Showing papers on "Morpholine published in 2011"
TL;DR: In this paper, photoionization (PI) and electron ionization (EI) molecular-beam mass spectrometry (MBMS) were combined to determine absolute mole-fraction profiles of numerous major and intermediate species with up to 6 heavy atoms.
66 citations
TL;DR: The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity.
Abstract: The scope and limitations of metal tetrafluoroborates have been studied for epoxide ring-opening reaction with amines, and Zn(BF(4))(2)·xH(2)O has been found to be a mild and efficient catalyst affording high yields under solvent-free conditions at rt with excellent chemo-, regio-, and stereoselectivities. The catalytic efficiency followed the order Zn(BF(4))(2)·xH(2)O ≫ Cu(BF(4))(2)·xH(2)O > Co(BF(4))(2)·6H(2)O ≫ Fe(BF(4))(2)·6H(2)O > LiBF(4) for reactions with cyclohexene oxide and Zn(BF(4))(2)·xH(2)O ≫ Co(BF(4))(2)·6H(2)O ≫ Fe(BF(4))(2)·6H(2)O > Cu(BF(4))(2)·xH(2)O for stilbene oxide, but AgBF(4) was ineffective. For reaction of styrene oxide with aniline, the metal tetrafluoroborates exhibited comparable regioselectivity (1:99-7:93) with preferential reaction at the benzylic carbon of the epoxide ring. A reversal of regioselectivity (91:1-69:31) in favor of the reaction at the terminal carbon of the epoxide ring was observed for reaction with morpholine. The regioselectivity was dependent on the electronic and steric factors of the epoxide and the pK(a) of the amine and independent of amine nucleophilicity. The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity. The methodology was used for synthesis of cardiovascular drug metoprolol as racemic and enriched enantiomeric forms.
64 citations
TL;DR: The chemical structures of the newly synthesized compound ware characterized by IR, 1H-N MR, 13C-NMR and mass spectral analysis and exhibited promising activities.
Abstract: 6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a-d. Reaction of 3a-d with phosphorus oxychloride yielded 6-chlorofurochromenylidenepyrimidinamines 4a-d, which were reacted with secondary amines to afford furochromenylideneamino-2,6-disubstituted pyrimidin-4-ones 5a-d. In addition, reaction of 5a-d with 3-chloropentane-2,4-dione gave 3-chloro-furochromenylpyrimidopyrimidines 6a-d. The latter were reacted with piperazine and morpholine to give 1-(furochromenyl)-pyrimidopyrimidine-3,6,8-triylpiperazines or -3,6,8-triylmorpholines 7a-d. The chemical structures of the newly synthesized compound ware characterized by IR, ¹H-NMR, ¹³C-NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of them, particularly 3-7, exhibited promising activities.
60 citations
TL;DR: In this paper, 2-Acetylpyridine-N(4)-morpholine thiosemicarbazone (HAcpMTSc) was synthesized and investigated as an inhibitor for mild steel corrosion in acid media.
Abstract: 2-Acetylpyridine-N(4)-morpholine thiosemicarbazone (HAcpMTSc) was synthesized and investigated as an inhibitor for mild steel corrosion in acid media. Various concentrations of the inhibitor in 1 M HCl solution were tested, and the corrosion inhibition efficiency to mild steel was estimated by means of weight loss measurements, potentiodynamic polarization, and electrochemical impedance spectroscopy. The adsorption equilibrium constant (Kads) and standard free energy of adsorption (ΔG°ads) were calculated. The nature of inhibition was studied by various spectroscopic techniques such as UV–visible, FTIR, and EPR spectroscopies and by using surface analysis methods (i.e., SEM-EDS).
56 citations
TL;DR: A series of metal-organic networks of CuSCN were prepared by direct reactions with substituted pyridine and aliphatic amine ligands, L, and thiocyanate bridging is seen in all but 1 of 11 new X-ray structures.
Abstract: A series of metal–organic networks of CuSCN were prepared by direct reactions with substituted pyridine and aliphatic amine ligands, L. Thiocyanate bridging is seen in all but 1 of 11 new X-ray structures. Structures are reported for (CuSCN)L sheets (L = 3-chloro- and 3-bromopyridine, N-methylmorpholine), ladders (L = 2-ethylpyridine, N-methylpiperidine), and chains (L = 2,4,6-collidine). X-ray structures of (CuSCN)L2 are chains (L = 4-ethyl- and 4-t-butylpyridine, piperidine, and morpholine). A unique N-thiocyanato monomer structure, (CuSCN)(3-ethylpyridine)3, is also reported. In most cases, amine ligands are thermally released at temperatures <100 °C. Strong yellow-to-green luminescence at ambient temperature is observed for the substituted pyridine complexes. High solid state quantum efficiencies are seen for many of the CuSCN-L complexes. Microsecond phosphorescence lifetimes seen for CuSCN-L are in direct contrast to the nanosecond-lifetime emission of CuSCN. MLCT associated with pyridine π* orbital...
