- Synthesis, characterization and biological activity evaluation of novel naphthalenylmethylen hydrazine derivatives as carbonic anhydrase inhibitors
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In the current study some derivatives of naphthalenylmethylen hydrazine were synthesized and possible in vitro hCA I and II enzymes inhibition effects were investigated. The designed compounds were synthesized by condensation of phenylhydrazine with 1-naphthaldehyde or 6-methoxy-2-naphthaldehyde and eight compounds (1a-h) were obtained. The novel Schiff bases derivatives (compounds 1a-1h) were effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II) with Ki values in the range of 80.60 ± 17.90 to 492.53 ± 95.23 nM for hCA I, 102.88 ± 18.44 to 461.09 ± 102.50 nM for hCA II. 1f compound shows a remarkable inhibitory effect of hCA I and hCA II isoenzymes among the new synthesized compounds. The new derivatives of naphthalenylmethylen hydrazine can be a potent inhibitor of both cytosolic CA isoenzymes which are commonly used in the pharmaceutical industries and medical areas.
- Dilek, Esra,Shirinzadeh, Hanif
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- Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines
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Herein, an efficient and simple catalytic method for the selective and partial reduction of aldazines using ruthenium catalyst [Ru(p-cymene)Cl2]2 (1) has been accomplished. Under mild conditions, aldazines undergo the addition of pinacolborane in the presence of a ruthenium catalyst, which delivered N-boryl-N-benzyl hydrazone products. Notably, the reaction is highly selective, and results in exclusive mono-hydroboration and desymmetrization of symmetrical aldazines. Mechanistic studies indicate the involvement of in situ formed intermediate [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1a) in this selective hydroboration.
- Gunanathan, Chidambaram,Pradhan, Subham,Thiyagarajan, Subramanian
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supporting information
p. 7147 - 7151
(2021/08/30)
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- Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions
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Abstract: A facile, environmentally and efficient Cs2CO3-mediated decomposition of N-tosylhydrazones reaction has been developed for the synthesis of functionalized azines under mild conditions. This method offers broad substrate scope, occurs as additive-free, without strong base conditions, utilizes readily available reactants, and forms products in good to high yields. Graphical Abstract: [Figure not available: see fulltext.]
- Luo, Zai-Gang,Liu, Peng,Fang, Yu-Yu,Xu, Xue-Mei,Feng, Cheng-Tao,Li, Zhong,Zhang, Xiao-Mei,He, Jie
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p. 1139 - 1148
(2017/02/10)
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- Utility of nitriles in synthesis of pyrido[2,3-d]pyrimidines, thiazolo[3,2-a]pyridines, pyrano[2,3-b]benzopyrrole, and pyrido[2,3-d] benzopyrroles
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3-Aryl-2-cyanoacrylonitriles (1a,b) reacted with 6-aminothiouracil, 2-ethoxy carbonylmethyl-4-oxo-Δ2-thiazoline, 2-cyanomethyl-4-oxo-Δ2- thiazoline and indan-2-one to give pyrido[2,3-d]pyrimidines, thiazolo[3,2-a]pyridines, pyrano [2,3-b]benzopyrrole and pyrido[2,3-b] benzopyrrole, respectively. The IR, MS and 1H-NMR of the synthesized compounds were discussed. The antimicrobial activity of some of the synthesized compounds was tested. Copyright Taylor & Francis Group, LLC.
- Mahmoud,El-Bordany,Hassan,El-Azm, F. S. M. Abu
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p. 2507 - 2521
(2008/03/13)
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- Orthoamide, LX [1]. N,N,N',N'-Tetraformylhydrazine- a Formylation Agent for Aromatic Compounds of Wide Scope
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The reagent system formed from N,N,N',N'-tetraformylhydrazine (3) and aluminum chloride allows the formylation of aromatic compounds. The scope of the method is comparable with the Olah formylation and the Gross-Rieche procedure, since benzene and fluorobenzene can be formylated. Two formyl groups are transferred from 3 to the aromatic nuclei when a molar ratio 4:1:4 (aluminum chloride/3/aromatic compound) is chosen.
- Kantlehner, Willi,Haug, Erwin,Scherr, Oliver,Stoyanov, Edmont V.,Mezger, Jochen,Ziegler, Georg
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p. 355 - 365
(2007/10/03)
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- A novel approach to 2-chloro-2-fluorostyrenes
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A new general catalytic olefination reaction (COR) of aromatic and heteroaromatic aldehydes and ketones was applied to synthesise 2-chloro-2-fluorostyrenes. The two-stage procedure includes the transformation of carbonyl compounds into hydrazones followed by treatment with CFCl3 mediated by copper catalysis. Trichlorofluoromethane was used as a chlorofluoromethylene transfer reagent. The reaction proceeds stereoselectively and the target alkenes were obtained in high yield. A proposed mechanism for the reaction is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Nenajdenko, Valentine G.,Shastin, Alexey V.,Korotchenko, Vasily N.,Varseev, Georgy N.,Balenkova, Elisabeth S.
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p. 302 - 308
(2007/10/03)
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- A novel approach to fluoro-containing alkenes
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A new and general one-pot transformation of aromatic aldehydes to fluorinated olefins containing -CH=C(Cl)CF3 or -CH=C(F)CClF2 moieties is described. Freons CCl3CF3 and CCl2FCClF2 were used as trifluoromethyl and difluoromethyl C2-building blocks respectively. A proposed mechanism for the reaction is discussed.
- Korotchenko, Vasily N,Shastin, Alexey V,Nenajdenko, Valentine G,Balenkova, Elisabeth S
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p. 7519 - 7527
(2007/10/03)
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- One-pot oxidation of azomethine compounds into arenecarboxylic acids
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Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.
- Giurg,Said,Syper,Mlochowski
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p. 3151 - 3159
(2007/10/03)
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- Fully conjugated and soluble polyazomethines containing 1.1′ binaphthyl groups
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Four monomers containing azomethine linkages and 1-naphthyl groups at the extremities were synthesized by coupling reaction of 1-naphthylaldehyde or 1-naphthylamine with two diamines and two dialdehydes, respectively. The corresponding polymers were obtained by chemical oxidation using anhydrous FeCl3. Both monomers and polymers were investigated by IR, UV and 1H-NMR methods.
- Grigora?, Mircea,Cianga, Ioan,Farcas, Aurica,Nǎstase, Georgiana,Ivǎnoiu, Maria
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p. 703 - 708
(2007/10/03)
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- Oxidative Transformations of Aldazines and Ketazines with Organic Peroxyacids
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Oxidation of aromatic aldazines and ketazines with various peroxycarboxylic acids was investigated.It was found that one part of azine molecule 2 was converted into carbonyl compound 1 or related acid 3 while the second part was transformed into carboxylic ester 4 related to peroxyacid used as an oxidant.It was revealed that aromatic azines could be used as a source of diazaarylmethanes and mechanisms of reactions studied were postulated. aldazines, carboxylic esters, ketazines, oxidation, peroxycarboxylic acids
- Mlochowski, J.,Giurg, M.
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p. 2333 - 2342
(2007/10/02)
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