Assessment of the Long-Range NMR C,H Coupling of a Series of Carbazolequinone Derivatives
Abstract
:1. Introduction
2. Results
2.1. Synthesis
2.2. Complete NMR Assignments of the 13C NMR
3. Discussion
4. Materials and Methods
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Saurí, J.; Liu, Y.; Parella, T.; Williamson, R.T.; Martin, G.E. Selecting the Most Appropriate NMR Experiment to Access Weak and/or Very Long-Range Heteronuclear Correlations. J. Nat. Prod. 2016, 79, 1400–1406. [Google Scholar] [CrossRef] [PubMed]
- Bax, A.; Summers, M.F. 1H and 13C Assignments from Sensitivity-Enhanced Detection of Heteronuclear Multiple-Bond Connectivity by 2D Multiple Quantum NMR. J. Am. Chem. Soc. 1986, 108, 2093–2094. [Google Scholar] [CrossRef]
- Bax, A.; Marion, D. Improved Resolution and Sensitivity in 1H-Detected Heteronuclear Multiple-Bond Correlation Spectroscopy. J. Magn. Reson. 1988, 78, 186–191. [Google Scholar] [CrossRef]
- Furrer, J. A Comprehensive Discussion of HMBC Pulse Sequences, Part 1: The Classical HMBC. Concepts Magn. Reson. Part A 2012, 40A, 101–127. [Google Scholar] [CrossRef]
- Reynolds, W.F.; Enriquez, R.G. Choosing the Best Pulse Sequences, Acquisition Parameters, Postacquisition. J. Nat. Prod. 2002, 65, 221–244. [Google Scholar] [CrossRef]
- Araya-Maturana, R.; Pessoa-Mahana, H.; Weiss-López, B. Very Long-Range Correlations (NJC,H n > 3) in HMBC Spectra. Nat. Prod. Commun. 2008, 3, 445–450. [Google Scholar] [CrossRef]
- Williamson, R.T.; Buevich, A.V.; Martin, G.E.; Parella, T. LR-HSQMBC: A Sensitive NMR Technique to Probe Very Long-Range Heteronuclear Coupling Pathways. J. Org. Chem. 2014, 79, 3887–3894. [Google Scholar] [CrossRef]
- Araya-maturana, R.; Gavín-sazatornil, J.A.; Heredia-moya, J.; Pessoa-Mahana, H.; Weiss-lópez, B. Long-Range Correlations (n j C,H n > 3) in the HMBC Spectra of 3-(4-Oxo-4H-chromen-3-YL)-acrylic Acid Ethyl Esters. J. Braz. Chem. Soc. 2005, 16, 657–661. [Google Scholar] [CrossRef]
- Buevich, A.V.; Williamson, R.T.; Martin, G.E. NMR Structure Elucidation of Small Organic Molecules and Natural Products: Choosing ADEQUATE vs HMBC. J. Nat. Prod. 2014, 77, 1942–1947. [Google Scholar] [CrossRef]
- Becerra-Martínez, E.; Pérez-Hernández, N.; Sánchez-Zavala, M.; Meléndez-Rodríguez, M.; Aristeo-Dominguez, A.; Suárez-Castillo, O.R.; Joseph-Nathan, P. Equilibrating Magnetic Dispersion and Magnet Homogeneity for the High-Resolution Proton Nuclear Magnetic Resonance of Monosubstituted Naphthalenes. Spectrosc. Lett. 2022, 55, 424–436. [Google Scholar] [CrossRef]
- Hollenberg, M.D. Proteinase-Activated Receptors (PARs): An Evolving Hormonal System. Drug Dev. Res. 2003, 59, 334–335. [Google Scholar] [CrossRef]