55 citations
TL;DR: Organocatalytic direct C3 alkenylation of indoles has been developed and simplicity and practicality constitute the most attractive advantages of this reaction.
54 citations
TL;DR: The antibacterial activities of the newly synthesized derivatives were investigated and all compounds were evaluated for their anti-inflammatory activity and the most potent derivatives were tested for their analgesic activity using indomethacin as a reference drug.
Abstract: This study is concerned with the synthesis of new 1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-thiadiazines derivatives. Derivatives 3a–i were obtained by condensation of 4-amino-3-(4-pyridine)-5-mercapto-1,2,4-triazole 1 with the appropriate aldehyde. Compounds 4a–i were synthesized in a one pot reaction involving compounds 3a–i, formaldehyde, and morpholine. Condensation of compound 1 with the appropriate acids or 4-substituted phenacyl bromide gave compounds 6a–d and 8a–f respectively. The chemical structures of the newly synthesized derivatives were elucidated using different spectral and elemental methods of analysis. All compounds were evaluated for their anti-inflammatory activity and the most potent derivatives were tested for their analgesic activity using indomethacin as a reference drug. In addition, ulcerogenicity and LD50 for the most active compounds were evaluated. Moreover, the antibacterial activities of the newly synthesized derivatives were investigated.
48 citations
TL;DR: Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones.
Abstract: Azidation of 1,2-anhydro sugars with NaN3 in CH3CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.
48 citations
TL;DR: In this paper, a series of dihydropyrano[c]chromene was obtained via condensation of aldehyde, malononitrile and 4-hydroxycoumarin in water catalyzed by morpholine.
Abstract: A series of dihydropyrano[c]chromene was obtained via condensation of aldehyde, malononitrile and 4-hydroxycoumarin in water catalyzed by morpholine, as a one-pot reaction. The significance of our findings relates to reducing the use of organic solvents, potentially toxic and hazardous materials, as well as its simplicity, good yields, mild conditions, and lower costs.
42 citations
TL;DR: The compounds 1b and 4b showed antimicrobial activity against three species of bacteria and for antifungal activity against yeast strains and the structural investigations of the compounds indicates that the compounds bind with AT nucleotides in DNA.
39 citations
TL;DR: A general strategy is developed for the stereoselective synthesis of C-substituted morpholine derivatives using intramolecular reductive etherification reaction and this method is extended to the first stereoselectedive total synthesis of (±)-chelonin C.
Abstract: A general strategy is developed for the stereoselective synthesis of C-substituted morpholine derivatives using intramolecular reductive etherification reaction. The method is extended to the first stereoselective total synthesis of (±)-chelonin C.
TL;DR: It is found that compounds possessing a nitrogen atom directly attached to the C-4 heterocycle ring possess in vitro Hsp90 inhibitory properties at least comparable to those of the structurally related 4,5-diarylisoxazole derivatives.
Abstract: A structural investigation on the isoxazole scaffold led to the discovery of 3,4-isoxazolediamide compounds endowed with potent Hsp90 inhibitory properties. We have found that compounds possessing a nitrogen atom directly attached to the C-4 heterocycle ring possess in vitro Hsp90 inhibitory properties at least comparable to those of the structurally related 4,5-diarylisoxazole derivatives. A group of compounds from this series of diamides combine potent binding affinity and cell growth inhibitory activity in both series of alkyl- and aryl- or heteroarylamides, with IC50 in the low nanomolar range. The 3,4-isoxazolediamides were also very effective in causing dramatic depletion of the examined client proteins and, as expected for the Hsp90 inhibitors, always induced a very strong increase in the expression levels of the chaperone Hsp70. In vivo studies against human epidermoid carcinoma A431 showed an antitumor effect of morpholine derivative 73 comparable to that induced by the reference compound 10.
TL;DR: In this article, a three-component, one-step method for the synthesis of 4-alkyl-3-aryl-2,6-dicyanoanilines involving reaction of alkyl aldehyde, malononitrile and aryl annealing in presence of morpholine is reported.
TL;DR: In this article, the energy of the chair conformers of Morpholine is ca. 7.5 kcal/mol lower than the skew-boat conformers, which implies that the chair conformer would be favorable in liquid Morpholine.
