- Synthesis of three imidazole derivatives and corrosion inhibition performance for copper
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Three imidazole derivatives, including 3-(4-(2,4-dichlorophenyl)-5-methyl-1H-imidazol-2-yl)pyridine (PDI), 2-(4-(2,4-dichlorophenyl)-5-methyl-1H-imidazol-2-yl)pyrazine (PAI) and 2-(4-(2,4-dichlorophenyl)-5-methyl-1H-imidazol-2-yl)pyrimidine (PMI), were synthesized. The structure of these compounds was confirmed by LC-MS, 1H NMR, 13C NMR and FTIR spectra. The inhibition performance in 3.5 wt% NaCl was investigated by electrochemical measurement and surface analysis. Results show that the corrosion efficiency of PDI (95.93%) was higher than PAI (69.61%) and PMI (20.46%), which is consistent with the adsorption energy calculated by molecular dynamics simulation. The corrosion inhibition mechanism could be explained by the metal–organic polymer film formed on the copper surface: on the one hand, the π-system formed by aromatic rings is tightly adsorbed on the copper substrates; on the other hand, the nitrogen atoms in the imidazole ring are coordinated with the metal ions in solution to form metal–organic polymer which could improve the compactness of the hydrophobic film.
- He, Kang,Hou, Yanggao,Lei, Jiaheng,Ma, Sicai,Yang, Ze,Zhu, Limeng
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- AMINOPYRIMIDINE DERIVATIVES AND THEIR USE AS ARYL HYDROCARBON RECEPTOR MODULATORS
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The present invention relates to novel compounds effective as modulators Aryl hydrocarbon receptor (AhR), pharmaceutical composition comprising the compounds for the modulation of AhR, or prevention or treatment of a disease, disorder, or condition associ
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Paragraph 636-642
(2021/10/02)
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- Investigation of the possible pharmacologically active forms of the nicotinic acetylcholine receptor agonist anabaseine
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Three major forms of the nicotinic agonist toxin anabaseine (cyclic iminium, cyclic imine and the monocationic open-chain ammonium-ketone) co-exist in almost equal concentrations at physiological pH.We asked the question: Which of these forms is pharmacologically active? First, we investigated the pH dependence of anabaseine inhibition of [3H]-methylcarbamylcholine binding at rat brain α4β2 nicotinic acetylcholine receptors (nAChRs). These experiments indicated that one or both monocationic forms interact with the orthosteric binding site for ACh. However, since they occur at equal concentrations near physiological pH, we employed another approach, preparing a stable analog of each form and examining its agonist activities and binding affinities at several vertebrate brain and neuromuscular nAChRs. Only 2-(3-pyridyl)-1,4,5,6-tetrahydropyrimidine monohydrogen chloride (PTHP), the cyclic iminium analog, displayed nAChR potencies and binding affinities similar to anabaseine. The cyclic imine analog 2,3'-bipyridyl and the open-chain ammonium-ketone analog 5-methylamino-1-(3-pyridyl)-1-pentanone (MAPP), displayed ≤1% of the activity predicted if the one form was solely active. The lower potency of weakly basic 2,3'-bipyridyl can be explained by the presence of a small concentration of its monocationic form. Since the open chain ammonium-ketone monocationic form of anabaseine has some structural similarity to the neurotransmitter GABA, we also tested the ability of anabaseine and its 1,2-dehydropyrrolidinyl analog myosmine to activate a mammalian GABAA receptor, but no activity was detected. We conclude that the monocationic cyclic iminium is the form which avidly binds and activates vertebrate nAChRs.
- Andrud, Kristin,Xing, Hong,Gabrielsen, Bjarne,Bloom, Linda,Mahnir, Vladimir,Lee, Stephen,Green, Benedict T.,Lindstrom, Jon,Kem, William
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- Synthesis and evaluation of 2-pyridinylpyrimidines as inhibitors of HIV-1 structural protein assembly
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In an effort to identify an HIV-1 capsid assembly inhibitor with improved solubility and potency, we synthesized two series of pyrimidine analogues based on our earlier lead compound N-(4-(ethoxycarbonyl)phenyl)-2-(pyridine-4-yl)quinazoline-4-amine. In vitro binding experiments showed that our series of 2-pyridine-4-ylpyrimidines had IC50values higher than 28 μM. Our series of 2-pyridine-3-ylpyrimidines exhibited IC50values ranging from 3 to 60 μM. The congeners with a fluoro substituent introduced at the 4-N-phenyl moiety, along with a methyl at C-6, represent potent HIV capsid assembly inhibitors binding to the C-terminal domain of the capsid protein.
- Ko?í?ek, Milan,?těpánek, Ond?ej,Parkan, Kamil,Berenguer Albi?ana, Carlos,Pávová, Marcela,Weber, Jan,Kr?usslich, Hans-Georg,Konvalinka, Jan,Machara, Ale?
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supporting information
p. 3487 - 3490
(2016/07/21)
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- Capsule-bowl conversion triggered by a guest reaction
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A new M20L8 coordination capsule was synthesized. Owing to the structural flexibility and dynamic properties, the capsule showed wide scope for guest encapsulation. Furthermore, unique capsule-bowl conversion occurred upon a large guest encapsulation or a guest reaction.
