35896-58-3Relevant academic research and scientific papers
Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues
Khrustalev, Victor N.,Muravsky, Egor A.,Semenov, Victor V.,Shinkarev, Ilia Yu.,Varakutin, Alexander E.
, p. 599 - 601 (2020/10/18)
A technologically advanced protocol has been developed for converting plant allyl(polyalkoxy)benzenes to methyl- and propyl(polyalkoxy)benzenes being intermediates in the syntheses of coenzyme Q0 analogues. The key stage of allyl and benzaldehyde moieties hydrogenation was carried out in a periodical autoclave mode on highly porous ceramic block Pd-catalysts. These catalysts possess large surface area, low hydraulic resistance, significant thermal and mechanical stabililty, multiple cycling and easy regeneration, which can dramatically reduce Pd consumption.
Efficient synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone: key intermediate for preparing Coenzyme Q
Qiu, Yong-Fu,Lu, Bin,Yan, Yi-Yu,Luo, Wan-Yue,Wang, Jin,Hu, Xiao
, p. 2745 - 2748 (2019/08/21)
The title compound, a key intermediate for preparing Coenzyme Qn family, was prepared in an excellent yield by a reaction sequence starting from the commercially available 3,4,5-trimethoxytoluene 1 via bromination, methoxylation and oxidation reactions. A
Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues
Wang, Jin,Xia, Fei,Jin, Wen-Bin,Guan, Jin-Yan,Zhao, Hang
, p. 214 - 218 (2016/08/25)
A new strategy for the efficient synthesis of C-5 heterocyclyl substituted Coenzyme Q analogues was developed by N-alkylation of bromomethylated quinone 11 with a series of amines 12 under metal-free conditions. In vitro antioxidant activities of these Coenzyme Q analogues were evaluated and compared with commercial antioxidant Coenzyme Q10 by employing DPPH assay. All these N-heterocyclyl substituted Coenzyme Q analogues are found to be exhibiting good antioxidant properties and may be used as potent antioxidants for combating oxidative stress.
QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS
-
Page/Page column 40, (2015/11/18)
The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment and/or prophylaxis of glaucoma and ocular hypertension.
Alkyne-tag Raman imaging for visualization of mobile small molecules in live cells
Yamakoshi, Hiroyuki,Dodo, Kosuke,Palonpon, Almar,Ando, Jun,Fujita, Katsumasa,Kawata, Satoshi,Sodeoka, Mikiko
supporting information, p. 20681 - 20689 (2013/02/23)
Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells. An examination of structure-Raman shift/intensity relationships revealed that alkynes conjugated to an aromatic ring and/or to a second alkyne (conjugated diynes) have strong Raman signals in the cellular silent region and can be excellent tags. Using these design guidelines, we synthesized and imaged a series of alkyne-tagged coenzyme Q (CoQ) analogues in live cells. Cellular concentrations of diyne-tagged CoQ analogues could be semiquantitatively estimated. Finally, simultaneous imaging of two small molecules, 5-ethynyl-2′-deoxyuridine (EdU) and a CoQ analogue, with distinct Raman tags was demonstrated.
Bis-coenzyme Q0: Synthesis, characteristics, and application
Wang, Xiuwen,Ma, Wei,Ying, Yilun,Liang, Jie,Long, Yi-Tao
supporting information; experimental part, p. 1064 - 1073 (2011/10/11)
A methylene-bridged bis-coenzyme Q0, bis(2,3-dimethoxy-5-methyl- l,4-benzoquinone)methane (Bis-CoQ0), that shows intramolecular electronic communications has been synthesized for the first time. By employing electrochemical, in situ UV/Vis, and electron paramagnetic resonance (EPR) spectroelectrochemical techniques, the unstable reduced intermediate speciesa-monoradicals, diamagnetic dianions and tetraanions of Bis-CoQ 0a-have been observed. The electron-transfer process can be defined as a three-step reduction process with a total of four electrons in solution in CH3CN. The chemical reaction in the third redox step process was confirmed by variable temperature cyclic voltammetry. In an aprotic CH 3CN solution, the peak potential separation between electron-transfer steps diminished sequentially with increasing concentration of water. The hydrogen-bonding interactions between water and the electrochemically reduced intermediates of Bis-CoQ0 can be estimated by peak potential shifts. The electronic communications of Bis-CoQ0 may have been blocked when one reduction peak was observed with proper quantities of water in CH 3CN solution. The antioxidant defense capacity of Bis-CoQ 0-protected cells has also been assessed.
In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues
Ma, Wei,Zhou, Hao,Ying, Yi-Lun,Li, Da-Wei,Chen, Guo-Rong,Long, Yi-Tao,Chen, Hong-Yuan
experimental part, p. 5990 - 6000 (2011/09/19)
Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.
Reversible redox of NADH and NAD+ at a hybrid lipid bilayer membrane using ubiquinone
Ma, Wei,Li, Da-Wei,Sutherland, Todd C.,Li, Yang,Long, Yi-Tao,Chen, Hong-Yuan
supporting information; experimental part, p. 12366 - 12369 (2011/10/02)
Here, we report the reversible interconversion between NADH and NAD + at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.
A green and efficient synthesis of 1-chloromethyl -2,3,4,5-tetramethoxy6- methylbenzene
Wang, Jin,Yang, Jian,Yang, Bo,Hu, Xiao,Sun, Jia-Qiang,Yang, Tao
, p. 717 - 718 (2011/04/22)
The title compound, a key intermediate for preparing coenzyme Q analogues, was prepared in excellent yield by a reaction sequence starting from the commercially available 3,4,5-trlmethoxybenzadehyde via Wolff-Kishner reduction, selective bromination, methoxylation and Blanc chloromethylation reaction.
