1H and 13C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

Chab, Faten Al; Fenêt, Bernard; Borgne, Marc Le; Jose, Joachim; Pinaud, Noël; Guillon, Jean; Ettouati, Laurent

doi:10.1002/mrc.4016

Cited by 3 publications

(8 citation statements)

References 11 publications

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“…Further perspectives for the importance of adequate precision in HNMR data reporting are provided by reported case studies of molecules that have been subjected previously to full spin analysis, recently referred to as HiFSA ( 1 H iterative full spin analysis): 9 the monoterpene β-pinene, 10 the sesquiterpenoid perezone and its analogues, 11 the diterpenoid ent-3β-hydroxytrachylobane, 12 a series of diterpenoid lactones (ginkgolides) and flavonoids from Ginkgo biloba L., 13,14 several alkaloids such as huperzine A, 15 indole derivatives, 16 anatabine 17 analogues from Nicotiana species, tropane derivatives, 18 flavonoids 19 and flavonolignans, and dimeric phenylpropanoids ([iso]silybins) from Silybum marianum (L.) Gaertn., 20 as well as mono- and oligosaccharides. 21 …”

Section: Approachmentioning

confidence: 99%

Essential Parameters for Structural Analysis and Dereplication by ¹H NMR Spectroscopy

et al. 2014

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The present study demonstrates the importance of adequate precision when reporting the δ and J parameters of frequency domain 1H NMR (HNMR) data. Using a variety of structural classes (terpenoids, phenolics, alkaloids) from different taxa (plants, cyanobacteria), this study develops rationales that explain the importance of enhanced precision in NMR spectroscopic analysis and rationalizes the need for reporting Δδ and ΔJ values at the 0.1–1 ppb and 10 mHz level, respectively. Spectral simulations paired with iteration are shown to be essential tools for complete spectral interpretation, adequate precision, and unambiguous HNMR-driven dereplication and metabolomic analysis. The broader applicability of the recommendation relates to the physicochemical properties of hydrogen (1H) and its ubiquity in organic molecules, making HNMR spectra an integral component of structure elucidation and verification. Regardless of origin or molecular weight, the HNMR spectrum of a compound can be very complex and encode a wealth of structural information that is often obscured by limited spectral dispersion and the occurrence of higher order effects. This altogether limits spectral interpretation, confines decoding of the underlying spin parameters, and explains the major challenge associated with the translation of HNMR spectra into tabulated information. On the other hand, the reproducibility of the spectral data set of any (new) chemical entity is essential for its structure elucidation and subsequent dereplication. Handling and documenting HNMR data with adequate precision is critical for establishing unequivocal links between chemical structure, analytical data, metabolomes, and biological activity. Using the full potential of HNMR spectra will facilitate the general reproducibility for future studies of bioactive chemicals, especially of compounds obtained from the diversity of terrestrial and marine organisms.

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Section: Approachmentioning

confidence: 99%

Essential Parameters for Structural Analysis and Dereplication by ¹H NMR Spectroscopy

et al. 2014

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“…However, owing to poor nuclear relaxation, several carbons were not assigned in the 13 C-NMR spectra of 7b and 7e , g . Nevertheless, a previous work [ 22 ] performed to study 1 H and 13 C-NMR assignments of indeno[1,2- b ]indole-10-one derivatives allowed us to achieve a complete spectral assignment for this scaffold.…”

Section: Resultsmentioning

confidence: 99%

“…1 H-NMR and 13 C-NMR spectra (broadband decoupling and DEPT-135) were recorded on a Brucker Avance 400 (400 MHz for 1 H and 100 MHz for 13 C) or a Brucker Avance 500 spectrometer (500 MHz for 1 H and 125 MHz for 13 C) using CDCl 3 or DMSO-d6 as solvents. NMR analysis of compounds 4 – 7 was performed with the same experiments described in [ 22 ]. Chemical shifts (δ) are referred to that of the solvent.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Biological Evaluation and Molecular Modeling of Substituted Indeno[1,2-b]indoles as Inhibitors of Human Protein Kinase CK2

et al. 2015

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Due to their system of annulated 6-5-5-6-membered rings, indenoindoles have sparked great interest for the design of ATP-competitive inhibitors of human CK2. In the present study, we prepared twenty-one indeno[1,2-b]indole derivatives, all of which were tested in vitro on human CK2. The indenoindolones 5a and 5b inhibited human CK2 with an IC50 of 0.17 and 0.61 µM, respectively. The indeno[1,2-b]indoloquinone 7a also showed inhibitory activity on CK2 at a submicromolar range (IC50 = 0.43 µM). Additionally, a large number of indenoindole derivatives was evaluated for their cytotoxic activities against the cell lines 3T3, WI-38, HEK293T and MEF.

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“…IR spectra were recorded on a Perkin Elmer 1310 spectrometer and a Spectrum One spectrometer using KBr pellets ( cm À1 ). 1 24 . Chemical shifts () are referred to that of the solvent.…”

Section: Generalmentioning

confidence: 99%

Screening of indeno[1,2-b]indoloquinones by MALDI-MS: a new set of potential CDC25 phosphatase inhibitors brought to light

Alchab

Sibille

Ettouati

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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¹H and ¹³C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

Abstract: The complete (1)H and (13)C assignments of eight bioactive indeno[1,2-b]indole-10-one derivatives were accomplished by the combined use of one-dimensional and two-dimensional NMR experiments.

Cited by 3 publications

References 11 publications

Essential Parameters for Structural Analysis and Dereplication by ¹H NMR Spectroscopy

Essential Parameters for Structural Analysis and Dereplication by ¹H NMR Spectroscopy

Synthesis, Biological Evaluation and Molecular Modeling of Substituted Indeno[1,2-b]indoles as Inhibitors of Human Protein Kinase CK2

Screening of indeno[1,2-b]indoloquinones by MALDI-MS: a new set of potential CDC25 phosphatase inhibitors brought to light

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1H and 13C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

Abstract: The complete (1)H and (13)C assignments of eight bioactive indeno[1,2-b]indole-10-one derivatives were accomplished by the combined use of one-dimensional and two-dimensional NMR experiments.

Cited by 3 publications

References 11 publications

Essential Parameters for Structural Analysis and Dereplication by 1H NMR Spectroscopy

Essential Parameters for Structural Analysis and Dereplication by 1H NMR Spectroscopy

Synthesis, Biological Evaluation and Molecular Modeling of Substituted Indeno[1,2-b]indoles as Inhibitors of Human Protein Kinase CK2

Screening of indeno[1,2-b]indoloquinones by MALDI-MS: a new set of potential CDC25 phosphatase inhibitors brought to light

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¹H and ¹³C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

Essential Parameters for Structural Analysis and Dereplication by ¹H NMR Spectroscopy

Essential Parameters for Structural Analysis and Dereplication by ¹H NMR Spectroscopy