Showing papers on "Morpholine published in 2016"
TL;DR: The theoretical calculation confirmed that morpholine is unable to function as either an electron donor or an electron acceptor to quench the BODIPY fluorescence in the neutral and basic condition via photo-induced electron transfer (PET) mechanism.
Abstract: Three uncommon morpholine-based fluorescent probes (A, B, and C) for pH were prepared by introducing morpholine residues to BODIPY dyes at 4,4′- and 2,6-positions, respectively. In contrast to morpholine-based fluorescent probes for pH reported in literature, these fluorescent probes display high fluorescence in a basic condition while they exhibit very weak fluorescence in an acidic condition. The theoretical calculation confirmed that morpholine is unable to function as either an electron donor or an electron acceptor to quench the BODIPY fluorescence in the neutral and basic condition via photoinduced electron transfer (PET) mechanism because the LUMO energy of morpholine is higher than those of the BODIPY dyes while its HOMO energy is lower than those of the BODIPY dyes. However, the protonation of tertiary amines of the morpholine residues in an acidic environment leads to fluorescence quenching of the BODIPY dyes via d-PET mechanism. The fluorescence quenching is because the protonation effectively ...
81 citations
TL;DR: A facile and effective fluoride post-treated route has been systematically applied for the preparation of hierarchical zeolite catalysts in three different SAPO-34 systems using morpholine, triethylamine and tetraethylammonium hydroxide as template, respectively.
80 citations
TL;DR: Among the newly synthesized triazole derivatives, the Schiff base 4d and the Mannich base 5d carrying nitro substituent on the thiophene ring showed promising antibacterial and antifungal activity, with lower MIC values than the standard antibacterial ampicillin.
Abstract: Compound 2 was synthesized by reacting CS2/KOH with compound 1. The treatment of compound 2 with hydrazine hydrate produced compound 3. Then, compound 3 was converted to Schiff bases (4a–d) by the handling with several aromatic aldehydes. The treatment of triazole compounds 4a–d containing Schiff base with morpholine gave compounds 5a–d. All compounds were tested for their antioxidant and antimicrobial activities. The antioxidant test results of DPPH• radical scavenging and ferric reducing/antioxidant power methods showed good antioxidant activity. The triazole-thiol (3) was the most active, and the effect of the substituent type of the thiophene ring on the activity was same for both Schiff bases (4a–d) and Mannich bases (5a–d). Among the newly synthesized triazole derivatives, the Schiff base 4d and the Mannich base 5d carrying nitro substituent on the thiophene ring showed promising antibacterial and antifungal activity, with lower MIC values than the standard antibacterial ampicillin.
72 citations
TL;DR: In this article, a morpholine-functionalised trithiocarbonate-based RAFT agent, MPETTC, was synthesised with an overall yield of 80% and used to prepare a poly(glycerol monomethacrlyate) (PGMA) chain transfer agent.
68 citations
TL;DR: The asymmetric (3 + 3) annulations of β'-acetoxy allenoates with either 3-oxo-nitriles or pyrazolones have been realized by using 6'-deoxy-6'-[(l)-N,N-(2,2'-oxidiethyl)-valine amido]quinine (6h) as the catalyst.
Abstract: The asymmetric (3 + 3) annulations of β′-acetoxy allenoates with either 3-oxo-nitriles or pyrazolones have been realized by using 6′-deoxy-6′-[(l)-N,N-(2,2′-oxidiethyl)-valine amido]quinine (6h) as the catalyst. The three functions of catalyst 6h, including Lewis base (quinuclidine N), H-bond donor (amide NH), and Bronsted base (morpholine N), cooperatively take crucial roles on the chemo- and enantioselectivity, allowing for the construction of 4H-pyran and 4H-pyrano[2,3-c]pyrazole in high yields and enantioselectivity.
68 citations
TL;DR: In this article, three new complexes of Ni(II) with tridentate Schiff base ligand, have been synthesized from reaction of the ligand sapH2 (salicylidene-2-aminophenol) with Ni(OAc)2·4H2O in the presence of relevant amine.
