21829-25-4Relevant articles and documents
Protective role of the novel hybrid 3,5-dipalmitoyl-nifedipine in a cardiomyoblast culture subjected to simulated ischemia/reperfusion
Santa-Helena, Eduarda,Teixeira, Stefanie,Castro, Micheli Rosa de,Cabrera, Diego da Costa,D'Oca, Caroline Da Ros Montes,D'Oca, Marcelo G. Montes,Votto, Ana Paula S.,Nery, Luiz Eduardo Maia,Gon?alves, Carla Amorim Neves
, p. 356 - 364 (2017)
This work investigated the acute effects of the calcium channel blocker nifedipine and its new fatty hybrid derived from palmitic acid, 3,5-dipalmitoyl-nifedipine, compared to endocannabinoid anandamide during the process of inducing ischemia and reperfusion in cardiomyoblast H9c2 heart cells. The cardiomyoblasts were treated in 24 or 96-well plates (according to the test being performed) and maintaining the treatment until the end of hypoxia induction. The molecules were tested at concentrations of 10 and 100?μM, cells were treated 24?h after assembling the experimental plates and immediately before the I/R. Cell viability, apoptosis and necrosis, and generation of reactive oxygen species were evaluated. Nifedipine and 3,5-dipalmitoyl-nifedipine were used to assess radical scavenging potential and metal chelation. All tested molecules managed to reduce the levels of reactive oxygen species compared to the starvation?+?vehicle group. In in vitro assays, 3,5-dipalmitoyl-nifedipine showed more antioxidant activity than nifedipine. These results indicate the ability of this molecule to act as a powerful ROS scavenger. Cell viability was highest when cells were induced to I/R by both concentrations of anandamide and the higher concentration of DPN. These treatments also reduced cell death. Therefore, it was demonstrated that the process of hybridization of nifedipine with two palmitic acid chains assigns a greater cardioprotective effect to this molecule, thereby reducing the damage caused by hypoxia and reoxygenation in cardiomyoblast cultures.
Catalytic effect of nanosized metal oxides on the Hantzsch reaction
Fedorova,Koryakova,Valova,Ovchinnikova,Titova,Rusinov,Charushin
, p. 566 - 572 (2010)
The effect of nanosized copper and aluminum oxides, which have a higher sorption capacity than that of bulk samples, on the Hantzsch reaction was studied. The adsorption of starting benzaldehydes and ethyl acetoacetate on the surface of copper and aluminum nanooxides resulted in the activation of these molecules and accelerated the Hantzsch reaction. In addition, considerable activation of ammonia and intermediates (chalcone and enamine) on the surface of aluminum nanooxide facilitated an increase in the rate and selectivity of the process. The experimental results were used to develop a one-pot method for the preparation of nifedipine and nitrendipine.
Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines
Gordeev, Mikhail F.,Patel, Dinesh V.,Gordon, Eric M.
, p. 924 - 928 (1996)
N-Immobilized enamino esters 2 derived from amine-functionalized PAL or Rink polystyrene resins react with preformed 2-arylidene β-keto esters or directly with β-keto esters and aldehydes to afford, upon trifluoroacetic acid cleavage, 1,4-dihydropyridine (DHP) derivatives in good yields. The mechanism of this transformation on solid support has been studied using 13C NMR and IR spectroscopies. This new solid-phase synthesis has been applied to the preparation of several bioactive DHPs and is designed to be amenable to the 'split and pool' protocol for combinatorial library synthesis.
Conformational preferences and dynamics of 4-isoxazolyl-1,4-dihydropyridine calcium channel antagonists as determined by variable-temperature NMR and NOE experiments
Palmer, Robert B.,Andro, Tina M.,Natale, Nicholas R.,Andersen, Niels H.
, p. 495 - 504 (1996)
A series of 14 4-(3′,5′-disubstituted isoxazolyl)-1,4-dihydropyridine calcium channel antagonists were examined using variable-temperature proton nuclear magnetic resonance spectroscopy and nuclear Overhauser effect (NOE) experiments. Two of these compounds, the 1,4-dihydro-2,6-dimethyl-4-[5′-methyl-3′-(4″-fluorophenyl) isoxazol-4′-yl]-3,5-pyridinedicarboxylic acid dimethyl ester (3a) and 1,4-dihydro-2,6-dimethyl-4-[5′-methyl-3′-(4″-bromophenyl) isoxazol-4′-yl]-3,5-pyridinedicarboxylic acid dimethyl ester (5a), were synthesized to assist in the clarification of ambiguities discovered in the low-temperature spectra of 1,4-dihydro-2,6-dimethyl-4-(5′-methyl-3′-phenylisoxazol-4′yl)- 3,5-pyridinedicarboxylic acid diethyl ester (2b). The solid-state structure of 3a is also reported. The solution-state rotameric preferences of the 14 compounds are reported and compared with those calculated at the AM1 level. C-4 - C-4′ bond rotation barriers were also calculated at the AM1 level for nine of the systems examined. Several species failed to display temperature-dependent signals associated with hindered rotation owing to highly biased rotameric equilibria at the temperatures required to freeze out the rotation. The seven experimental rotation barriers (ΔG≠ from ≤26 to 40.4 kJ mol-1) reported are 1-6.8 kJ mol-1 higher than ΔH≠ calculated at the AM1 level).