- Wang, X.-Y.; Yang, H.-H.; Chang, L.-K.; Chiu, T.-H.; Liu, F.-C.; Lin, I.J.B. Synthesis and Structures of Benzyl- and Amido-Substituted N-Heterocyclic Palladium Carbene.Pdf. Chem. Sel. 2022, 7, e202201700. [Google Scholar] [CrossRef]
- Vien, L.T.; Hanh, T.T.H.; Quang, T.H.; Cuong, N.T.; Cuong, N.X.; Oh, H.; Van Sinh, N.; Nam, N.H.; Minh, C. Van Oroxindols A and B, Two Novel Secoabietane Diterpenoids from Oroxylum Indicum. Phytochem. Lett. 2020, 40, 101–104. [Google Scholar] [CrossRef]
- Burns, D.C.; Reynolds, W.F. Minimizing the Risk of Deducing Wrong Natural Product Structures from NMR Data. Magn. Reson. Chem. 2021, 59, 500–533. [Google Scholar] [CrossRef] [PubMed]
- Surup, F.; Wiebach, V.; Kuhnert, E.; Stadler, M. Truncaquinones A and B, Asterriquinones from Annulohypoxylon Truncatum. Tetrahedron Lett. 2016, 57, 2183–2185. [Google Scholar] [CrossRef]
- Schulte-Herbrüggen, T.; Meissner, A.; Papanikos, A.; Meldal, M.; Sørensen, O.W. Optimizing delays in the MBOB, broadband HMBC, and broadband XLOC NMR pulse sequences. J. Magn. Reson. 2002, 156, 282–294. [Google Scholar] [CrossRef] [PubMed]
- Furihata, K.; Seto, H. Decoupled HMBC (D-HMBC), an Improved Technique of HMBC. Tetrahedron Lett. 1995, 36, 2817–2820. [Google Scholar] [CrossRef]
- Furihata, K.; Seto, H. 3D-HMBC, a New NMR Technique Useful for Structural Studies of Complicated Molecules. Tetrahedron Lett. 1996, 37, 8901–8902. [Google Scholar] [CrossRef]
- Furihata, K.; Seto, H. Constant Time HMBC (CT-HMBC), a New HMBC Technique Useful for Improving Separation of Cross Peaks. Tetrahedron Lett. 1998, 39, 7337–7340. [Google Scholar] [CrossRef]
- Hadden, C.E.; Martin, G.E.; Krishnamurthy, V.V. Improved Performance Accordion Heteronuclear Multiple-Bond Correlation Spectroscopy—IMPEACH-MBC. J. Magn. Reson. 1999, 140, 274–280. [Google Scholar] [CrossRef]
- Hadden, C.E.; Martin, G.E.; Krishnamurthy, V.V. Constant Time Inverse-Detection Gradient Accordion Rescaled Heteronuclear Multiple Bond Correlation Spectroscopy: CIGAR-HMBC. Magn. Reson. Chem. 2000, 38, 143–147. [Google Scholar] [CrossRef]
- Wagner, R.; Berger, S. ACCORD–HMBC: A Superior Technique for Structural Elucidation. Magn. Reson. Chem. 1998, 36, S44–S46. [Google Scholar] [CrossRef]
- Marcarino, M.O.; Zanardi, M.M.; Cicetti, S.; Sarotti, A.M. NMR calculations with quantum methods: Development of new tools for structural elucidation and beyond. Acc. Chem. Res. 2020, 53, 1922–1932. [Google Scholar] [CrossRef] [PubMed]