- Wang, Shitao,Sawada, Tomohisa,Fujita, Makoto
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supporting information
p. 11653 - 11656
(2016/10/04)
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- COMPOUNDS FOR USE IN INHIBITING HIV CAPSID ASSEMBLY
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The present invention relates a compound or a pharmaceutically acceptable salt or solvate thereof for use in inhibiting HIV capsid assembly, wherein the compound is a pyrimidine being at least substituted in two positions, preferably in 2 and 4 position o
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Page/Page column 29
(2014/09/03)
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- 2,4-Diaryl-4,6,7,8-tetrahydroquinazolin-5(1H)-one derivatives as anti-HBV agents targeting at capsid assembly
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A series of novel 2,4-diaryl-4,6,7,8-tetrahydroquinazolin-5(1H)-one derivatives were designed and synthesized as potent inhibitors of HBV capsid assembly. These compounds arose from efforts to rigidify an earlier series of heteroaryldihydropyrimidines (HA
- Zhu, Xuejun,Zhao, Guoming,Zhou, Xiaoping,Xu, Xiaoqian,Xia, Guangqiang,Zheng, Zhibing,Wang, Lili,Yang, Xiaohong,Li, Song
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scheme or table
p. 299 - 301
(2010/04/05)
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- Synthesis and SAR of 6-chloro-4-fluoroalkylamino-2-heteroaryl-5-(substituted)phenylpyrimidines as anti-cancer agents
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The synthesis and SAR of a series of 6-chloro-4-fluoroalkylamino-2-heteroaryl-5-(substituted)phenylpyrimidines as anti-cancer agents are described. This series of 2-heteroarylpyrimidines was developed by modifying a series of anti-tumor [1,2,4]triazolo[1,5-a]pyrimidines and 2-cyanoaminopyrimidines we reported earlier. For the 2-heteroaryl group, the best activity is obtained when the heteroaryl group has a nitrogen atom at the ortho-position to the pyrimidyl core. The structure-activity relationship for the rest of the molecule in this 2-heteroarylpyrimidine series mimics that of the [1,2,4]triazolo[1,5-a]pyrimidine series. Like triazolopyrimidines and 2-cyanoaminopyrimidines, the 2-heteroarylpyrimidines retain the capability to overcome multidrug resistance due to Pgp. Mechanism of action studies showed that the lead compounds behaved in the same manner as triazolopyrimidines and 2-cyanoaminopyrimidines. The lead compounds in this series are more potent than the corresponding triazolopyrimidines in vitro and in vivo. Compound 21 (PTI-868) showed tumor growth inhibition in several nude mouse xenograft models, and was selected to advance to preclinical development.
- Zhang, Nan,Ayral-Kaloustian, Semiramis,Nguyen, Thai,Hernandez, Richard,Lucas, Judy,Discafani, Carolyn,Beyer, Carl
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experimental part
p. 111 - 118
(2011/02/25)
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- 2, 6 BISHETEROARYL-4-AMINOPYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
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4-Aminopyrimidine derivatives of formula (I) FORMULA heteroaryl groups, including pharmaceutically acceptable salts thereof, wherein R1 and R2 are adenosine A2A receptor antagonists useful in the treatment of movement disorders such as Parkinson's disease.
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Page/Page column 97
(2010/02/12)
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- 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof
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Novel 6-heterocyclyl-pyrazolo[3,4-d]pyrimidin-4-ones, useful in treating cardiovascular disease, are prepared by reacting a 5-amino-1H-pyrazole-4-carboxamide with heterocyclylcarboxaldehyde or by reacting a 5-amino-1H-pyrazole-4-carbonitrile with a heterocyclylcarboxamidine, followed by diazotization and hydrolysis of the resulting 4-amino-6-heterocyclyl-pyrazolo[3,4-d]pyrimidine.
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- Substituted 5-amino-1,2,4-thiadiazoles with pharmaceutical activity
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Pharmaceutical compounds of the following formula are described: in which R1 is hydrogen, C1 4 alkyl, C1 4 alkoxy-C1 4 alkyl, hydroxy-C1 4 alkyl, optionally substituted phenyl, optionally substituted phenyl-C1 4 alkyl or a heterocycle selected from: where R3 is hydrogen, C1 4 alkyl, C1 4 alkoxy, nitro, halo, cyano, trifluoromethyl, carboxyl or -CONH2, and R4 is C1 4 alkyl; and R2 is hydrogen, C1 4 alkyl, phenyl or thienyl substituted with a carboxyl or C1 4 alkoxy-carbonyl group, an acyl group of the formula R5CO- where R5 is hydrogen, C1 4 alkyl, C1 4 alkoxy-C1 4 alkyl, halo C1 4 alkyl, C1 4 alkoxy, halo-C1 4 alkoxy, phenyl, phenyl-C1 4 alkyl, -NHC1 4 alkyl, -NH phenyl or where R6 is C1 4 alkyl, or a group of the formula -CH=C(COC1 4 alkoxy)2; or a salt thereof.
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- Preparation of Triazolopyrimidines as Potential Antiasthma Agents
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With the use of the human basophil histamine release assay, 5-aryl-2-aminotriazolopyrimidines were found to be active as mediator release inhibitors.These compounds were prepared by reacting arylamidines with sodium ethyl formylacetate or with ethyl propiolate to give pyrimidinones.Treatment with phosphorus oxychloride gave a chloropyrimidine, which was converted to a hydrazinopyrimidine with hydrazine.Cyclization, using cyanogen bromide, gave the triazolopyrimidines, after a Dimroth rearrangement.Following a structure-activity evaluation, the5--2-amino (8-10), 5-(3-bromophenyl)-2-amino (8-13), 5--2-amino (8-11), and 5-(4-pyridinyl)-2-amino (6-7) compounds were found to have the best activity.They were chosen for further pharmacological and toxicological study.
- Medwid, Jeffrey B.,Paul, Rolf,Baker, Jannie S.,Brockman, John A.,Du, Mila T.,et al.
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p. 1230 - 1241
(2007/10/02)
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