- Discovery of Biphenyl-Sulfonamides as Novel β- N-Acetyl- d -Hexosaminidase Inhibitors via Structure-Based Virtual Screening
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Novel insecticidal targets are always in demand due to the development of resistance. OfHex1, a β-N-acetyl-d-hexosaminidase identified in Ostrinia furnacalis (Asian corn borer), is involved in insect chitin catabolism and has proven an ideal target for insecticide development. In this study, structure-based virtual screening, structure simplification, and biological evaluation are used to show that compounds with a biphenyl-sulfonamide skeleton have great potential as OfHex1 inhibitors. Specifically, compounds 10k, 10u, and 10v have Ki values of 4.30, 3.72, and 4.56 μM, respectively, and thus, they are more potent than some reported nonglycosyl-based inhibitors such as phlegmacin B1 (Ki = 26 μM), berberine (Ki = 12 μM), 2 (Ki = 11.2 μM), and 3 (Ki = 28.9 μM). Furthermore, inhibitory kinetic assessments reveal that the target compounds are competitive inhibitors with respect substrate, and based on toxicity predictions, most of them have potent drug properties. The obtained results indicate that the biphenyl-sulfonamide skeleton characterized by simple chemical structure, synthetic tractability, potent activity, and low toxicity has potential for further development in pest management targeting OfHex1.
- Chen, Tao,Li, Wen-Qin,Liu, Zheng,Jiang, Wen,Liu, Tian,Yang, Qing,Zhu, Xiao-Lei,Yang, Guang-Fu
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p. 12039 - 12047
(2021/10/20)
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- Cellulose supported Pd(II) complex catalyzed carbon-carbon bonds formation
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Corn-cobs are an agro-industrial waste and composed of cellulose mostly. In this study cellulose was isolated from the waste corn-cobs and modified to polymeric hydroxamic acid palladium complex 1 and characterized by using a variety of spectroscopic methods such as field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The complex 1 exhibited high catalytic activity towards Suzuki and Heck coupling reactions of activated and deactivated aryl halides to give the respective coupling products with high yield. Moreover, the complex 1 was recovered and recycled five times with no considerable loss of catalytic overall performance.
- Sarkar, Shaheen M.,Rashid,Karim, Kaykobad Md. Rezaul,Mustapha, Siti Noor Hidayah,Lian, Yuen Mei,Zamri, Normaiza,Khan, Md. Maksudur Rahman,O'Reilly, Emmet J.,Rahman, Md. Lutfor
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p. 2856 - 2861
(2019/01/03)
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- Delineating the Role of Substituents on the Coordination Behavior of Aroylhydrazone Ligands in PdII Complexes and their Influence on Suzuki–Miyaura Coupling in Aqueous Media
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Reactions of piperonal aroylhydrazone ligands (HL1–HL4) with [PdCl2(PPh3)2] in CH3OH and CHCl3 afforded four new Pd(II) complexes (1–4) featuring diverse coordination behaviors. These complexes 1–4 were fully characterized by elemental analyses, UV/Visible, FT-IR and 1H/13C NMR spectra. The variant coordination modes of piperonal aroylhydrazone ligands with Pd(II) ion in these complexes were unambiguously confirmed by single-crystal XRD study. Though the ligands HL1–HL4 are of similar nature, one of them (HL4) possessing an electron withdrawing nitro group as substitution in the peripheral part of the hydrazone displayed an uncommon ligation towards the palladium ion. An experimentally observed molecular architects were in turn rationalized by density functional theory (DFT) calculations as well as natural bonding analysis (NBO). All these Pd(II) complexes were evaluated for their catalytic potential towards Suzuki–Miyaura cross-coupling reaction of sterically congested arylboronic acids with (hetero)arylhalides under an open-flask conditions in aqueous media with low catalyst loading. Advantageously, the selected catalyst was active up to five cycles without significant loss in activity.
- Vignesh, Arumugam,Shalini, Chinnuswamy,Dharmaraj, Nallasamy,Kaminsky, Werner,Karvembu, Ramasamy
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p. 3869 - 3882
(2019/09/17)
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- Atom-efficient Pd-catalyzed cross-couplings of chloroarenes with triarylbismuth reagents
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Various Pd-catalyzed protocols have been developed for the atom-efficient cross-coupling of chloroarenes with triarylbismuth reagents. Using the developed protocols, an efficient synthesis of unsymmetrical biaryls in good to excellent yields was achieved by employing electron-deficient chloroarenes and a range of triarylbismuth reagents.
