cas 365-24-2, 4,4'-Difluorobenzhydrol | Articles data

Articles about 365-24-2Total 54 be found

Article title
Article abstract
Author
Journal number and time
Download

High triplet energy exciton blocking materials based on triphenylamine core for organic light-emitting diodes
A series of novel high triplet energy materials have been designed and synthesized from the simple starting compounds through a simple one-step Friedel–Crafts reaction by using triphenylamine and methoxy, fluoro substituted diphenylmethanoles and triphenylmethanol as the starting materials. The synthesized compounds exhibit the ionization potentials in an interval of 5.4–5.7?eV in the solid state, the wide bang-gaps of 3.6?eV and the high triplet energies of about 3.0?eV. The photophysical properties have been confirmed by DFT. The introduction of a material with the lowest ionization potential as the high triplet energy exciton blocking thin layer of the green organic light-emitting diode doubled the quantum efficiency of the device. The best fabricated green device exhibited the maximum current, power, and external quantum efficiencies of 80.1?Cd?A?1 and 31.4?Lm?W?1, 23.2%, respectively. The triplet-triplet annihilation and triplet-polaron quenching effects for the devices without and with exciton blocking layer have been analyzed.
Bagdziunas, Gintautas,Surka, Mindaugas,Ivaniuk, Khrystyna
p. 122 - 129
(2017)
Read Online

First catalytic enantioselective synthesis of the cocaine abuse therapeutic agent (S)-(+)-1-(4-{2-[bis(4-fluorophenyl)methoxy]ethyl}piperazin-1-yl)-2-phenyl-2-propanol
(S)-(+)-1-(4-{2-[Bis(4-fluorophenyl)methoxy]ethyl}piperazin-1-yl)-2-phenyl-2-propanol, which is a promising candidate as a cocaine abuse therapeutic agent, is prepared in several steps. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to either 2-chloro or 2-bromoacetophenone catalyzed by the use of different chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The synthesis of a new isoborneolsulfonamide ligand bearing a trifluromethyl substituent and its use in this addition is also presented.
Forrat, Vicente J.,Ramon, Diego J.,Yus, Miguel
p. 400 - 405
(2007)
Read Online

Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.
Chen, Gong,Qiao, Tianjiao,Wang, Yaxin,Zhang, Jian,Zhao, Jianyou
supporting information
p. 3297 - 3302
(2021/10/14)

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots
We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.
Xi, Zi-Wei,Yang, Lei,Wang, Dan-Yan,Feng, Chuan-Wei,Qin, Yufeng,Shen, Yong-Miao,Pu, Chaodan,Peng, Xiaogang
p. 2474 - 2488
(2021/02/05)

Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions
Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.
Cao, Dawei,Xia, Shumei,Pan, Pan,Zeng, Huiying,Li, Chao-Jun,Peng, Yong
supporting information
p. 7539 - 7543
(2021/10/12)

MAGL inhibitor as well as preparation method and application thereof
The invention relates to a compound shown as a formula I in the description and a pharmaceutically acceptable salt thereof, a preparation method, an intermediate for preparing the compound, a composition containing the compound or salt, and application of the compound for preparing drugs for treating MAGL-mediated diseases and symptoms.
-
Paragraph 0027-0029

(2021/03/30)

Simple synthesis of [Ru(CO3)(NHC)(p-cymene)] complexes and their use in transfer hydrogenation catalysis
A novel, efficient and facile protocol for the synthesis of a series of [Ru(NHC)(CO3)(p-cymene)] complexes is reported. This family of Ru-NHC complexes was obtained from imidazol(in)ium tetrafluoroborate or imidazolium hydrogen carbonate salts in moderate to excellent yields, employing sustainable weak base. The ruthenium complexes were successfully utilized in the transfer hydrogenation of ketones as highly active multifunctional catalysts.
Cazin, Catherine S. J.,Guillet, Sébastien G.,Liu, Yaxu,Ma, Xinyuan,Nolan, Steven P.
p. 13012 - 13019
(2021/10/12)