67 citations
TL;DR: A series of (allyl)palladium(II) complexes of anionic N-heterocyclic carbenes that contain a weakly coordinating borate moiety (WCA-NHC) were prepared by deprotonation of the carbene IPr with n-butyllithium in the 4 position, which was followed by addition of B(C6F5)3 and reaction of the resulting lithium carbene-borate with [(η3-allyl]Pd(μ-Cl)]2 (ally l = 2-
50 citations
TL;DR: Phenolic bis Mannich bases having the chemical structure of 1-[3,5-bis-aminomethyl-4-hydroxyphenyl]-3-(4-halogenophenyl)-2-propen-1-ones may serve as lead molecules for further anticancer drug candidate developments.
Abstract: Phenolic bis Mannich bases having the chemical structure of 1-[3,5-bis-aminomethyl-4-hydroxyphenyl]-3-(4-halogenophenyl)-2-propen-1-ones (1a-c, 2a-c, 3a-c) were synthesized (Numbers 1, 2, and 3 represent fluorine, chlorine, and bromine bearing compounds, respectively, while a, b, and c letters represent the compounds having piperidine, morpholine, and N-methyl piperazine) and their cytotoxic and carbonic anhydrase (CA, EC 4.2.1.1) enzyme inhibitory effects were evaluated. Lead compounds should possess both marked cytotoxic potencies and selective toxicity for tumors. To reflect this potency, PSE values of the compounds were calculated. According to PSE values, the compounds 2b and 3b may serve as lead molecules for further anticancer drug candidate developments. Although the compounds showed a low inhibition potency toward hCA I (25–43%) and hCA II (6–25%) isoforms at 10 μM concentration of inhibitor, the compounds were more selective (1.5–5.2 times) toward hCA I isoenzyme. It seems that the compo...
47 citations
TL;DR: In this article, a series of new donor-acceptor molecules based on acridone-amine containing four aryl substituted 2,7-diaminoacridones (1,4) and morpholine substituted acridon compounds (5) were synthesized in good yields using palladium catalysed Buchwald-Hartwig C-N amination.
Abstract: A series of new donor–acceptor molecules based on acridone-amine containing four aryl substituted 2,7-diaminoacridones (1–4) and morpholine substituted acridone compounds (5) were synthesized in good yields using palladium catalysed Buchwald–Hartwig C–N amination. Their absorption, photoluminescence and electrochemical properties were investigated in solution and in thin films. Photophysical properties were found to be affected by the electron donating capability of the substituents on the diaryl amines. Absorption showed intramolecular charge transfer transitions (ICT) in a range of 447–479 nm. These acridone amine derivatives emit in the green region (500–527 nm). Reversible oxidation waves were observed for compounds 1–5 in cyclic voltammetry. The HOMO (−4.95 to −5.11 eV) and LUMO (−2.36 to −2.56 eV) energy levels of 1–5 were calculated. The EHOMO for compounds 1–5 are similar with the most widely used hole transporting materials NPD, TPD and spiro-OMe-TAD. Hence we believe that these compounds have the potential to be used as hole transporting materials in optoelectronic devices.
45 citations
TL;DR: In this paper, the properties of octachlorocyclotetraphosphazene derivatives were characterized by MS, FTIR, 1H, 13C and 31P NMR, HSQC and HMBC techniques.
