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Published Online:https://doi.org/10.4155/fmc-2022-0225
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Reference

  • 1. Van de Waterbeemd H, Smith DA, Beaumont K, Walker DK. Property-based design: optimization of drug absorption and pharmacokinetics. J. Med. Chem. 44(9), 1313–1333 (2001).
  • 2. Li D, Paul VF, Takashi M. Bridging solubility between drug discovery and development. Drug Discov.Today 17(9-10), 486–495 (2012).
  • 3. Schneider G. Automating drug discovery. Nat Rev Drug Discov. 17, 97–113 (2018).
  • 4. Das B, Baidya ATK, Mathew A et al. Structural modification aimed for improving solubility of lead compounds in early phase drug discovery. Bioorg. Med. Chem. 56, 116614 (2022).
  • 5. Ishikawa M, Hashimoto Y. Improving the water-solubility of compounds by molecular modification to disrupt crystal packing. The Practice of Medicinal Chemistry (4th Edition). Wermuth CGAldous DRaboisson PRognan D (Eds.). Academic Press, London, UK, 747–765 (2015).
  • 6. Charalabidis A, Sfouni M, Bergström C, Macheras P. The biopharmaceutics classification system (BCS) and the biopharmaceutics drug disposition classification system (BDDCS): beyond guidelines. Int. J. Pharm. 566, 264–281 (2019).
  • 7. Saal C, Petereit AC. Optimizing solubility: kinetic versus thermodynamic solubility temptations and risks. Eur. J. Pharm. Sci. 47, 589–595 (2012).
  • 8. Testa B, Crivori P, Reist M, Carrupt PA. The influence of lipophilicity on the pharmacokinetic behavior of drugs: Concepts and examples. Perspectives in Drug Discovery and Design 19(1), 179–211 (2000).
  • 9. Naylor MR, Ly AM, Handford MJ et al. Lipophilic permeability efficiency (LPE) reconciles the opposing roles of lipophilicity in membrane permeability and aqueous solubility. J. Med. Chem. 61, 11169–11182 (2018).
  • 10. Lu Y, Li C-M, Wang Z. Design, synthesis, and SAR studies of 4-substituted methoxylbenzoyl-aryl-thiazoles analogues as potent and orally bioavailable anticancer agents. J. Med. Chem. 54, 4678–4693 (2011).
  • 11. Kuhn B, Mohr P, Stahl M. Intramolecular hydrogen bonding in medicinal chemistry. J. Med. Chem. 53, 2601–2611 (2010).
  • 12. Etter MC. Encoding and decoding hydrogen-bond patterns of organic compounds. Acc. Chem. Res. 23, 120–126 (1990).
  • 13. Pinal R. Effect of molecular symmetry on melting temperature and solubility. Org. Biomol. Chem. 2, 2692–2699 (2004).
  • 14. Nikam SS, Cordon JJ, Ortwine DF et al. Design and synthesis of novel quinoxaline-2, 3-dione AMPA/GlyN receptor antagonists: amino acid derivatives. J. Med. Chem. 42, 2266–2271 (1999).
  • 15. Fujita Y, Yonehara M, Tetsuhashi M et al. β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity. Bioorg Med Chem. 18, 1194–1203 (2010).
  • 16. Bachovchin KA, Sharma A, Bag S et al. Improvement of aqueous solubility of lapatinib-derived analogues: identification of a quinolinimine lead for human African trypanosomiasis drug development. J. Med. Chem. 62, 665–687 (2018).
  • 17. Lewin G, Maciuk A, Moncomble AI, Cornard J-P. Enhancement of the water solubility of flavone glycosides by disruption of molecular planarity of the aglycone moiety. J. Nat. Prod. 76, 8–12 (2013).
  • 18. Kumari S, Carmona AV, Tiwari AK, Trippier PC. Amide bond bioisosteres: strategies, synthesis, and successes. J. Med. Chem. 63, 12290–12358 (2020).
  • 19. Rubio-Ruiz B, Pérez-López AM, Sebastián V, Unciti-Broceta A. A minimally masked inactive prodrug of panobinostat that is bioorthogonally activated by gold chemistry. Bioorg. Med. Chem. 41, 116217–116223 (2021).
  • 20. Jornada DH, dos Santos Fernandes GF, Chiba DE et al. The prodrug approach: a successful tool for improving drug solubility. Molecules 21, 42–73 (2016).