183208-35-7Relevant articles and documents
Full functionalization of the 7-azaindole scaffold by selective metalation and sulfoxide/magnesium exchange
Barl, Nadja M.,Sansiaume-Dagousset, Elodie,Karaghiosoff, Konstantin,Knochel, Paul
, p. 10093 - 10096 (2013)
Filling positions: 7-Azaindoles are important targets in the pharmaceutical industry. All five carbon positions of the azaindole ring system can be functionalized in a predictable manner starting from the appropriately substituted azaindole 1 by directed metalation and halogen/magnesium and sulfoxide/magnesium exchange. The products are fully substituted azaindoles of type 2.
Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity
Verdonck, Sven,Pu, Szu-Yuan,Sorrell, Fiona J.,Elkins, Jon M.,Froeyen, Mathy,Gao, Ling-Jie,Prugar, Laura I.,Dorosky, Danielle E.,Brannan, Jennifer M.,Barouch-Bentov, Rina,Knapp, Stefan,Dye, John M.,Herdewijn, Piet,Einav, Shirit,De Jonghe, Steven
, p. 5810 - 5831 (2019/07/04)
There are currently no approved drugs for the treatment of emerging viral infections, such as dengue and Ebola. Adaptor-associated kinase 1 (AAK1) is a cellular serine-threonine protein kinase that functions as a key regulator of the clathrin-associated host adaptor proteins and regulates the intracellular trafficking of multiple unrelated RNA viruses. Moreover, AAK1 is overexpressed specifically in dengue virus-infected but not bystander cells. Because AAK1 is a promising antiviral drug target, we have embarked on an optimization campaign of a previously identified 7-azaindole analogue, yielding novel pyrrolo[2,3-b]pyridines with high AAK1 affinity. The optimized compounds demonstrate improved activity against dengue virus both in vitro and in human primary dendritic cells and the unrelated Ebola virus. These findings demonstrate that targeting cellular AAK1 may represent a promising broad-spectrum antiviral strategy.
Simple preparation method of 5-halogenated-7-azaindole
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Paragraph 0046-0049, (2019/10/01)
The invention discloses a simple preparation method of 5-halogenated-7-azaindole. The method comprises: carrying out a 1,4-addition reaction on 4,4-dialkoxy n-butyronitrile (II) and 2,3-dihalogenatedacrolein (III) in the presence of a solvent and a catalyst to generate 2,3-dihalogenated-4-cyano-6,6-dialkoxy n-hexanal (IV), and carrying out a cyclization reaction on the 2,3-dihalogenated-4-cyano-6,6-dialkoxy n-hexanal, an alkali, ammonia and an ammonium salt to prepare the 5-halogenated-7-azaindole (I). According to the present invention, the method has characteristics of inexpensive and easily available raw materials, short process route, less wastewater discharge, easy environmental protection, convenient reaction operation, high reaction selectivity, high product purity, high yield andlow cost, and is suitable for the environmentally-friendly industrial production of 5-halogenated-7-azaindole.