Abstract: The reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with N-alkyl-N-mono-ferrocenyldiamines, FcCH2NH(CH2)nNHR1 [n = 2, Fc = ferrocene, R1 = Me (1); n = 2, R1 = Et (2) and n = 3, R1 = Me (3)], led to the formation of monoferrocenyl-spirocyclotetraphosphazenes (4–6). When the reactions were carried out with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), the fully substituted products (4a–6c) were obtained in high yields. The structures of all the phosphazene derivatives were characterized by MS, FTIR, 1H, 13C and 31P NMR, HSQC and HMBC techniques. The crystal structures of 4a and 5a were determined by X-ray crystallography. The electrochemically reversible one-electron oxidation of Fc redox centers was observed for cyclotetraphosphazenes. The fully substituted phosphazenes (4a–6c) were evaluated for their antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and compounds 4a–6a and 5c were found to be active. The antibacterial activities of phosphazenes 4a–6c against G(+) and G(−) bacteria and their antifungal activities against yeast strains were carefully scrutinized. The results indicate that compounds 4a–6a, 6b, 4c and 5c are very effective against yeast strains. The anticandidal activities of 6a and 6b make them promising anticandidal agents. The interactions of these compounds with plasmid DNA and their cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were also investigated.
38 citations
TL;DR: The present study successfully demonstrated the use of azaspiro substructure in the medicinal chemistry of antibacterial and antitubercular agents.
TL;DR: In this paper, a one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3-c ]pyrazoles, which were generally catalyzed by organic alkalis.
TL;DR: Piperidine, piperazine and morpholine as archetypes for secondary heterocyclic amines, a structural unit that is often present in pharmaceuticals, were investigated in their reaction with ozone and three products have been found.
TL;DR: Interestingly, all six piperazine appended dibenzo[b,d]thiophene-1,2,3-triazoles 11a-f exhibited Mtb inhibition activity with MIC 1.56-12.5μg/mL, which indicated Mycobacterium tuberculosis inhibition among the appendages is in the order, p Piperazine>thiomorpholine>morpholine.
TL;DR: In this paper, the reaction of glyceraldehyde with alkynes delivers furfuryl alcohol derivatives within only one reaction step in the presence of a gold(III) catalyst.
Abstract: The reaction of glyceraldehyde with alkynes delivers furfuryl alcohol derivatives within only one reaction step in the presence of a gold(III) catalyst. The reaction cascade is initiated by an intermolecular gold-catalyzed A3 coupling sequence in which morpholine is used as additive. Intramolecular cyclization and subsequent aromatization under elimination of the amine then deliver the target molecules. The protocol offers a valuable alternative to the common routes that are based on functionalization of already existing furan cores.
TL;DR: A series of pyrrole analogues of combretastatin (CA-4) were synthesized and tested for their anti-proliferative activity, with 1,2- and 2,3-diaryl-1H-pyrroles which are both geometrically similar to CA-4.
TL;DR: In this paper, the reactivity of azelaic acid with carboxylic acid, alcohol, amine, and amide based co-formers was screened and five new multicomponent crystal forms of AA were obtained by liquid assisted grinding and conventional solution methods.
Abstract: The reactivity of the active pharmaceutical ingredient azelaic acid (AA) with carboxylic acid, alcohol, amine, and amide based co-formers was screened. Five new multicomponent crystal forms of AA were obtained by liquid assisted grinding and conventional solution methods. The obtained forms: (i) a co-crystal with 4,4′-bipyridine (AA:BIP, 1), (ii) an anhydrous and an hydrated molecular salt with piperazine (AA:PIP, 2 and 3), and (iii) two anhydrous molecular salts with morpholine (AA:MORPH, 4) and 1,4-diazobicyclo[2.2.2]octane (AA:DABCO, 5), were fully characterized by X-ray diffraction and solid-state (SS) NMR. In all new forms the carboxylic-carboxylic R22(8) homosynthon present in AA is broken, and NH2···OCOOH or +NH2···OCOO- hydrogen bonds (HBs) become the fundamental pillars in the new supramolecular arrangements. The X-ray structure of 4 exhibits a static disorder in the hydrogen atoms engaged in an HB between two COOH moieties of AA. Density functional theory geometry optimization of the hydrogen po...
TL;DR: In this paper, substituted morpholines have been efficiently synthesised in good yields from nitrogen tethered alkanol-epoxide mediated by boron trifluoride etherate.