Formation of a hydride containing amido-zincate using pinacolborane
Amido-zincates containing hydrides are underexplored yet potentially useful complexes. Attempts to access this type of zincate through combining amido-organo zincates and pinacolborane (HBPin)viaZn-C/H-BPin exchange led instead to preferential formation of amide-BPin and/or [amide-BPin(Y)]?(Y = Ph, amide, H), when the amide is hexamethyldisilazide or 2,2,6,6-tetramethylpiperidide and the hydrocarbyl group was phenyl or ethyl. In contrast, the use of a dipyridylamide (dpa) based arylzinc complex led to Zn-C/H-BPin metathesis being the major outcome. Independent synthesis and full characterisation of two LnLi[(dpa)ZnPh2] (L = THF,n= 3; L = PMDETA,n= 1) complexes,1and3, respectively, enabled reactivity studies that demonstrated that these species display zincate type reactivity (by comparison to the lower reactivity of the neutral complex (Me-dpa)ZnPh2,4, Me-dpa = 2,2′-dipyridyl-N-methylamine). This included1performing the rapid deprotonation of 4-ethynyltoluene and also phenyl transfer to α,α,α-trifluoroacetophenone in contrast to neutral complex4. Complex1reacted with one equivalent of HBPin to give predominantly PhBPin (ca.90%) and a lithium amidophenylzincate containing a hydride unit, complex7-A, as the major zinc containing product. Complex7-Atransfers hydride to an electrophile preferentially over phenyl, indicating it reacts as a hydridozincate. Attempts to react1with >1 equivalent of HBPin or with catecholborane led to more complex outcomes, which included significant borane and dpaZn substituent scrambling, two examples of which were crystallographically characterised. While this work provides proof of principle for Zn-C/H-BPin exchange as a route to form an amido-zincate containing a hydride, amido-organozincates that undergo more selective Zn-C/H-BPin exchange still are required.
Ingleson, Michael J.,Nichol, Gary S.,Uzelac, Marina,Yuan, Kang
supporting information
p. 14018 - 14026
(2021/10/19)

Photo-induced phosphorus radical involved semipinacol rearrangement reaction: Highly synthesis of γ-oxo-phosphonates
Hydroxyphosphoric acids display the unique biological activities, and they have some attractive prospects as clinical drug moleculars. Herein, a new approach for the synthesis of γ-oxo-phosphonates (the precursor of hydroxyphosphoric acid) has been established through the semipinacol rearrangement tactic involved the photo-induced phosphorus radical process. Most important, this transformation is avoid of the external oxidants, and occurs very well under the sunlight irradiation, meanwhile the γ-oxo-phosphonate was easily derivatized to obtain γ-hydroxyphosphoric acid, thus highlights the synthesis value of this method.
Wang, Chunhai,Huang, Xiaoling,Liu, Xueting,Gao, Suqian,Zhao, Bin,Yang, Shangdong
supporting information
p. 677 - 680
(2019/08/27)

A facile and highly efficient transfer hydrogenation of ketones and aldehydes catalyzed by palladium nanoparticles supported on mesoporous graphitic carbon nitride
A novel transfer hydrogenation methodology for the reduction of ketones (14 examples) and benzaldehyde derivatives (12 examples) to the corresponding alcohols using Pd nanoparticles supported on mesoporous graphitic carbon nitride (mpg-C3N4/Pd) as a reusable catalyst and ammonia borane as a safe hydrogen source in an aqueous solution MeOH/H2O (v/v = 1/1) is described. The catalytic hydrogenation reactions were conducted in a commercially available high-pressure glass tube at room temperature, and the corresponding alcohols were obtained in high yields in 2–5 min. Moreover, the presented transfer hydrogenation protocol shows partial halogen selectivity with bromo-, fluoro-, and chloro-substituted carbonyl analogs. In addition, the present catalyst can be reused up to five times without losing its efficiency, and scaling-up the reaction enables α-methylbenzyl alcohol to be produced in 90% isolated yield.
Ni?anc?, Bilal,Da?alan, Ziya
p. 14 - 19
(2019/11/14)

Discovery of Aryl Formyl Piperidine Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase Inhibitors
Most of the current monoacylglycerol lipase (MAGL) inhibitors function by an irreversible mechanism of action, causing a series of side effects. Herein, starting from irreversible inhibitors, 25 compounds were synthesized and evaluated in vitro for MAGL inhibition, among which, compound 36 showed the most potent inhibitory activity (IC50 = 15 nM). Crucially, docking studies demonstrated that the m-chlorine-substituted aniline fragment occupied a hydrophobic subpocket enclosed by side chains of Val191, Tyr194, Val270, and Lys273, which creatively identify a new key anchoring point for the development of new MAGL inhibitors. Furthermore, in vivo evaluation innovatively revealed that this reversible inhibitor 36 significantly ameliorated depressive-like behaviors induced by reserpine. To the best of our knowledge, this is the first time that reversible inhibitors of MAGL were developed to support MAGL as a potential therapeutic target for depression.
Zhi, Zhuoer,Zhang, Wenting,Yao, Jingchun,Shang, Yanguo,Hao, Qingjing,Liu, Zhong,Ren, Yushan,Li, Jie,Zhang, Guimin,Wang, Jinxin
p. 5783 - 5796
(2020/07/14)

Trivalent Rare-Earth Metal Amide Complexes as Catalysts for the Hydrosilylation of Benzophenone Derivatives with HN(SiHMe2)2 by Amine-Exchange Reaction
The rare-earth metal complexes Ln(L1)[N(SiHMe2)2](thf) (Ln=La, Ce, Y; L1=N,N′′-bis(pentafluorophenyl)diethylenetriamine dianion) were synthesized by treating Ln[N(SiHMe2)2]3(thf)2 with L1H2. The lanthanum and cerium derivatives are active catalysts for the hydrosilylation of benzophenone derivatives with HN(SiHMe2)2. An amine-exchange reaction was revealed as a key step of the catalytic cycle, in which Ln?Si?H β-agostic interactions are proposed to promote insertion of the carbonyl moiety into the Si?H bond.
Shinohara, Koichi,Tsurugi, Hayato,Anwander, Reiner,Mashima, Kazushi
supporting information
p. 14130 - 14136
(2020/10/06)

