Tuning rate of the Bergman cyclization of benzannelated enediynes with ortho substituents

被引:94
作者
Alabugin, IV [1 ]
Manoharan, M [1 ]
Kovalenko, SV [1 ]
机构
[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
关键词
D O I
10.1021/ol0255054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The Bergman cyclization of benzannelated enediynes is highly sensitive to ortho substitution. This finding opens possibilities for the rational design of conformer-specific and pH-dependent DNA-cleaving agents.
引用
收藏
页码:1119 / 1122
页数:4
相关论文
共 46 条
[1]  
[Anonymous], 1998, ENCY COMPUTATIONAL C
[2]   CDPI3-ENEDIYNE AND CDPI3-EDTA CONJUGATES - A NEW CLASS OF DNA CLEAVING AGENTS [J].
BOGER, DL ;
ZHOU, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3018-3024
[3]  
Borders D B, 1995, ENEDIYNE ANTIBIOTICS
[4]   A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes [J].
Bowles, DM ;
Anthony, JE .
ORGANIC LETTERS, 2000, 2 (01) :85-87
[5]   Studies toward the synthesis of natural and unnatural dienediynes 1. Approaches to a functionalised bicyclic ring system [J].
Caddick, S ;
Delisser, VM ;
Doyle, VE ;
Khan, S ;
Avent, AG ;
Vile, S .
TETRAHEDRON, 1999, 55 (09) :2737-2754
[6]  
Charton M., 1971, PROG PHYS ORG CHEM, V8, P235
[7]   A Bergman cyclization approach to polymers for thin-film lithography [J].
Chen, XH ;
Tolbert, LM ;
Hess, DW ;
Henderson, C .
MACROMOLECULES, 2001, 34 (12) :4104-4108
[8]  
Choy N, 1999, HETEROCYCLES, V51, P13
[9]   Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes [J].
Choy, N ;
Kim, CS ;
Ballestero, C ;
Artigas, L ;
Diez, C ;
Lichtenberger, F ;
Shapiro, J ;
Russell, KC .
TETRAHEDRON LETTERS, 2000, 41 (36) :6955-6958
[10]   Prediction of singlet-triplet splittings for aryne biradicals from H-1 hyperfine interactions in aryl radicals [J].
Cramer, CJ ;
Squires, RR .
JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (49) :9191-9194