117616-08-7Relevant articles and documents
The enantioselective, organocatalyzed Diels-Alder reaction of 2-Vinlindoles with α,β-unsaturated aldehydes: An efficient route to functionalized tetrahydrocarbazoles
Zheng, Changwu,Lu, Yingpeng,Zhang, Junkang,Chen, Xingkuan,Chai, Zhuo,Ma, Wenying,Zhao, Gang
supporting information; experimental part, p. 5853 - 5857 (2010/09/04)
(Figure Presented) Prolinol catalysts: A highly enantioand diastereoselective prolinol-catalyzed Diels-Alder reaction of 2-vinylindoles and α,β-unsaturated aldehydes is developed (see scheme). This methodology allows the development of further applications of prolinols in asymmetric synthesis. The resulting densely functionalized enantiomerically pure tetrahydrocarbazoles are useful in the total synthesis of natural products such as the core structure of the akuammiline alkaloid vincorine.
4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione inhibitors of the checkpoint kinase Wee1. structure-activity relationships for chromophore modification and phenyl ring substitution
Palmer, Brian D.,Thompson, Andrew M.,Booth, R. John,Dobrusin, Ellen M.,Kraker, Alan J.,Lee, Ho H.,Lunney, Elizabeth A.,Mitchell, Lorna H.,Ortwine, Daniel F.,Smaill, Jeff B.,Swan, Leesa M.,Denny, William A.
, p. 4896 - 4911 (2007/10/03)
High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]-carbazole-1,3(2H,6H)- dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.
Intramolecular Peterson Olefination of ortho-Trimethylsilylmethyl Anilides: a New Synthesis of N-Methylindoles
Bartoli, Giuseppe,Bosco, Marcella,Dalpozzo, Renato,Todesco, Paolo E.
, p. 807 - 808 (2007/10/02)
A modified Madelung synthesis of indoles by cyclisation of ortho-trimethylsilylmethyl anilides under mild conditions is reported.