Synthesis of Benzylic Alcohols by C-H Oxidation
Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.
Tanwar, Lalita,B?rgel, Jonas,Ritter, Tobias
supporting information
p. 17983 - 17988
(2019/11/14)

Synthesis and evaluation of potent and selective MGL inhibitors as a glaucoma treatment
Monoacylglycerol lipase (MGL) inhibition provides a potential treatment approach to glaucoma through the regulation of ocular 2-arachidonoylglycerol (2-AG) levels and the activation of CB1 receptors. Herein, we report the discovery of new series of carbamates as highly potent and selective MGL inhibitors. The new inhibitors showed potent nanomolar inhibitory activity against recombinant human and purified rat MGL, were selective (>1000-fold) against serine hydrolases FAAH and ABHD6 and lacked any affinity for the cannabinoid receptors CB1 and CB2. Protein-based 1H NMR experiments indicated that inhibitor 2 rapidly formed a covalent adduct with MGL with a residence time of about 6 h. This interconversion process “intrinsic reversibility” was exploited by modifications of the ligand's size (length and bulkiness) to generate analogs with “tunable’ adduct residence time (τ). Inhibitor 2 was evaluated in a normotensive murine model for assessing intraocular pressure (IOP), which could lead to glaucoma, a major cause of blindness. Inhibitor 2 was found to decrease ocular pressure by ～4.5 mmHg in a sustained manner for at least 12 h after a single ocular application, underscoring the potential for topically-administered MGL inhibitors as a novel therapeutic target for the treatment of glaucoma.
Alapafuja, Shakiru O.,Malamas, Michael S.,Shukla, Vidyanand,Zvonok, Alexander,Miller, Sally,Daily, Laura,Rajarshi, Girija,Miyabe, Christina Yume,Chandrashekhar, Honrao,Wood, JodiAnne,Tyukhtenko, Sergiy,Straiker, Alex,Makriyannis, Alexandros
p. 55 - 64
(2018/11/23)

Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase
Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2.
Winters, Maria,DuHadaway, James B.,Pham, Khoa N.,Lewis-Ballester, Ariel,Badir, Shorouk,Wai, Jenny,Sheikh, Eesha,Yeh, Syun-Ru,Prendergast, George C.,Muller, Alexander J.,Malachowski, William P.
supporting information
p. 455 - 464
(2018/11/25)

Synthesis, molecular docking studies, and antimicrobial evaluation of new structurally diverse ureas
A series of new urea derivatives (3a-p) have been synthesized from readily available isocyanates and amines in good to high yields. All synthesized compounds were fully characterized using 1H NMR, 13C NMR, IR, and mass spectrometry. Additionally, the structure of the compound (3n) was confirmed by single-crystal X-ray diffraction. Furthermore, all compounds were evaluated for antimicrobial activity against five bacteria and two fungi. Last but not the least, molecular docking studies with Candida albicans dihydropteroate synthetase were performed and the results are presented herein.
Patil, Mahadev,Poyil, Anurag Noonikara,Joshi, Shrinivas D.,Patil, Shivaputra A.,Patil, Siddappa A.,Bugarin, Alejandro
supporting information
p. 302 - 311
(2019/03/26)

Design, synthesis, and molecular docking study of new piperazine derivative as potential antimicrobial agents
Herein, we describe the successful design and synthesis of seventeen new 1,4-diazinanes, compounds commonly known as piperazines. This group of piperazine derivatives (3a-q) were fully characterized by 1H NMR, 13C NMR, FT-IR, and LCMS spectral techniques. The molecular structure of piperazine derivative (3h) was further established by single crystal X-ray diffraction analysis. All reported compounds were evaluated for their antibacterial and antifungal potential against five bacterial (Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Pseudomonas aeruginosa) and two fungal strains (Candida albicans and Cryptococcus neoformans). The complete bacterial screening results are provided. As documented, piperazine derivative 3e performed the best against these bacteria. Additionally, data obtained during molecular docking studies are very encouraging with respect to potential utilization of these compounds to help overcome microbe resistance to pharmaceutical drugs, as explicitly noted in this manuscript.
Patil, Mahadev,Noonikara Poyil, Anurag,Joshi, Shrinivas D.,Patil, Shivaputra A.,Patil, Siddappa A.,Bugarin, Alejandro
supporting information

(2019/09/06)

