Ethanone Oxime Research Articles

Chiral N, N′-dioxide-iron(II) complexes catalyzed enantioselective oxa-Michael addition of α,β-unsaturated aldehydes

The enantioselective oxa-Michael addition reaction of 1-(4-methoxyphenyl) ethanone oxime to various α,β-unsaturated aldehydes was accomplished by using chiral N, N′-dioxide-FeSO 4·7H 2O (1:1) complex. Aromatic acid was employed as additive to increase the yield of the reaction. The corresponding adducts were obtained in moderate yields with up to 76% ee under mild conditions.

Oxoperoxo molybdenum(VI)- and tungsten(VI) complexes with 1-(2′-hydroxyphenyl) ethanone oxime: Synthesis, structure and catalytic uses in the oxidation of olefins, alcohols, sulfides and amines using H 2O 2 as a terminal oxidant

High yield synthesis of two new oxodiperoxo-molybdate, PPh 4[MoO(O 2) 2(HPEOH)] ( 1), and -tungstate, PPh 4[WO(O 2) 2(HPEOH)] ( 2), complexes with 1-(2′-hydroxyphenyl) ethanone oxime (HPEOH 2) as organic ligand has been achieved by adding methanol solution of the ligand to the pale-yellow solution obtained by dissolving molybdic-/tungstic-acid (freshly prepared) in hydrogen peroxide and precipitating the complexes using tetraphenylphosphonium chloride. The orange-yellow complexes have been characterized by elemental analysis, IR, 1H NMR, UV–Vis spectroscopy and finally by X-ray structure analysis. Both the complexes function as facile olefin epoxidation catalysts with hydrogen peroxide as terminal oxidant and bicarbonate as a co-catalyst at room temperature. Catalytic potentiality of 1 and 2 is also exhibited in the case of oxidation of alcohols, amines and sulfides. The catalysts are very much efficient especially in olefin epoxidation giving high yield, TON (turnover number) and TOF (turnover frequency). The method described is environmentally benign and cost-effective in all the cases.

Asymmetric synthesis of N-1-(heteroaryl)ethyl- N-hydroxyureas

The asymmetric synthesis of two 5-lipoxygenase inhibitors ( R)- N-1-(benzofuran-2-yl)ethyl- N-hydroxyurea, 99% ee, and ( R)- N-1-(benzo[ b]thiophen-2-yl)ethyl- N-hydroxyurea, 95% ee, is described. The enantioselective reduction of 1-(benzofuran-2-yl)ethanone oxime O-benzyl ether and 1-(benzo[ b]thiophen-2-yl)ethanone oxime O-benzyl ether with borane oxazaborolidine, generated from (1 R,2 S,3 R,4 S)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, was used for the formation of the stereogenic centres.

Synthesis, crystal structure, insecticidal activity and DFT study on the geometry and vibration of O-( E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1 H-1,2,3-triazol-4-yl}ethyleneamino- O-ethyl- O-phenylphosphorothioate

The title compound, O-( E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1 H-1,2,3-triazol-4-yl}ethyleneamino- O-ethyl- O-phenylphosphorothioate, has been synthesized via the condensation reaction of 1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1 H-1,2,3-triazol-4-yl}ethanone oxime and O-ethyl- O-phenylphosphorochloridothioate in the presence of NaOH powder in refluxing EtOH. Its structure was characterized by 1H NMR, FTIR, Raman, elemental analysis and X-ray single crystal diffraction. The results of preliminary bioassays indicated that the title compound displays good insecticidal activity. Density functional (DFT) calculations have been carried out for the title compound by using the Becke-Lee-Yang-Parr's three-parameter hybrid functional (B3LYP) method at 6-31G** and 6-31G* basis sets. The calculated results show that the predicted geometry can well reproduce the structural parameters. The vibrational wave numbers of the title compound were calculated at same level. Predicted vibrational frequencies have been assigned and compared with experimental IR and Raman spectra and they are supported each other.

1,2-Diaryl(3-pyridyl)ethanone oximes. Intermolecular hydrogen bonding networks revealed by X-ray diffraction.

