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1.
Peter Segl’a Jozef Miklovič Dušan Mikloš Viera Mrázová Lenka Krupková Daniela Hudecová Zuzana Ondrušová Jozef Švorec Ján Moncol Milan Melník 《Transition Metal Chemistry》2009,34(1):15-22
The synthesis and characterization of six new 2-methylthionicotinate (2-MeSnic) copper(II) monomeric complexes [Cu(2-MeSnic)2L2] (L is furo[3,2-c]pyridine—fpy, 2-methylfuro[3,2-c]pyridine—Mefpy, 2,3-dimethylfuro[3,2-c]pyridine—Me2fpy or benzo[4,5]furo[3,2-c]pyridine—Bfp), [Cu(2-MeSnic)2(fpy)2(H2O)], as well as [Cu(2-MeSnic)2(CF3Phfpy)2(H2O)2] (CF3Phfpy is 2-(3-trifluoromethylphenyl)furo[3,2-c]pyridine) are reported. The characterizations were based on elemental analysis,
infrared, electronic and EPR spectra. The crystal structure of one of the complexes has been determined. The CuII atoms of [Cu(2-MeSnic)2(fpy)2(H2O)] are six-coordinated in a highly distorted tetragonal–bipyramidal arrangement by two nitrogen atoms, one from each fpy,
in trans-positions, by three oxygen atoms of the carboxyl groups of 2-MeSnic ligands (one monodentate, one asymmetrically bidentate),
one axial position being occupied by the oxygen of a water molecule. The antimicrobial effects have been tested on various
strains of bacteria, yeasts and filamentous fungi. A comparison of the IC50 and MIC values has shown a decrease of inhibition activities of tested compounds in the order: [Cu(2-MeSnic)2(Bfp)2] > Bfp > [Cu(2-MeSnic)2(CF3Phfpy)2(H2O)2] > [Cu(2-MeSnic)2(Me2fpy)2] > CF3Phfpy > [Cu(2-MeSnic)2(Mefpy)2] > Me2fpy > [Cu(2-MeSnic)2(fpy)2(H2O)] > [Cu(2-MeSnic)2(H2O)]2 > Mefpy > fpy = 2-MeSnicH = CuSO4.
Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. 相似文献
2.
L’. Lajdová E. Jóna J. Miklovič P. Segl’a L’. Kvasnicová S. Šnircová R. Janík S. C. Mojumdar 《Journal of Thermal Analysis and Calorimetry》2010,100(3):857-860
The stoichiometry of thermal decomposition of the complexes Co(NCS)2(fpy)4 (I), Co(NCS)2(Mefpy)4 (II) and Co(NCS)2(bfpy)4 (III) (where fpy = furo[3,2-c]pyridine, Mefpy = methylfuro[3,2-c]pyridine, bfpy = benzo-[2, 3]furo[3,2-c]pyridine) have been investigated in nitrogen atmosphere from room temperature (RT) to 800 °C by means of TG and DTA. The results revealed that release of heterocyclic ligands occurs in one step. Infrared data suggested that fpy, Mefpy and bfpy were coordinated to Co(II) through the nitrogen atom of the respective heterocyclic ring and anionic ligands through nitrogen atom of the NCS groups. 相似文献
3.
L’. Lajdová E. Jóna S. Šnircová J. Miklovič P. Segl’a M. Pajtášová D. Ondrušová S. C. Mojumdar 《Journal of Thermal Analysis and Calorimetry》2009,96(1):59-62
The stoichiometry of thermal decomposition of the complexes Ni(NCS)2(fpy)4 (I), Ni(NCS)2(bfpy)4 (II) and Ni(NCS)2(CF3Phfpy)4 (III) (where fpy=furopyridine, bfpy=benzo-[2,3]furo[3,2-c]pyridine, CF3Phfpy=2-(3-fluoromethylphenyl) furo[3,2-c]pyridine) have been investigated in nitrogen atmosphere from room temperature to
500°C by means of TG and DTG. The results revealed that release of the heterocyclic ligands occurs in two steps. IR data suggested
that fpy, bfpy and CF3Phfpy ligands were coordinated to Ni(II) through the N atom of the respective heterocyclic rings and same is the case with
the anionic NCS group. 相似文献
4.