Two-component boronic acid catalysis for increased reactivity in challenging Friedel-Crafts alkylations with deactivated benzylic alcohols
A general and efficient boronic acid catalyzed Friedel-Crafts alkylation of arenes with benzylic alcohols was previously developed for the construction of unsymmetrical diarylmethane products (X. Mo, J. Yakiwchuk, J. Dansereau, J. A. McCubbin and D. G. Hall, J. Am. Chem. Soc., 2015, 137, 9694). Highly electron-deficient benzylic alcohols, however, were ineffective coupling partners due to the increased difficulty of C-O bond ionization. Herein, we report the use of perfluoropinacol as an effective co-catalyst to improve the reactivity of a boronic acid catalyst in the Friedel-Crafts benzylations of electronically deactivated primary and secondary benzylic alcohols. According to spectroscopic studies, it is believed that perfluoropinacol condenses with the arylboronic acid catalyst to form a highly electrophilic and Lewis acidic boronic ester. This in situ formed species enables a more facile ionization of the benzylic alcohols likely through a mode of activation promoted by a Lewis acid assisted hydronium Br?nsted acid generated from the interactions of the transient boronic ester with hexafluoroisopropanol solvent and water.
Ang, Hwee Ting,Rygus, Jason P. G.,Hall, Dennis G.
supporting information
p. 6007 - 6014
(2019/06/24)

Electrochemical Hydrogenation with Gaseous Ammonia
As a carbon-free and sustainable fuel, ammonia serves as high-energy-density hydrogen-storage material. It is important to develop new reactions able to utilize ammonia as a hydrogen source directly. Herein, we report an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen source and carbon electrodes. A variety of heterocycles and functional groups, including for example sulfide, benzyl, benzyl carbamate, and allyl carbamate were well tolerated. Fast stepwise electron transfer and proton transfer processes were proposed to account for the transformation.
Li, Jin,He, Lingfeng,Liu, Xu,Cheng, Xu,Li, Guigen
supporting information
p. 1759 - 1763
(2019/01/16)

Synthesis and biological evaluation of new N-substituted 4-(arylmethoxy)piperidines as dopamine transporter inhibitors
The library of new N-substituted 4-(arylmethoxy)piperidines as dopamine transporter inhibitors was designed and synthesized. H-Bond donors in piperidine ring were found to be important for reduced locomotor activity in mice. 4-[Bis(4-fluorophenyl)methoxy]piperidine has IC50 17.0 ± 1.0 nm for dopamine transporter and locomotor activity, which is lower than that for cocaine.
Lapa, Gennady B.,Lapa, Alla A.
p. 203 - 205
(2019/04/25)

Different Selectivities in the Insertions into C(sp2)?H Bonds: Benzofulvenes by Dual Gold Catalysis Competition Experiments
An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)?H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C?H positions. A bidirectional synthesis with two competing ortho-aryl C?H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C?H bonds with a benzylic methyl group also showed perfect selectivity.
Plajer, Alex J.,Ahrens, Lukas,Wieteck, Marcel,Lustosa, Danilo M.,Babaahmadi, Rasool,Yates, Brian,Ariafard, Alireza,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information
p. 10766 - 10772
(2018/08/03)

Carbenium ion formation by fragmentation of electrochemically generated oxonium ions
Fragmentation of electrochemically generated oxonium ions can be exploited to form carbenium ions at a low oxidation potential in the presence of a nucleophile. The application of this concept is demonstrated for the allylation of carbenium ions generated by the anodic oxidation of stannylmethylethers.
Lielpetere, Anna,Jirgensons, Aigars
supporting information
p. 5094 - 5096
(2018/07/29)

Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination
This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.
Heinz, Christoph,Lutz, J. Patrick,Simmons, Eric M.,Miller, Michael M.,Ewing, William R.,Doyle, Abigail G.
supporting information
p. 2292 - 2300
(2018/02/19)

Large-scale synthesis of novel sterically hindered acenaphthene-based α-diimine ligands and their application in coordination chemistry
An efficient method to synthesize novel highly sterically hindered acenaphthene-based α-diimine ligands bearing bulky diarylmethyl moiety was achieved by two-step reactions. These reactions could be carried out on a scale of 100 g with no chromatography involved. On the basis of this method, a series of novel highly sterically hindered acenaphthene-based α-diimine Pd(II) and Ni(II) complexes, imidazolium precursors and the corresponding NHCs-metal complexes were also successfully synthesized. These novel complexes can offer great potential for metal-catalyzed polymerizations and organic reactions.
Guo, Lihua,Kong, Wenyu,Xu, Yanjian,Yang, Yuliang,Ma, Rui,Cong, Li,Dai, Shengyu,Liu, Zhe
supporting information
p. 58 - 67
(2018/02/14)

AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage
A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
Hu, Chen,Hong, Gang,Qian, Xiaofei,Kim, Kwang Rim,Zhu, Xiaoyan,Wang, Limin
supporting information
p. 4984 - 4991
(2017/07/10)

Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates
C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.
Wang, Fen,Wang, He,Wang, Qiang,Yu, Songjie,Li, Xingwei
supporting information
p. 1306 - 1309
(2016/04/01)

