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. 2019 Jun 12:15:1281-1288.
doi: 10.3762/bjoc.15.126. eCollection 2019.

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

Maryna V Murlykina  1   2   3 , Oleksandr V Kolomiets  1   2 , Maryna M Kornet  4 , Yana I Sakhno  1 , Sergey M Desenko  1   2 , Victoriya V Dyakonenko  1 , Svetlana V Shishkina  1   2 , Oleksandr A Brazhko  4 , Vladimir I Musatov  1 , Alexander V Tsygankov  5 , Erik V Van der Eycken  3   6 , Valentyn A Chebanov  1   2   3
Affiliations

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

Maryna V Murlykina et al. Beilstein J Org Chem. .

Abstract

Substituted 1H-pyrazolo[3,4-b]pyridine-4- and 1H-pyrazolo[3,4-b]pyridine-6-carboxamides have been synthetized through a Doebner-Ugi multicomponent reaction sequence in a convergent and versatile manner using diversity generation strategies: combination of two multicomponent reactions and conditions-based divergence strategy. The target products contain as pharmacophores pyrazolopyridine and peptidomimetic moieties with four points of diversity introduced from readily available starting materials including scaffold diversity. A small focused compound library of 23 Ugi products was created and screened for antibacterial activity.

Keywords: Doebner reaction; Ugi reaction; antibacterial activity; pyrazolo[3,4-b]pyridine carboxylic acids.

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Figures

Scheme 1
Scheme 1
An overview of heterocyclic acids used in the Ugi reaction.
Scheme 2
Scheme 2
Synthesis of pyrazolopyridine carboxylic acids 4 [45] and 7 [45] in Doebner-type reaction.
Figure 1
Figure 1
Molecular structure of N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-6-(4-methoxyphenyl)-3-methyl-N-p-tolyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (11n) according to X-ray diffraction data. Non-hydrogen atoms are presented as thermal ellipsoids with 50% probability.
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