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Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors.

Scheiper B, Matter H, Steinhagen H, Böcskei Z, Fleury V, McCort G
Bioorg Med Chem Lett 21 5480-6 (2011)
Related entries: 3oot, 3oqf, 3oqk

Cited: 8 times
EuropePMC logo PMID: 21840218

Abstract

The control of hypertension and associated cardiovascular risk factors is possible by selective inhibition of the aspartyl protease renin due to its unique position in the renin-angiotensin system. Starting from a previously disclosed series of potent and nonchiral indole-3-carboxamides, we further explored this motif by structure-based drug design guided by X-ray crystallography in combination with efficient parallel synthesis. This resulted in the discovery of 4- or 6-azaindole derivatives with remarkable potency for renin inhibition. The best compound from these series showed an IC(50) value of 1.3 nM.

Articles - 3sfc mentioned but not cited (2)

  1. Alternatively Spliced Homologous Exons Have Ancient Origins and Are Highly Expressed at the Protein Level. Abascal F, Ezkurdia I, Rodriguez-Rivas J, Rodriguez JM, del Pozo A, Vázquez J, Valencia A, Tress ML. PLoS Comput. Biol. 11 e1004325 (2015)
  2. Exploring the pH-Dependent Structure-Dynamics-Function Relationship of Human Renin. Ma S, Henderson JA, Shen J. J Chem Inf Model 61 400-407 (2021)


Reviews citing this publication (2)

  1. Recent progress on the discovery of non-peptidic direct renin inhibitors for the clinical management of hypertension. Yokokawa F. Expert Opin Drug Discov 8 673-690 (2013)
  2. Synthetic strategies, SAR studies, and computer modeling of indole 2 and 3-carboxamides as the strong enzyme inhibitors: a review. Chehardoli G, Bahmani A. Mol Divers 25 535-550 (2021)

Articles citing this publication (4)

  1. Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N'-protected piperazines via organocatalysis. O'Reilly MC, Lindsley CW. Tetrahedron Lett. 53 1539-1542 (2012)
  2. Facile synthesis of 4- and 7-azaindoles from the corresponding imines by palladium-catalyzed cascade C-C and C-N coupling. Pham NN, Dang TT, Ngo NT, Villinger A, Ehlers P, Langer P. Org. Biomol. Chem. 13 6047-6058 (2015)
  3. Computational modeling and design of renin inhibitors. Subramanian G. Bioorg. Med. Chem. Lett. 23 460-465 (2013)
  4. Impact of Applicability Domains to Generative Artificial Intelligence. Langevin M, Grebner C, Güssregen S, Sauer S, Li Y, Matter H, Bianciotto M. ACS Omega 8 23148-23167 (2023)


Related citations provided by authors (1)

  1. Discovery and optimization of a new class of potent and non-chiral indole-3-carboxamide-based renin inhibitors.. Scheiper B, Matter H, Steinhagen H, Stilz U, Böcskei Z, Fleury V, McCort G Bioorg Med Chem Lett 20 6268-72 (2010)

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