A second pharmaceutical intermediates monofluoro-benzene Gui Qin method for synthesizing the fluorophenyl methanol (by machine translation)
The invention discloses a pharmaceutical intermediate monofluoro-benzene Gui Qin two pairs of fluorophenyl methanol synthesis method, in the dimethylamine solution, adding 4,4 the two [...]monofluoro-benzene ketone and isobutyl alcohol lithium, the reflux reaction under elevated temperature conditions, then distilled under reduced pressure, boil off dimethylamine, by adding ethyl acetate solution, separation oil objects, object leans the oil then add cyclonexane solution, separating solid, filtration, recrystallization, washing, dehydrating agent dehydration, to obtain colourless crystal two pairs of fluorophenyl methanol. The method proposed in the background technology compared with the synthetic method, the yield of the reaction is greatly improved, at the same time, a new synthetic method in order to further improve the yield provides new ideas. (by machine translation)
-
Paragraph 0016; 0018; 0019; 0020; 0021; 0022

(2016/11/28)

Synthesis and biological evaluation of aryloxyacetamide derivatives as neuroprotective agents
A series of new aryloxyacetamide derivatives 10a-s and 14a-m are designed and synthesized. Their protective activities against the glutamate-induced cell death were investigated in differentiated rat pheochromocytoma cells (PC12 cells). Most compounds exhibited neuroprotective effects, especially for 10m, 10r, 14b and 14c, which showed potential protection of PC12 cells at three doses (0.1, 1.0, 10 μM). MTT assay, Hoechst 33342/PI double staining, and high content screening (HCS) revealed that pretreatment of the cells with 10m, 10r, 14b and 14c has significantly decreased the extent of cell apoptosis in a dose-dependent manner. The results of western blot analysis demonstrated these compounds suppressed apoptosis of glutamate-induced PC12 cells via caspase-3 pathway. These compounds can be lead compounds for further discovery of neuroprotective agents for treating cerebral ischemic stroke. Basic structure-activity relationships are also presented.
Zhong, Yan,Xu, Yi,Zhang, Ai-Xia,Li, Xiao-Feng,Xu, Zhao-Ying,Li, Ping,Wu, Bin
supporting information
p. 2526 - 2530
(2016/07/07)

Synthetic method of diaryl methanol compound
The invention discloses a synthetic method of a diaryl methanol compound. Compared with a reported method for obtaining the diaryl methanol compound through catalytic reduction by taking diaryl ketone as an initial raw material, the method is characterized by taking substituted benzyl bromide and substituted phenylboronic acid which are cheap and easy to obtain as initial raw materials, reacting for 4 hours in an alkaline solution, water or a mixed solvent of the water and an organic solvent under room temperature in air, and carrying out simple separation and purification operation, thus obtaining a pure product. A catalyst adopted in the method is a palladium compound/an in-situ catalytic system prepared from phosphorus- and oxygen-containing carboxylic acids ligands, the catalytic system is cheap in price, high in catalytic activity and good in selectivity and is stable in the air and a water solution, the diaryl methanol compound is compounded through a method of catalyzing the substituted benzyl bromide and the substituted phenylboronic acid and a 'one-pot reaction method' of hydrogen peroxide, the reaction steps are less, after-treatment is simple, the product is easy to separate and purify, the yield is high, and the mixed solvent is prepared from cheap and easy-to-obtain water and the organic solvent, so that the environment is not polluted, and environment protection is realized.
-
Paragraph 0044-0046

(2017/04/03)

UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions
UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
Zheng, Lewei,Huang, Hongli,Yang, Chao,Xia, Wujiong
supporting information
p. 1034 - 1037
(2015/03/30)

Boron Trifluoride?Diethyl Ether-Catalyzed Etherification of Alcohols: A Metal-Free Pathway to Diphenylmethyl Ethers
A novel boron trifluoride?diethyl ether (BF3?OEt2)-catalyzed etherification procedure has been developed in which primary and secondary alcohols are easily converted into diphenylmethyl ethers with yields of up to 99%.
Li, Jiaqiang,Zhang, Xiaohui,Shen, Hang,Liu, Qing,Pan, Jing,Hu, Wen,Xiong, Yan,Chen, Changguo
supporting information
p. 3115 - 3120
(2015/11/03)

Dual gold catalysis: Synthesis of polycyclic compounds via C-H insertion of gold vinylidenes
New and interesting polycyclic compounds have been synthesized from non-conjugated diyne systems by dual gold catalysis. A quaternary carbon center in the backbone and the accompanying Thorpe-Ingold effect enabled the unprecedented insertion of sp3 and sp2 C-H bonds that for the first time were incorporated within the backbone of the diyne system and allowed the construction of complex polycyclic carbon scaffolds inaccessible by previous approaches in which the C-H bonds for the insertion were situated at the other end of the alkyne.
Wieteck, Marcel,Tokimizu, Yusuke,Rudolph, Matthias,Rominger, Frank,Ohno, Hiroaki,Fujii, Nobutaka,Hashmi, A. Stephen K.
supporting information
p. 16331 - 16336
(2015/01/09)

