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Ring size changes in the development of class I HDAC inhibitors
Five pathways involving different ring structures led to generation of fourteen thienylbenzamides (7–20) which display the structure-activity relationships of class I HDAC inhibitors. All the synthesised compounds inhibit HDAC1 and HDAC2 selectively over other isoforms and many inhibit DLD1 and HCT116 cells more effectively than a parent compound. Compounds 8 and 16 inhibit HCT116 cells by activation of the apoptosis pathway.
Cho, Er-Chieh,Lee, Hsueh-Yun,Liu, Chi-Yuan,Tang, Di-Wei
p. 1387 - 1401
(2021/07/06)

A Practical Procedure for Regioselective Bromination of Anilines
A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.
Takahashi, Yusuke,Seki, Masahiko
p. 1828 - 1832
(2021/04/15)

Novel compound and organic light emitting device comprising the same
The present invention provides: a novel compound each comprising an amino group at both ends of a molecule; and an organic light emitting device comprising the same. When the compound of chemical formula 1 of the present invention is applied to the organic light emitting device, it is possible to improve efficiency, lower driving voltage, and improve lifespan characteristics of the organic light emitting device.COPYRIGHT KIPO 2020
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Paragraph 0392-0395

(2020/05/26)

A Novel Conjugated Polymer Consists of Benzimidazole and Benzothiadiazole: Synthesis, Photophysics Properties, and Sensing Properties for Pd2+
A conjugated polymer PPBIBTE based on benzimidazole and benzothiadiazole was synthesized through palladium-catalyzed sonogashira cross-coupling reaction. The chemical structures of the monomers and the polymer were indicated by 1H NMR, and investigation of photophysics properties and sensing optical properties for metal ions were observed by ultraviolet–visible and photoluminescence spectroscopy. PPBIBTE showed remarkable selectivity for Pd2+ by “turn-off” fluorescence sensing progress. In addition, the Stern–Volmer and Benesi-Hildebrand plots were used to reveal the interaction between the polymer and Pd2+, while job's method was applied to calculate the determination of stoichiometry. The results demonstrate that PPBIBTE can utilize static quenching for Pd2+ by forming a 1:1 complex. And it is a potential sensing material as fluorescence chemosensor for Pd2+ with high selectivity and sensitivity.
Hu, Zijun,Liu, Kuan
(2020/02/05)

METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE
PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0139-0144

(2020/07/28)

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
supporting information
p. 6001 - 6009
(2019/04/17)

Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach
A simple, environmentally benign methodology has been developed to synthesize some bromoorganic compounds which have potential as antimicrobial agents. The required compounds were obtained through microwave (MW) irradiation, on-water reactions and using cetyltrimethylammonium tribromide (CTMATB) as the bromine source. The high yield of the product could be achieved within short reaction times, thus representing the main attribute of the present synthetic approach. The compounds were evaluated for in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Bacillus subtilis. Further, in silico studies were carried out to elucidate the interactions of the compounds with the bacterial proteins.
Longkumer, Naruti,Richa, Kikoleho,Karmaker, Rituparna,Kuotsu, Visekhonuo,Supong, Aola,Jamir, Latonglila,Bharali, Pranjal,Sinha, Upasana Bora
p. 276 - 283
(2019/07/12)

Sodium persulfate-promoted site-selective synthesis of mononitroarylamines under transition-metal-free conditions
A practical preparation of nitroarylamines from protected arylamines was herein disclosed. In this system, sodium nitrite acted as a nitration reagent in the presence of sodium persulfate without any transition-metal catalysts. This efficient site-selective protocol took place at room temperature for a short time through a free radical pathway.
Xie, De-Xun,Yu, Hui-Juan,Liu, Hui,Xue, Wei-Cai,Qin, Yuan-Shou,Shao, Guang
p. 1157 - 1165
(2019/01/24)

