21392-51-8Relevant articles and documents
Preparation of novel pyrrolo[2,3-b]pyridine derivatives via a new concise synthetic approach
Guo, Na,Jia, Haiyong,You, Xing,Jiang, Du,Lu, Kui,Yu, Peng
, p. 1143 - 1147 (2015)
The pyrrolo[2,3-b]pyridine core structure, a bioisostere of quinolones, is found in several molecules that possess important biological activity. We describe here a new, concise, three-step synthesis of pyrrolo[2,3-b]pyridines starting from L-alanine. A series of 4,7-dihydro-4-oxo-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid derivatives, which have not been previously reported, were synthesized using this approach.
Identification of new pyrrolo[2,3-d]pyrimidines as potent VEGFR-2 tyrosine kinase inhibitors: Design, synthesis, biological evaluation and molecular modeling
Adel, Mai,Serya, Rabah A.T.,Lasheen, Deena S.,Abouzid, Khaled A.M.
, p. 612 - 629 (2018/09/29)
Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in cancer angiogenesis. In the current study, a series of novel pyrrolo[2,3-d]pyrimidine based-compounds was designed and synthesized as VEGFR-2 inhibitors, in accordance to the structure activity relationship (SAR) studies of known type II VEGFR-2 inhibitors. The newly synthesized compounds were evaluated for their ability to inhibit VEGFR-2 kinase enzyme in vitro. All the tested compounds demonstrated highly potent dose-related VEGFR-2 inhibition with IC50 values in nanomolar range. Among these compounds, pyrrolo[2,3-d]pyrimidine derivatives carrying biaryl urea moieties (12d and 15c) exhibited IC50 values of 11.9 and 13.6 nM respectively. Additionally, most of the newly synthesized final compounds were tested on 60 human cancer cell lines. Docking of these compounds into the inactive conformation of VEGFR-2 was performed which showed comparable binding modes to that of the FDA approved VEGFR-2 kinase inhibitors. These newly discovered potent kinase inhibitors could be considered as potential candidates for the development of new targeted anticancer agent.
Broad spectrum chemistry as practised by Novartis process research
Mickel, Stuart J.,Fischer, Reto,Marterer, Wolfgang
, p. 640 - 648 (2007/10/03)
Three actual examples from the current product palette within Novartis Process Research will demonstrate the some of the variety and challenges encountered in modern chemical development.
Large-scale synthesis of a pyrrolo[2,3-d]pyrimidine via Dakin-West reaction and Dimroth rearrangement
Fischer, Reto W.,Misun, Marian
, p. 581 - 586 (2013/09/07)
Pyrrolo[2,3-d]pyrimidines have been widely investigated as pharmaceutically active compounds. In this article, we present a short and efficient synthesis of 4-(3-chlorophenylamino)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine starting from cheap alanine and malononitrile. To the best of our knowledge, the first application of a Dakin-West reaction on plant scale is demonstrated by elaboration of a modified procedure avoiding uncontrolled release of carbon dioxide. Pyrimidine ring formation is achieved in a simple one-pot reaction which is followed by an equally simple isomerization. The whole synthesis requires neither chromatographies nor extractions, no waste treatment and no special equipment, resulting in a remarkably ecological as well as economical process.
Synthesis of 4-oxopyrrolopyrimidine-3-carboxylic acid derivatives as potential antimicrobial agents
Bayomi, Said M.,Al-Obaid, Abdul Rahman M.,Jado, Ahmad I.,Loutfy, Essam A.
, p. 814 - 816 (2007/10/02)
A route for the synthesis of various derivatives of 4-oxopyrrolopyrimidine-3-carboxylic acid from 2-amino-3-cyano-4,5-dimethylpyrrole and 2-amino-3-cyano-4-arylpyrroles is described.