Stereoselective synthesis of (z)-1-benzhydryl-4-cinnamylpiperazines via the wittig reaction
A synthetic method of producing (E)- and (Z)-isomers of 1-benzhydryl-4-cinnamylpiperazines in a specific ratio from corresponding benzhydrylpiperazine is described. Of the three compounds synthesized (5a-c), the ratio of E/Z-isomers remained around 15:85. The key intermediates, 1-benzhydryl-4-(2,2-dimethoxyethyl)piperazine derivatives (3a-c), were prepared by nucleophilic substitution reaction of benzhydrylpiperazines (2a-c) with chloroacetaldehyde dimethylacetal in good yield (up to 88%). Hydrolysis of 3a-c gave the corresponding aldehydes 4a-c, which when subjected to the Wittig reaction followed by column purification to afford 1a-c (E-isomers) and 6a-c (Z-isomers) in pure form. The isolated compounds were characterized by NMR and mass spectral analysis. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright
Shivprakash,Reddy, G. Chandrasekara
supporting information
p. 600 - 609
(2014/01/17)

Synthesis and cytotoxicity studies of novel benzhydrylpiperazine carboxamide and thioamide derivatives
Synthesis and cytotoxic activities of 32 benzhydrylpiperazine derivatives with carboxamide and thioamide moieties were reported. In vitro cytotoxic activities of compounds were screened against hepatocellular (HUH-7), breast (MCF-7) and colorectal (HCT-116) cancer cell lines by sulphorhodamine B assay. In general, 4-chlorobenzhydrylpiperazine derivatives were more cytotoxic than other compounds. In addition, thioamide derivatives (6a-g) have higher growth inhibition than their carboxamide analogs.
Gurdal, Enise Ece,Durmaz, Irem,Cetin-Atalay, Rengul,Yarim, Mine
p. 205 - 214
(2014/04/03)

Synthesis of 1-benzhydryl piperazine derivatives and evaluation of their ACE inhibition and antimicrobial activities
This study presents the synthesis of 14 new 1,4-disubstituted piperazine derivatives from allyl bromides of Baylis-Hillman adduct and 4,4-disubstituted benzhydryl piperazines. All the synthesized compounds were further screened for in vitro ACE inhibitor and antimicrobial activities. Among the synthesized piperazine derivatives, compound 12h showed moderate ACE inhibitor activity as compared to the standard, angiotensin-converting enzyme inhibitor (Sigma). The kinetic data (K m, K i and V max values) of enzyme inhibition for compound 12h and ACE inhibitor standard were also determined. Similarly, all compounds were screened against different bacterial strains. Compounds 12a, 12b, 12d, 12h and 12i showed excellent to moderate activity against various tested bacterial strains. Compounds 12b and 12i showed broad spectrum of antibacterial activity against Pseudomonas aeruginosa, Staphylococcus aureus, S. aureus MLS 16, Escherichia coli, Bacillus subtilis and Klebsiella planticola, while compounds 12a, 12d and 12i showed promising activity against P. aeruginosa (MIC value of 8.96 μM), S. aureus (MIC value of 42.2 μM) and S. aureus MLS 16 (MIC value of 81.3 μM), respectively. The remaining compounds showed activity at a concentration of >491 μM.
Santhoshi, Amlipur,Kumar, Singam Naveen,Sujitha, Pombala,Poornachandra, Yedla,Sadhu, Partha Sarathi,Kumar, C. Ganesh,Rao, Vaidya Jayathirtha
p. 3207 - 3219
(2014/05/06)

LAUFLUMIDE AND THE ENANTIOMERS THEREOF, METHOD FOR PREPARING SAME AND THERAPEUTIC USES THEREOF
The invention relates to the molecule having formula (I), as well as the enantiomers thereof, and to the use of same in the treatment of ADHD, narcolepsy or idiopathic hypersomnia.
-
Paragraph 0114

(2013/11/19)

Magnesium-catalysed hydroboration of aldehydes and ketones
The heteroleptic magnesium alkyl complex [CH{C(Me)NAr}2Mg nBu] (Ar = 2,6-iPr2C6H3) is reported as a highly efficient pre-catalyst for the hydroboration of aldehydes and ketones with pinacolborane. The Royal Society of Chemistry 2012.
Arrowsmith, Merle,Hadlington, Terrance J.,Hill, Michael S.,Kociok-Koehn, Gabriele
supporting information; experimental part
p. 4567 - 4569
(2012/06/05)

Synthesis of fluorenone derivatives through Pd-catalyzed dehydrogenative cyclization
Palladium-catalyzed dual C-H functionalization of benzophenones to form fluorenones by oxidative dehydrogenative cyclization is reported. This method provides a concise and effective route toward the synthesis of fluorenone derivatives, which shows outstanding functional group compatibility.
Li, Hu,Zhu, Ru-Yi,Shi, Wen-Juan,He, Ke-Han,Shi, Zhang-Jie
supporting information
p. 4850 - 4853,4
(2012/12/12)