- Plazinski, W.; Angles d’Ortoli, T.; Widmalm, G. Conformational flexibility of the disaccharide β-l-Fucp-(1→4)-α-d-Glcp-OMe as deduced from NMR spectroscopy experiments and computer simulations. Org. Biomol. Chem. 2023, 21, 6979–6994. [Google Scholar] [CrossRef] [PubMed]
- Adamson, J.; Nazarski, R.B.; Jarvet, J.; Pehk, T.; Aav, R. Shortfall of B3LYP in Reproducing NMR JCH Couplings in Some Isomeric Epoxy Structures with Strong Stereoelectronic Effects: A Benchmark Study on DFT Functionals. ChemPhysChem 2018, 19, 631–642. [Google Scholar] [CrossRef]
- Thomson, R.H. Naturally Occuring Quinones IV; Blackie Academic: London, UK, 1997. [Google Scholar]
- Krueger, F.R.; Werther, W.; Kissel, J.; Schmid, E.R. Assignment of quinone derivatives as the main compound class composing ‘interstellar’ grains based on both polarity ions detected by the ‘Cometary and Interstellar Dust Analyser’ (CIDA) onboard the spacecraft STARDUST. Rapid Commun. Mass Spectrom. 2004, 18, 103–111. [Google Scholar] [CrossRef] [PubMed]
- Monroy-Cárdenas, M.; Andrades, V.; Almarza, C.; Vera, M.J.; Martínez, J.; Pulgar, R.; Amalraj, J.; Araya-Maturana, R.; Urra, F.A. A New Quinone-Based Inhibitor of Mitochondrial Complex I in D-Conformation, Producing Invasion Reduction and Sensitization to Venetoclax in Breast Cancer Cells. Antioxidants 2023, 12, 1597. [Google Scholar] [CrossRef]
- Kumagai, Y.; Shinkai, Y.; Miura, T.; Cho, A.K. The chemical biology of naphthoquinones and its environmental implications. Annu. Rev. Pharmacol. Toxicol. 2012, 52, 221–247. [Google Scholar] [CrossRef]
- Bolton, J.L.; Trush, M.A.; Penning, T.M.; Dryhurst, G.; Monks, T.J. Role of Quinones in Toxicology. Chem. Res. Toxicol. 2000, 13, 135–160. [Google Scholar] [CrossRef]
- Patel, O.P.S.; Beteck, R.M.; Legoabe, L.J. Antimalarial application of quinones: A recent update. Eur. J. Med. Chem. 2021, 210, 113084. [Google Scholar] [CrossRef]
- Zhang, L.; Zhang, G.; Xu, S.; Song, Y. Recent advances of quinones as a privileged structure in drug discovery. Eur. J. Med. Chem. 2021, 223, 113632. [Google Scholar] [CrossRef] [PubMed]
- Aouacheria, A.; Néel, B.; Bouaziz, Z.; Dominique, R.; Walchshofer, N.; Paris, J.; Fillion, H.; Gillet, G. Carbazolequinone Induction of Caspase-Dependent Cell Death in Src-Overexpressing Cells. Biochem. Pharmacol. 2002, 64, 1605–1616. [Google Scholar] [CrossRef] [PubMed]
- Agarwal, S.K.; Singh, S.S.; Verma, S.; Kumar, S. Antifungal Activity of Anthraquinone Derivatives from Rheum Emodi. J. Ethnopharmacol. 2000, 72, 43–46. [Google Scholar] [CrossRef] [PubMed]
- Chrysayi-Tokousbalides, M.; Kastanias, M.A. Cynodontin: A Fungal Metabolite with Antifungal Properties. J. Agric. Food Chem. 2003, 51, 4920–4923. [Google Scholar] [CrossRef] [PubMed]
