TUMOR-TARGETED BORANES .3. SYNTHESIS OF CARBAMATE-LINKED NITROIMIDAZOLYL CARBORANES DESIGNED FOR BORON NEUTRON-CAPTURE THERAPY OF CANCER

被引:22
作者
SCOBIE, M [1 ]
THREADGILL, MD [1 ]
机构
[1] UNIV BATH,SCH PHARM & PHARMACOL,BATH BA2 7AY,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 15期
关键词
D O I
10.1039/p19940002059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cancer (BNCT), Carbamoylation of 2-[2-[2-(2-nitroimidazol-1-yl)ethoxy]ethoxy]ethanol 5 and 1-(chloromethyl)-2-(2-nitroimidazol-1-yl)ethanol 6 with carboran-1-yl isocyanate (generated in situ by a Curtius rearrangement of carborane-1-carbonyl azide) gave the corresponding carbamate-linked nitroimidazolylcarboranes 16 and 17. A similar reaction of 4-carboranylphenyl isocyanate with 6 afforded the corresponding carbamate 24.
引用
收藏
页码:2059 / 2063
页数:5
相关论文
共 32 条
[21]  
SOLOWAY AH, 1961, J PHARMACOL EXP THER, V134, P117
[22]   FROM BORON ANALOGS OF AMINO-ACIDS TO BORONATED DNA - POTENTIAL NEW PHARMACEUTICALS AND NEUTRON-CAPTURE AGENTS [J].
SPIELVOGEL, BF ;
SOOD, A ;
SHAW, BR ;
HALL, IH .
PURE AND APPLIED CHEMISTRY, 1991, 63 (03) :415-418
[23]  
Stanko V. I., 1966, ZH OBSHCH KHIM, V36, P1779
[24]   SYN-SELECTIVITY IN THE EPOXIDATION OF 1-(CYCLOHEX-2-ENYL)-2-NITROIMIDAZOLE MEDIATED BY HYDROGEN-BONDING [J].
THREADGILL, MD ;
WEBB, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (04) :269-271
[25]   SYNTHESIS AND INVITRO EVALUATION OF BORONATED URIDINE AND GLUCOSE DERIVATIVES FOR BORON NEUTRON-CAPTURE THERAPY [J].
TJARKS, W ;
ANISUZZAMAN, AKM ;
LIU, L ;
SOLOWAY, AH ;
BARTH, RF ;
PERKINS, DJ ;
ADAMS, DM .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (09) :1628-1633
[26]  
WILBUR DS, 1991, 4TH P INT S SYNTH AP
[27]  
WILBUR DS, 1993, ADV NEUTRON CAPTURE
[28]   BORON HYDRIDE DERIVATIVES FOR NEUTRON-CAPTURE THERAPY - ANTIBODY APPROACH [J].
WONG, HS ;
TOLPIN, EI ;
LIPSCOMB, WN .
JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (08) :785-791
[29]   A GENERAL, CONVENIENT WAY TO CARBORANE-CONTAINING AMINO-ACIDS FOR BORON NEUTRON-CAPTURE THERAPY [J].
WYZLIC, IM ;
SOLOWAY, AH .
TETRAHEDRON LETTERS, 1992, 33 (49) :7489-7490
[30]   SYNTHESIS OF CARBORANES CONTAINING NUCLEOSIDE BASES - UNEXPECTEDLY HIGH CYTOSTATIC AND CYTOCIDAL TOXICITY TOWARDS CANCER-CELLS [J].
YAMAMOTO, Y ;
SEKO, T ;
NAKAMURA, H ;
NEMOTO, H ;
HOJO, H ;
MUKAI, N ;
HASHIMOTO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (02) :157-158