Abstract: Morpholine is a typical six-membered saturated heterocycle with the molecular formula HN(CH2CH2)2O. In this work, the conformations of Morpholine in liquid and adsorbed on the surface of gold nanoparticles were studied by means of Raman spectroscopy and theoretical calculations. Ab initio calculations indicate that the energy of the chair conformers of Morpholine is ca. 7.5 kcal/mol lower than the skew-boat conformers, which implies that the chair conformers would be favorable in liquid Morpholine. Comparison of the observed Raman spectra of liquid Morpholine, its solution, and the predicted spectra of the chair conformers (equatorial and axial) revealed that both of the chair conformers coexist in its liquid, and the content of the equatorial-chair conformer may reduce in the solution. Considering the concentration-dependent Surface-Enhanced Raman Scattering (SERS) spectral profile, the surface selection rule, and the theoretical calculations, it has been inferred that at higher concentrations Morpholine...
TL;DR: The synthesized Ruthenium(II) hydrazone Schiff base complexes have exhibited catalytic activity for oxidation of benzyl alcohol to benzaldehyde and cyclo hexanol to cyclohexanone in the presence of N-methyl morpholine N-oxide (NMO) as co-oxidant.
TL;DR: In this paper, a new approach to the regioselective synthesis of polyfunctional 3H-pyrroles from 4-oxoalkane-1,1,2,2-tetracarbonitriles is described.
TL;DR: The triplet quantum yield of SiPc unit in the supra-molecule is unexpectedly high, and the predominant spectral signal in microsecond-scale is triplet-triplet (T(1)-T(n)) absorption.
Abstract: Silicon phthalocyanine (SiPc) with two axially attached morpholine (MP) units was prepared, and its photophysics was studied by laser flash photolysis, steady state and time-resolved fluorescence m...
TL;DR: Two new Schiff and Mannich bases were prepared from condensation reaction of new Schiff base 3-(1′-N-dithiooxamide)iminoisatin (SBH) with morpholine or diphenylamine respectively in presence of formaldehyde and their structures were characterized by IR, 1HNMR, mass spectrometry, and CHN analyses.
Abstract: Two new Schiff and Mannich bases, namely, 1-Morpholinomethyl-3(1′ -N-dithiooxamide)iminoisatin (LIH) and 1-diphenylaminomethyl-3-1′-N-dithiooxamide)iminoisatin (LIIH), were prepared from condensation reaction of new Schiff base 3-(1′-N-dithiooxamide)iminoisatin (SBH) with morpholine or diphenylamine respectively in presence of formaldehyde . The structures were characterized by IR, 1HNMR, mass spectrometry, and CHN analyses. Metal complexes of the two ligands were synthesized, and their structures were characterized by elemental analyses, atomic absorption, IR and UV-visible spectra, molar conductivity, and magnetic moment determination. All complexes showed octahedral geometries except palladium complexes which were square planar. The biological activity of the prepared compounds and some selected metal complexes was tested against three types of bacteria and against cell line of human epidermoid larynx carcinoma (Hep-2).
TL;DR: In this article, palladium nanoparticles were used on silica-bonded N-propyl morpholine (PNP-SBNPM) as a heterogeneous catalyst for synthetically sized 1,4-distyrylbenzene derivatives.
Abstract: Some new 1,4-distyrylbenzene derivatives were synthe- sized by using immobilized palladium nanoparticles on silica-bond- ed N-propyl morpholine (PNP-SBNPM) as a heterogeneous catalyst. These one-pot reactions afforded a range of stereoselec- tive, symmetrical (E)-1,4-distyrylbenzene derivatives with high yields (78-90%). The green catalyst system is recyclable and allows facile product isolation. The recycled catalyst could be reused six times without appreciable loss of catalytic activity.
TL;DR: In this article, a one-pot synthetic method for the synthesis of naphthalene derivatives from easily available 1,4-diaryl-1,3-butadiynes was proposed.
TL;DR: The synthesis of novel, unsymmetrical, octasubstituted metal-free and metallophthalocyanines (zinc, cobalt) bearing one chlorine, one morpholine moieties and six 4- tert -butylphenoxy substituents was achieved by a statistical condensation reaction of two corresponding phthalonitriles.
TL;DR: In this article, a new class of N-basic side chains was obtained from 2,3-dihydro-2H-3-oxobenzo[d]isothiazole and aliphatic or aromatic aldehydes.
