An efficient, concise synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings

References

• Yoshida, Y.; Takeuchi, H.; Nakagawa, K.; Fujii, T.; Arichi, N.; Oishi, S.; Ohno, H.; Inuki, S. Construction of a Bicyclo[2.2.2]Octene Skeleton via a Visible-Light-Mediated Radical Cascade Reaction of Amino Acid Derivatives with N-(2-Phenyl)Benzoyl Groups. Org. Lett. 2023, 25, 4846–4851. DOI: 10.1021/acs.orglett.3c01586.
   PubMed Web of Science ®Google Scholar
• Nicolaou, K. C.; Toh, Q.-Y.; Chen, D. Y.-K. An Expedient Asymmetric Synthesis of Platencin. J. Am. Chem. Soc. 2008, 130, 11292–11293. DOI: 10.1021/ja804588r.
   PubMed Web of Science ®Google Scholar
• Herlah, B.; Hoivik, A.; Jamšek, L.; Valjavec, K.; Yamamoto, N.; Hoshino, T.; Kranjc, K.; Perdih, A. Design, Synthesis and Evaluation of Fused Bicyclo[2.2.2]Octene as a Potential Core Scaffold for the Non-Covalent Inhibitors of SARS-CoV-2 3CLpro Main Protease. Pharmaceuticals (Basel) 2022, 15, 539. DOI: 10.3390/ph15050539.
   PubMedGoogle Scholar
• Suzuki, T.; Watanabe, S.; Ikeda, W.; Kobayashi, S.; Tanino, K. Biomimetic Total Syntheses of (+)-Chloropupukeananin, (-)-Chloropupukeanolide D, and Chloropestolides. J. Org. Chem. 2021, 86, 15597–15605. DOI: 10.1021/acs.joc.1c02108.
   PubMed Web of Science ®Google Scholar
• Mykhailiuk, P. K. Saturated Bioisosteres of Benzene: Where to Go Next? Org. Biomol. Chem. 2019, 17, 2839–2849. DOI: 10.1039/c8ob02812e.
   PubMed Web of Science ®Google Scholar
• Han, J.; Escorihuela, J.; Fustero, S.; Landa, A.; Soloshonok, V. A.; Sorochinsky, A. Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives. Molecules 2022, 27, 3797. DOI: 10.3390/molecules27123797.
   PubMed Web of Science ®Google Scholar
• Chen, Y.; Wu, Q.; Jin, Z.; Qin, Y.; Meng, F.; Zhao, G. Review of Voltage-Gated Calcium Channel α2δ Subunit Ligands for the Treatment of Chronic Neuropathic Pain and Insight into Structure-Activity Relationship (SAR) by Pharmacophore Modeling. Curr. Med. Chem. 2022, 29, 5097–5112. DOI: 10.2174/0929867329666220407093727.
   PubMed Web of Science ®Google Scholar
• Gajcy, K.; Lochyński, S.; Librowski, T. A Role of GABA Analogues in the Treatment of Neurological Diseases. Curr. Med. Chem. 2010, 17, 2338–2347. DOI: 10.2174/092986710791698549.
   PubMed Web of Science ®Google Scholar
• Blakemore, D. C.; Bryans, J. S.; Carnell, P.; Field, M. J.; Kinsella, N.; Kinsora, J. K.; Meltzer, L. T.; Osborne, S. A.; Thompson, L. R.; Williams, S. C. Synthesis and in Vivo Evaluation of 3,4-Disubstituted Gababutins. Bioorg. Med. Chem. Lett. 2010, 20, 248–251. DOI: 10.1016/j.bmcl.2009.10.121.
   PubMed Web of Science ®Google Scholar
• Blakemore, D. C.; Bryans, J. S.; Carnell, P.; Carr, C. L.; Chessum, N. E. A.; Field, M. J.; Kinsella, N.; Osborne, S. A.; Warren, A. N.; Williams, S. C. Synthesis and in Vivo Evaluation of Bicyclic Gababutins. Bioorg. Med. Chem. Lett. 2010, 20, 461–464. DOI: 10.1016/j.bmcl.2009.11.118.