The study of interactions with a halogen atom: influence of NH2 group insertion on the crystal structures of meta-bromonitrobenzene derivatives
Halogen atoms in molecular crystals may be involved in various interactions, often playing a very important role in structure stabilization. By introducing electron-donating groups, such as NH2, the electron density of the molecule is changed and thus interactions with the bromine substituent may alter. Herein, the crystal structures of meta-bromonitrobenzene and its NH2-substituted derivatives are analyzed. In all four described structures, namely m-bromonitrobenzene [Charlton & Trotter (1963). Acta Cryst.16, 313], 4-bromo-2-nitroaniline (C6H5BrN2O2, 1), 2-bromo-6-nitroaniline (2) and 2-bromo-4-nitroaniline [Arshad et al. (2009). Acta Cryst. E65, o480], the Br atom is engaged in different interactions (Bra€|?€, Bra€|O, Bra€|Br and Ca€”Ha€|Br, respectively). The Hirshfeld surface analysis (HS) and Reduced Density Gradient NonCovalent Interaction (RDG NCI) plots are used to prove the relevance, directionality and stabilizing nature of these interactions. Their modifications have been associated with the position of the amino group in the molecular structure and its influence on charge distribution analyzed with electrostatic potential surfaces (EPS). The diversification of the interactions has been correlated with a ??-hole potential value that enables a switching of the Br-atom character from electrophilic to nucleophilic.
Marek, Paulina H.,Urban, Mateusz,Madura, Izabela D.
p. 1509 - 1517
(2018/10/31)

Novel compound and organic light emitting device comprising the same
The present invention provides a novel compound containing amino groups at both ends of a molecule and an organic light emitting device having the novel compound. The present invention also provides the organic light emitting device comprising: a first electrode; a second electrode facing the first electrode; and at least one organic material layer provided between the first electrode and the second electrode.COPYRIGHT KIPO 2019
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Paragraph 0395-0398

(2019/01/31)

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol
Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.
Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
p. 930 - 938
(2018/01/28)

Protecting-Group-Free Total Synthesis and Biological Evaluation of 3-Methylkealiiquinone and Structural Analogues
The modular protecting-group-free total synthesis of 3-methylkealiiquinone, an analogue of the marine alkaloid kealiiquinone, was accomplished in seven steps. A regioselectively constructed functionalized arylbenzimidazolone moiety and dimethyl squarate were used as the only two building blocks. A thermal ring expansion via 6π-conrotatory ring closure to build the quinone fragment gave rise to the desired linear analogue of the natural compound along with a nondescribed structurally attractive angular naphtho[1,2-d]imidazole regioisomer. The IC50 values for the compounds were determined on three cancer cell lines.
Ramadoss, Velayudham,Alonso-Castro, Angel Josabad,Campos-Xolalpa, Nimsi,Solorio-Alvarado, César R.
p. 10627 - 10635
(2018/09/06)

Method for synthesizing monobrominated aniline compound
The invention discloses a method for synthesizing a monobrominated aniline compound. The method comprises the following steps: by taking an aniline compound as a raw material, and taking zinc aluminum hydrotalcite ZnAl-BrO3-LDHs with a bromate inserted layer and an alkali metal bromide as bromine sources in a mixed solvent of water and an organic solvent, reacting for 1-3h at 10-50 DEG C; after ending the reaction, extracting a reaction mixed solution A by using dichloromethane; adding a column chromatography silica gel into dichloromethane phase; removing the solvent in the manner of reduced pressure distillation; and acquiring a mono-bromination objective product in the manner of column chromatography separation by using an eluent composed of petroleum ether and ethyl acetate at the ratio of 10:1. The invention realizes a high-selectivity oxidative bromination method by adopting an aniline compound under the effects of ZnAl-BrO3-LDHs and potassium bromide; the monobrominated aniline compound is prepared; the reaction popularity is high and the raw material is low in cost and is easily acquired; the reaction condition is mild; the reaction yield is high; the atom utilization ratio is high; and the chemical selectivity is excellent and the environment is protected.
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Paragraph 0032; 0033; 0034; 0035; 0064; 0065; 0066-0083

(2017/09/26)

