607-67-0Relevant articles and documents
Synthesis, spectroscopic investigations and computational study of monomeric and dimeric structures of 2-methyl-4-quinolinol
Pourmousavi, Seied Ali,Kanaani, Ayoub,Ghorbani, Fatemeh,Damghani, Kobra Khorsi,Ajloo, Davood,Vakili, Mohamad
, p. 1237 - 1274 (2016)
The present study aimed to determine an efficient and solvent-free method to synthesize 2-methyl-4-quinolinol (2MQ, also known as 4-hydroxy-2-methylquinoline) and includes spectroscopic investigations and computational studies. Molecular geometry and vibrational wavenumbers of 2MQ were investigated using the density functional (DFT/B3LYP) method with 6-311++G(d,p) and 6-311++G(2d,p) basis sets. According to calculations, the keto form of 2MQ is more stable than the annual form, and the dimeric conformation is predicted to be more stable than the monomeric conformations. A detailed analysis of the nature of the hydrogen bonding, using topological parameters such as electronic charge density, Laplacian, kinetic and potential energy density evaluated at the bond critical point, is also presented. The 1H nuclear magnetic resonance chemical shifts of the molecule were calculated by the GIAO method. The molecule orbital contributions were studied by using total (TDOS) and partial (PDOS) density of states. The UV-visible spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were investigated by the time-dependent DFT (TD-DFT) approach. The linear polarizability (α) and the first-order hyperpolarizability (β) values of the investigated molecule were computed using DFT quantum mechanical calculations. The results show that the 2MQ molecule may have a nonlinear optical comportment with non-zero values. The stability and charge delocalization of the molecule was studied by natural bond orbital analysis. In addition, a molecular electrostatic potential map of the title compound was studied for predicting the reactive sites. Local reactivity descriptors, such as Fukui functions, local softness and electrophilicity indices analyses, were studied to determine the reactive sites within the molecule.
Hydrolyses of 2- and 4-Fluoro N-Heterocycles. 4. Proton Inventories of the Hydrolyses of 2-Fluoro-1-methylpyridinium Iodide, 4-Fluoroquinaldine, and 2-Chloro-1-methylpyrimidinium Triflate
Muscio, Oliver J.,Meng, Jialun,Wang, Haisheng,Shi, Songyuan
, p. 6454 - 6459 (1992)
Rate constants for the hydrolyses of 2-fluoro-1-methylpyridinium iodide (3), 4-fluoroquinaldine (4), and 2-chloro-1-methylpyrimidinium triflate (5) in 2 * 10-3 M aqueous sulfuric acid, in D2O/D2SO4, and in mixed H2O/H2SO4-D2O/D2SO4 media are reported.Significant solvent deuterium kinetic isotope effects are evident, with kH/kD = 2.07 for 3, 1.62 for 4, and 2.12 for 5.The results of the proton inventories for the hydrolyses of 3 and 5 are best fit by a form of the Gross-Butler equation for three nearly equivalent sites with fractionation factors of 0.78.The proton inventory of 4 does not yield a unique solution to the Gross-Butler equation, but the results are also consistent with three transition state sites with nearly equal fractionation factors of 0.72-0.78, as well as an additional transition-state site with Φ > 1 and a reactant site with Φ /= 1.These proton inventories are consistent with mechanisms in which nucleophilic addition of water in the rate-determining step is assisted by proton-transfer to a second water molecule, with development of an "immature hydronium ion" in the transition state.Mechanisms with cyclic proton transfer are also consistent, but are less satisfactory as hydrolysis routes.
Triphenylamine - quinoline derivatives and adopts its modification for detecting the oncogene related G - quadruplex optical fiber sensor
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Paragraph 0047-0051, (2019/07/10)
The invention belongs to the field of molecular biology, in particular to triphenylamine - quinoline derivatives and adopts its modification for detecting the oncogene related G - quadruplex optical fiber sensor, the present invention provides a new structure of the triphenylamine - quinoline derivatives, the quinoline derivative by the method of the present invention modified with activated hydroxyl of the surface layer of the optical fiber sensor of the optical fiber, the optical fiber sensor can be quickly specific detection HRAS G - quadruplex and HTG - 21 G - quadruplex, makes up for the optical fiber DNA sensor detecting G4 - DNA vacancies of the chain, since many of the cancer disease is due to the initiation of the cells in vivo G4 - DNA over-expression of the chain, the invention is specific detection G4 DNA offers a high-efficient and swift sensor, the sensor is expected to be applied to the biological and clinical analysis.
Syntheses and evaluation of new Quinoline derivatives for inhibition of hnRNP K in regulating oncogene c-myc transcription
Shu, Bing,Zeng, Ping,Kang, Shuangshuang,Li, Peng-Hui,Hu, Dexuan,Kuang, Guotao,Cao, Jiaojiao,Li, Xiaoya,Zhang, Meiling,An, Lin-Kun,Huang, Zhi-Shu,Li, Ding
, p. 1 - 17 (2019/01/04)
Aberrant overexpression of heterogeneous nuclear ribonucleoprotein K (hnRNP K) is a key feature in oncogenesis and progression of many human cancers. hnRNP K has been found to be a transcriptional activator to up-regulate c-myc gene transcription, a critical proto-oncogene for regulation of cell growth and differentiation. Therefore, down-regulation of c-myc transcription by inhibiting hnRNP K through disrupting its binding to c-myc gene promoter is a potential approach for cancer therapy. In the present study, we synthesized and screened a series of Quinoline derivatives and evaluated their binding affinity for hnRNP K. Among these derivatives, (E)-1-(4-methoxyphenyl)-3-(4-morpholino-6-nitroquinolin-2-yl)prop-2-en-1-one (compound 25) was determined to be the first-reported hnRNP K binding ligand with its KD values of 4.6 and 2.6 μM measured with SPR and MST, respectively. Subsequent evaluation showed that the binding of compound 25 to hnRNP K could disrupt its unfolding of c-myc promoter i-motif, resulting in down-regulation of c-myc transcription. Compound 25 showed a selective anti-proliferative effect on human cancer cell lines with IC50 values ranged from 1.36 to 3.59 μM. Compound 25 exhibited good tumor growth inhibition in a Hela xenograft tumor model, which might be related to its binding with hnRNP K. These findings illustrated that inhibition of DNA-binding protein hnRNP K by compound 25 could be a new and selective strategy of regulating oncogene transcription instead of targeting promoter DNA secondary structures such as G-quadruplexes or i-motifs.
