Kobus, M., Friedrich, T., Zorn, E., Burmeister, N. & Maison, W. Medicinal chemistry of drugs with N‑Oxide functionalities. J. Med. Chem. 67, 5168–5184 (2024).Article
CAS
PubMed
PubMed Central
Google Scholar
Klein-Junior, L. C. et al. Targeted isolation of monoterpene indole alkaloids from Palicourea sessilis. J. Nat. Prod. 80, 3032–3037 (2017).Article
CAS
PubMed
Google Scholar
Bartolucci, C. et al. Structural determinants of torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-alzheimer drug ganstigmine (CHF-2819). J. Med. Chem. 49, 5051–5058 (2006).Article
CAS
PubMed
Google Scholar
Yeung, P. K. F., Mosher, S. J., Macrae, D. A. & Klassen, G. A. Effect of diltiazem and its metabolites on the uptake of adenosine in blood: an in-vitro investigation. J. Pharm. Pharmacol. 43, 685–689 (1991).Article
CAS
PubMed
Google Scholar
Liu, P. et al. New compound structure and preparation method and application thereof, Patent No. CN101885726A, (November, 17, 2010).Gao, W. et al. Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents. Bioorg. Med. Chem. Lett. 17, 4338–4342 (2007).Article
CAS
PubMed
Google Scholar
Tábi, T., Vécsei, L., Youdim, M. B., Riederer, P. & Szökő, É. Selegiline: A molecule with innovative potential. J. Neural Transm. 127, 831–842 (2020).Article
PubMed
Google Scholar
Lévai, F. et al. In Vitro formation of selegiline-N-oxide as a metabolite of selegiline in human, hamster, mouse, rat, guinea-pig, rabbit and dog. Eur. J. Drug. Metab. Pharmacokinet. 29, 169–178 (2004).Article
PubMed
Google Scholar
Liu, X. H., Lin, L. L. & Feng, X. M. Chiral N,N’-dioxides: new ligands and organocatalysts for catalytic asymmetric reactions. Acc. Chem. Res. 44, 574–587 (2011).Article
CAS
PubMed
Google Scholar
Malkov, A. V. & Kocovsky, P. Chiral N-oxides in asymmetric catalysis. Eur. J. Org. Chem. 1, 29–36 (2007).Article
Google Scholar
Chen, D. F., Gong, L. Z. & Feng, X. M. Chiral N.,N-dioxide ligands: uniqueness and impacts. Org. Chem. Front. 10, 3676–3683 (2023).Article
CAS
Google Scholar
Traverse, J. F., Zhao, Y., Hoveyda, A. H. & Snapper, M. L. Proline-based N-oxides as readily available and modular chiral catalysts. enantioselective reactions of allyltrichlorosilane with aldehydes. Org. Lett. 7, 3151–3154 (2005).Article
CAS
PubMed
Google Scholar
Bickel, M. H. The Pharmacology and biology of N-oxides. Pharmacol. Rev. 21, 325–355 (1969).CAS
PubMed
Google Scholar
Albini, A. Alkaloid N-oxides. Heterocycles 34, 1973–2002 (1992).Article
CAS
Google Scholar
Lebar, M. D. et al. Identification and functional analysis of the aspergillic acid gene cluster in Aspergillus flavus. Fungal Genet. Biol. 116, 14–23 (2018).Article
CAS
PubMed
Google Scholar
Patterson, L. H. Bioreductively activated antitumor N-oxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy. Drug. Metab. Rev. 34, 581–592 (2002).Article
CAS
PubMed
Google Scholar
O’Neil, I. Science of Synthesis, 40, 859–891 (Thieme 2009)Bernier, D., Wefelscheid, U. K. & Woodward, S. Properties, preparation and synthetic uses of amine N-oxides. an update. Org. Prep. Proced. Int. 41, 173–210 (2009).Article
CAS
Google Scholar
Limnios, D. & Kokotos, C. G. 2,2,2-Trifluoroacetophenone as an organocatalyst for the oxidation of tertiary Amines and azines to N-Oxides. Chem. Eur. J. 20, 559–563 (2014).Article
CAS
PubMed
Google Scholar
Łukomska, M., Rybarczyk-Pirek, A. J., Jabłon´skib, M. & Palusiak, M. The nature of NO-bonding in N-oxide group. Phys. Chem. Chem. Phys. 17, 16375–16387 (2015).Article
