Scaffold morphing leading to evolution of 2,4-diaminoquinolines and aminopyrazolopyrimidines as inhibitors of the ATP synthesis pathway

MedChemComm
2016.0

Abstract

The success of bedaquiline as an anti-tubercular agent for the treatment of multi-drug resistant tuberculosis has validated ATP synthesis pathway and in particular ATP synthase as an attractive target. However, limitations associated with its use in the clinic and the drug-drug interactions with rifampicin have prompted research efforts towards identifying alternate ATP synthesis inhibitors with differentiated mechanism of action. A biochemical assay was employed to screen AstraZeneca's corporate compound collection to identify inhibitors of mycobacterial ATP synthesis. The high throughput screen resulted in the identification of 2, 4-diaminoquinazolines as inhibitors of ATP synthesis pathway. A structure activity relationship for quinazolines was established and the knowledge was utilized to morph quinazoline core into quinoline and pyrazolopyrimidine to expand the scope of chemical diversity. The morphed scaffolds exhibited a 10-fold improvement in the enzyme potency and over 100 fold improvement in selectivity against inhibition of mammalian mitochondrial ATP synthesis. These novel compounds were bactericidal and demonstrated growth retardation of Mycobacterium tuberculosis in the acute mouse model of tuberculosis infection.

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