The synthesis of a set of 1-aryl-2-aryl(3-pyridyl)ethanones 1-5 and the corresponding ketoximes 6-9 is reported. Structural studies of oximes 6, 7 and 9 were performed in solution using 1H-NMR and in the solid state by X-ray crystallography, providing evidence of H-bonding networks. The crystal packing was controlled by homomeric intermolecular oxime···oxime H-bond interactions for 6 and cooperative oxime···N(pyridyl) and CH/π interactions for 7 and 9.

Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3-substituted-4,5-dihydropyrazol-1-yl)ethanone oxime ester derivatives

A series of novel 1-(5-substituted-3-substituted-4,5-dihydropyrazol-1-yl)ethanone oxime ester derivatives are synthesized. The results show that compounds 14 and 26c can strongly inhibit Staphylococcus aureus DNA gyrase and Escherichia coli DNA gyrase (with IC 50 of 0.25 and 0.125 μg/mL against S. aureus DNA gyrase, 0.125 and 0.25 μg/mL against E. coli DNA gyrase). On the basis of the biological results, structure–activity relationships are also discussed.

Stereoselective synthesis and biological activities of O‐(E)‐1‐{1‐[(6‐chloropyridin‐3‐yl)methyl]‐5‐methyl‐1H‐1,2,3‐triazol‐4‐yl}ethyleneamino‐O‐ethyl‐O‐arylphosphorothioates

AbstractTo find novel lead compounds having high insecticidal activity, a series of phosphorothioate derivatives containing 1,2,3‐triazole and pyridine rings were synthesized by the reaction of 1‐{1‐[(6‐chloropyridin‐3‐yl)methyl]‐5‐methyl‐1H‐1,2,3‐triazol‐4‐yl}ethanone oxime with phosphorochloridothioates. Their structures were confirmed by IR, 1H NMR, 31P NMR, mass spectrometry, and elemental analyses. The structure of 6c was determined by single crystal X‐ray diffraction, which is thermodynamically stable E isomer. The results of preliminary bioassay indicate that some title compounds possess insecticidal activity to some extent. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:15–20, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20367

Synthesis and characterization of some novel 4-furyl substituted 3-imidazoline 3-oxides

Novel 4-furyl substituted 3-imidazoline 3-oxides were synthesized by the reaction of 2-bromo-1- (2-furanyl)ethanone oxime with aromatic amines and aldehydes, including formaldehyde, using one pot procedures involving the reactions of in situ formed α-amino oximes with aldehydes and also by one pot procedures involving the reactions of in situ formed imines with α-halo oximes.

Synthesis, cytotoxicity, and anti-inflammatory evaluation of 2-(furan-2-yl)-4-(phenoxy)quinoline derivatives. Part 4

A number of 2-(furan-2-yl)-4-phenoxyquinoline derivatives have been synthesized and evaluated for anti-inflammatory evaluation. 4-[(2-Furan-2-yl)quinolin-4-yloxy]benzaldehyde ( 8), with an IC 50 value of 5.0 μM against β-glucuronidase release, was more potent than its tricyclic furo[2,3- b]quinoline isomer 3a (>30 μM), its 4′-COMe counterpart 7 (7.5 μM), and its oxime derivative 13a (11.4 μM) and methyloxime derivative 13b (>30 μM). For the inhibition of lysozyme release, however, oxime derivative 12a (8.9 μM) and methyloxime derivative 12b (10.4 μM) are more potent than their ketone precursor 7 and their respective tricyclic furo[2,3- b]quinoline counterparts 4a and 4b. Among them, 4-{4-[(2-furan-2-yl)-quinolin-4-yloxy]phenyl}but-3-en-2-one ( 10) is the most active against lysozyme release with an IC 50 value of 4.6 μM, while 8 is the most active against β-glucuronidase release with an IC 50 value of 5.0 μM. ( E)-1-{3-[(2-Furan-2-yl)quinolin-4-yloxy]phenyl}ethanone oxime ( 11a) is capable of inhibiting both lysozyme and β-glucuronidase release with IC 50 values of 7.1 and 9.5 μM, respectively. For the inhibition of TNF-α formation, 1-{3-[(2-furan-2-yl)quinolin-4-yloxy]phenyl}ethanone ( 6) is the most potent with an IC 50 value of 2.3 μM which is more potent than genistein (9.1 μM). For the inhibitory activity of fMLP-induced superoxide anion generation, 11a (2.7 μM), 11b (2.8 μM), and 13b (2.2 μM) are three of the most active. None of above compounds exhibited significant cytotoxicity.