TL;DR: The phosphazene derivatives inhibit the restriction endonuclease cleavage of plasmid DNA by BamHI and HindIII enzymes and digestion results demonstrate that the compounds bind with G/G and A/A nucleotides.
Abstract: The condensation reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with N-alkyl-N′-mono(4-nitrobenzyl)diamines (1–3), NO2PhCH2NH(CH2)
n
NHR1 (R1 = CH3 or C2H5), led to the formation of the mono(4-nitrobenzyl)spirocyclotriphosphazenes (4–6). The tetra-pyrrolidino (4a–6a), piperidino (4b–6b), and 1,4-dioxa-8-azaspiro[4,5]decaphosphazenes (4c–6c) were prepared from(for) the reactions of partly substituted compounds (4, 5, and 6) with excess pyrrolidine, piperidine, and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The partly substituted geminal (4d and 5d) and cis-morpholino (6d) phosphazenes were isolated from the reactions of excess morpholine in boiling THF and o-xylene, but the expected fully substituted compounds were not obtained. The structures of all the phosphazene derivatives were determined by elemental analyses, MS, FTIR, 1H, 13C{1H}, 31P{1H} NMR, HSQC, and HMBC techniques. The crystal structures of 4, 6, 4a, and 5a were verified by X-ray diffraction analysis. In addition, in vitro cytotoxic activities of fully substituted phosphazenes (4a–6c) against HeLa cervical cancer cell lines (ATCC CCL-2) and the compounds 4a and 4c against breast cancer cell lines (MDA-MB-231) and L929 fibroblast cells were evaluated, respectively. Apoptosis effect was determined by MDA-MB-231 cancer cell lines and fibroblast cells. The MIC values of the compounds were in the ranges of 9.8–19.5 µM. The compounds 6, 5a, 6a, 5b, and 6d have greater MIC activity against bacterial and yeast strain. The investigation of DNA binding with the phosphazenes was studied using plasmid DNA. The phosphazene derivatives inhibit the restriction endonuclease cleavage of plasmid DNA by BamHI and HindIII enzymes. BamHI and HindIII digestion results demonstrate that the compounds bind with G/G and A/A nucleotides.
TL;DR: A new series of morpholine derivatives has been identified as selective DA D3 receptor antagonists; their in vitro profile and pharmacokinetic data are provided.
TL;DR: In this paper, a comprehensive thermodynamic model has been developed for calculating phase equilibria and speciation in aqueous mixtures containing neutralizing amines and corresponding amine hydrochlorides.
Journal Article•
TL;DR: In this paper, the top-of-the-line corrosion inhibition mechanism in the presence of amines: diethylamine and morpholine was investigated and the surface charge was investigated by determining the potential of zero charge (PZC).
Abstract: The principal objective of this work is to investigate and understand the top of the line corrosion (TLC) inhibition mechanism in the presence of amines: diethylamine and morpholine. TLC can be defined as corrosion of carbon steel under water condensation conditions in the presence of acid gases such as CO2, which can be a problem in wet natural gas transportation lines. In order to define the possible interactions between the tested amines and the steel surface, the surface charge was investigated by determining the potential of zero charge (PZC). The PZC was measured by means of electrochemical impedance spectroscopy (EIS) in a 1 wt% NaCl solution at different pH values. The possible inhibitive properties of diethylamine and morpholine were first tested under full immersion in the water phase—a condition corresponding to the so-called “bottom of the line” situation in gas pipelines, using linear polarization resistance and EIS. This was followed by tests in the gas phase under water condensing condition...
TL;DR: A novel HIV protease inhibitor was designed using a morpholine core as the aspartate binding group, which afforded a series of potent orally bioavailable inhibitors of which MK-8718 was identified as a compound with a favorable overall profile.
Abstract: A novel HIV protease inhibitor was designed using a morpholine core as the aspartate binding group. Analysis of the crystal structure of the initial lead bound to HIV protease enabled optimization of enzyme potency and antiviral activity. This afforded a series of potent orally bioavailable inhibitors of which MK-8718 was identified as a compound with a favorable overall profile.
