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Diaminoimidazopyrimidines: Access via the Groebke–Blackburn–Bienaymé Reaction and Structural Data Mining
Author(s) -
Konstantinidou Markella,
Boiarska Zlata,
Butera Roberto,
Neochoritis Constantinos G.,
Kurpiewska Katarzyna,
KalinowskaTłuscik Justyna,
Dömling Alexander
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000933
Subject(s) - pharmacophore , chemistry , scope (computer science) , drug discovery , scaffold , combinatorial chemistry , computer science , computational biology , database , stereochemistry , programming language , biochemistry , biology
Imidazopyrimidines with diverse substitution patterns are a prime class of heterocycles, present in many commercially available or late‐stage clinical trials drugs. Here, we describe a fast access to diaminoimidazopyrimidines by means of a powerful multicomponent reaction; the Groebke–Blackburn–Bienaymé reaction. We provide the design of such libraries of compounds, identifying all the structural motifs, and subsequently their synthesis. Scope and limitations are discussed, in addition to data mining in the Cambridge Structural Database and pharmacophore search with Crossminer. The presented approach highlights the vast amount of data available in the databases and provides potential future scaffold hopping alternatives for compounds with similar binding patterns. Further studies are ongoing to introduce more “drug‐like” properties into this scaffold and to investigate cellular mechanism‐based anti‐cancer behaviours.