ELECTROCHEMISTRY OF POTENTIAL BIOREDUCTIVE ALKYLATING QUINONES .2. ELECTROCHEMICAL PROPERTIES OF 2,5-BIS(1-AZIRIDINYL)-3,6-BIS(ETHOXYCARBONYLAMINO)-1,4-BENZOQUINONE AND SOME MODEL COMPOUNDS

被引:26
作者
DRIEBERGEN, RJ [1 ]
HOLTHUIS, JJM [1 ]
BLAUW, JS [1 ]
KELDER, SJP [1 ]
VERBOOM, W [1 ]
REINHOUDT, DN [1 ]
VANDERLINDEN, WE [1 ]
机构
[1] UNIV TWENTE,DEPT CHEM TECHNOL,7500 AE ENSCHEDE,NETHERLANDS
关键词
Aziridinylquinones; Bis(1-aziridinyl)bis(ethoxycarbonylamino)-benzoquinone; Controlled potential electrolysis; Quinones;
D O I
10.1016/S0003-2670(00)83570-9
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
The reduction mechanism of 2,5-bis(1-aziridinyl)-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone (Diaziquone, AZQ) and several model compounds of the mono- and bis(1-aziridinyl)quinone type at the dropping mercury electrode in aqueous solutions was studied. In addition, the influence of methyl substitution of the aziridinyl moiety at the 2-position on the protonation of the aziridine nitrogen was investigated. Substituent effects on quinone reduction and aziridine protonation prior to and following quinone reduction were studied qualitatively. © 1990.
引用
收藏
页码:285 / 307
页数:23
相关论文
共 33 条
[1]   STUDIES RELATED TO ANTITUMOR ANTIBIOTICS .6. CORRELATION OF COVALENT CROSS-LINKING OF DNA BY BIFUNCTIONAL AZIRIDINOQUINONES WITH THEIR ANTINEOPLASTIC ACTIVITY [J].
AKHTAR, MH ;
BEGLEITER, A ;
JOHNSON, D ;
LOWN, JW ;
MCLAUGHLIN, L ;
SIM, SK .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2891-2905
[2]  
ANHALT A, 1962, J ELECTROANAL CHEM, V4, P218
[3]  
BAUER E, 1964, CHEM ZVESTI, V18, P454
[4]  
BERG H, 1958, Z Krebsforsch, V62, P495, DOI 10.1007/BF00525474
[5]  
BERG H, 1962, CHEM ZVESTI, V16, P342
[6]  
BERG H, 1962, Z CHEM, V8, P237
[7]  
BOSANQUET AG, 1985, INVEST NEW DRUG, V3, P43
[8]   INVESTIGATION ON ISOMERIZATION OF 2-AMINO-3-AZIRIDINO-1,4-NAPHTHOQUINONES TO BENZO[G]QUINOXALINES [J].
CASINI, G ;
CLAUDI, F ;
GRIFANTI.M ;
MARTELLI, S .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (03) :377-386
[9]  
DAHNE S, 1964, TETRAHEDRON LETT, P3355
[10]  
Dermer O.C., 1969, ETHYLENIMINE OTHER A, P106