Development of small-molecule probes that selectively kill cells induced to express mutant RAS
Synthetic lethal screening is a chemical biology approach to identify small molecules that selectively kill oncogene-expressing cell lines with the goal of identifying pathways that provide specific targets against cancer cells. We performed a high-throughput screen of 303,282 compounds from the National Institutes of Health-Molecular Libraries Small Molecule Repository (NIH-MLSMR) against immortalized BJ fibroblasts expressing HRASG12V followed by a counterscreen of lethal compounds in a series of isogenic cells lacking the HRASG12V oncogene. This effort led to the identification of two novel molecular probes (PubChem CID 3689413, ML162 and CID 49766530, ML210) with nanomolar potencies and 4-23-fold selectivities, which can potentially be used for identifying oncogene-specific pathways and targets in cancer cells.
We?wer, Michel,Bittker, Joshua A.,Lewis, Timothy A.,Shimada, Kenichi,Yang, Wan Seok,MacPherson, Lawrence,Dandapani, Sivaraman,Palmer, Michelle,Stockwell, Brent R.,Schreiber, Stuart L.,Munoz, Benito
supporting information; experimental part
p. 1822 - 1826
(2012/04/04)

Bifunctional rhenium complexes for the catalytic transfer-hydrogenation reactions of ketones and imines
The silyloxycyclopentadienyl hydride complexes [Re(H)(NO)(PR 3)(C5H4OSiMe2tBu)] (R=iPr (3a), Cy (3b)) were obtained by the reaction of [Re(H)(Br)(NO)(PR3) 2] (R=iPr, Cy) with Li[C5H4OSiMe 2tBu]. The ligand-metal bifunctional rhenium catalysts [Re(H)(NO)(PR3)(C5H4OH)] (R=iPr (5a), Cy (5b)) were prepared from compounds 3a and 3b by silyl deprotection with TBAF and subsequent acidification of the intermediate salts [Re(H)(NO)(PR 3)(C5H4O)][NBu4] (R=iPr (4a), Cy (4b)) with NH4Br. In nonpolar solvents, compounds 5a and 5b formed an equilibrium with the isomerized trans-dihydride cyclopentadienone species [Re(H)2(NO)(PR3)(C5H4O)] (6a,b). Deuterium-labeling studies of compounds 5a and 5b with D2 and D 2O showed H/D exchange at the HRe and HO positions. Compounds 5a and 5b were active catalysts in the transfer hydrogenation reactions of ketones and imines with 2-propanol as both the solvent and H2 source. The mechanism of the transfer hydrogenation and isomerization reactions was supported by DFT calculations, which suggested a secondary-coordination-sphere mechanism for the transfer hydrogenation of ketones. The Re-al deal: Bifunctional rhenium complexes [Re(H)(NO)(PR 3)(C5H4OH)] (R=Cy, iPr) of Shvo-type were prepared and used as catalysts for the transfer hydrogenation of ketones and imines. TOFs up to 1164 h-1 were obtained for ketones and up to 79 h-1 for imines. DFT calculations suggested a secondary-coordination- sphere mechanism for the transfer hydrogenation of ketones.
Landwehr, Anne,Dudle, Balz,Fox, Thomas,Blacque, Olivier,Berke, Heinz
experimental part
p. 5701 - 5714
(2012/06/18)

N-heterocyclic carbene-catalyzed cross-coupling of aromatic aldehydes with activated alkyl halides
N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, α-halo ketones and esters can also be used as aldehyde reaction partners.
Padmanaban, Mohan,Biju, Akkattu T.,Glorius, Frank
supporting information; experimental part
p. 98 - 101
(2011/03/19)

Sodium bisulfite: An efficient catalyst for ether formation via dehydration of aromatic/aliphatic alcohol
Straightforward etherification of benzyl alcohols (1) via intermolecular dehydration can be efficiently catalyzed by sodium bisulfite under solvent-free conditions. In the presence of 0.3 mol% or 0.6 mol% amount of sodium bisulfite, symmetric and unsymmetric ethers are prepared from the corresponding alcohols in high yields (up to 95%). Etherification of benzhydryl alcohols is also discussed. Copyright
Wang, Hui,Zhu, Xingfei,Lu, Yangning,Li, Yue,Gao, Xiang
experimental part
p. 1180 - 1184
(2012/04/23)

A simple and efficient synthesis of the antimigraine drug lomerizine
The synthesis of the antimigraine drug 1-[bis(4-fluorophenyl)methyl]-4-(2, 3,4-trimethoxybenzyl)piperazine has been carried out in very good yields. The five-step synthesis started from bis(4-fluorophenyl)methanone. This route can be applied for large-scale preparation of lomerizine. Georg Thieme Verlag Stuttgart.
Narsaiah, A. Venkat,Kumar, J. Kranthi
experimental part
p. 1989 - 1991
(2010/08/13)

Chemo-and stereoselective iron-catalyzed hydrosilylation of ketones
The reduction of ketones with polymethylhydrosiloxane (PMHS) gives the corresponding alcohols in good to excellent yield applying iron-based catalyst systems. In the case of prochiral ketones, the use of Fe(OAc) 2/(S,S)-Me-DuPhos leads to high enantioselectivity up to 99% ee. The reaction proceeds in the presence of several functional groups such as esters, halides as well as conjugated double bonds, with high chemoselectivity. The advantage of this protocol is that the reaction requires no activating agents or additives.
Addis, Daniele,Shaikh, Nadim,Zhou, Shaolin,Das, Shoubhik,Junge, Kathrin,Beller, Matthius
experimental part
p. 1687 - 1691
(2011/08/05)