PubMed
Google Scholar
Baumeister, T. et al. Continuous flow synthesis of amine oxides by oxidation of tertiary amines. React. Chem. Eng. 4, 1270–1276 (2019).Article
CAS
Google Scholar
Toda, F., Mori, K., Stein, Z. & Goldberg, I. Optical resolution of amine N-oxide by diastereoisomeric complex formation with optically active host compound. Tetrahedron Lett. 30, 1841–1844 (1989).Article
CAS
Google Scholar
Drabowicz, J., Dudziński, B., Mikołajczyk, M., Colonna, S. & Gaggero, N. Chiral t-butylphenylphosphinothioic acid in NMR analysis of tertiary amine oxides with a stereogenic nitrogen atom. Tetrahedron. Asymmetry 8, 2267–2270 (1997).Article
CAS
Google Scholar
Liu, W., Wang, D., Zhang, D. & Yang, X. Catalytic kinetic resolution and desymmetrization of amines. Synlett. 33, 1788–1812 (2022).Article
CAS
Google Scholar
Wang, G., Lu, R., He, C. & Liu, L. Kinetic resolution of indolines by asymmetric hydroxylamine formation. Nat. Commun. 12, 2512 (2021).Article
ADS
CAS
PubMed
PubMed Central
Google Scholar
Colonna, S., Banfi, S. & Annunziata, R. Enantio- and diastereoselectivity in the periodate oxidation of sulfides catalyzed by bovine serum albumin. J. Org. Chem. 51, 891–895 (1986).Article
CAS
Google Scholar
Colonna, S., Gaggero, N., Drabowicz, J., Łyżwa, P. & Mikolajczyk, M. The first efficient bovine serum albumin catalyzed asymmetric oxidation of tertiary amines to the corresponding N-oxides via kinetic dynamic resolution. Chem. Commun. 18, 1787–1788 (1999).Article
Google Scholar
Ottolina, G., Bianchi, S., Belloni, B., Carrea, G. & Danieli, B. First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase. Tetrahedron Lett. 40, 8483–8486 (1999).Article
CAS
Google Scholar
Bergstad, K. & Baeckvall, J.-E. Mild and efficient flavin-catalyzed H2O2 oxidation of tertiary amines to amine N-oxides. J. Org. Chem. 63, 6650–6655 (1998).Article
CAS
Google Scholar
Zhang, S. et al. Biomimetic dynamic kinetic asymmetric N-oxidation with H2O2 and O2. ACS Catal. 13, 11954–11962 (2023).Article
CAS
Google Scholar
Bhadra, S. & Yamamoto, H. Catalytic asymmetric synthesis of N-chiral amine oxides. Angew. Chem. Int. Ed. 55, 13043–13046 (2016).Article
CAS
Google Scholar
Zong, L. & Tan, C.-H. Phase-transfer and ion-pairing catalysis of pentanidiums and bisguanidiniums. Acc. Chem. Res. 50, 842–856 (2017).Article
CAS
PubMed
Google Scholar
Ye, X. & Tan, C.-H. Enantioselective transition metal catalysis directed by chiral cations. Chem. Sci. 12, 533–539 (2021).Article
CAS
Google Scholar
Wang, C., Zong, L. & Tan, C.-H. Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium. J. Am. Chem. Soc. 137, 10677–10682 (2015).Article
CAS
PubMed
Google Scholar
Ye, X. et al. Enantioselective sulfoxidation catalyzed by a bisguanidinium diphosphatobisperoxotungstate ion pair. Angew. Chem. Int. Ed. 55, 7101–7105 (2016).Article
CAS
Google Scholar
Zong, L. et al. Bisguanidinium dinuclear oxodiperoxomolybdosulfate ion-pair-catalyzed enantioselective sulfoxidation. Nat. Commun. 7, 13455–13464 (2016).Article
ADS
PubMed
PubMed Central
Google Scholar
Chin, K. F. et al. Bisguanidinium-catalyzed epoxidation of allylic and homoallylic amines under phase transfer conditions. ACS Catal. 10, 2684–2691 (2020).Article
CAS
Google Scholar
Bickelhaupt, F. M. & Houk, K. N. Analyzing reaction rates with the distortion/interaction-activation strain model. Angew. Chem. Int. Ed. 56, 10070–10086 (2017).Article
CAS
Google Scholar