Synthesis of 5H-Pyrazolo[4,3-c]quinolines

Ivachtchenko, Alexandre V.; Silin, Olexiy V.; Савченко, Т. И.; Kovalenko, Sergiy M.; Nikitchenko, V. M.

doi:10.3987/com-04-10092

Cited by 16 publications

(5 citation statements)

References 2 publications

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“…The regioisomeric mixture of compounds 26 and 29 derived from the oxidation of 21 was treated with concentrated aqueous ammonia. 50 This ammonolysis reaction afforded respective regioisomeric products 30 and 31 as an almost chromatographically inseparable mixture (Scheme 1). However, a small amount of compound 30 could be isolated.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Furanosesquiterpenes and Related Natural Products from Myoporum Species: Isolation and Semisynthesis

Gyeltshen

Deans

et al. 2023

J. Nat. Prod.

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Myoporum species are recognized as toxic plants. Essential oils from the leaves of these species contain furanosesquiterpenes, which comprise the active toxins. In this report, natural products isolation studies of three Myoporum species (M. insulare, M. parvifolium, and M. montanum) afforded two previously unreported furanosesquiterpenes (24 and 25) and three unprecedented γ-lactone-containing analogues (26–28), along with nine previously reported furanosesquiterpenes and five other natural products. Among the 14 furanosesquiterpenes and related compounds isolated in this study, we observed three distinct types of furanosesquiterpene structures isolated from each of these Myoporum species. Semisyntheses of four sesquiterpene natural products were completed from (−)-ngaione over two steps in each case. This included the synthesis of the lactam-containing sesquiterpene myoporumine A.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Furanosesquiterpenes and Related Natural Products from Myoporum Species: Isolation and Semisynthesis

Gyeltshen

Deans

et al. 2023

J. Nat. Prod.

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“…The Optical Excalibur bench contains a interferometer (it is piezoelectric aligned dynamically), far-, mid-and near-infrared ranges, dual internal detector snd sources, four Raman ports, emission and external beams, and a host of accessories. Mass spectra are recorded in MX-1303 [7][8].…”

Section: A Materials and Methodsmentioning

confidence: 99%

Synthesis, X-Ray Characterization, IR Vibrational Frequencies, NMR Chemical Shifts And DFT Properties Of 2,7-Dimethyl-2,7-Dicyanide-3,6-Diazaoctane

Chuliyev¹,

Yusupova²,

Kodirov³

et al. 2020

IJITEE

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In our research work, we have synthesized 2,7-dimethyl-2,7-dicyanide-3,6-diazaoctane and confirmed its structure by using X-ray diffraction and spectrometric experiments. The experimentally obtained results were compared with theoretically results. The electronic properties of 2,7-dimethyl-2,7-dicyanide-3,6-diazaoctane have been analyzed by DFT. The energy band gap is computed at -1.800349 eV for the 2,7-dimethyl-2,7-dicyanide-3,6-diazaoctane shows that this molecular structure is lower kinetic stability and more reactivity. Molecular electrostatic potential map of electron density on an isosurface of electrostatic potential for the 2,7-dimethyl-2,7- dicyanide-3,6-diazaoctane indicates electron rich reactive sites were located over nitrogen (N≡C) atoms belong cyanide groups. Our research results will be important for syntheses new α-aminonitriles organic compounds and calculate theoretical properties of them.

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“…Thus, hybrids of fluoroquinolones with derivatives of phenylthiazole, quinazoline, thiazolidine, thiadiazole, pyrimidine, dithienylethene, and 1,2,4-triazole are widely described in the literature (Suaifan & Mohammed, 2019;Jia & Zhao, 2021). Our scientific team has been fruitfully working in this direction (Bylov et al, 1999;Silin et al, 2004;Savchenko et al, 2007;Hryhoriv et al, 2022;Vaksler et al, 2022). At the same time, a thorough analysis of literature sources demonstrates that modification of the 3-position of fluoroquinolones is promising and insufficiently researched (Oniga et al, 2018).…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, analysis of molecular and crystal structures, estimation of intermolecular interactions and biological properties of 1-benzyl-6-fluoro-3-[5-(4-methylcyclohexyl)-1,2,4-oxadiazol-3-yl]-7-(piperidin-1-yl)quinolin-4-one

et al. 2023

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The title compound, C30H33N4O2F, can be obtained via a two-step synthetic scheme involving 1-benzyl-6-fluoro-4-oxo-7-(piperidin-1-yl)-1,4-dihydroquinoline-3-carbonitrile as a starting compound that undergoes substitution with hydroxylamine and subsequent cyclization with 4-methylcyclohexane-1-carboxylic acid. It crystallizes from 2-propanol in the triclinic space group P\overline{1} with a molecule of the title compound and one of 2-propanol in the asymmetric unit. After the molecular structure was clarified using NMR and LC/MS, the molecular and crystalline arrangements were defined with SC-XRD. A Hirshfeld surface analysis was performed for a better understanding of the intermolecular interactions. One strong (O—H...O) and three weak [C—H...F (intramolecular) and two C—H...O] hydrogen bonds were found. The contributions of short contacts to the Hirshfeld surface were estimated using two-dimensional fingerprint plots showing that O...H/H...O, C...H/H...C and C...C contacts are the most significant for the title compound and O...H for the 2-propanol. The crystal structure appears to have isotropically packed tetramers containing two molecules of the title compound and two molecules of 2-propanol as the building unit according to analysis of the distribution of pairwise interaction energies. A molecular docking study was carried out to evaluate the interactions of the title compound with the active centers of macromolecules corresponding to viral targets, namely, anti-hepatitis B activity [HBV, capsid Y132A mutant (VCID 8772) PDB ID: 5E0I] and anti-COVID-19 main protease activity (PDB ID: 6LU7). The data obtained revealed a noticeable affinity towards them that exceeded that of the reference ligands.

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Synthesis of 5H-Pyrazolo[4,3-c]quinolines

Cited by 16 publications

References 2 publications

Furanosesquiterpenes and Related Natural Products from Myoporum Species: Isolation and Semisynthesis

Furanosesquiterpenes and Related Natural Products from Myoporum Species: Isolation and Semisynthesis

Synthesis, X-Ray Characterization, IR Vibrational Frequencies, NMR Chemical Shifts And DFT Properties Of 2,7-Dimethyl-2,7-Dicyanide-3,6-Diazaoctane

Synthesis, analysis of molecular and crystal structures, estimation of intermolecular interactions and biological properties of 1-benzyl-6-fluoro-3-[5-(4-methylcyclohexyl)-1,2,4-oxadiazol-3-yl]-7-(piperidin-1-yl)quinolin-4-one

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