Abstract
Tetrahydropyrrolo-3,4-azoles and tetrahydropyrrolo-2,3-azoles represent an interesting family of heterocycles that offer potential utility in drug design as either scaffolds or pharmacophoric elements. The tetrahydropyrrolo[3,4-c]pyrazole ring system is the most explored representative of this class of heterobicycle which is represented in the marketed dipeptidyl peptidase-4 inhibitor omarigliptin and the Phase 2 clinical candidate danusertib, an Aurora kinase inhibitor. In this chapter, we provide an overview of the synthesis of tetrahydropyrrolo-3,4-azoles and summarize their applications in drug design and discovery. In contrast, the tetrahydropyrrolo-2,3-azole series has been only sparsely explored with no significant systematic study or defined application in drug design.
Author supplied keywords
- 1,4,5,6-Tetrahydropyrrolo[3,4-d][1,2,3]triazole
- 1,4,5,6-Tetrahydropyrrolo[3,4-d]imidazole
- 4,5-Dihydro-6H-pyrrolo[3,4-d]thiazol-6-one
- 5,6-Dihydro-4H-pyrrolo[3,4-c]isothiazole
- 5,6-Dihydro-4H-pyrrolo[3,4-c]isoxazole
- 5,6-Dihydro-4H-pyrrolo[3,4-d]isothiazole
- 5,6-Dihydro-4H-pyrrolo[3,4-d]isoxazole
- 5,6-Dihydro-4H-pyrrolo[3,4-d]oxazole
- 5,6-Dihydro-4H-pyrrolo[3,4-d]thiazol-4-one
- 5,6-Dihydro-4H-pyrrolo[3,4-d]thiazole
- Tetrahydropyrrolo-2,3-azole
- Tetrahydropyrrolo-3,4-azole
- Tetrahydropyrrolo[3,4-c]pyrazole
Cite
CITATION STYLE
Meanwell, N. A., & Sistla, R. (2021). A survey of applications of tetrahydropyrrolo-3,4-azoles and tetrahydropyrrolo-2,3-azoles in medicinal chemistry. In Advances in Heterocyclic Chemistry (Vol. 134, pp. 31–100). Academic Press Inc. https://doi.org/10.1016/bs.aihch.2020.10.004
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