Zur Kenntnis der Basen des Steinkohlenteer‐Schweröls. Über das 7‐Aza‐indol im Steinkohlenteer

Kruber, O.

doi:10.1002/cber.19430760118

Cited by 24 publications

(6 citation statements)

References 7 publications

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“…7-Azaindole was first obtained from coal tar in 1943. 22 Variolin B, a marine alkaloid containing azaindole moiety, isolated from the Antarctic sponge Kirkpatrickia varialosa, exhibited anti-cancer properties. [23][24][25] Its synthetically designed derivatives have been employed as potential protein kinase inhibitors which are important drug targets in various oncology studies.…”

Section: Introductionmentioning

confidence: 99%

Laser spectroscopic characterization of supersonic jet cooled 2,7-diazaindole

Baweja,

Kalal,

Maity

2023

Phys. Chem. Chem. Phys.

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Section: Introductionmentioning

confidence: 99%

Laser spectroscopic characterization of supersonic jet cooled 2,7-diazaindole

Baweja,

Kalal,

Maity

2023

Phys. Chem. Chem. Phys.

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“…The 7-azaindole was first obtained from coal tar in 1943. 22 Variolin B, a marine alkaloid which was isolated from an Antarctic sponge Kirkpatrickia varialosa exhibited anticancer properties. [23][24][25] Its synthetically designed derivatives have been employed as potential protein kinase inhibitors which are important drug targets in various oncology studies.…”

Section: Introductionmentioning

confidence: 99%

Laser Spectroscopic Characterization of Supersonic Jet Cooled 2,7-Diazaindole (27DAI)

Baweja

Kalal

Maity

2023

Preprint

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This article presents an extensively curated rich set of gas phase spectroscopic data of 2,7-diazaindole in the ground and excited states. Single vibronic level fluorescence spectroscopy (SVLF) was performed to determine the ground state vibrations of the molecule, which depicted a large Franck-Condon activity of the bands beyond 2600 cm-1. For the excited state, laser-induced fluorescence (LIF) and resonant two-colour two-photon ionization spectroscopy (R2PI) were performed. The band origin 〖(0〗_0^0) for S1←S0 transition appeared at 33910±1 cm-1 . The Frank-Condon active vibrational modes in the spectra were seen till 〖(0〗_0^0)+ 1600 cm-1 region, which suggested the similar ground and excited state geometries. The lower energy asymmetric vibrational modes at 207, 252 and 358 cm-1, observed in the excited state were absent in the SVLF spectrum. IR-UV double Hole Burning spectroscopy confirmed the absence of any other isomeric species in the molecular beam. Ionization potential (I.P) of the molecule was found to be 8.9310.001 eV, recorded using photoionization efficiency spectroscopy. The above value is significantly higher than the related azaindole derivatives. The ground and excited state N-H stretching frequencies of the molecule were determined using fluorescence-dip infrared spectra (FDIR) and resonant ion-dip infrared spectroscopy (IDIR), obtained at 3523 and 3467 cm-1, respectively. The lower value of NH in the electronic excited state implies the higher acidity of the group compared to the ground state. Moreover, to understand the excited state properties of the molecule, a comparative analysis of the experimental LIF/2C-R2PI spectra was done against Franck-Condon simulated spectra at three different levels of theories. The vibrational frequencies calculated at B3LYP-D4/def2-TZVPP showed the most accurate prediction on comparison with the experimentally detected symmetric modes in the ground state. However, in the excited state, the low energy asymmetric modes were correctly determined at B3LYP/def-SVP level of theory. This is most probably due to the distortion observed at the pyrazolyl ring leading to the appearance of asymmetric vibrational modes. However, all the three methods have shown nearly similar correlation with the experimental frequencies in the excited state, which was evident from their similar scaling factors.

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“…Indole derivatives represent a large and highly structurally diverse group of secondary metabolites of both terrestrial and marine origins with a wide range of biological activities. , However, their isosteres containing nitrogen atoms instead of carbons in the benzene ring of indoles are rare among natural products, with 7-azaindole from coal tar being the first example. Related secondary metabolites, variolins A–D, with azaindole moieties fused into polycyclic systems were previously isolated from the marine sponge Kirkpatrickia varialosa . , In comparison, synthetic azaindole compounds constitute a large and steadily growing group of new pharmaceutical precursors, , showing biological activities such as inhibition of Cdc7 kinase and blood coagulation factors …”

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confidence: 99%

Guitarrins A–E and Aluminumguitarrin A: 5-Azaindoles from the Northwestern Pacific Marine Sponge Guitarra fimbriata

et al. 2019

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Guitarrins A−E (1−5), the first natural 5azaindoles, and aluminumguitarrin A (1a), the first aluminumcontaining compound from marine invertebrates, were isolated from the sponge Guitarra f imbriata. The structures of these compounds were established using detailed analysis of 1D and 2D NMR data, mass spectra, and X-ray analysis of 1 and 1a. Compound 3 was proved to be a natural inhibitor of alkaline phosphatase.

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Zur Kenntnis der Basen des Steinkohlenteer‐Schweröls. Über das 7‐Aza‐indol im Steinkohlenteer

Cited by 24 publications

References 7 publications

Laser spectroscopic characterization of supersonic jet cooled 2,7-diazaindole

Laser spectroscopic characterization of supersonic jet cooled 2,7-diazaindole

Laser Spectroscopic Characterization of Supersonic Jet Cooled 2,7-Diazaindole (27DAI)

Guitarrins A–E and Aluminumguitarrin A: 5-Azaindoles from the Northwestern Pacific Marine Sponge Guitarra fimbriata

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