Importance of 5/6-aryl substitution on the pharmacological profile of 4?-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1?-biphenyl]-2-carboxylic acid derived PPARγ agonists
In this structure-activity relationship study, the influence of aryl substituents at position 5 or 6 on the pharmacological profile of the partial PPARγ agonist 4‘-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1‘-biphenyl]-2-carboxylic acid was investigated. This lead was previously identified as the essential part of telmisartan to induce PPARγ activation. Para-OCH3-phenyl substitution strongly increased potency and efficacy independent of the position. Both compounds represent full agonists because of strong hydrophobic contacts with the amino acid Phe363 in the ligand binding domain. Partial agonists with higher potency than telmisartan or the lead were obtained with OH or Cl substituents at the phenyl ring. Molecular modeling suggested additional hydrogen or halogen bonds with Phe360 located at helix 7. It is assumed that these interactions fix helix 7, thereby promoting a partial agonist conformation of the receptor. The theoretical considerations correlate very well with the results from the luciferase transactivation assay using hPPARγ-LBD as well as those from a time-resolved fluorescent resonance energy transfer (TR-FRET) assay in which the coactivator (TRAP220, PGC-1α) recruitment and corepressor (NCoR1) release pattern was investigated.
Obermoser, Victoria,Mauersberger, Robert,Schuster, Daniela,Czifersky, Monika,Lipova, Marina,Siegl, Monika,Kintscher, Ulrich,Gust, Ronald
supporting information
p. 590 - 603
(2016/12/09)

Palladium(II)-catalyzed, heteroatom-directed, regioselective C-H nitration of anilines using pyrimidine as a removable directing group
A new palladium-catalyzed, heteroatom-directed strategy for C-H nitration of anilines is described. This C-H functionalization reaction is highly ortho-selective and results in very good yields. The highlight of the work is the use of pyrimidine as the removable directing group. This approach constitutes one of the rare methods of ortho-nitration of anilines, a reaction that is normally very difficult to achieve via traditional approaches.
Pawar, Govind Goroba,Brahmanandan, Abhilashamole,Kapur, Manmohan
p. 448 - 451
(2016/02/18)

The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions
Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]
Salmasi, Reihaneh,Gholizadeh, Mostafa,Salimi, Alireza,Garrison, Jered C.
p. 2019 - 2028
(2016/09/16)

Polymer light-emitting devices based on europium(III) complex with 11-bromo-dipyrido[3,2-a:2′,3′-c]phenazine
Polymer light-emitting diodes (PLEDs) containing Eu(DBM)3(BrDPPz) (DBM is dibenzoylmethane, and BrDPPz is 11-bromo-dipyrido[3,2-a:2′,3′-c]phenazine) doped in a blend of poly(9,9-dioctylfluorene) (PFO) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) as the host matrix are reported. Eu(DBM)3(BrDPPz) exhibited high thermal stability and intense UV-Vis absorption. Narrow-bandwidth red emission at 612 nm with a full width at half-maximum (FWHM) of 14.0 nm was observed from Eu(DBM)3(BrDPPz) in these double-layered PLEDs at dopant concentrations from 1 wt% to 8 wt%. For the PLED containing 1 wt% Eu(DBM)3(BrDPPz), a maximum luminance of 829 cd/m2 at 153.5 mA/cm2, highest external quantum efficiency of 1.70% at 2.1 mA/cm2 and maximum luminance of 0.74 cd/A at 4.31 mA/cm2 were obtained.
Fan, Qunping,Liu, Yu,Hao, Zhaoran,Li, Chun,Wang, Yafei,Tan, Hua,Zhu, Weiguo,Cao, Yong
p. 1152 - 1158
(2015/08/06)

Copper-catalyzed mild nitration of protected anilines
A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.
Hernando, Elier,Castillo, Rafael R.,Rodríguez, Nuria,G?mez Arrayás, Ram?n,Carretero, Juan C.
p. 13854 - 13859
(2016/02/18)

Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones
A series of new 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)- ones have been synthesized and evaluated for dual D2 and 5-HT1A receptor binding affinities. The synthesized ligands are structurally related to bifeprunox, a potential atypical antipsychotic, having potent D2 receptor antagonist and 5-HT1A receptor agonist properties. The Suzuki-Miyaura reaction of cyclic vinyl boronate with appropriate aryl halide yielded arylpiperidine, which was eventually transformed to piperidinyl-1H-benzo[d]imidazol-2(3H)-one. The reductive amination of the latter with appropriate biarylaldehdyes rendered the synthesis of 5-piperidinyl-1H-benzo[d]imidazol-2(3H)-ones. Likewise, the Buchwald-Hartwig coupling reactions of 1-boc-piperazine with appropriate aryl halide and subsequent removal of the boc group rendered arylpiperazine. The reductive amination of the latter with appropriate biarylaldehdyes accomplished the synthesis of 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. The structure-activity relationship studies showed that cyclopentenylpyridine and cyclopentenylbenzyl groups contribute significantly to the dual D2 and 5-HT1A receptor binding affinities of these compounds.
Ullah, Nisar
p. 281 - 291
(2014/04/03)

