89536-71-0Relevant articles and documents
Exploring new scaffolds for the dual inhibition of hiv-1 rt polymerase and ribonuclease associated functions
Alcaro, Stefano,Cirone, Italo,Corona, Angela,Cottiglia, Filippo,Deplano, Serenella,Distinto, Simona,Esposito, Francesca,Mátyus, Péter,Maccioni, Elias,Meleddu, Rita,Onali, Alessia,Ortuso, Francesco,Sanna, Erica,Secci, Daniela,Sequeira, Lisa,Tramontano, Enzo
, (2021)
Current therapeutic protocols for the treatment of HIV infection consist of the combination of diverse anti-retroviral drugs in order to reduce the selection of resistant mutants and to allow for the use of lower doses of each single agent to reduce toxicity. However, avoiding drugs interactions and patient compliance are issues not fully accomplished so far. Pursuing on our investigation on potential anti HIV multi-target agents we have designed and synthesized a small library of biphenylhydrazo 4-arylthiazoles derivatives and evaluated to investigate the ability of the new derivatives to simultaneously inhibit both associated functions of HIV reverse transcriptase. All compounds were active towards the two functions, although at different concentrations. The substitution pattern on the biphenyl moiety appears relevant to determine the activity. In particular, compound 2-{3[(2-{4-[4-(hydroxynitroso)phenyl]-1,3-thiazol-2-yl} hydrazin-1-ylidene) methyl]-4-methoxyphenyl} benzamide bromide (EMAC2063) was the most potent towards RNaseH (IC50 = 4.5 mM)-and RDDP (IC50 = 8.0 mM) HIV RT-associated functions.
Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction
?zdemir, ?smail,Akko?, Mitat,Alt?n, Serdar,Bu?day, Nesrin,Ya?ar, Sedat
, (2021/08/03)
A novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe3O4@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy?(TEM), Energy Dispersive X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES)?analysis was used to determine the exact amount of Pd (0.33?wt%) in Fe3O4@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst's structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki–Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a K2CO3 at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products in excellent yields with spectacular TOFs values (up to 1,960,339?h?1); in the presence of 1?mg of Fe3O4@SBA-15@NHC-Pd catalyst (contains 3.1 × 10–6?mol% Pd) at room temperature in aqueous media. After reusability experiments, it is found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. Graphic Abstract: [Figure not available: see fulltext.]
Magnetite@MCM-41 nanoparticles as support material for Pd-N-heterocyclic carbene complex: A magnetically separable catalyst for Suzuki–Miyaura reaction
Akko?, Mitat,Bu?day, Nesrin,Alt?n, Serdar,Ya?ar, Sedat
, (2021/03/22)
The Magnetite@MCM-41@NHC@Pd catalyst was obtained with Pd metal bound to the NHC ligand anchored to the surface of Fe3O4@MCM-41. It was characterized by Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy disperse X-ray analysis (EDX), thermogravimetric analysis (TGA), differential thermal analysis (DTA), and scanning electron microscopy (SEM). The amount of Pd in the Magnetite@MCM-41@NHC@Pd was measure by inductively coupled plasma–optical emission spectroscopy (ICP-OES) analysis. The catalytic activity of Magnetite@MCM-41@NHC@Pd heterogeneous catalyst done on Suzuki–Miyaura reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions afforded excellent yields and up to 408404 Turnover Frequency (TOF) h?1 in the presence of 2 mg of Magnetite@MCM-41@NHC@Pd catalyst (0.0564 mmol g?1, 0.01127 mmol% Pd) at room temperature in 2-propanol/H2O (1:2). Moreover, Magnetite@MCM-41@NHC@Pd catalyst was recover by applying the magnet and reused for another reaction. The catalyst showed excellent structural and chemical stability and reused ten times without a substantial loss in its catalytic performance.
N-heterocyclic carbene Pd(II) complex supported on Fe3O4@SiO2: Highly active, reusable and magnetically separable catalyst for Suzuki-Miyaura cross-coupling reactions in aqueous media
Akko?, Mitat,Bu?day, Nesrin,Alt?n, Serdar,Kiraz, Nadir,Ya?ar, Sedat,?zdemir, ?smail
, (2021/05/05)
A new type magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was fabricated and characterized by Fourier Transform Infrared (FTIR) spectroscopy, Transmission Electron Microscopy (TEM), X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Energy Disperse X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA), and Scanning Electron Microscopy (SEM). The loading amount of Palladium (Pd) to magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs was measured by Inductively Coupled Plasma-Optical Emission Spectroscopy (ICP-OES) analysis. The catalytic activity of magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was examined on Suzuki-Miyaura cross-coupling reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions yielded excellent results and high TOF (up to 76528 h?1) in the presence of 2 mg of Fe3O4@SiO2@NHC@Pd-MNPs catalyst (0.0197 mmolg?1, 0.00394 mmol%Pd) at 80 °C in 2-propanol/H2O (1:2). In addition, the magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs catalyst was easily recovered by using an external Nd-magnet and reused for the Suzuki cross-coupling reactions. The catalyst showed strong structural and chemical stability and was reused six times without losing its catalytic activity substantially.
Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
Kaga, Atsushi,Hayashi, Hirohito,Hakamata, Hiroyuki,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 11807 - 11811 (2017/09/20)
A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.
A gallium-catalyzed cycloisomerization/Friedel-Crafts tandem
Li, Hui-Jing,Guillot, Regis,Gandon, Vincent
, p. 8435 - 8449 (2011/03/19)
Under noble (Au, Pt, Ru) and group 13 (Ga, In) metals catalysis, 1,6-arenynes rearrange to give 1,2-dihydronaphthalenes in a high yielding, regiocontrolled fashion. When the reaction is carried out in the presence of electron-rich arenes (anisole, phenol, indole derivatives), Friedel-Crafts addition may follow the cycloisomerization step. Only GaX3 salts proved able to catalyze these two C-C bond formation events. This specificity of gallium has been exploited for the synthesis of valuable polycyclic compounds that would be very difficult to prepare otherwise. For instance, tetrahydroisoquinolines and tetrahydrobenzoazepines have been obtained by selective 6-exo-dig or 7-endo-dig cyclization of N-tethered 1,6-arenynes. DFT calculations were carried out to shed light on the mechanism and provide a rationale for this regiodivergency. Computations also reveal the fundamental role of the tether in the stabilization of carbocationic species. Differential reactivities of other types of substrates in gallium- and gold-catalyzed cascades are also exposed, showing that the two approaches are complementary. In particular, bimolecular Friedel-Crafts additions are facilitated under gallium catalysis.
2-ARYLOXYETHYL GLYCINE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORT INHIBITORS
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Page/Page column 101, (2010/02/14)
The present invention relates to certain 2-aryloxyethyl glycine derivatives that exhibit activity as inhibitors of the glycine type-1 transporter, to pharmaceutical compositions containing them and to their use in the treatment of neurological and neuropsychiatric disorder.
1-substituted phenyl-1-(1h-imidazol-4-yl) alcohols, process for producing the same and use thereof
-
, (2008/06/13)
To provide a composition having a steroid C17,20-lyase inhibitory activity and useful as an agent for the prophylaxis or treatment of prostatism and tumors such as breast cancer. A compound represented by the formula: wherein R is a hydrogen atom or a protecting group, R1is a lower alkyl group or a cyclic hydrocarbon group, R2is an aromatic hydrocarbon group optionally having substituents or an aromatic heterocyclic group optionally having substituents, R3is a hydrocarbon group optionally having substituents, a hydroxyl group optionally having substituents, a thiol group optionally having substituents, an amino group optionally having substituents, an acyl group or a halogen atom, and n is an integer of 0 to 4, and a salt thereof have a steroid C17,20-lyase inhibitory activity, and are useful as an agent for the pophylaxis or treatment of prostatism and tumors such as beast cancer and the like.
1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character
Rangisetty,Dukat,Dowd,Herrick-Davis,DuPre,Gadepalli,Teitler,Kelley,Sharif,Glennon
, p. 3283 - 3291 (2007/10/03)
Certain phenylethylamines, such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; 1a), are high-affinity 5-HT2 agonists. Previous structure - affinity studies have concluded that both the 2,5-dimethoxy substitution pattern and the nature of substituents at the 4-position are important determinants of high affinity. We recently demonstrated that replacement of the bromo group of DOB with a 3-(phenyl)propyl substituent results in retention of affinity and that, counter to established structure - affinity relationships, the 2,5-dimethoxy substitution pattern is no longer a requirement for the binding. The present investigation extends these findings by examining a series of analogues, 3, lacking a 5-methoxy group. It was additionally found that shifting the phenylalkyl substituent from the 4- to the 5-position (e.g., 4i) also results in retention of affinity. For example, 1-(2-methoxy-5-(3-phenylpropyl)-2-aminopropane (6; the α-methyl derivative of 4i) binds at 5-HT2A receptors with high affinity (Ki = 13 nM) and possesses 5-HT2A antagonist character. Thus, not only is the 2,5-dimethoxy substitution pattern not a requirement for the binding of certain phenylethylamines at 5-HT2A receptors, the presence of a 4-position substituent (previously thought to serve as a modulator of affinity of DOB-like agents) is also not required. Striking differences in the 5-HT2A binding requirements of the present compounds as compared to DOB-like agents suggest multiple substituent-dependent modes of binding.
Synthesis of Diphenyl-substituted Flavonoid Compounds on Both Benzene Rings
Matsumura, Hisashi,Tsuchiya, Toshio,Imafuku, Kimiaki
, p. 3519 - 3520 (2007/10/02)
Condensation of o-hydroxyacetophenone and its 3- and 5-phenyl-substituted compounds with 2- or 4-methoxy-biphenyl-3-carbaldehyde gave six mono- and diphenyl-substituted 2'-hydroxychalcones (5a-f), which were cyclized with alkali to afford the flavonones.T
