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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 54, 2024 - Issue 3
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Research Articles

Synthesis and characterization of four diastereomers of β-lactamase inhibitor drug intermediate

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Pages 198-206 | Received 14 Oct 2023, Published online: 05 Dec 2023

References

  • Brooks, W.; Guida, W.; Daniel, K. The Significance of Chirality in Drug Design and Development. Curr. Top. Med. Chem. 2011, 11, 760–770. DOI: 10.2174/156802611795165098.
  • Turnaturi, R.; Pasquinucci, L.; Chiechio, S.; Grasso, M.; Marrazzo, A.; Amata, E.; Dichiara, M.; Prezzavento, O.; Parenti, C. Exploiting the Power of Stereochemistry in Drug Action: 3-[(2S,6S,11S)-8-Hydroxy-6,11-Dimethyl-1,4,5,6-Tetrahydro-2,6-Methano-3-Benzazocin-3-(2H)-yl]-N-Phenylpropanamide as Potent Sigma-1 Receptor Antagonist. ACS Chem. Neurosci. 2020, 11, 999–1005. DOI: 10.1021/acschemneuro.9b00688.
  • Fabbretti, A.; Gualerzi, C.; Brandi, L. How to Cope with the Quest for New Antibiotics. FEBS Lett. 2011, 585, 1673–1681. DOI: 10.1016/j.febslet.2011.04.029.
  • Tao, W.; Liang-Dong, D.; Ding-Jian, W.; Xiang, L.; Xin-Zhi, C.; Guo-Feng, W. Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2S,5R)-5-((Benzyloxy)Amino) Piperidine-2-Carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam. Org. Process Res. Dev. 2018, 22, 1738–1744.
  • Tao, W.; Liang-Dong, D.; Ding-Jian, W.; Xiang, L.; Xin-Zhi, C.; Guo-Feng, W. A New Synthetic Route to Avibactam: lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation. Org. Process Res. Dev. 2018, 22, 267–272. DOI: 10.1021/acs.oprd.7b00290.
  • David, E.; Ehmann, H.; Jahic, P.; Rong-Fang, R.; Jun, H.; Gunther, K.; Grant, K.; Walkup, S. Avibactam is a Covalent, Reversible, Non-β-Lactam β-Lactamase Inhibitor. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 11663–11668. DOI: 10.1073/pnas.1205073109.
  • Zhanel, G. G.; Lawson, C. D.; Adam, H.; Schweizer, F.; Zelenitsky, S.; Lagacé-Wiens, P. R. S.; Denisuik, A.; Rubinstein, E.; Gin, A. S.; Hoban, D. J.; et al. Ceftazidime-Avibactam: A Novel Cephalosporin/β-Lactamase Inhibitor Combination. Drugs 2013, 73, 159–177. DOI: 10.1007/s40265-013-0013-7.
  • Coleman, K. Diazabicyclooctanes (DBOs): a Potent New Class of Non-β-Lactam β-Lactamase Inhibitors. Curr. Opin. Microbiol. 2011, 14, 550–555. DOI: 10.1016/j.mib.2011.07.026.
  • Stachyra, T.; Péchereau, M.-C.; Bruneau, J.-M.; Claudon, M.; Frère, J.-M.; Miossec, C.; Coleman, K.; Black, M. T. Mechanistic Studies of the Inactivation of TEM-1 and P99 by NXL104, a Novel Non-β-Lactam β-Lactamase Inhibitor. Antimicrob Agents Chemother. 2010, 54, 5132–5138. DOI: 10.1128/AAC.00568-10.
  • Markus, F.; Sandro, N.; Folkert, R.; Anthony, C.; Robert, S.; Heiner, S.; Guido, K. Scale-Up Synthesis of IID572: A New β-Lactamase Inhibitor. Org. Process Res. Dev. 2020, 24, 1244–1253.
  • Ball, M.; Boyd, A.; Ensor, G. J.; Evans, M.; Golden, M.; Linke, S. R.; Milne, D.; Murphy, R.; Telford, A.; Kalyan, Y.; et al. Development of a Manufacturing Route to Avibactam, a β-Lactamase Inhibitor. Org. Process Res. Dev. 2016, 20, 1799–1805. DOI: 10.1021/acs.oprd.6b00268.
  • Shen, Y.; Li, L.; Pan, Z.; Wang, Y.; Li, J.; Wang, K.; Wang, X.; Zhang, Y.; Hu, T.; Zhang, Y. Protecting-Group-Free Total Synthesis of (−)-Jiadifenolide: development of a [4 + 1] Annulation toward Multisubstituted Tetrahydrofurans. Org Lett. 2011, 13, 5480–5483.
  • Patel, M.; Deshpande, P.; Bhawasar, S.; Bhagwat, S.; Jafri, A.; Mishra, A.; Pavase, L.; Gupta, S.; Kale, R.; Joshi, S. 1,6-diazabicyclo[3,2,1]Octan-7-One Derivatives and Their Use in the Treatment of Bacterial Infections. US patent: WO2013030733 2013.

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