Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 46, 2016 - Issue 12
664
Views
10
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

Strategies toward optimization of the metabolism of a series of serotonin-4 partial agonists: investigation of azetidines as piperidine isosteres

, , , , &
Pages 1112-1121 | Received 19 Dec 2015, Accepted 06 Feb 2016, Published online: 07 Mar 2016

References

  • Brodney MA, Johnson DE, Sawant-Basak A, et al (2012). Identification of multiple 5-HT4 partial agonist clinical candidates for the treatment of Alzheimer's disease. J Med Chem 55:9240–54
  • Carlson TJ, Jones JP, Peterson L, et al (1995). Stereoselectivity and isotope effects associated with cytochrome P450-catalyzed oxidation of (S)-nicotine. The possibility of initial hydrogen atom abstraction in the formation of the delta 1', 5-nicotinium ion. Drug Metab Dispos: Biological Fate Chem 23:749–56
  • Cervinka O (1987) Heterocyclic enamines. In: Enamines: Synthesis, Structure, and Reactions. (Ed. AG Cook), 2nd Edn., Marcel Dekker, New York, pp 441-530
  • Feng B, Xu JJ, Bi YA, et al (2009). Role of hepatic transporters in the disposition and hepatotoxicity of a HER2 tyrosine kinase inhibitor CP-724,714. Toxicol Sci 108:492–500
  • Fitzgerald LW, Burn TC, Brown BS, et al (2000). Possible role of valvular serotonin 5-HT(2B) receptors in the cardiopathy associated with fenfluramine. Mol Pharmacol 57:75–81
  • Greffe G, Chalabreysse L, Mouly-Bertin C, et al (2007). Valvular heart disease associated with fenfluramine detected 7 years after discontinuation of treatment. Ann Thorac Surg 83:1541–3
  • Guengerich FP. (2002). Rate-limiting steps in cytochrome P450 catalysis. Biol Chem 383:1553–64
  • Guengerich FP, Yun CH, Macdonald TL. (1996). Evidence for a 1-electron oxidation mechanism in N-dealkylation of N,N-dialkylanilines by cytochrome P450 2B1. Kinetic hydrogen isotope effects, linear free energy relationships, comparisons with horseradish peroxidase, and studies with oxygen surrogates. J Biol Chem 271:27321–9
  • Hubbs JL, Fuller NO, Austin WF, et al (2015). Minimization of drug-drug interaction risk and candidate selection in a natural product-based class of gamma-secretase modulators. Bioorg Med Chem Lett 25:1621–6
  • Johnson DE, Drummond E, Grimwood S, et al (2012). The 5-hydroxytryptamine4 receptor agonists prucalopride and PRX-03140 increase acetylcholine and histamine levels in the rat prefrontal cortex and the power of stimulated hippocampalθ oscillations. J Pharmacol Exp Ther 341:681–91
  • Kedderis GL, Hollenberg PF. (1983). Characterization of the N-demethylation reactions catalyzed by horseradish peroxidase. J Biol Chem 258:8129–38
  • Ohwada T, Hirao H, Ogawa A. (2004). Theoretical analysis of Lewis basicity based on local electron-donating ability. Origin of basic strength of cyclic amines. J Org Chem 69:7486–94
  • Okazaki O, Guengerich FP. (1993). Evidence for specific base catalysis in N-dealkylation reactions catalyzed by cytochrome P450 and chloroperoxidase. Differences in rates of deprotonation of aminium radicals as an explanation for high kinetic hydrogen isotope effects observed with peroxidases. J Biol Chem 268:1546–52
  • Packiarajan M, Ferreira CG, Hong SP, et al (2012). Azetidinyl oxadiazoles as potent mGluR5 positive allosteric modulators. Bioorg Med Chem Lett 22:6469–74
  • Sawant-Basak A, Coffman KJ, Walker GS, et al (2013). Metabolism of a serotonin-4 receptor partial agonist 4-{4-[4-tetrahydrofuran-3-yloxy)-benzo[d]isoxazol-3-yloxymethyl]-piperidin-1-ylme thyl}-tetrahydropyran-4-ol (TBPT): identification of an unusual pharmacologically active cyclized oxazolidine metabolite in human. J Pharm Sci 102:3277–93
  • Shaffer CL, Morton MD, Hanzlik RP. (2001). N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group. J Am Chem Soc 123:8502–8
  • Sun H, Scott DO. (2011). Metabolism of 4-aminopiperidine drugs by cytochrome P450s: molecular and quantum mechanical insights into drug design. ACS Med Chem Lett 2:638–43
  • Zhang X, Hou C, Hufnagel H, et al (2012). Discovery of a 4-azetidinyl-1-thiazoyl-cyclohexane CCR2 antagonist as a development candidate. ACS Med Chem Lett 3:1039–44

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.