- Synthesis, protease inhibition, and antileishmanial activity of new benzoxazoles derived from acetophenone or benzophenone and synthetic precursors
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Abstract: This work reports the synthesis, protease inhibition, and antileishmanial activity of ten benzoxazole derivatives, which were obtained in a three-step synthetic route from 4-hydroxy-acetophenone and 4-hydroxy-benzophenone. These benzoxazoles, the synthetic intermediates, and the starting ketones were evaluated for their inhibitory effect on the activity of cysteine (papain, rCPB2.8, and rCPB3.0) and serine (trypsin) proteases. All compounds showed significant values of IC50 against these enzymes (in the range of 0.0086–0.7612 μM for papain and 0.0075–0.5032 μM for trypsin), being more active than the standard inhibitors (1.7821 and 7.2318 μM, for E64 and TLCK, respectively). Following, all compounds were evaluated in vitro for their leishmanicidal activity against promastigote form of Leishmania amazonensis. The most active compounds were further evaluated against amastigote form and for its toxicity against murine macrophages. The benzoxazole 4d, a benzophenone derivative, and the intermediate 4-hydroxy-3-nitroacetophenone 2b showed significant antileishmanial activity (IC50 = 90.3 μM and IC50 = 130.9 μM, respectively) with selectivity indexes (5.22 and 18.09, respectively) compared to or better than those of two established leishmanicidal drugs, pentamidine (0.58) and amphotericin B (5.31). Graphical Abstract: [InlineMediaObject not available: see fulltext.].
- Folquitto, Laís R. S.,Nogueira, Priscila F.,Espuri, Patrícia F.,Gontijo, Vanessa S.,de Souza, Thiago B.,Marques, Marcos J.,Carvalho, Diogo T.,Júdice, Wagner A. S.,Dias, Danielle F.
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p. 1149 - 1159
(2017/05/04)
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- Benzophenone based fluorophore for selective detection of Sn2?+ ion: Experimental and theoretical study
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Synthesis of novel benzophenone-based chemosensor is presented for the selective sensing of Sn2?+ ion. Screening of competitive metal ions was performed by competitive experiments. The specific cation recognition ability of chemosensor towards
- Jadhav, Amol G.,Shinde, Suvidha S.,Lanke, Sandip K.,Sekar, Nagaiyan
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p. 291 - 296
(2016/12/18)
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- An eco-friendly Co(OAc)2-catalyzed aerobic oxidation of 4-benzylphenols into 4-hydroxybenzophenones
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An undecorated Co(OAc)2-catalyzed aerobic oxidation system has been reported that enables direct transformation of 4-benzylphenols into the corresponding 4-hydroxybenzophenones. The procedure is especially suitable for electron-withdrawing group-containing substrates, which are commonly inefficient to conduct this category of oxidation. Based on well-defined p-benzoquinone methides and the confirmed ethereal intermediate, a plausible mechanism was depicted.
- Huang, Jian-Gang,Guo, Ying,Jiang, Jian-An,Liu, Hong-Wei,Ji, Ya-Fei
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p. 7115 - 7124
(2015/02/19)
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- Melamine-(H2SO4)3 and PVP-(H 2SO4)n as solid acids: Synthesis and application in the first mono- and di-nitration of bisphenol A and other phenols
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Melamine and poly vinylpyrrolidone (PVP) reacted with neat sulfuric acid readily to form two new organic solid acids namely melamine-(H 2SO4)3 and PVP-(H2SO 4)n. These solid acids were used for the first nitration of bisphenol A as well as other phenols in the presence of NH4NO 3. Mono- and di-nitro bisphenol A have been characterized with IR and 1H NMR techniques.
- Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali,Azimi, Seyedeh Bahareh,Alizadeh, Ebadollah
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experimental part
p. 827 - 830
(2012/02/14)
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- PEG-N2O4: An efficient nitrating agent for the selective mono- and dinitration of phenols under mild conditions
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N2O4 was easily impregnated on polyethyleneglycol to give a stable reagent. The polyethyleneglycol-N2O4 (PEG-N2O4) system was used as an effective nitrating agent for the nitration of phenols. Mono- and dinitrophenols can be obtained via direct nitration of phenols in the presence of PEG-N2O4 at room temperature in moderate to high yields. Copyright Taylor & Francis Group, LLC.
- Zolfigol, Mohammad Ali,Madrakian, Elaheh,Ghaemi, Ezat,Niknam, Khodabakhsh
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p. 3366 - 3374
(2008/12/22)
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- Ionic complex of N2O4 with 18-crown-6: A highly efficient and selective reagent for nitration of phenols
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Interaction of gaseous N2O4 with 18-crown-6 affords the stable crystalline complex of NO+ · 18-crown-6 · H(NO3)2· This ionic complex is an efficient nitrating agent for the selective mono-, di-, and trinitration of phenol and also for the selective mono-, and dinitration of substituted phenols.
- Iranpoor,Firouzabadi,Heydari
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p. 3295 - 3302
(2007/10/03)
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- A convenient synthesis of 2-nitrophenols from 1,2-dichlorobenzenes
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Aromatic nucleophilic substitution of 1,2-dichlorobenzenes 1 possessing a strong electron-withdrawing group in the 4-position with a nitrite ion give the corresponding 2-nitrophenols 5.
- Zilberman,Ioffe,Gozlan
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p. 659 - 660
(2007/10/02)
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- Vicarious Nucleophilic Hydroxylation of Aromatic Nitro Compounds with Organic Hydroperoxides
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Nitrobenzene, α-nitronaphthalene, m-dinitrobenzene, 1,3,5-trinitrobenzene, m-nitrobenzophenone, m-nitrobenzonitrile, methyl m-nitrobenzoate and m-nitro diphenylsulphone can be hydroxylated with cumene or tert-butyl hydroperoxide in dipolar aprotic solvents in the presence of strong bases.The hydroxyl group is introduced preferably in p-position to the nitro group.Attempts to hydroxylate benzophenone, anthraquinone, 2-ethyl anthraquinone, anthraquinone 2-sulphonate, benzonitrile and diphenyl sulphone under the same conditions failed. 1-Nitroanthraquinone delivered 1-hydroxy, 1,2-dihydroxy and 1,4-dihydroxy anthraquinone.
- Brose, Thomas,Holzscheiter, Felix,Mattersteig, Gunter,Pritzkow, Wilhelm,Voerckel, Volkmar
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p. 497 - 504
(2007/10/02)
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