- Kim, Y.M.; Lee, C.H.; Kim, H.G.; Lee, H.S. Anthraquinones Isolated from Cassia Tora (Leguminosae) Seed Show an Antifungal Property against Phytopathogenic Fungi. J. Agric. Food Chem. 2004, 52, 6096–6100. [Google Scholar] [CrossRef] [PubMed]
- Ferreira, E.S.B.; Hulme, A.N.; McNab, H.; Quye, A. The Natural Constituents of Historical Textile Dyes. Chem. Soc. Rev. 2004, 33, 329–336. [Google Scholar] [CrossRef] [PubMed]
- Er, S.; Suh, C.; Marshak, M.P.; Aspuru-Guzik, A. Computational design of molecules for an all-quinone redox flow battery. Chem. Sci. 2015, 6, 885–893. [Google Scholar] [CrossRef]
- Lee, J.; Kim, H.; Park, M.J. Long-Life, High-Rate Lithium-Organic Batteries Based on Naphthoquinone Derivatives. Chem. Mater. 2016, 28, 2408–2416. [Google Scholar] [CrossRef]
- Itoigawa, M.; Kashiwada, Y.; Ito, C.; Furukawa, H.; Tachibana, Y.; Bastow, K.F.; Lee, K.-H. Antitumor Agents. 203. Carbazole Alkaloid Murrayaquinone A and Related Synthetic Carbazolequinones as Cytotoxic Agents. J. Nat. Prod. 2000, 63, 3–7. [Google Scholar] [CrossRef]
- Khan, Q.A.; Lu, J.; Hecht, S.M. Calothrixins, a new class of human DNA topoisomerase i poisons. J. Nat. Prod. 2009, 72, 438–442. [Google Scholar] [CrossRef]
- Bernardo, P.H.; Chai, C.L.L.; Heath, G.A.; Mahon, P.J.; Smith, G.D.; Waring, P.; Wilkes, B.A. Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones. J. Med. Chem. 2004, 47, 4958–4963. [Google Scholar] [CrossRef] [PubMed]
- Murata, T.; Kohno, S.; Ito, C.; Itoigawa, M.; Sugiura, A.; Hikita, K.; Kaneda, N. Inhibitory effect of carbazolequinone derivatives on lipopolysaccharide and interferon-γ-induced nitric oxide production in mouse macrophage RAW264.7 cells. J. Pharm. Pharmacol. 2013, 65, 1204–1213. [Google Scholar] [CrossRef] [PubMed]
- Araya-Maturana, R.; Cassels, B.K.; Delgado-Castro, T.; Hurtado-Guzmán, C.; Jullian, C. Complete assignment of the 13C NMR spectra of a series of 5,8-disubstituted 4,4-dimethylanthracene-1,9,10(4h)-triones. Magn. Reson. Chem. 1999, 37, 312–316. [Google Scholar] [CrossRef]
- Córdova-Delgado, M.; Fuentes-Retamal, S.; Palominos, C.; López-Torres, C.; Guzmán-Rivera, D.; Ramírez-Rodríguez, O.; Araya-Maturana, R.; Urra, F.A. Fri-1 is an anti-cancer isoquinolinequinone that inhibits the mitochondrial bioenergetics and blocks metabolic shifts by redox disruption in breast cancer cells. Antioxidants 2021, 10, 1618. [Google Scholar] [CrossRef] [PubMed]
- Martínez-Cifuentes, M.; Clavijo-Allancan, G.; Zuñiga-Hormazabal, P.; Aranda, B.; Barriga, A.; Weiss-López, B.; Araya-Maturana, R. Protonation sites, tandem mass spectrometry and computational calculations of o-carbonyl carbazolequinone derivatives. Int. J. Mol. Sci. 2016, 17, 1071. [Google Scholar] [CrossRef]