Ivana Bradiaková Naďa Prónayová Anton Gatial Alžbeta Krutošíková 《Chemical Papers》2008,62(4):428-434
(E)-3-{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}propenoic acid (I) was prepared from 5-[3-(tri-fluoromethyl)phenyl]furan-2-carbaldehyde under the Doebner’s conditions. The obtained acid was
converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to 2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with H2NNH2-Pd/C to the title compound V. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. On treatment of VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction), corresponding 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine-1-carbonitrile (VII) resulted. 5-Amino-2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-ium-4-methylbenzene sulfonate (VIII) was prepared by direct N-amination of the title compound V with 1-[(aminooxy)sulfonyl]-4-methylbenzene in dichloromethane. Then, VIII was transformed to a non-isolated zwitterionic N-imid IX which afforded the corresponding furo[3,2-c]pyrazolo[1,5-a]pyridine carboxylic acid esters X, XI by 1,3-dipolar cycloaddition reactions with dimethyl but-2-ynedionate (DBD) or ethyl propiolate. The structures of all compounds
were confirmed by their IR and NMR spectra.
Presented at the 1st International Conference “Applied Natural Sciences” on the occasion of 10th anniversary of the University
of St. Cyril and Methodius, Trnava, 7–9 November 2007. 相似文献
5.
S. C. Mojumdar J. Miklovič A. Krutošíková D. Valigura J. M. Stewart 《Journal of Thermal Analysis and Calorimetry》2005,81(1):211-215
Summary The thermal decomposition of the complexes Ni(SCN)2(fp)4·2H2O (I), Ni(SCN)2(mfp)4 (II) and Ni(SCN)2(dmfp)3 (III) (where fp=furo[3,2-c]pyridine, mfp=2-methylfuro[3,2-c]pyridine and dmfp=2,3-dimethylfuro[3,2-c]pyridine) have been investigated in dynamic air from room temperature to 1000°C by means of TG, DTG and DTA. The chemical composition of the complexes, solid intermediates and the resultant products of thermolysis have been identified by means of elemental analysis and complexometric titration. The results revealed that NiO was left as residue at the end of the thermal degradation experiments. IR data suggested that fp, mfp and dmfp were coordinated to Ni(II) through the N atom of the respective heterocyclic ring. 相似文献
6.
Stefan Nikolić Sanja Grgurić-Šipka Ivana S. Djordjević Rahma Dahmani Dragana Dekanski Sašenka Vidičević 《Journal of Coordination Chemistry》2019,72(1):148-163
In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene?=?benzene or toluene and XY?=?bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes). 相似文献
7.
We have established that 2,4-dimethylbenzo[b]furo[3,2-c]pyrylium and 2,4-dimethylbenzo[b]thieno[3,2-c]pyrylium salts can undergo recyclization to 3-dialkylamino derivatives of dibenzofuran and dibenzothiophene when treated
with secondary amines. We compare the physicochemical and spectral characteristics of the compounds obtained with the recyclization
products of 1,3-dimethylbenzo[b]furo[2,3-c]- and 1,3-dimethylbenzo[b]thieno[2,3-c]pyrylium salts.
L. M. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk
340114. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 182–185, February, 1998. 相似文献
8.
The Knoevenagel condensations of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde with seven compounds containing an active
methyl or methylene group have been studied. The compounds used were: methyl 2-cyanoacetate, malononitrile, 2-furylacetonitrile,
acetophenone, 2-thioxo-1,3-thiazolidin-4-one (rhodanine), 5,5-dimethylcyclohexane-1,3-dione (dimedone), and methyl 2-azidoacetate.
The effect of microwave irradiation on the condensation reactions was studied and compared with “’classical”’ conditions.
Thermolysis of methyl 2-azido-3-{5-[3-(trifluoromethyl)phenyl]-2-furyl}propenoate afforded methyl 2-[3-(trifluoromethyl)phenyl)]-4H-furo[3,2-b]pyrrole-5-carboxylate.
