Synthesis and Diversification of 1,2,3-Triazole-Fused 1,4-Benzodiazepine Scaffolds

被引:87
作者
Donald, James R. [1 ]
Martin, Stephen F. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Texas Inst Drug & Diagnost Dev, Austin, TX 78712 USA
基金
美国国家卫生研究院;
关键词
DIVERSE HETEROCYCLIC SCAFFOLDS; PRIVILEGED STRUCTURES; MULTICOMPONENT REACTIONS; DRUG DISCOVERY; ANTAGONISTS; CONDENSATION; ANTHRAMYCIN; DERIVATIVES; CHEMISTRY; DESIGN;
D O I
10.1021/ol1028404
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A substituted heterocyclic scaffold comprising a 1,4-benzodiazepine fused with a 1,2,3-triazole ring has been synthesized and diversified via a variety of refunctionalizations. The strategy features the rapid assembly of the scaffold by combining 3-4 reactants in an efficient multicomponent assembly process, followed by an intramolecular Huisgen cycloaddition.
引用
收藏
页码:852 / 855
页数:4
相关论文
共 34 条
[1]   A new modular and flexible approach to [1,2,3]triazolo[1,5-a][1,4]benzodiazepines [J].
Alajarin, Mateo ;
Cabrera, Jose ;
Pastor, Aurelia ;
Villalgordo, Jose M. .
TETRAHEDRON LETTERS, 2007, 48 (20) :3495-3499
[2]  
Baldwin J. J., 1995, World Patent, Patent No. [WO 9514471 (A1), 9514471]
[3]   The properties of known drugs .1. Molecular frameworks [J].
Bemis, GW ;
Murcko, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (15) :2887-2893
[4]   A new and practical procedure for the Bruylants reaction.: Zinc-mediated synthesis of tertiary homoallylamines and β-aminoesters [J].
Bernardi, L ;
Bonini, BF ;
Capitò, E ;
Dessole, G ;
Fochi, M ;
Comes-Franchini, M ;
Ricci, A .
SYNLETT, 2003, (12) :1778-1782
[5]   1,2,3-triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding [J].
Bertelli, L ;
Biagi, G ;
Giorgi, I ;
Livi, O ;
Manera, C ;
Scartoni, V ;
Martini, C ;
Giannaccini, G ;
Trincavelli, L ;
Barili, PL .
FARMACO, 1998, 53 (04) :305-311
[6]  
Boulouard M., 1998, Pharmacy and Pharmacology Communications, V4, P43
[7]  
Broggini G, 1999, HETEROCYCLES, V51, P1295
[8]   A POTENT NONPEPTIDE CHOLECYSTOKININ ANTAGONIST SELECTIVE FOR PERIPHERAL-TISSUES ISOLATED FROM ASPERGILLUS-ALLIACEUS [J].
CHANG, RSL ;
LOTTI, VJ ;
MONAGHAN, RL ;
BIRNBAUM, J ;
STAPLEY, EO ;
GOETZ, MA ;
ALBERSSCHONBERG, G ;
PATCHETT, AA ;
LIESCH, JM ;
HENSENS, OD ;
SPRINGER, JP .
SCIENCE, 1985, 230 (4722) :177-179
[9]   Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones [J].
Cledera, P ;
Avendaño, C ;
Menéndez, JC .
TETRAHEDRON, 1998, 54 (40) :12349-12360
[10]  
COONEY JV, 1981, J ORG CHEM, V46, P2570, DOI 10.1021/jo00325a027