- Martínez-Cifuentes, M.; Clavijo-Allancan, G.; Di Vaggio-Conejeros, C.; Weiss-López, B.; Araya-Maturana, R. On-water reactivity and regioselectivity of quinones in C-N coupling with amines: Experimental and theoretical study. Aust. J. Chem. 2014, 67, 217–224. [Google Scholar] [CrossRef]
- Bodenhausen, G.; Ruben, D.J. Natural abundance nitrogen-15 NMR by enhanced heteronuclear spectroscopy. Chem. Phys. Lett. 1980, 69, 185–189. [Google Scholar] [CrossRef]
Compound | CQ-1 | CQ-2 | CQ-3 | CQ-4 | CQ-5 | CQ-6 |
---|---|---|---|---|---|---|
X | H | OMe | Cl | Br | COMe | F |
C1 | 114.4 | 115.6 | 116.2 | 116.5 | 114.4 | 116.1 |
C2 | 127.1 | 118.4 | 127.2 | 129.8 | 126.5 | 115.9 |
C3 | 124.6 | 157.6 | 129.1 | 117.1 | 133.3 | 160.1 |
C4 | 122.4 | 102.3 | 121.3 | 124.4 | 123.9 | 106.8 |
C5 | 123.9 | 123.9 | 124.8 | 125.4 | 123.4 | 124.4 |
C6 | 138.2 | 138.2 | 136.6 | 136.8 | 140.4 | 134.9 |
C7 | 116.6 | 116.6 | 116.0 | 115.8 | 117.5 | 116.4 |
C8 | 183.1 | 183.1 | 183.0 | 183.0 | 183.2 | 182.9 |
C9 | 159.0 | 159.0 | 158.9 | 158.9 | 158.8 | 159.0 |
C10 | 130.3 | 130.4 | 130.4 | 130.4 | 130.3 | 130.4 |
C11 | 178.1 | 177.8 | 177.9 | 177.9 | 177.9 | 177.9 |
C12 | 135.7 | 135.6 | 136.7 | 136.5 | 137.2 | 137.0 |
C13 | 183.6 | 183.7 | 183.5 | 183.5 | 183.5 | 183.6 |
C14 | 127.0 | 127.0 | 127.0 | 127.0 | 127.0 | 127.0 |
C15 | 158.6 | 158.6 | 158.6 | 158.6 | 158.7 | 158.6 |
C16 | 39.5 | 39.5 | 39.5 | 39.5 | 39.5 | 39.5 |
gem-Me | 26.7 | 26.6 | 26.6 | 26.6 | 26.6 | 26.6 |
OMe | 55.8 | |||||
MeCO | 31.1 |
CQ-1 | CQ-2 | CQ-3 | CQ-4 | CQ-5 | CQ-6 | |
---|---|---|---|---|---|---|
H1 | 7.56 | 7.46 | 7.58 | 7.53 | 7.64 | 7.59 |
H2 | 7.42 | 7.06 | 7.44 | 7.56 | 8.00 | 7.31 |
H3 | 7.35 | - | - | - | - | - |
H4 | 8.11 | 7.52 | 8.06 | 8.22 | 8.70 | 7.77 |
H14 | 6.26 | 6.25 | 6.26 | 6.27 | 6.28 | 6.26 |
H15 | 7.01 | 7.06 | 7.02 | 7.02 | 7.02 | 7.01 |
H4 | 2J C3 2.1 | 3J C7 2.0 | 3J C2 5.6 | 3J C6 7.3 | |
H1 | 3J C3 9.1 | 4J C12 6.1 | 4J C4 2.0 | ||
H2 | 2J C3 1.9 | 3J C4 4.9 | 3J C6 10.0 | ||
H15 | 2J C16 2.5 | 3J C17/18 2.4 | 3J C9 7.2 | 3J C13 10.1 | 4J C10 2.0 |
H14 | 3J C16 7.5 | 3J C10 4.1 | 4J C17/18 2.0 | 4J C11 2.1 | 4J C11 2.1 |
H17/18 | 3J C17/18 4.9 | 2J C16 3.8 | 4J C14 2.3 | 3J C9 3.6 |
H4 | 2J C3 2.9 | 3J C6 7.4 | 4J C1 2.0 | ||||
H1 | 3J C5 2.9 | 3JC3 11.0 | 4J C4 2.6 | 4J C7 5.7 | |||
H2 | 2J C1 2.0 | 2J C3 2. 3 | 3J C4 5.6 | 3J C6 10.0 | |||
H15 | 2J C16 2.3 | 3JC17/18 2.1 | 3J C9 7.3 | 3J C8 2.8 | 3JC13 10.1 | 4J C10 2.0 | 5J C7 2.3 |