Polymer-anchored peroxo compounds of molybdenum and tungsten as efficient and versatile catalysts for mild oxidative bromination
A polymer supported peroxomolybdate(VI) compound of the type [MoO 2(O2)(CN)2]-PAN [PAN = poly(acrylonitrile)] (PANMo) was obtained by reacting H2MoO4 with 30% H 2O2 and the macromolecular ligand, PAN at near neutral pH. The macrocomplex has been characterized by elemental analysis (CHN and EDX analysis), spectral (IR, UV-Vis and 13C NMR, 95Mo NMR), thermal (TGA-DTG) as well as SEM studies. The catalytic activity of PANMo and its previously reported tungsten containing analog PANW, in oxidative bromination of organic substrates has been explored. The supported complexes could serve as efficient heterogeneous catalysts for the oxidative bromination of a variety of structurally diverse aromatic compounds, with H 2O2 as terminal oxidant, to afford bromo organics in impressive yields under environmentally clean conditions. The catalysts afforded regeneration and could be reused for a minimum of six reaction cycles.
Boruah, Jeena Jyoti,Das, Siva Prasad,Borah, Rupam,Gogoi, Sandhya Rani,Islam, Nashreen S.
p. 246 - 254
(2013/05/23)

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid
An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.
Miyamoto, Hiroshi,Hirano, Tomohiro,Okawa, Yoichiro,Nakazaki, Atsuo,Kobayashi, Susumu
supporting information
p. 9481 - 9493
(2013/10/08)

Fast and efficient bromination of aromatic compounds with ammonium bromide and Oxone
A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product. Georg Thieme Verlag Stuttgart . New York.
Naresh, Mameda,Arun Kumar, Macharla,Mahender Reddy, Marri,Swamy, Peraka,Nanubolu, Jagadeesh Babu,Narender, Nama
p. 1497 - 1504
(2013/06/27)

Selective oxidation of sulfides and oxidative bromination of organic substrates catalyzed by polymer anchored Cu(II) complex
A new polymer-anchored Cu(II) complex has been synthesized and characterized. The catalytic performance of the complex has been tested for the oxidation of sulfides and in oxidative bromination reaction with hydrogen peroxide as the oxidant. Sulfides have been selectively oxidized to the corresponding sulfoxides in excellent yields and in the presence of KBr as the bromine source, organic substrates have been selectively converted to mono bromo substituted compounds using polymer-anchored Cu(II) catalyst. This catalyst showed excellent catalytic activity, high selectivity, and recyclability. The polymer-anchored Cu(II) catalyst could be easily recovered by filtration and reused more than five times without appreciable loss of its initial activity.
Islam,Roy, Anupam Singha,Mondal, Paramita,Tuhina, Kazi,Mobarak, Manir,Mondal, John
supporting information; experimental part
p. 127 - 131
(2012/01/17)

Discovery and optimization of benzotriazine Di-N-oxides targeting replicating and nonreplicating mycobacterium tuberculosis
Compounds bactericidal against both replicating and nonreplicating Mtb may shorten the length of TB treatment regimens by eliminating infections more rapidly. Screening of a panel of antimicrobial and anticancer drug classes that are bioreduced into cytotoxic species revealed that 1,2,4-benzotriazine di-N-oxides (BTOs) are potently bactericidal against replicating and nonreplicating Mtb. Medicinal chemistry optimization, guided by semiempirical molecular orbital calculations, identified a new lead compound (20q) from this series with an MIC of 0.31 μg/mL against H37Rv and a cytotoxicity (CC 50) against Vero cells of 25 μg/mL. 20q also had equivalent potency against a panel of single-drug resistant strains of Mtb and remarkably selective activity for Mtb over a panel of other pathogenic bacterial strains. 20q was also negative in a L5178Y MOLY assay, indicating low potential for genetic toxicity. These data along with measurements of the physiochemical properties and pharmacokinetic profile demonstrate that BTOs have the potential to be developed into a new class of antitubercular drugs.
Chopra, Sidharth,Koolpe, Gary A.,Tambo-Ong, Arlyn A.,Matsuyama, Karen N.,Ryan, Kenneth J.,Tran, Tran B.,Doppalapudi, Rupa S.,Riccio, Edward S.,Iyer, Lalitha V.,Green, Carol E.,Wan, Baojie,Franzblau, Scott G.,Madrid, Peter B.
p. 6047 - 6060
(2012/09/05)