   PubMed Web of Science ®Google Scholar
• Blakemore, D. C.; Bryans, J. S.; Carnell, P.; Chessum, N. E. A.; Field, M. J.; Kinsella, N.; Kinsora, J. K.; Osborne, S. A.; Williams, S. C. Synthesis and in Vivo Evaluation of 3-Substituted Gababutins. Bioorg. Med. Chem. Lett. 2010, 20, 362–365. DOI: 10.1016/j.bmcl.2009.10.089.
   PubMed Web of Science ®Google Scholar
• Zoidis, G.; Papanastasiou, I.; Dotsikas, I.; Sandoval, A.; Dos Santos, R. G.; Papadopoulou-Daifoti, Z.; Vamvakides, A.; Kolocouris, N.; Felix, R. The Novel GABA Adamantane Derivative (AdGABA): Design, Synthesis, and Activity Relationship with Gabapentin. Bioorg. Med. Chem. 2005, 13, 2791–2798. DOI: 10.1016/j.bmc.2005.02.030.
   PubMed Web of Science ®Google Scholar
• Bryans, J. S.; Davies, N.; Gee, N. S.; Dissanayake, V. U.; Ratcliffe, G. S.; Horwell, D. C.; Kneen, C. O.; Morrell, A. I.; Oles, R. J.; O'Toole, J. C.; et al. Identification of Novel Ligands for the Gabapentin Binding Site on the α2δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents. J. Med. Chem. 1998, 41, 1838–1845. DOI: 10.1021/jm970649n.
   PubMed Web of Science ®Google Scholar
• Powers, D. C.; Leber, P. A.; Gallagher, S. S.; Higgs, A. T.; McCullough, L. A.; Baldwin, J. E. Thermal Chemistry of Bicyclo[4.2.0]Oct-2-Enes. J. Org. Chem. 2007, 72, 187–194. DOI: 10.1021/jo061964x.
   PubMed Web of Science ®Google Scholar
• Leber, P. A.; Lasota, C. C.; Strotman, N. A.; Yen, G. S. Effect of a Methoxy Substituent on the Vinylcyclobutane Carbon Migration. J. Org. Chem. 2007, 72, 912–919. DOI: 10.1021/jo0621017.
   PubMed Web of Science ®Google Scholar
• Kerns, J. K.; Nie, H.; Bondinell, W.; Widdowson, K. L.; Yamashita, D. S.; Rahman, A.; Podolin, P. L.; Carpenter, D. C.; Jin, Q.; Riflade, B.; et al. Azepanone-Based Inhibitors of Human Cathepsin S: Optimization of Selectivity via the P2 Substituent. Bioorg. Med. Chem. Lett. 2011, 21, 4409–4415. DOI: 10.1016/j.bmcl.2011.06.045.
   PubMed Web of Science ®Google Scholar
• Kozikowski, A. P.; Schmiesing, R. J. Synthesis of an Alleged Constituent of New Brunswick Cranberry Leaves: The so-Called Cannivonine. J. Org. Chem. 1983, 48, 1000–1007. DOI: 10.1021/jo00155a014.
   Web of Science ®Google Scholar
• Powell, L.; Mahmood, A.; Robinson, G. E. Dialkyl Sulfide Stabilisation in a Catalytic Dicuprate 1,6-Dienone Addition Process. Org. Process Res. Dev. 2011, 15, 49–52. DOI: 10.1021/op1002648.
   Web of Science ®Google Scholar
• Fossey, J. S.; Richards, C. J. Synthesis of 2,6-Bis(2-Oxazolinyl)Phenylplatinum(II) NCN Pincer Complexes by Direct Cyclometalation. Catalysts for Carbon-Carbon Bond Formation. Organometallics 2004, 23, 367–373. DOI: 10.1021/om0305162.
   Web of Science ®Google Scholar
• Lbarzo, J.; Ortuño, R. M. 1,2-Dibromoethane in the Synthesis of 2-Bromoesters: Bromination vs Alkylation. Tetrahedron 1994, 50, 9825–9830. DOI: 10.1016/S0040-4020(01)85547-2.
   Web of Science ®Google Scholar