Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization

被引:35
作者
Jones, GB [1 ]
Wright, JM
Hynd, G
Wyatt, JK
Warner, PM
Huber, RS
Li, AW
Kilgore, MW
Sticca, RP
Pollenz, RS
机构
[1] Northeastern Univ, Dept Chem, Boston, MA 02115 USA
[2] Clemson Univ, Dept Chem, GHS Med Chem Lab, Clemson, SC 29634 USA
[3] Univ S Florida, Dept Biol, Tampa, FL 33620 USA
关键词
D O I
10.1021/jo0256888
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).
引用
收藏
页码:5727 / 5732
页数:6
相关论文
共 64 条
[1]   Design, synthesis and biological activity of novel enediynyl monocyclic beta-lactams [J].
Basak, A ;
Khamrai, UK .
TETRAHEDRON LETTERS, 1996, 37 (14) :2475-2478
[2]   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
[3]   The synthesis and reactivity of novel azetidinyl enediynes [J].
Basak, A ;
Khamrai, UK ;
Mallik, U .
CHEMICAL COMMUNICATIONS, 1996, (06) :749-750
[4]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[5]   POLYNUCLEAR AROMATIC HYDROCARBON CARCINOGENS AS ANTIESTROGENS IN MCF-7 HUMAN BREAST-CANCER CELLS - ROLE OF THE AH RECEPTOR [J].
CHALOUPKA, K ;
KRISHNAN, V ;
SAFE, S .
CARCINOGENESIS, 1992, 13 (12) :2233-2239
[6]   Photochemical and thermal Bergman cyclization of a pyrimidine enediynol and enediynone [J].
Choy, N ;
Blanco, B ;
Wen, JH ;
Krishan, A ;
Russell, KC .
ORGANIC LETTERS, 2000, 2 (24) :3761-3764
[7]   UDFT and MCSCF descriptions of the photochemical Bergman cyclization of enediynes [J].
Clark, AE ;
Davidson, ER ;
Zaleski, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (11) :2650-2657
[8]   Aryl hydrocarbon receptor imported into the nucleus following ligand binding is rapidly degraded via the cytosplasmic proteasome following nuclear export [J].
Davarinos, NA ;
Pollenz, RS .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (40) :28708-28715
[9]   Synthesis of a heterocyclic aza-enediyne and its DNA-cleavage properties [J].
David, WM ;
Kumar, D ;
Kerwin, SM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (22) :2509-2512
[10]   FREE-RADICAL MECHANISMS INVOLVED IN THE FORMATION OF SEQUENCE-DEPENDENT BISTRANDED DNA LESIONS BY THE ANTITUMOR ANTIBIOTICS BLEOMYCIN, NEOCARZINOSTATIN, AND CALICHEAMICIN [J].
DEDON, PC ;
GOLDBERG, IH .
CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (03) :311-332