1,154
Views
48
CrossRef citations to date
0
Altmetric
Reviews

What does the aromatic ring number mean for drug design?

, MA PhD FRSC (Professor, External Collaboration Manager) & , BSc PhD FRSC (Professor of Medicinal Chemistry) (External Collaboration Manager) (Professor of Medicinal Chemistry) (External Collaboration Manager)

Bibliography

  • Ritchie TJ, MacDonald SJ. The impact of aromatic ring count on compound developability: are too many aromatic rings a liability in drug design? Drug Discov Today 2009;14(21-22):1011-20
  • Ritchie TJ, MacDonald SJ, Young RJ, Pickett SD. The impact of aromatic ring count on compound developability: further insights by examining carbo- and hetero-aromatic and -aliphatic ring types. Drug Discov Today 2011;16(3-4):164-71
  • Ritchie TJ, MacDonald SJ, Peace S, et al. The developability of heteroaromatic and heteroaliphatic rings - do some have a better pedigree as potential drug molecules than others? Med Chem Comm 2012;3(9):1062-9
  • Meanwell N. Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem Res Toxicol 2011;24:1420-56
  • Lovering F, Bikker J, Humblet C. Escape from flatland: increasing saturation as an approach to improving clinical success. J Med Chem 2009;52:6752
  • Leeson PD, St-Galley SA, Wenlock MC. Impact of ion class and time on oral drug molecular properties. Med Chem Comm 2011;2:91
  • Belema M, Lopez OD, Bender JA, et al. Discovery and development of hepatitis c virus ns5a replication complex inhibitors. J Med Chem 2014;57(5):1643-72
  • Lipinski CA, Lombardo F, Dominy BW, Feeny PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3025
  • Meyer EA, Castellano RK, Diederich F. Interactions with aromatic rings in chemical and biological recognition. Angew Chem Int Ed Engl 2003;42(11):1210-50
  • Wheeler SE. Understanding substituent effects in noncovalent interactions involving aromatic rings. Acc Chem Res 2013;2013:46(4):1029-38
  • ,·Kombarov R, Altieri AGenis D, et al. BioCores: identification of a drug/natural product-based privileged structural motif for small-molecule lead discovery. Mol Divers 2010;14:193-200
  • DeSimone RW, Currie KS, Mitchell SA, et al. Privileged structures: applications in drug discovery. Comb Chem High Throughput Screen 2004;7:473-93
  • Lee S, Raw AS, Yu L. Significance of drug substance physicochemical properties in regulatory quality by design. Drugs Pharm Sci 2008;178(Preformulation in Solid Dosage Form Development):571-83
  • Ponnuswamy MN, Gromiha MM, Sony SM, Saraboji K. Conformational aspects and interaction studies of heterocyclic drugs. Topics in Heterocyclic Chemistry 2006;3(QSAR and Molecular Modeling Studies in Heterocyclic Drugs I):81-147
  • Edwards PJ, Sturino C. Managing the liabilities arising from structural alerts: a safe philosophy for medicinal chemists. Curr Med Chem 2011;18(20):3116-35
  • Cola I, Landis J. Can the pharmaceutical industry reduce attrition rates? Nat Rev Drug Discov 2004;3:711-16
  • Leeson PD, Springthorpe B. The influence of drug-like concepts on decision-making in medicinal chemistry. Nat Rev Drug Discov 2007;6(11):881-90
  • Hughes JD, Blagg J, Price DA, et al. Physiochemical drug properties associated with in vivo toxicological outcomes. Bioorg Med Chem Lett 2008;18(17):4872-5
  • Keserue GM, Makara GM. The influence of lead discovery strategies on the properties of drug candidates. Nat Revs Drug Discov 2009;8(3):203-12
  • Hann MM. Molecular obesity, potency and other addictions in drug discovery. Med Chem Commun 2011;2:349-55
  • Abad-Zapatero C. Ligand efficiency indices for effective drug discovery. Expert Opin Drug Discov 2007;2(4):469-88
  • Arnott JA, Planey SL. The influence of lipophilicity in drug discovery and design. Expert Opin Drug Discov 2012;7(10):863-75
  • Walters PW. Going further than Lipinski’s rule. Expert Opin Drug Discov 2012;7(2):99-107
  • Sonbol MB, Firwana B, et al. Comprehensive review of JAK kinase in myeloproliferative neoplasms. Ther Adv Hematol 2013;1):15-35
  • Reichetzeder C, Tsuprykov O, Hocher B. Endothelin receptor antagonists in clinical research – lessons learned from preclinical and clinical kidney studies. Life Sci 2014; Epub ahead of print
  • Hill AP, Young RJ. Getting physical in drug discovery: a contemporary perspective on solubility and hydrophobicity. Drug Discov Today 2010;15(15-16):648-55
  • Young RJ, Green DV, Luscombe CN, Hill AP. Getting physical in drug discovery II: the impact of chromatographic hydrophobicity measurements and aromaticity. Drug Discov Today 2011;16(17-18):822-30
  • Medina-Franco J L. Interrogating novel areas of chemical space for drug discovery using chemoinformatics. Drug Dev Res 2012;73:430-8
  • Ruddigkeit L, van Deursen R, Blum LC, Reymond J-L. Enumeration of 166 billion organic small molecules in the chemical universe database GDB-17. J Chem Inf Model 2012;52:2864-75
  • Taylor RD, MacCoss M, Lawson AD. Rings in drugs. J Med Chem 2014; Epub ahead of print
  • Pitt WR, Parry DM, Perry BG, Groom CR. Heteroaromatic rings of the future. J Med Chem 2009;52:2952-63
  • Ritchie TJ, Luscombe CN, Macdonald SJ. Analysis of the calculated physicochemical properties of respiratory drugs: can we design for inhaled drugs yet? J Chem Inf Model 2009;49(4):1025-32

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.