METHODS FOR TREATING CHRONIC FATIGUE SYNDROME AND MYALGIC ENCEPHALOMYELITIS
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, (2021/03/13)
In one aspect the invention relates to a method of treatment selected from the group consisting of: (a) treating a symptom such as pain in a subject identified or diagnosed as having Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS); (b) treating a symptom such as pain in a subject having dysfunctional TRPM3 ion channel activity; (c) restoring NK cell function in a subject having dysfunctional TRPM3 ion channel activity; and (d) restoring calcium homeostasis in a subject having dysfunctional TRPM3 ion channel activity. The method comprises the step of administering to the subject a therapeutically effective amount of at least one therapeutic compound selected from the group consisting of: (i) an opioid receptor antagonist; (ii) an opioid antagonist; and (iii) a therapeutic compound that restores TRPM3 ion channel activity. In some embodiments the therapeutic compound is naltrexone hydrochloride.
Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
, p. 9561 - 9568 (2021/08/06)
A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
Aqueous CO2fixation: construction of pyridine skeletons in cooperation with ammonium cations
Fan, Weibin,Guo, Shiwei,Huang, Deguang,Li, Yinghua,Xiang, Shiqun,Zhang, Wei
supporting information, p. 7950 - 7955 (2021/10/29)
A simple and green method is explored for the synthesis of fused pyridines by [2 + 2 + 1 + 1] the cycloaddition of ketones with an ammonium cation under a CO2atmosphere. The reactions employed ammonium cation as a nitrogen source and CO2gas as a carbon source in an aqueous solution. Monoethanolamine (MEA) was used as an additive to increase the solubility of CO2in an aqueous solution. The scope and versatility of the method are demonstrated with 38 examples. Products are found to be photosensitive and show potential applications as organic optoelectronic materials. A selectfluor-promoted reaction mechanism is proposed based on the experimental studies. Our work is superior as it is a metal-free system, uses CO2as a carbon source and MEA as an additive in aqueous synthesis.
Preparation method of nifedipine
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Paragraph 0051-0061, (2020/07/02)
The invention provides a preparation method of nifedipine, belonging to the technical field of organic drug synthesis. According to the preparation method of nifedipine, under the action of a nitrogen-containing heterocyclic carboxylic acid catalyst, an intermediate methyl (o-nitrobenzylidene)acetoacetate and 3-aminocrotonic acid methyl ester are subjected to an addition reaction in a C1-C4 loweraliphatic alcohol solvent so as to prepare nifedipine. The time of the addition reaction is obviously shortened, and particularly, the content of special impurities in a crude nifedipine product is obviously reduced, so a subsequent refining process is greatly simplified, and an efficient, simple, convenient and novel method is provided for the batch production of the nifedipine in the future.
Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex
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Paragraph 0041; 0070-0071, (2019/12/02)
The invention belongs to the technical field of catalytic organic synthesis, and particularly relates to a preparation method and application of a novel ionic beta-naphthol aldehyde Schiff base zirconium complex. Zirconium atoms are coordinated with a beta-naphthol aldehyde Schiff base ligand and water molecules, and two perfluoroalkyl (aryl) sulfonic acid groups are combined with central atom zirconium through covalent bonds and ionic bonds respectively. The preparation method comprises the following steps: dissolving beta-naphthol aldehyde Schiff base zirconium dichloride in a solvent, adding a silver salt under the protection of N2, reacting the mixture for 1-4 hours in a dark place at room temperature, performing filtration, adding n-hexane into filtrate until layering, putting the solution into a refrigerator, and freezing the solution for 24 hours to separate out the beta-naphthol aldehyde Schiff base zirconium complex. The beta-naphthol aldehyde Schiff base zirconium complex hashigh air stability and strong Lewis acidity, and can efficiently catalyze the Hantzsch reaction of aldehyde, beta-ketoester and ammonium acetate to synthesize 1,4-dihydropyridine derivatives.
Method for synthesizing 1,4-dihydropyridines derivatives
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Paragraph 0138; 0139, (2017/10/27)
The invention relates to a method for synthesizing 1,4-dihydropyridines derivatives. According to the method, a fluorescence-marked nonmetal organic boron-nitrogen lewis acid-alkali dual-functional complex is used as a catalyst, so that the pollution of heavy metals is effectively avoided; the catalyst can be recycled, and a residual amount of the catalyst in a product can be rapidly detected; and the source of raw materials is wide, the target yield is close to 100 percent, the reaction process is a homogenous reaction, and a product is obtained by virtue of chromatographic separation. The whole reaction system can be directly amplified, and the industrialization prospect is significant.