- Rao, Maddali L.N.,Meka, Suresh
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supporting information
(2019/07/30)
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- Thioether–NHC-Ligated PdII Complex for Crafting a Filtration-Free Magnetically Retrievable Catalyst for Suzuki–Miyaura Coupling in Water
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A new benzimidazolium salt, 1-[benzylaminocarbonylmethyl]-3-(2-phenylsulfanylethyl)-1H-benzimidazolium chloride (L), which is a precursor of a novel thioether-functionalized NHC, has been synthesized by subjecting 1H-benzimidazole to a sequence of reactions with 1,2-dichloroethane, sodium thiophenolate, and N-benzyl-2-chloroacetamide, successively. The moisture/air-insensitive complex [Pd(L–HCl)Cl2] (1) was prepared by the reaction of L with PdCl2. The molecular structure of 1, established by X-ray crystallography, revealed a square-planar geometry around Pd. Complex 1 was screened for Suzuki–Miyaura coupling reactions of various aryl/heteroaryl bromides (yields of up to 94 % in 2 h) in water at room temperature. Furthermore, complex 1 was immobilized onto the surface of aminopropyl-functionalized silica-coated magnetite nanoparticles [NPs, Fe3O4@SiO2-(CH2)3-NH2] by a stepwise modification strategy to develop the heterogeneous magnetically retrievable catalyst Fe3O4@SiO2-1′, in which the amide functionality present in the side-arm of the NHC within the NHC–PdII complex serves as linker. This magnetic nanosupport, bearing palladium complexes incorporating a novel thioether-based NHC ligand that functions in aqueous aerobic medium and can be easily separated, renders Fe3O4@SiO2-1′ a most desirable catalyst for the Suzuki–Miyaura coupling reaction. It was also observed that the catalyst was effective for up to seven cycles and was easily separated from the reaction medium by the use of an external magnet, further increasing its appeal.
- Nayan Sharma, Kamal,Satrawala, Naveen,Kumar Joshi, Raj
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p. 1743 - 1751
(2018/05/14)
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- Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides
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Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.
- Barbero, Margherita,Dughera, Stefano
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p. 5758 - 5769
(2018/09/10)
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- Mono- and dinuclear cyclopalladates as catalysts for Suzuki–Miyaura cross-coupling reactions in predominantly aqueous media
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Suzuki–Miyaura cross-coupling reactions of aryl halides with arylboronic acids were performed in predominantly aqueous media employing two mono- and two dinuclear cyclopalladated complexes as catalysts. These complexes are [Pd(HL)Cl] (I), [Pd(L)(PPh3)] (II), [Pd2(μ-dppb)(L)2] (III) and [Pd2(μ-dppf)(L)2] (IV); where H2L, dppb and dppf represent 4-methoxy-N′-(mesitylidene)benzohydrazide, 1,4-bis(diphenylphosphino)butane and 1,1′-bis(diphenylphosphino)ferrocene, respectively. The reactions were conducted using potassium carbonate as base in presence of tetrabutylammonium bromide (TBAB) at 70/90 °C in dimethylformamide–water (1:20) mixture. Among the four catalysts used, the dinuclear complex IV turned out to be the most effective and afforded moderate to excellent yields with broad substrate scope.
- Babu, G. Narendra,Pal, Samudranil
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p. 1000 - 1005
(2017/02/18)
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- Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water
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A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling- was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.
- Kutonova, Ksenia V.,Jung, Nicole,Trusova, Marina E.,Filimonov, Victor D.,Postnikov, Pavel S.,Br?se, Stefan
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p. 1680 - 1688
(2017/03/21)
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- Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for Suzuki-Miyaura cross-coupling reactions in water
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The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.
- Kodicherla, Balaswamy,Perumgani C., Pullaiah,Keesara, Srinivas,Mandapati, Mohan Rao
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supporting information
p. 95 - 100
(2014/09/30)
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- Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for suzuki-miyaura cross-coupling reactions in water
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The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.
- Balaswamy, Kodicherla,Pullaiah, Perumgani C.,Srinivas, Keesara,Rao, Mandapati Mohan
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p. 95100 - 95100
(2014/12/10)
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- Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for Suzuki-Miyaura cross-coupling reactions in water
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The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.
- Kodicherla, Balaswamy,Perumgani C., Pullaiah,Keesara, Srinivas,Mandapati, Mohan Rao
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- Unique solvent-dependent fluorescence of nitro-group-containing naphthalene derivatives with weak donor-strong acceptor system
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We synthesized nitro-group-containing π-conjugated naphthalene derivatives with a weak donor-strong acceptor system and investigated their photophysical properties. The nitro group was introduced into naphthalene through the phenyl or phenylethynyl moiety at the C2 and C7 positions as the strong acceptor moiety, and a methoxy group was introduced into naphthalene directly at the position opposite to the nitro group, as a weak donor moiety. While 2-(4-nitrophenyl)naphthalene did not show fluorescence in various solvents, 2-methoxy-6-(4-nitrophenyl)naphthalene showed fluorescence in weakly polar solvents (ΦF = 0.11 in CH2Cl2), with a large Stokes shift (Δν = 12,000 cm-1). Additionally, 2-methoxy-6-(4-nitrophenyl)naphthalene did not show fluorescence in polar solvents (acetonitrile) and non-polar solvents (toluene). This unique solvent-dependent fluorescence is remarkable for environmental fluorescence sensor applications.
