Synthesis and reactivity of enediynyl amino acids and peptides: a novel concept in lowering the activation energy of Bergman cyclisation by H-bonding and electrostatic interactions

被引:23
作者
Basak, A [1 ]
Bag, SS [1 ]
Bdour, HMM [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
D O I
10.1039/b308976m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel enediynyl amino acids and peptides 3 and 5 - 8 were synthesized and their thermal reactivity towards Bergman cyclization studied and compared with the earlier reported amino acid 4, which demonstrated, for the first time, the effect of H-bonding and electrostatic interactions in lowering the activation energy of Bergman cyclization.
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页码:2614 / 2615
页数:2
相关论文
共 28 条
[1]   Synthesis and thermal reactivity of a novel macrocyclic enediyne and its copper(II) complex [J].
Basak, A ;
Shain, JC .
TETRAHEDRON LETTERS, 1998, 39 (19) :3029-3030
[2]   Benzene fused monocyclic enediynyl amides: Synthesis, reactivity and DNA-cleavage activity in comparison to the corresponding sulfonamides [J].
Basak, A ;
Mandal, S ;
Das, AK ;
Bertolasi, V .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (06) :873-877
[3]   Nitrogen substituted cyclic enediynes: synthesis, thermal reactivity and complexation with metal ions [J].
Basak, A ;
Shain, JC ;
Khamrai, UK ;
Rudra, KR ;
Basak, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1955-1964
[4]   Synthesis and thermal behaviour of a novel diazaenediyne and its copper(II)-complex [J].
Basak, A ;
Shain, J .
TETRAHEDRON LETTERS, 1998, 39 (12) :1623-1624
[5]   DNA-cleavage studies on N-substituted monocyclic enediynes:: Enhancement of potency by incorporation of intercalating or electron poor aromatic ring and subsequent design of a novel phototriggerable acyclic enediyne [J].
Basak, A ;
Bdour, HM ;
Shain, JC ;
Mandal, S ;
Rudra, KR ;
Nag, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (12) :1321-1325
[6]  
Basak A, 1999, J INDIAN CHEM SOC, V76, P679
[7]   The synthesis and reactivity of novel azetidinyl enediynes [J].
Basak, A ;
Khamrai, UK ;
Mallik, U .
CHEMICAL COMMUNICATIONS, 1996, (06) :749-750
[8]  
Basak A., 2002, J CHEM SOC P1, V15, P1805
[9]   Metalloenediynes: Ligand field control of thermal Bergman cyclization reactions [J].
Benites, PJ ;
Rawat, DS ;
Zaleski, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7208-7217
[10]   Structure and thermal reactivity of a novel Pd(0) metalloenediyne [J].
Coalter, NL ;
Concolino, TE ;
Streib, WE ;
Hughes, CG ;
Rheingold, AL ;
Zaleski, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3112-3117