TL;DR: In this article, an efficient synthesis of 2,4-diary lyrroles was described, using a mixture of a 4-nitro-1,3-Diarylbutan-1-one and ammonium acetate in the presence of morpholine and sulfur.
Abstract: An efficient synthesis of 2,4-diarylpyrroles is described. Heating a mixture of a 4-nitro-1,3-diarylbutan-1-one and ammonium acetate in the presence of morpholine and sulfur afforded the corresponding 2,4-diarylpyrroles in excellent yields.
TL;DR: The synthesis and structure-activity relationship of a series of chiral alkoxymethyl morpholine analogs are reported, leading to the identification of (S)-2-(((6-chloropyridin-2-yl)oxy)methyl)-4-((6-fluoro-1H-indol-3-yl(yl)methyl)morpholine as a novel potent and selective dopamine D4 receptor antagonist with selectivity against the other dopamine receptors tested.
TL;DR: In this paper, the synthesis of Schiff bases was performed from the reaction of the corresponding triazol-3-thioles with various aromatic aldehydes, and the treatment of the Schiff bases containing 1,2,4-triazoles with morpholine or thiomorpholine generated the corresponding Mannich bases.
Abstract: 5-(Pyridine-3-yl)-1,3,4-oxadiazole-2-thiole 2, obtaining starting from nicotinic acid hydrazide were converted to the corresponding Mannich bases (3a–c) by the reaction with several heterocyclic amines in the presence of formaldehyde. 1,2,4-Triazole-3-thiole, (4) prepared from 1,3,4-oxadiazole-2-thiole (2) was converted to the corresponding Mannich bases (5a–e) by several steps. The synthesis of Schiff bases (6a–d) was performed from the reaction of the corresponding triazol-3-thioles with various aromatic aldehydes. The treatment of Schiff bases containing 1,2,4-triazoles 6c and 6d with morpholine or thiomorpholine generated the corresponding Mannich bases 7a, b and 8a, b. The synthesized compounds were screened for their antimicrobial, antilipase, and antiurease activities. Some of them were found to possess good-moderate antimicrobial, antiurease, and/or antilipase activity.
TL;DR: A palladium on carbon-catalyzed approach to regioselectively alter the cleavage sites of the C-C bonds of cinnamaldehyde derivatives by a slight change in the reaction conditions in isopropanol under an O2 atmosphere is demonstrated.
Abstract: We have demonstrated a palladium on carbon-catalyzed approach to regioselectively alter the cleavage sites of the C-C bonds of cinnamaldehyde derivatives by a slight change in the reaction conditions in isopropanol under an O2 atmosphere. Styrene derivatives could be selectively formed by the addition of Na2CO3 in association with the dissociation of carbon monoxide, while benzaldehyde derivatives were generated by the addition of CuCl and morpholine instead of Na2CO3.
TL;DR: In this paper, a dry gel method was used to synthesize small particles of less than 500nm within a short reaction time of 30 min, which were characterized by X-ray diffraction, field-emission scanning electron microscopy, energy-dispersive Xray spectroscopy, and gas sorption analysis.
TL;DR: In this paper, a novel bis benzoxazin-4-one derivative has been synthesized and utilized to construct a new series of bis quinazolin-4(3H)-one derivatives via the reactions with different nitrogen nucleophiles.
TL;DR: A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(i) catalyst under mild conditions to create morpholine derivatives with good diastereoselectivities in high yields.
Abstract: A convenient synthetic method for the construction of morpholine derivatives from easily available aziridines and propargyl alcohols has been successfully developed A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(I) catalyst under mild conditions The gold(I) catalyst served as a π acid and also a σ acid to realize the dual activation of both reactants in this reaction The obtained unsaturated morpholine products could be easily hydrogenated to achieve target morpholine derivatives with good diastereoselectivities in high yields