290368-03-5Relevant academic research and scientific papers
Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: A mild and flexible strategy to design 2-aza tryptamines
Arnautu, Anca,Collot, Valérie,Ros, Javier Calvo,Alayrac, Carole,Witulski, Bernhard,Rault, Sylvain
, p. 2695 - 2697 (2002)
This paper describes a Sonogashira-type cross-coupling reaction of 3-iodoindazoles with various terminal alkynes as a general route to 3-alkynylindazoles. The coupling reaction is illustrated by the preparation of new indazolylpropiolic or propargylic derivatives. Scope and limitation of the method are outlined.
Suzuki-type cross-coupling reaction of unprotected 3-iodoindazoles with pinacol vinyl boronate: An expeditive C-3 vinylation of indazoles under microwave irradiation
Vera, Gonzalo,Diethelm, Benjamín,Terraza, Claudio A.,Recabarren-Gajardo, Gonzalo
, (2018/09/26)
Herein we report an expeditive C-3 vinylation of unprotected 3-iodoindazoles under microwave irradiation. Ten C-5 substituted 3-vinylindazole derivatives, nine of them novel, were synthesized through this method, which proceeds in moderate to excellent yields starting from C-5 substituted 3-iodoindazole derivatives. In all cases, the C-3 vinylated derivative was the only isolated product. This methodology allows access to 3-vinylated indazoles selectively and directly without the need of N-protection. 3-Vinylindazoles could be interesting synthetic intermediates allowing access to biologically active molecules.
ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans
Youngsaye, Willmen,Hartland, Cathy L.,Morgan, Barbara J.,Ting, Amal,Nag, Partha P.,Vincent, Benjamin,Mosher, Carrie A.,Bittker, Joshua A.,Dandapani, Sivaraman,Palmer, Michelle,Whitesell, Luke,Lindquist, Susan,Schreiber, Stuart L.,Munoz, Benito
supporting information, p. 1501 - 1507 (2013/10/22)
The National Institutes of Health Molecular Libraries and Probe Production Centers Network (NIH-MLPCN) screened >300,000 compounds to evaluate their ability to restore fluconazole susceptibility in resistant Candida albicans isolates. Additional counter screens were incorporated to remove substances inherently toxic to either mammalian or fungal cells. A substituted indazole possessing the desired bioactivity profile was selected for further development, and initial investigation of structure-activity relationships led to the discovery of ML212.
Synthesis of 1,3-diarylsubstituted indazoles utilizing a Suzuki cross-coupling/deprotection/N-arylation sequence
Salovich, James M.,Lindsley, Craig W.,Hopkins, Corey R.
supporting information; experimental part, p. 3796 - 3799 (2010/08/07)
Herein we report a general synthesis of 1,3-diarylsubstituted indazoles utilizing a two-step Suzuki crosscoupling/deprotection/N-arylation sequence. This procedure proceeds in excellent overall yield starting from the 3-iodo-N-Boc indazole derivative allowing for rapid access to these compounds.
Heck cross-couplingg reaction of 3-iodoindazoles with methyl acrylate: A mild and flexible strategy to design 2-azatryptamines
Collot, Valérie,Varlet, Didier,Rault, Sylvain
, p. 4363 - 4366 (2007/10/03)
In order to design 2-azabioisosteres of tryptamine, serotonin or melatonin, the conditions of the Heck coupling reaction of 3-iodoindazoles with methyl acrylate are studied. This reaction authorizes the synthesis of 3-indazolylpropenoates as key intermediates to prepare 3-indazolylpropionic acids and 3-indazolylethylamines. The flexible synthetic strategy allows molecular diversity. (C) 2000 Elsevier Science Ltd.