Synthesis and Anticancer Evaluation of Certain 4‐Anilinofuro[2,3‐b]quinoline and 4‐Anilinofuro[3,2‐c]quinoline Derivatives.

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Synthesis of novel 4-substituted-7-trifluoromethylquinoline derivatives with nitric oxide releasing properties and their evaluation as analgesic and anti-inflammatory agents

Six derivatives of the general formula 2- or 4-(7-trifluoromethylquinolin-4-ylamino) benzoic acid N′-(nitrooxyacetyl or propionyl) hydrazide and an oxime of the formula 1-[4-(7-trifluoromethylquinolin-4-ylamino)phenyl]ethanone oxime were synthesized and tested for their in vivo anti-inflammatory, analgesic, and ulcerogenic properties, as well as their in vitro nitric oxide release ability. Compound 2-(7-trifluoromethylquinolin-4-ylamino)benzoic acid N′-(2-nitrooxy propionyl)hydrazide 12 showed an anti-inflammatory activity comparable to that of indomethacin in the carrageenan-induced rat paw edema test, and equipotency to glafenine in the acetic acid mice induced writhing model at 100 mg/kg p.o., respectively. All the final compounds showed no tendency to induce stomach ulceration in rats; nitric oxide seems to contribute to their excellent safety profile.

Synthesis and anticancer evaluation of certain 4-anilinofuro[2,3- b]quinoline and 4-anilinofuro[3,2- c]quinoline derivatives

Certain linear 4-anilinofuro[2,3- b]quinoline and angular 4-anilinofuro[3,2- c]quinoline derivatives were synthesized and evaluated in vitro against the full panel of NCI's 60 cancer cell lines. For the linear 4-anilinofuro[2,3- b]quinoline derivatives, 1-[4-(furo[2,3- b]quinolin-4-ylamino)phenyl]ethanone ( 5a) is the most cytotoxic with a mean GI 50 value of 0.025 μM. Substitution at either furo[2,3- b]quinoline ring ( 2a, 2b, and 5b) or 4-anilino moiety ( 3– 7) led to a decrease of cytotoxicity. For the angular 4-anilinofuro[3,2- c]quinoline derivatives, ( E)-1-[3-(furo[3,2- c]quinolin-4-ylamino)phenyl]ethanone oxime ( 14a) exhibited potent inhibitory activities on UO-31, UACC-257, and UACC-62, with GI 50 values of 0.03, < 0.01, and < 0.01 μM respectively. The same cytotoxicity profile was observed for its methyl counterpart, 14b, in which the GI 50 values against UO-31, UACC-257, and UACC-62 was < 0.01, 0.04 and < 0.01 μM respectively. These results deserve full attention especially because 14a and 14b are relatively non-cytotoxic with the mean GI 50 value of 7.73 and 8.91 μM respectively.