Fluorene- and benzimidazole-based blue light-emitting copolymers: Synthesis, photophysical properties, and PLED applications
Blue light-emitting materials are receiving considerable academic and industrial interest due to their potential applications in optoelectronic devices. In this study, blue light-emitting copolymers based on 9,9'-dioctylfluorene and 2,2'-(1,4-phenylene)-bis(benzimidazole) moieties were synthesized through palladium-catalyzed Suzuki coupling reaction. While the copolymer consisting of unsubstituted benzimidazoles (PFBI0) is insoluble in common organic solvents, its counterpart with N-octyl substituted benzimidazoles (PFBI8) enjoys good solubility in toluene, tetrahydrofuran, dichloromethane (DCM), and chloroform. The PFBI8 copolymer shows good thermal stability, whose glass transition temperature and onset decomposition temperature are 103 and 428 °C, respectively. Its solutions emit blue light efficiently, with the quantum yield up to 99% in chloroform. The electroluminescence (EL) device of PFBI8 with the configuration of indium-tin oxide/poly(ethylenedioxythiophene): poly(styrene sulfonic acid)/PFBI8/1,3,5-tris(1-phenyl-1H-benzimidazole-2-yl) benzene/LiF/Al emits blue light with the maximum at 448 nm. Such unoptimized polymer light-emitting diode (PLED) exhibits a maximum luminance of 1534 cd/m2 with the current efficiency and power efficiency of 0.67 cd/A and 0.20 lm/W, respectively. The efficient blue emission and good EL performance make PFBI8 promising for optoelectronic applications. 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 A conjugated polymer based on 9,9'-dioctylfluorene and N-octyl substituted 2,2'-(1,4-phenylene)- bis(benzimidazole) moieties (PFBI8) was synthesized. Its solutions emit blue light efficiently, with the quantum yield up to 99% in chloroform. It is also morphologically and thermally stable, with glass transition temperature and decomposition temperature as high as 103 and 428 °C, respectively. The polymer light-emitting diode using PFBI8 as the active emitting layer exhibits blue emission (448 nm) with the maximum luminance, current efficiency and power efficiency of 1534 cd/m2, 0.67 cd/A, and 0.20 lm/W, respectively. Copyright
Zhu, Haifeng,Tong, Hui,Gong, Yongyang,Shao, Shiyang,Deng, Chunmei,Yuan, Wang Zhang,Zhang, Yongming
experimental part
p. 2172 - 2181
(2012/07/17)

Regioselective chlorination and bromination of unprotected anilines under mild conditions using copper halides in ionic liquids
By using ionic liquids as solvents, the chlorination or bromination of unprotected anilines at the para-position can be achieved in high yields with copper halides under mild conditions, without the need for potentially hazardous operations such as supplementing oxygen or gaseous HCl.
Wang, Han,Wen, Kun,Nurahmat, Nurbiya,Shao, Yan,Zhang, He,Wei, Chao,Li, Ya,Shen, Yongjia,Sun, Zhihua
supporting information; experimental part
p. 744 - 748
(2012/06/30)

An instant and facile bromination of industrially-important aromatic compounds in water using recyclable CaBr2-Br2 system
Various industrially-important brominated intermediates have been instantly synthesized using aq. CaBr2-Br2 system as an efficient and recyclable brominating reagent under aqueous conditions at room temperature without the need for metal catalysts or acidic additives. Structurally-diverse phenol and aniline derivatives with strong electron-withdrawing groups such as carboxylic, nitro and formyl show remarkable reactivity to the brominating reagent and brominated in 92-98% yield with high purity (>99%) in a very short reaction time. Organic solvent-free conditions, a feature of the green chemistry, were successively used not only for the reactions but also for the isolation of products at the end of the reaction. The recycling of HBr by its neutralization, thereby generating additional amounts of industrially-important CaBr2 has been designed and developed. The brominating reagent has been recycled and regenerated, and the process was repeated up to 4 cycles after the fresh batch using the regenerated brominating reagent having almost identical selectivity and isolated yields, which seems to be the most promising methodology from the viewpoint of the green approach to organic synthesis.
Kumar, Lalit,Mahajan, Tanu,Agarwal
experimental part
p. 2187 - 2196
(2011/09/16)