- Hachiya, Sojiro,Asai, Kengo,Konishi, Gen-Ichi
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supporting information
p. 1839 - 1841
(2013/05/09)
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- Design and synthesis of boronic acid inhibitors of endothelial lipase
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Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL.
- O'Connell, Daniel P.,Leblanc, Daniel F.,Cromley, Debra,Billheimer, Jeffrey,Rader, Daniel J.,Bachovchin, William W.
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scheme or table
p. 1397 - 1401
(2012/03/26)
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- ZnCl2-catalyzed [4 + 2] benzannulation of 2-ethynylbenzaldehydes with alkynes: Selective synthesis of naphthalene derivatives
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Zn-catalyzed [4 + 2] benzannulation of 2-ethynylbenzaldehydes with alkynes is described for the selective synthesis of naphthalene derivatives. In the presence of ZnCl2, a variety of 2-ethynylbenzaldehydes underwent the [4 + 2] benzannulation reactions with alkynes to selectively afford the corresponding naphthalene derivatives in moderate to good yields.
- Fang, Xiao-Li,Tang, Ri-Yuan,Zhang, Xing-Guo,Zhong, Ping,Deng, Chen-Liang,Li, Jin-Heng
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experimental part
p. 352 - 356
(2011/02/16)
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- The 1,3-diaminobenzene-derived aminophosphine palladium pincer complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A highly active Suzuki-Miyaura catalyst with excellent functional group tolerance
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The rapidly prepared 1,3-diaminobenzenederived aminophosphine pincer complex {C6H3 [NHP(piperidinyl)2] 2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side-product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable. Experimental observations indicate that palladium nanoparticles are the catalytically active form of 1.
- Bolliger, Jeanne L.,Frech, Christian M.
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experimental part
p. 1075 - 1080
(2010/06/17)
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- Palladium-catalyzed cross-coupling of 2,3-naphthoxadisilole with aryl halides
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Palladium-catalyzed cross-coupling between 2,3-naphthoxadisilole and aryl halides in the presence of tetrabutylammonium fluoride afforded 2-aryl naphthalenes. This is first report that oxadisilole served as a partner in the palladium-catalyzed cross-coupling reactions. The reaction mechanism was also studied.
- Ding, Han,Chen, Yali,Cao, Weiguo,Wu, Kaicheng,Chen, Jie,Lee, Albert W. M.
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experimental part
p. 984 - 991
(2010/05/18)
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- Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts
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(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).
- Goossen, Luksa J.,Rodriguez, Nuria,Lange, Paul P.,Linder, Christophe
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supporting information; experimental part
p. 1111 - 1114
(2010/04/29)
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- Phosphine-free palladium(II)-catalyzed arylation of naphthalene and benzene with aryl iodides
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(Chemical Equation Presented) A phosphine-free arylation of naphthalene and benzene with aryl iodides to give biaryls in moderate to good yields is carried out in the presence of catalytic Pd(OAc)2 and stoichiometric CF 3CO2 Ag in TFE or/and TFA.
- Qin, Chunxia,Lu, Wenjun
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supporting information; experimental part
p. 7424 - 7427
(2009/05/07)
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- Diels-Alder reactions of 2′-hydroxychalcones with ortho-benzoquinodimethane: A new synthesis of 3-aryl-2-naphthyl 2-hydroxyphenyl ketones
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Diels-Alder reactions of the 2′-hydroxychalcones 1a-e with oriho-benzoquinodimethane (3) yielded the 3-aryl-1,2,3,4-tetrahydro-2-naphthyl 2-hydroxyphenyl ketones 4a-e in good yields. The dehydrogenation of the cycloadducts 4a-e to 3-aryl-2-naphthyl 2-hydroxyphenyl ketones 5a-e was studied. Good results were obtained when DDQ was used as oxidant and microwave irradiation as energy source. Several benzoxanthone derivatives were also obtained as minor products. Structures of all new compounds were established by extensive NMR studies. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Brito, Cristela M.,Pinto, Diana C. G. A.,Silva, Artur M. S.,Silva, Ana M. G.,Tome, Augusto C.,Cavaleiro, Jose A. S.
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p. 2558 - 2569
(2007/10/03)
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- Generation of Aryl Radicals by the Oxidation of α-(Arylazo)triphenylmethanes by Cerium(IV) Ammonium Nitrate
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The one-electron oxidation of α-(arylazo)triphenylmethanes by cerium(IV) ammonium nitrate (CAN) generated aryl radicals along with the triphenylmethyl cation.When the reaction was carried out in the presence of appropriate radical-trapping agents, such as arenes and olefins, the corresponding addition products were obtained in moderate yield.The oxidation of the arylazo compounds with CAN was accelerated by the addition of acids.
- Arai, Noriyoshi,Narasaka, Koichi
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p. 1707 - 1714
(2007/10/02)
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