Formation of cobalt(II) complexes with five pyridine oximes in aqueous solution

Complex formation equilibria of cobalt(II) with pyridine-2-carboxamidoxime (1), pyridine-2-acetamidoxime (2), pyridine-2-aldoxime (3), 1-(2-pyridinyl)ethanone oxime (4) and 6-methylpyridine-2-aldoxime (5) were studied in 0.1 M NaCl solution at 25°C by potentiometric titrations with use of a glass electrode. Experimental data were analysed with the least-squares computer program SUPERQUAD to determine the complexes formed and their stability constants. With ligands 1−4 Co(II) forms mono, bis and (except for 2) tris complexes of the type and deprotonated/hydrolyzed products of the bis and tris complexes, Co(HL)L+ and Co(HL)2L+. The deprotonated complexes have a low spin structure (t 2 g 6 e g ) and are readily oxidized after the easy loss of the sole e g electron. Their formation with increasing pH involves slow attainment of equilibrium in the pH range 3−5. Only with ligand 3 could studies be continued to pH 8−10 by using very low cobalt(II) ion concentrations. There, CoL2 is formed quantitatively, while complexes Co(HL)L2 and could not be observed. Ligand 1 also forms the complex Co2(HL)2H2L5+ and ligand 2 the complex Co(H2L)3+ with the positively charged ligand (H2L+). Ligand 5 forms the complexes Co(HL)2+, CoL2, Co2L2OH+, and Co2L3OH mainly in the pH range 6−10. The stabilities of these complexes and also their oxidation reactions are reduced by the steric requirements of the 6-methyl groups of the ligand.

AgI and CuI binuclear macrocyclic complexes with 1-(3-pyridyl)ethanone oxime.

Bis[micro-1-(3-pyridyl)ethanone oxime-kappa(2)N:N']bis[nitratosilver(I)], [Ag(2)(NO(3))(2)(C(7)H(8)N(2)O)(2)], crystallizes as a centrosymmetric binuclear macrocylic complex containing silver(I) ions bridged by the organic 1-(3-pyridyl)ethanone oxime ligand. The ligand coordinates via the pyridine and the oxime N atoms. A similar metal-ligand arrangement was found in the copper(I) complex catena-poly[[bis[micro-1-(3-pyridyl)ethanone oxime-kappa(2)N:N']dicopper(I)]-di-micro-iodo], [Cu(2)I(2)(C(7)H(8)N(2)O)(2)](n), but here the centrosymmetric macrocycles are connected by double anion bridges, resulting in the formation of a one-dimensional coordination polymer.

Formation of Zinc(II) and Cadmium(II) Complexes with Pyridine Oxime Ligands in Aqueous Solution

Complex formation equilibria involving pyridine-2-carboxaldehyde oxime (1), 1-(2-pyridinyl)ethanone oxime (2) and 6-methylpyridine-2-carboxaldehyde oxime (3), HL, with zinc(II) and cadmium(II) ions were studied in aqueous 0.1 M NaCl solution at 25° C by potentiometric titrations with a glass electrode. Experimental data were analysed with the least-squares computer program SUPERQUAD to determine the complexes formed and their stability constants. With Ligands 1 and 2 the sets of complexes for Zn(II) and Cd(II) are essentially the same, mono- and dinuclear oxime complexes and their deprotonated/hydrolysed products HpMq(HL)2q+p r. Owing to the steric requirements of the 6-methyl group, sets of complexes formed with 3 are distinctly different. For zinc(II), only dinuclear oximato species HpZn2(HL)4q+p 2 ( p = − 2, − 3, − 4) are found, while for the larger cadmium(II) ion mononuclear oximato species CdL+ and CdL2 are detected in addition to the dinuclear complex HpCd2(HL)4q+p 2 ( p = − 3).

Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives

Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a–c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Those active compounds 4a,b, 6, 8, 10a,b, 11a,b, 12a,b were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that cytotoxicity decreases in the order of 6-anilinoindoloquinolines>indoloquinolin-2(1H)-ones>pyrroloquinolin-2(1H)-ones>benzofuroquinolin-2(1H)-ones. Among them, 1-[3-(11H-indolo[3,2-c]quinolin-6ylamino)phenyl]ethanone oxime hydrochloride (11a) and its 2-chloro derivative (11b) were most active, with mean GI50 values of 1.70 and 1.35μM, respectively. Both compounds 11a,b were also found to inhibit the growth of SNB-75 (CNS cancer cell) with a GI50 value of less than 0.01μM, and, therefore, were selected for further evaluation for in vivo antitumor activity.

Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities

In this study, oxime and oxime ether derivatives of anticonvulsant nafimidone [1-(2-naphthyl)-2-(imidozole-1-yl)ethanone] were prepared as potential anticonvulsant compounds. Nafimidone oxime was synthesized by the reaction of nafimidone and hydroxylamine hydrochloride. O-Alkylation of the oxime by various alkyl halides gave the oxime ether derivatives. Anticonvulsant activity of the compounds was determined by maximal electroshock (MES) and subcutaneous metrazole (scMet) tests in mice and rats according to procedures of the Antiepileptic Drug Development (ADD) program of the National Institutes of Health (NIH). In addition to anticonvulsant evaluation, compounds were also screened for possible antibacterial and antifungal activities because of the structural resemblance to the azole antifungals, especially to oxiconazole. All compounds were evaluated against three human pathogenic fungi and four bacteria using the microdilution method. Most of the compounds exhibited both anticonvulsant and antimicrobial activities; the O-alkyl substituted compounds ( 2, 3, 4 and 5) were found to be more active than the O-arylalkyl substituted compounds in both screening paradigms.

Synthesis and Study of New Clathrochelates with 1-Phenyl-2-(1′-Piperidinyl) Ethanone Oxime Ligand

The synthesis and characterization of new complex compounds of [M(L-H)X2], [ML(L-H)]X and [M(L-H)2] types (M= Co, Ni, Cu, X = Cl, CH3COO) and L=1-phenyl-2-(1'-piperidinyl) ethanone oxime is presented. In reactions of [ML(L-H)]X (M = Ni, Cu) with Lewis acids like TiCl4 and SnCl4 semiclathrochelates of [M(L-H)2MCl2] type (M′ = Ti, Sn) were obtained and characterized (electronic, FT-IR, RPE, NMR spectra, conductivity measurements, as well as TD-analysis). Such complexes should be potential oxygen molecular carriers.

Effects of MCI-727 on pancreatic exocrine secretion and acute pancreatitis in two experimental rat models.

The effects of a newly developed compound having antiulcer action, (Z)-2-(4-methylpiperazin-1-yl)-1-[4-(2-phenyl-ethyl)phenyl]-eth anone oxime hydrochloride monohydrate (MCI-727), on pancreatic exocrine secretion were studied in anesthetized rats and evaluated its preventive and therapeutic effects on acute pancreatitis in two experimental rat models. Intraduodenal administration of MCI-727 [25, 50, or 100 mg/kg body weight (wt)] stimulated a dose-dependent increase in pancreatic juice and bicarbonate output without increasing the protein output or plasma cholecystokinin concentration. MCI-727-stimulated pancreatic exocrine secretion was completely abolished by antisecretin serum but not by the cholecystokinin receptor antagonist loxiglumide (50 mg/kg body wt/h) or cholinergic receptor antagonist atropine (100 mu g/kg body wt/h). In rats with acute pancreatitis induced by four subcutaneous injections of 20 mu g/kg body wt cerulein at hourly intervals over 3 h, MCI-727 administered orally at a dose of 100 mg/kg body wt 30 min before the first cerulein injection significantly reduced the increases in serum amylase and lipase activity and pancreatic wet weight and induced improvements in the results of histologic examination. Moreover, when given 30 min before and 90 min after the first cerulein injection, MCI-727 had even more dramatic protective effects on all these parameters. In addition, even when administered immediately after the last cerulein injection, MCI-727 effectively ameliorated all these alterations of acute pancreatitis. However, MCI-727 had no apparent beneficial effects on the biochemical and histologic alterations of acute pancreatitis in the severe form induced by retrograde intraductal injection of 1.0 ml/kg body wt of 4% sodium taurocholate. These findings suggest that oral administration of MCI-727 stimulates pancreatic exocrine secretion by endogenous secretin release and that it has therapeutic as well as preventive effects on mild forms of acute pancreatitis in rats.

ChemInform Abstract: Addition Reactions of Acetylenic Esters Upon 1‐(2‐Thienyl)‐ and 1‐(3‐ Thienyl)‐ethanone Oximes and Upon 6,7‐Dihydrobenzo(b)thiophen‐4(5H)‐ one and 5,6‐Dihydrobenzo(b)thiophen‐7(4H)‐one Oximes. Formation of 2‐( Thienyl)pyrroles and 4,5‐Dihydro‐1H‐thieno(g)indoles.

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