(2E)-3-{ 5-[3-(Trifluoromethyl)phenyl]-2-furyl}propenoic acid was converted to the corresponding azide, which was cyclized
on heating into 2-[3-(trifluoromethyl)phenyl)]-4,5-dihydrofuro[3,2-c]pyridin-4-one. The latter after successive action of
POCl3 and NH2NH2-Pd/C gave 2-[3-(trifluoromethyl)-phenyl]furo[3,2-c]pyridine.
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 825–831, June, 2006. 相似文献
9.
Shunsaku Shiotani 《Journal of heterocyclic chemistry》1993,30(4):1035-1039
The preparation of 2-aminomethyl- 3a-d , 2-acetamidomethyl- 4a-d , 2-N,N-dimethylaminomethyl- 5a-d , 2-(1-hydroxy-2-nitroethyl)- 6a-d , 2-(1-hydroxyl-2-aminoethyl)- 7a-d and 2-(1-hydroxy-2-N,N-dimethylaminoethyl)- 8b-d derivatives of furo[2,3-b]-, furo[3,2-b]-, furo[2,3-c]- and furo[3,2-c]pyridine is described. 相似文献
10.
Donald F. Worth S. C. Perricone Edward F. Elslager 《Journal of heterocyclic chemistry》1970,7(6):1353-1356
The boron trifluoride catalyzed 1,4-addition of 2,3-dihydro-5-methylfuran to N-(p-methoxybenzylidene)-5-indanamine (VI) gave 2 pairs of epimers, dl-3,3a,4,5,7,8,9,10b-octahydro-4-(p-methoxyphenyl)-10b-methyl-2H-cyclopenta[g]furo[3,2-c]quinoline (VIIa and b) and dl-3,3a, 4,-5,8,9,10,10c-octahydro-4-(p-methoxyphenyl)-10c-methyl-2H-cyclopenta[f]furo[3,2-c]quinoline (VIIIa and b). When 4-(benzylideneamino)-1-naphthol (IXa) was condensed with 2,3-dihydro-5-methylfuran in an analogous manner, a mixture of two isomers of dl-1,2,2a,3,4,5a-hexahydro-5a-methyl-2-phenylbenzo[h]furo[3,2-c]quinolin-7-ol [Xa and b (R ? H)] was obtained. Likewise, 4-[(p-hydroxybenzylidene)amino]-1-naphthol (IXb) and 4-(p-methoxybenzylidene)amino]-1-naphthol (IXc) gave a mixture of two isomers of dl-1,2,2a,3,4,5a-hexahydro-2-(p-hydroxyphenyl)-5a-methylbenzo[h]furo[3,2-c]quinolin-7-ol [Xa and b (R ? OH)] and dl-1,2,2a,3,4,5a-hexahydro-2-(p-methoxyphenyl)-5a-methylbenzo [h]furo[3,2-c]quinolin-7-ol [Xa and b (R ? OCH3)], respectively. The condensation of N-(p-methoxybenzylidene)-5-acenaphthenamine (XI) with 2,3-dihydro-5-methylfuran afforded a mixture of two isomers of dl-2,3,3a,4,5,9,10,-11b-octahydro-4-(p-methoxyphenyl)-11b-methylfuro[3,2-c]indeno[1,7-gh]quinoline (XIIa and b). Structural assignments for all of the products were made from NMR spectra. None of these compounds possessed appreciable biological activity. 相似文献
11.
Alzbeta Krutosikova Miloslava Dandarova Jana Chylova Daniel Vegh 《Monatshefte für Chemie / Chemical Monthly》1992,123(8-9):807-815
Summary A number of furo[3,2-c]pyridines (4a–4d) and benzo[b]derivative (4e), as well as pyrrolo[2,3-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.