H14 | 2J C13 2.1 | 3J C16 7.5 | 3J C10 4.2 | 4J C17/18 2.1 | 4J C9 2.2 | 4J C11 2.5 | |
H17/18 | 2J C16 3.3 | 3JC17/18 4.9 | 3J C15 3.7 |
HN | 2J C12 5.6 | 2J C6 3.1 | 3J C5 2.9 | 3J C7 4.9 | |||
H4 | 3J C7 2.6 | 3J C2 7.5 | 3J C6 6.8 | 4J C1 2.8 | |||
H1 | 2J C2 3.6 | 3J C5 5.6 | |||||
H2 | 2J C1 3.4 | 3J C4 8.0 | 3J C6 9.7 | ||||
H3 | 2J C2 2.5 | 3 J C1 8.2 | 3J C5 9.1 | 4J C6 2.5 | |||
H15 | 2J C16 2.8 | 3J C17/18 2.1 | 3J C9 7.1 | 3J C13 10.5 | 4J C10 1.8 | 4J C8 2.4 | 5J C7 2.3 |
H14 | 2J C13 1.8 | 3J C16 7.4 | 3J C10 4.1 | 4JC17/18 1.8 | 5J C9 2.0 | 4J C111.8 | |
H17/18 | 2J C16 3.4 | 3J C17/18 4.3 | 3J C9 3.5 | 4J C14 1.8 |
H4 | 2J C3 3.5 | 3J C7 2.1 | 3J C2 4.6 | 3J C6 8.0 | ||
H1 | 3J C5 5.3 | 3J C3 10.0 | 4J C12 5.8 | |||
H2 | 2J C3 2.2 | 3J C4 4.5 | 3J C6 9.0 | |||
H15 | 2J C16 3.0 | 3J C17/18 3.2 | 3J C9 7.5 | 3J C13 10.0 | 4J C10 2.7 | 5J C7 2.1 |
H14 | 2J C13 3.0 | 3J C16 8.0 | 3J C10 3.5 | 4JC17/18 2.9 | 4J C9 3.0 | 4J C11 3.4 |
H17/18 | 2J C16 3.1 | 3J C17/18 3.5 | 3J C9 3.5 |
H4 | 3J C7 2.2 | 3J C2 7.3 | 3J C6 7.6 | 3J CO 3.6 | 4J C1 2.8 | ||
H1 | 3J C3 7.0 | 3J C5 5.3 | 4J CO 1.9 | 5J C8 2.0 | |||
H2 | 3J C4 6.0 | 3J C6 10.1 | 3J CO 2.8 | ||||
H15 | 2J C16 2.7 | 3J C17/18 2.1 | 3J C9 7.2 | 3J C13 10.4 | 4J C10 2.0 | 4J C8 3.0 | |
H14 | 2J C13 1.9 | 3J C16 7.6 | 3J C10 3.9 | 4J C17/18 3.0 | 4J C9 2.0 | 4J C11 2.1 | 5J C12 3.0 |
H17/18 | 2J C16 3.7 | 3J C17/18 5.0 | 3J C9 4.0 | ||||
CH3-CO | 2J CO 6.0 |
H4 | 2J C3 5.0 | 2J C5 5.0 | 3J C7 2.0 | 3J C6 7.6 | |||
H1 | 3J C3 4.4 | 3J C5 6.1 | 4J C4 2.3 | ||||
H2 | 2J C3 4.1 | 3J C6 10.1 | 3J C4 3.9 | 4J C5 4.1 | |||
H15 | 2J C16 2.2 | 3J C17/18 2.0 | 3J C9 7.1 | 3J C13 10.5 | 4J C10 2.0 | 4J C8 2.7 | 5J C7 2.3 |
H14 | 2J C13 2.1 | 3J C16 7.7 | 3J C10 4.1 | 4J C17/18 2.0 | 4J C9 2.0 | 4J C11 2.5 | |
H17/18 | 2J C16 3.6 | 3J C17/18 4.8 | 3J C9 3.9 |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Monroy-Cárdenas, M.; Gavín, J.A.; Araya-Maturana, R. Assessment of the Long-Range NMR C,H Coupling of a Series of Carbazolequinone Derivatives. Int. J. Mol. Sci. 2023, 24, 17450. https://doi.org/10.3390/ijms242417450
Monroy-Cárdenas M, Gavín JA, Araya-Maturana R. Assessment of the Long-Range NMR C,H Coupling of a Series of Carbazolequinone Derivatives. International Journal of Molecular Sciences. 2023; 24(24):17450. https://doi.org/10.3390/ijms242417450
Chicago/Turabian StyleMonroy-Cárdenas, Matías, José A. Gavín, and Ramiro Araya-Maturana. 2023. "Assessment of the Long-Range NMR C,H Coupling of a Series of Carbazolequinone Derivatives" International Journal of Molecular Sciences 24, no. 24: 17450. https://doi.org/10.3390/ijms242417450