - A NOVEL INVESTIGATIONAL ANTIMICROTUBULE AGENT [J].
ROWINSKY, EK ;
CAZENAVE, LA ;
DONEHOWER, RC .
JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (15) :1247-1259
[5]   MODIFIED TAXOLS .5. REACTION OF TAXOL WITH ELECTROPHILIC REAGENTS AND PREPARATION OF A REARRANGED TAXOL DERIVATIVE WITH TUBULIN ASSEMBLY ACTIVITY [J].
SAMARANAYAKE, G ;
MAGRI, NF ;
JITRANGSRI, C ;
KINGSTON, DGI .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5114-5119
[6]  
Sharts C.M., 1974, ORG REACT N Y, V21, P125
[7]   BIOLOGICALLY-ACTIVE TAXOL ANALOGS WITH DELETED A-RING SIDE-CHAIN SUBSTITUENTS AND VARIABLE C-2' CONFIGURATIONS [J].
SWINDELL, CS ;
KRAUSS, NE ;
HORWITZ, SB ;
RINGEL, I .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :1176-1184
[8]  
YAROVENKO NN, 1959, J GEN CHEM USSR, V329, P2125