Synthesis and reactivity studies of a new reagent, ethyltriphenylphosphonium tribromide
A new reagent, ethyltriphenyl phosphonium tribromide (ETPPTB), has been synthesized and studied. Results show that the reagent is quite efficient for various reactions such as organic bominations, acylations, and isothiocyanate preparation. Copyright
Jamir, Latonglila,Alimenla,Kumar, Anil,Sinha, Dipak,Sinha, Upasana B.
experimental part
p. 147 - 155
(2011/03/17)

Exploration of larger central ring linkers in furamidine analogues: Synthesis and evaluation of their DNA binding, antiparasitic and fluorescence properties
The effects of replacing the central furan ring of furamidine with indole and benzimidazole on their DNA binding affinity, antiparasitic activity and fluorescence are reported. The bis-cyanophenylindoles required to make the corresponding amidines were prepared by sequential Stille and/or Suzuki coupling reactions. The bis-cyanophenylbenzimidazoles were obtained by coupling 4-cyanobenzaldehydes with the appropriate cyano substituted phenylenediamine. The bis-nitriles were converted to the diamidines by reaction with LiN[Si(CH3)3]2 or by Pinner methodology. Specifically, we have prepared new series of 2,6- and 2,5-diaryl indoles (6a,b, 12 and 17a-d) and the related benzimidazoles (24, 30 and 35). The new compounds bind in the DNA minor groove in DNA AT base pair sequences and eight of the ten new analogues exhibit ΔTm values comparable to or higher than that of furamidine. Six of ten of the new compounds exhibit lower IC 50 values against Trypanosoma brucei rhodesiense (T. b. r.) and eight of ten exhibit lower IC50 values against Plasmodium falciparum (P. f.) than furamidine. Four of the ten show greater efficacy than furamidine in the rigorous T. b. r. STIB900 mouse model for African trypanosomiasis. Generally, the fluorescence properties of the new analogues are similar to that of DAPI.
Farahat, Abdelbasset A.,Paliakov, Ekaterina,Kumar, Arvind,Barghash, Alaa-Eldin M.,Goda, Fatma E.,Eisa, Hassan M.,Wenzler, Tanja,Brun, Reto,Liu, Yang,Wilson, W. David,Boykin, David W.
scheme or table
p. 2156 - 2167
(2011/05/06)

Silica-supported quinolinium tribromide: A recoverable solid brominating reagent for regioselective monobromination of aromatic amines
Silica-supported quinolinium tribromide was synthesized and found to be an efficient, stable, and recoverable solid brominating reagent for the regioselective monobromination of aromatic amines. This protocol has advantages of high yield, mild condition and simple work-up procedure.
Li, Zheng,Sun, Xiunan,Wang, Lue,Li, Yanbo,Ma, Yuanhong
scheme or table
p. 496 - 501
(2010/08/06)

Mild, efficient, and regioselective monobromination of arylamines and phenols using [BBIm]Br3 as a new reagent
We report here an efficient method for the synthesis and characterization of the room-temperature ionic liquid 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3) (2) and its application as an efficient reagent and solvent for regioselective bromination of arylamines and phenols under mild conditions. The bromination was carried out in the absence of organic solvents, and in most cases, the only extraction solvent needed was water. The spent 1,3-di-n-butylimidazolium bromide (1) was easily recycled.
Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
experimental part
p. 647 - 653
(2011/02/27)

A simple, safe and efficient synthesis of Tyrian purple (6,6'-Dibromoindigo)
6,6'-Dibromoindigo is a major component of the historic pigment Tyrian purple, arguably the most famous dye of antiquity. Over the last century, chemists have been interested in developing practical syntheses of the compound We describe herein a new, reasonably simple and efficient synthesis of Tyrian purple which opens the way to the production of large quantities of the dye with minimal hazards and at low cost.
Wolk, Joel L.,Frimer, Aryeh A.
experimental part
p. 5561 - 5580
(2010/12/20)

INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.
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Page/Page column 18

(2010/08/22)