Abstract: A new class of N-basic side chains was obtained from 2,3-dihydro-2H-3-oxobenzo[d]isothiazole and aliphatic or aromatic aldehydes. Secondary amines (morpholine, N-methylpiperazine and ethyl isonipecotate) afforded tertiary N-basic side chains (4–6), while dibasic secondary amines (such as piperazine) gave bis-tertiary N-basic side chains (2). On the other hand, the use of mono- or dibasic primary amines namely; aniline, anisidine, phenyl hydrazine, o-hydroxy benzoic acid hydrazide, hydrazine hydrate, and ethylenediamine (instead of secondary amines) afforded secondary N-basic side chain as mono component or as bis component 7a-c, 9a-c, 11 and 12a-c. In addition, secondary Mannich base was synthesized via Michael addition to the corresponding aldimine. The new compounds were investigated for antioxidant and antimicrobial activities. Compounds 2, 7c and 12a exhibited significant antimicrobial activity, whereas compounds 7a, 7b, 9b, 9c and 11 exhibited high antioxidant activity as compared to ascorbic acid, These compounds showed the best protective effect against DNA damage induced by bleomycin.
TL;DR: Azine derivative D4 was found to be the most potent among all the compounds tested and the cytotoxicity increased 1.73 fold compared with the mono-Mannich base Ig4 in PC-3 cells.
Abstract: Mono-Mannich bases derived from acetophenones, 1-aryl-3-amino-1-propanone hydrochlorides (Ig1-Ig4), and their corresponding azine derivatives, N, N'-bis(3-amino-1-aryl-propylidene) hydrazine dihydrochlorides (D1-D4), were designed and synthesized as cellular thiol alkylating agents. The aryl portion was replaced by a phenyl group in Ig1, Ig2, Ig3, D1, D2, and D3, and by a p-hydroxyphenyl group in Ig4 and D4. The amine side chain was replaced by a dimethylamine group in Ig1, D1, Ig4 and D4, by a piperidine group in Ig2 and D2, and by a morpholine group in Ig3 and D3. The cytotoxic activity of the compounds was tested against the androgen-independent prostate cancer cell line PC-3. The relationship between cytotoxicity and pKa value of the amine group and partition coefficients of the compounds was also investigated. Azine derivative D4 was found to be the most potent among all the compounds tested and the cytotoxicity increased 1.73 fold compared with the mono-Mannich base Ig4 in PC-3 cells. On the other hand, conversion of mono-Mannich bases Ig1-Ig3 to their corresponding azine derivatives D1-D3 decreased the cytotoxicity considerably. Substitution of the hydroxyl group at the para position of the aromatic ring in azine derivative D4 increased the cytotoxicity, and a rational explanation in this regard is described in length. The results emerged from this investigation guide the future expansion of these series of compounds.
TL;DR: In this article, a mechanism involving a concomitant attack of the amine at the metal center and at the coordinated isocyanide was proposed on the basis of a detailed kinetic study.
TL;DR: In this paper, two cyclotetraphosphazene derivatives were synthesized by the reaction of octachlorocyclotetraprapazene with the potassium salt of 4-hydroxybenzaldehyde, and subsequent reduction of aldehyde groups to alcohol groups using sodium borohydride.
Abstract: Two novel cyclotetraphosphazene derivatives were synthesized by the reaction of octachlorocyclotetraphosphazene with the potassium salt of 4-hydroxybenzaldehyde, and subsequent reduction of aldehyde groups to alcohol groups using sodium borohydride. The bromination reaction was carried out using PBr3 to give N4P4(OC6H4-p-CH2Br)8 (4). This compound was employed in reaction with imidazole or morpholine to produce eight-armed, star-branched title compounds. The target compounds were characterized by 1H, 31P, and 13C NMR as well as IR and ESI-MS. The Cu complex of 5a was effective in oxidative cleavage reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT
TL;DR: The prepared compounds were tested for their interaction with DNA; bromovisnagin 2 showed the highest affinity and compounds 6, 15, 8a, > 14, > 16b, 17a, and 16a showed moderate activity in decreasing potency.