Synthesis of novel 1-benzhydryl-4-(3-(piperidin-4-yl)propyl) piperidine sulfonamides as anticonvulsant agents
A series of novel 1-benzhydryl-4-(3-(piperidin-4-yl)propyl)piperidine sulphonamide derivatives 8(a-j) was synthesized in good yield and met the structural requirements essential for anticonvulsant properties. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. All the compounds were evaluated for their possible anticonvulsant activity by Maximal Electroshock Seizure (MES) test and their neurotoxic effects were determined by rotorod test. Majority of the compounds were active in MES tests. Compounds 8f and 8g have shown a significant and protective effect on seizure, when compared with standard drug phenytoin. Compound 8f and 8g without a fluoro group showed anticonvulsant activity in MES test as compared with compound 8a and 8b with fluoro substituents. From this study, it is quite apparent that there are at least three parameters for the activity of anticonvulsant drugs, that is, a lipophilic domain, a distal hydrophobic center and two-electron donor (-C-N=) system.
Vinaya,Veeresh,Ananda Kumar,Prasanna,Ranganatha,Benaka Prasad,Patil,Rangappa
scheme or table
p. 109 - 115
(2011/02/22)

Synthesis and anticonvulsant activity of some cinnamylpiperazine derivatives
A series of cinnamylpiperazine derivatives was synthesized using different benzophenone as starting material. The structures of the compounds were proved by their IR, 1H-NMR spectroscopic data and mass spectra data. The anticonvulsant activities of these compounds were evaluated with maximal electroshock (MES) test and rotarod test with intraperitoneal injection on KunMing mice. Among all the flunarizine analogues, no one exhibited better anticonvulsant activity than flunarizine. Flunarizine (4i) exhibited anticonvulsant activity with ED50 of 38.1 mg/kg, TD50 of 164.3 mg/kg and PI of 4.3 through administration intraperitoneal, and with ED50 of 56.8 mg/kg, TD50 of 456.3 mg/kg and PI of 8.0 through oral administration.
Hu, Chuan,Sun, Zhi-Gang,Wei, Cheng-Xi,Quan, Zhe-Shan
scheme or table
p. 661 - 664
(2011/11/29)

MODULATORS OF C3A RECEPTOR AND METHODS OF USE THEREOF
Provided are compounds that are modulators of C3a receptor activity, compositions containing the compounds and methods of use of the compounds and compositions. In certain embodiments, the compounds are pyridones. In certain embodiments, provided are methods for treatment or amelioration of diseases associated with modulation of C3a receptor activity.
-
Page/Page column 99

(2008/12/07)

CYCLIC AMINE COMPOUND
An object of the present invention is to provide a cyclic amine compound which has a potent inhibitory effect on the binding of a2C-adrenoceptor and is useful in preventing and treating disorders attributable to a2C-adrenoceptor.The above-described object is solved by the following cyclic amine compound, etc., wherein X is O, S, SO, SO2 or NR2, etc.; R1 is a hydrogen atom, a cyano group, a carboxyl group, a C2-C13 alkoxycarbonyl group, a carbamoyl group, etc.; Ar1 and Ar2 are the same or different and each represent an aryl or heteroaryl group which may be substituted by 1 to 3 substituents and so on; ring B is a benzene ring may be substituted by 1 to 3 substituents and so on; n is an integer from 1 to 10; and p and q are the same or different and each represent an integer of 1 or 2.
-
Page/Page column 19-20

(2008/06/13)

The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines
The synthesis of potent 4-aryl methoxypiperidinol inhibitors of the dopamine transporter is described. Symmetrical para substituents of the benzene rings are important for high potency in binding to the dopamine transporter. 4-[Bis(4-fluorophenyl) methoxy]-1-methylpiperidine has an IC50 of 22.1 ± 5.73 nM and increases locomotor activity in mice.
Lapa, Gennady B.,Byrd, Gary D.,Lapa, Alla A.,Budygin, Evgeny A.,Childers, Steven R.,Jones, Sara R.,Harp, Jill J.
p. 4915 - 4918
(2007/10/03)

Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists
This paper describes the synthesis of several novel T-type calcium channel antagonists that inhibit calcium influx into the cell, which in turn regulates unknown aspects of the cell cycle pathway that are responsible for cellular proliferation. A library of compounds was synthesized anda brief structure activity relationship will be described. From these studies we have identified a compound (1) that displays anti-proliferative activity in the low micromolar range across a variety of cancer cell lines.
McCalmont, William F.,Heady, Tiffany N.,Patterson, Jaclyn R.,Lindenmuth, Michael A.,Haverstick, Doris M.,Gray, Lloyd S.,Macdonald, Timothy L.
p. 3691 - 3695
(2007/10/03)