An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions
1-Butyl-3-methylpyridinium tribromide, [BMPy]Br3 proves to be a highly efficient, regioselective reagent/solvent for nuclear bromination of various anilines and phenols. The synthesis and characterization of the room temperature ionic liquid [BMPy]Br3 (2) is described. The bromination was carried out in the absence of organic solvents and in most cases the only extraction solvent needed was water. The spent 1-butyl-3-methylpyridinium bromide (1) was easily recycled.
Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
scheme or table
p. 1007 - 1009
(2009/05/11)

Effect of structural factors and solvent nature in bromination of anilines
Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.
Bagmanov
experimental part
p. 1570 - 1576
(2011/06/20)

Synthesis and property studies of cyclotrisazobenzenes
Azobenzenophanes are fascinating macrocycles, which are of special interest due to their unique photochromic behavior. Cyclotrisazobenzenes 2 (R = H, Br, tBu) were prepared to probe how much strain the photoisomerization of the azobenzene motive can tolerate. The macrocycles were synthesized in an overall yield of 10-20% from oriho-phenylenediamine (6). Solid-state structures of cyclotrisazobenzenes 2a and 2b were obtained. Irradiation under various conditions did not induce any isomerization.
Reuter, Raphael,Hostettler, Nik,Neuburger, Markus,Wegner, Hermann A.
supporting information; experimental part
p. 5647 - 5652
(2010/02/28)

Simple catalyst-free regio- and chemoselective monobromination of aromatics using NBS in polyethylene glycol
NBS in polyethylene glycol has been efficiently utilized for regio- and chemoselective bromination of activated aromatics at room temperature to form the corresponding bromo products in excellent yields. Copyright Taylor & Francis Group, LLC.
Venkateswarlu, Katta,Suneel, Kanaparthy,Das, Biswanath,Reddy, Kuravallapalli Nagabhushana,Reddy, Thummala Sreenivasulu
experimental part
p. 215 - 219
(2009/04/07)

1, 2 DISUBSTITUTED HETEROCYCLIC COMPOUNDS
1,2-disubstituted heterocyclic compounds which are inhibitors of phosphodiesterase 10 are described. Also described are processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of mammals, including human(s) for central nervous system (CNS) disorders and other disorders which may affect CNS function. Among the disorders which may be treated are neurological, neurodegenerative and psychiatric disorders including, but not limited to, those associated with cognitive deficits or schizophrenic symptoms.
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Page/Page column 99-100

(2010/01/30)

Total synthesis of (-)-flustramine B via one-pot intramolecular ullmann coupling and claisen rearrangement
Total synthesis of (-)-flustramine B was achieved via one-pot intramolecular Ullmann coupling and Claisen rearrangement. A striking feature of this method of synthesis is that the sequential intramolecular Ullmann coupling and Claisen rearrangement reactions proceeds with concomitant deprotection of the methoxymethyl (MOM) group to afford spirocyclic oxindole with perfect asymmetric transmission in good overall yield.
Hirano, Tomohiro,Iwakiri, Kanako,Miyamoto, Hiroshi,Nakazaki, Atsuo,Kobayashi, Susumu
experimental part
p. 805 - 820
(2009/12/01)

INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.
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Page/Page column 60

(2009/04/25)

A convenient and selective method for the para-bromination of aromatic compounds with potassium bromide in the presence of poly(4-vinylpyridine)- supported peroxodisulfate in nonaqueous solution
A convenient and selective procedure for the para-bromination of aromatic compounds has been developed using potassium bromide in the presence of poly(4-vinylpyridine)-supported peroxodisulfate in nonaqueous solution.
Tajik,Mohammadpoor-Baltork,Hassan-Zadeh,Rafiee Rashtabadi
p. 1282 - 1284
(2008/03/27)

Structure-activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors
The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding has been previously reported. The structure-activity relationships around the carboxylic acid substituent are described herein. This acid was replaced by several alternative functional groups in attempts to retain bioactivity while reducing protein binding. Only groups with an acidic proton retained activity, and analogs containing those groups maintained the protein binding inherent to this class of antibacterial agents.
Ruble, J. Craig,Wakefield, Brian D.,Kamilar, Gregg M.,Marotti, Keith R.,Melchior, Earline,Sweeney, Michael T.,Zurenko, Gary E.,Romero, Donna L.
p. 4040 - 4043
(2008/02/08)