Abstract: Bromination of visnagin (1) afforded 9-bromovisnagin (2) which on its alkaline hydrolysis afforded the 3-acetyl benzofuran derivative (3). The condensation of (3) with hydrazine hydrate, phenylhydrazine and/or hydroxylamine hydrochloride afforded the corresponding pyrazole derivatives (4a, b) and isoxazole derivative (4c). On the other hand, when compound 3 was condensed with some aromatic aldehydes, this yielded corresponding α, β-unsaturated keto derivatives (5a–e). Furthermore, when 1 was subjected to chlorosulfonation, the visnaginsulfonylchloride derivative 6 was afforded, which on amidation using morpholine, a sulonamido derivative (7) was obtained. Alkaline hydrolysis of the latter compound yielded 7-N-morpholinosulsamidobenzofuran (8) which was condensed with some aromatic aldehydes to yield the corresponding chalcone compounds (9a–e). Demethylation of visnagin afforded norvisnagin (10). The reaction of 10 with ethylbromoacetate in dry acetone yielded the ester benzopyran derivative (11) which reacted with hydrazine hydrate to afford the corresponding hydrazide derivative (12) and this was condensed with 3,4,5-trimethoxybenzaldehyde to give the corresponding hydrazone (13). A thaizolidinone derivative (14) was obtained by condensation of (13) with thioglycolic acid. Chloromethylation of norvisnagin afforded a 4-chloromethyl derivative (15) which reacted with different primary and secondary amines to yield the corresponding ethylamino derivative (16a, b). Moreover, mannich bases (16a, b) and (17a–c) were obtained by reacting norvisnagin with different primary and secondary amines in the presence of formalin but benzoylation of (16a, b) and (17a–c) afforded 4-oxybenzoyl derivative (18a–e). The prepared compounds were tested for their interaction with DNA; bromovisnagin 2 showed the highest affinity and compounds 6, 15, 8a, > 14, > 16b, 17a, and 16a showed moderate activity in decreasing potency. Moreover, compound 2 also was the most active as antiviral agent toward HS-I virus and compounds 6, 7, 15, 14, 16a, and 18a were found to be moderately active. CD50 of the active compounds were also measured.
TL;DR: In this article, the DISQUAC interaction parameters of cyclohexylamine and morpholine + organic solvent mixtures have been investigated in terms of DisQUAC and of the Kirkwood-Buff formalism.
Abstract: Cyclic amine or morpholine + organic solvent mixtures have been investigated in terms of DISQUAC and of the Kirkwood–Buff formalism. The amines considered are cyclohexylamine; (c-CH2)uNH (u = 2–7) and (c-CH2)uN–CH3 (u = 4,5). The organic solvents are alkanes and methanol or ethanol. The DISQUAC interaction parameters are reported. The model describes correctly a whole set of thermodynamic properties: vapor–liquid equilibria (VLE); excess Gibbs energies, GmE; excess enthalpies, HmE; excess heat capacities at constant pressure, CP,mE; and partial excess enthalpies at infinite dilution, H1E,∞, as well as the main features of the Kirkwood–Buff integrals. In (c-CH2)uNH + C6H12 mixtures, amine–amine interactions become weaker with increased u values. This is supported by the corresponding decrease of HmE and H1E,∞ and of the effective dipole moment. Interactions between amine molecules are also weakened when passing from a primary cyclic amine to an isomeric tertiary cyclic amine. The existence of an aromatic r...
Patent•
04 Feb 2011
TL;DR: The present paper relates to polymorphs and solvates of the hydrochloride salt of 4- [2-[[5-methyl-1]-(2-naphthalenyl)-1 H-pyrazol-3-yl]oxy]ethyl]morpholine (P027), processes for their preparation, and pharmaceutical compositions comprising them as discussed by the authors.
Abstract: The present invention relates to polymorphs and solvates of the hydrochloride salt of 4- [2-[[5-methyl-1 -(2-naphthalenyl)-1 H-pyrazol-3-yl]oxy]ethyl]morpholine (P027), processes for their preparation, and to pharmaceutical compositions comprising them.
TL;DR: In this article, the synthesis and structural studies of an [O,N,O, N′]-type phenolic ligand (H2L) and two new uranyl complexes of this ligand are described.
TL;DR: Twenty novel cinnamamide derivatives were designed and synthesized using as lead compound pyrimorph, whose morpholine moiety was replaced by β-phenylethylamine, and most of the title compounds exhibited moderate nematicidal activities.
Abstract: Twenty novel cinnamamide derivatives were designed and synthesized using as lead compound pyrimorph, whose morpholine moiety was replaced by β-phenylethylamine. All the compounds were characterized by their spectroscopic data. The fungicidal and insecticidal activities were also evaluated. The preliminary results showed that all the title compounds had certain fungicidal activities against seven plant pathogens at a concentration of 50 μg/mL, and compounds 11a and 11l showed inhibition ratios of up to 90% against R. solani. Most of the title compounds exhibited moderate nematicidal activities. In general, the morpholine ring may be replaced by other amines and a chlorine atom in the pyridine ring is helpful to fungicidal activity.