2g26 › Citations

Ketopiperazine-based renin inhibitors: optimization of the "C" ring.

Holsworth DD, Cai C, Cheng XM, Cody WL, Downing DM, Erasga N, Lee C, Powell NA, Edmunds JJ, Stier M, Jalaie M, Zhang E, McConnell P, Ryan MJ, Bryant J, Li T, Kasani A, Hall E, Subedi R, Rahim M, Maiti S
Bioorg Med Chem Lett 16 2500-4 (2006)
Related entries: 2fs4, 2g1n, 2g1o, 2g1r, 2g1s, 2g1y, 2g20, 2g21, 2g22, 2g24, 2g27

Cited: 15 times
EuropePMC logo PMID: 16480874

Abstract

A systematic investigation of the S3 sub-pocket activity requirements was conducted. It was observed that linear and sterically small side chain substituents are preferred in the S3 sub-pocket for optimal renin inhibition. Polar groups in the S3-sub-pocket were not well tolerated and caused a reduction in renin inhibitory activity. Further, compounds with clog P's < or = 3 demonstrated a dramatic reduction in CYP3A4 inhibitory activity.

Articles - 2g26 mentioned but not cited (1)

  1. research-article Recognition and Cleavage of Human tRNA Methyltransferase TRMT1 by the SARS-CoV-2 Main Protease. D'Oliviera A, Dai X, Mottaghinia S, Geissler EP, Etienne L, Zhang Y, Mugridge JS. bioRxiv 2023.02.20.529306 (2023)


Reviews citing this publication (1)

  1. Recent syntheses of 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. Nammalwar B, Bunce RA. Molecules 19 204-232 (2013)

Articles citing this publication (13)

  1. What is the relationship between the global structures of apo and holo proteins? Brylinski M, Skolnick J. Proteins 70 363-377 (2008)
  2. Potential virtual lead identification in the discovery of renin inhibitors: application of ligand and structure-based pharmacophore modeling approaches. Thangapandian S, John S, Sakkiah S, Lee KW. Eur J Med Chem 46 2469-2476 (2011)
  3. Application of 3D QSAR CoMFA/CoMSIA and in silico docking studies on novel renin inhibitors against cardiovascular diseases. Politi A, Durdagi S, Moutevelis-Minakakis P, Kokotos G, Papadopoulos MG, Mavromoustakos T. Eur J Med Chem 44 3703-3711 (2009)
  4. Size of the aliphatic chain of sodium houttuyfonate analogs determines their affinity for renin and angiotensin I converting enzyme. Yuan L, Wu J, Aluko RE. Int. J. Biol. Macromol. 41 274-280 (2007)
  5. Discovery of 6-ethyl-2,4-diaminopyrimidine-based small molecule renin inhibitors. Holsworth DD, Jalaie M, Belliotti T, Cai C, Collard W, Ferreira S, Powell NA, Stier M, Zhang E, McConnell P, Mochalkin I, Ryan MJ, Bryant J, Li T, Kasani A, Subedi R, Maiti SN, Edmunds JJ. Bioorg. Med. Chem. Lett. 17 3575-3580 (2007)
  6. Discovery of new renin inhibitory leads via sequential pharmacophore modeling, QSAR analysis, in silico screening and in vitro evaluation. Al-Nadaf AH, Taha MO. J. Mol. Graph. Model. 29 843-864 (2011)
  7. The discovery and synthesis of potent zwitterionic inhibitors of renin. Aspiotis R, Chen A, Cauchon E, Dubé D, Falgueyret JP, Gagné S, Gallant M, Grimm EL, Houle R, Juteau H, Lacombe P, Laliberté S, Lévesque JF, MacDonald D, McKay D, Percival MD, Roy P, Soisson SM, Wu T. Bioorg. Med. Chem. Lett. 21 2430-2436 (2011)
  8. Structure-based design of substituted piperidines as a new class of highly efficacious oral direct Renin inhibitors. Ehara T, Irie O, Kosaka T, Kanazawa T, Breitenstein W, Grosche P, Ostermann N, Suzuki M, Kawakami S, Konishi K, Hitomi Y, Toyao A, Gunji H, Cumin F, Schiering N, Wagner T, Rigel DF, Webb RL, Maibaum J, Yokokawa F. ACS Med Chem Lett 5 787-792 (2014)
  9. An integrated computational workflow for efficient and quantitative modeling of renin inhibitors. Subramanian G, Rao SN. Bioorg. Med. Chem. 20 851-858 (2012)
  10. Decades-old renin inhibitors are still struggling to find a niche in antihypertensive therapy. A fleeting look at the old and the promising new molecules. Ramya K, Suresh R, Kumar HY, Kumar BRP, Murthy NBS. Bioorg Med Chem 28 115466 (2020)
  11. Design, synthesis and biological evaluation of renin inhibitors guided by simulated annealing of chemical potential simulations. Cloudsdale IS, Dickson JK, Barta TE, Grella BS, Smith ED, Kulp JL, Guarnieri F, Kulp JL. Bioorg. Med. Chem. 25 3947-3963 (2017)
  12. Computational modeling and design of renin inhibitors. Subramanian G. Bioorg. Med. Chem. Lett. 23 460-465 (2013)
  13. 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)


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