NaIO4/KI/NaCl: a new reagent system for iodination of activated aromatics through in situ generation of iodine monochloride
A new reagent system consisting of NaIO4/KI/NaCl in aq AcOH has been found to be effective in iodinating a variety of activated aromatic substrates via in situ-generated iodine monochloride, to furnish iodoaromatics in excellent yields. This iodination procedure has been applied successfully for a cost-effective synthesis of 3,3′-diaminobenzidine, a key intermediate for preparing proton conducting membranes for fuel cell applications, with high yield and a purity of 99.7%.
Emmanuvel, Lourdusamy,Shukla, Ravi Kant,Sudalai, Arumugam,Gurunath, Suryavanshi,Sivaram, Swaminathan
p. 4793 - 4796
(2007/10/03)

An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst
A simple, efficient and rapid method has been developed for high-yielding regioselective nuclear monobromination of aromatic and heteroaromatic compounds using NBS in the presence of sulfonic-acid-functionalized silica at room temperature. The catalyst works under heterogeneous conditions and can be recycled.
Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish
p. 8693 - 8697
(2007/10/03)

Sulfonamide-based compounds as protein tyrosine kinase inhibitors
Various sulfonamide-based compounds are able to selectively inhibit the Src family of tyrosine kinases. These compounds are useful in the treatment of various diseases including hyperproliferative diseases, hematologic diseases, osteoporosis, neurological diseases, autoimmune diseases, allergic/immunological diseases, or viral infections.
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Page/Page column 6/16; 7; 12

(2008/06/13)

Tetrameric DABCO-bromine: An efficient and versatile reagent for bromination of various organic compounds
Tetrameric DABCO-bromine is a powerful brominating agent but shows reasonable selectivity with certain substrates. The selective bromination for activated aromatic compounds and alkenes is reported. Synthesis of α-bromo ketones and nitriles has also been achieved by using this reagent and the results are also reported. All products reported were obtained in good to excellent yields.
Heravi, Majid M.,Derikvand, Fatemeh,Ghassemzadeh, Mitra
p. 125 - 128
(2007/10/03)

Regioselective and high-yielding bromination of aromatic compounds using hexamethylenetetramine-bromine
A regioselective and highly efficient method for bromination of aromatic compounds in the presence of a stoichiometric amount of hexamethylenetetramine- bromine (HMTAB) as an efficient reagent in dichloromethane is reported. The selectivity depends on the temperature and nature of the substituent on the substrate. The reactivity of this reagent was increased by supporting it to silica gel for bromination of less activated compounds.
Heravi, Majid M.,Abdolhosseini, Nafiseh,Oskooie, Hossein A.
p. 8959 - 8963
(2007/10/03)

A new recyclable ditribromide reagent for efficient bromination under solvent free condition
1,2-Dipyridiniumditribromide-ethane (DPTBE) has been synthesized and explored as a new efficient brominating agent. The crystalline ditribromide reagent is stable for months and acts as a safe source of bromine requiring just 0.5 equiv for complete bromination. It has high active bromine content per molecule and shows a remarkable reactivity compared to other tribromide reagents toward various substrates by just grinding the reagent and substrates in a porcelain mortar at room temperature. No organic solvent has been used during any stage of the reaction for substrates giving product as solid. Product can easily be isolated by just washing the highly water soluble 1,2- dipyridiniumdibromide-ethane (DPDBE) from the brominated product. The spent reagent can be recovered, regenerated, and reused without any significant loss.
Kavala, Veerababurao,Naik, Sarala,Patel, Bhisma K.
p. 4267 - 4271
(2007/10/03)

Bromination of aromatic compounds with potassium bromide in the presence of poly(4-vinylpyridine)-supported bromate in nonaqueous solution
A simple, efficient, and mild method for selective bromination of activated aromatic compounds using potassium bromide in the presence of poly(4-vinylpyridine)-supported bromate in nonaqueous solution is reported. The results obtained revealed excellent to good selectiveity between ortho and para positions of methoxyarenes, anilines, and phenols. Copyright Taylor & Francis, Inc.
Tajik, Hassan,Shirini, Farhad,Hassan-Zadeh, Parwin,Rashtabadi, Hassan Rafiee
p. 1947 - 1952
(2007/10/03)

Polymer-supported organotin reagents for regioselective halogenation of aromatic amines
(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.
Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul
p. 2870 - 2873
(2007/10/03)