Kondensierte O-, N-Heterocyclen durch Umwandlung von Azidoacrylaten
Zusammenfassung Eine Anzahl von Furo[3,2-c]pyridinen (4a –4d), ein Benzo[b]derivat (4e) und Pyrrolo[2,3:4,5]furo[3,2-c]pyridin (8) wurden durch die Reaktion von Phenylisocyanaten mit den entsprechenden Iminophosphoranen dargestellt, die aus Ethyl-azidoheteroacrylaten und Triphenylphosphin leicht zugänglich sind. Die entsprechenden Azidoacrylate wurden zur Synthese einiger Furo[3,2-b:4,5-b]dipyrrole (6) verwendet. Die Reaktionen einiger dieser Verbindungen werden beschrieben.相似文献
12.
Bin Peng Hui Chao Bin Sun Feng Gao Liang-Nian Ji Jian Zhang 《Transition Metal Chemistry》2007,32(2):271-277
Two novel cobalt(III) mixed-polypyridyl complexes
[Co(bpy)2(dpta)]3+ and [Co(bpy)2(amtp)]3+ (bpy = 2,2′-bipyridine, dpta = dipyrido-[3,2-a;2′,3′-c]-thien-[3,4-c]azine, amtp = 3-amino-1,2,4-triazino[5,6-f]-1,10-phenanthroline)
have been synthesized and characterized. The interaction of CoIII complexes with calf thymus DNA was investigated by spectroscopic and viscosity measurements. Results suggest that the two
complexes bind to DNA via an intercalative mode. Moreover, CoIII complexes have been found to promote the photocleavage of plasmid DNA pBR322 under irradiation at 365 nm. The mechanism studies
reveal that hydroxyl radical (OH•) is likely to be the reactive species responsible for the cleavage of plasmid DNA by [Co(bpy)2(dpta)]3+ and superoxide anion radical (O
2
•−
) acts as the key role in the cleavage reaction of plasmid DNA by [Co(bpy)2(amtp)]3+. 相似文献
13.
By reaction of lactim ethers with N-substituted cyanoacetamides, the corresponding enaminoamides were obtained, cyclization of which by dimethylformamide acetal gave derivatives of pyrrolo[3,2-c]pyridine, 1,6-naphthyridine, and pyrido[4,3-b]azepine, having a substituent at the nitrogen atom of the pyridone ring. N-substituted furo[3,2-c]pyridines were synthesized from the diethyl acetals of butyrolactone and 3-(dimethylaminomethylene)butyrolactone and dimethylformamide acetal.For communication 44, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 929–932, July, 1985. 相似文献
14.
An efficient and novel microwave-assisted synthesis of furo[3,2-c]chromen-4-ones and 7,8,9,10-tetrahydro-6H-benzofuro[3,2-c]chromen-6-ones via 4-hydroxycoumarins with α-chloroketones or α-bromocyclohexanone in the presence of acetic acid (AcOH)/ammonium acetate (NH4OAc) using DMF as solvent under microwave irradiation is described. Systematically, antifungal biological tests showed that most of the compounds exhibited potent antifungal activity against Botrytis cinerea, Collecterichum capsica, Alternaria solani, Gibberella zeae, and Rhizoctorzia solani at the concentration of 50 µg/mL. The corresponding EC50 values of these analogues have been detected, and compound 4i showed better antifungal activity against tested fungi Botrytis cinerea and Collecterichum capsica than the reference Osthol. 相似文献
15.
An interesting series of cobalt(II) complexes of the new ligands: 4[N-(benzalidene)amino]antipyrinethiosemicarbazone (BAAPTS), 4[N-(2′-hydroxy-benzalidene)amino]antipyrinethiosemicarbazone (HBAAPTS) and 4[N-(2′-hydroxy-1′-naphthalidene)amino]antipyrinethiosemicarbazone (HNAAPTS) were synthesized by reaction with Co(II) salts in
ethanol. The general stoichiometry of the complexes was found to be [CoX2(H2O)(L)] and [Co(L)2](ClO4)2, where X = Cl, NO3, NCS or CH3COO and L = BAAPTS, HBAAPTS or HNAAPTS. The complexes were characterized by elemental analysis, molar conductivity measurement,
molecular weight determination, magnetic moments at room temperature, infrared and electronic spectra. All the thiosemicarbazones
behave as neutral tridentate (N, N, S) donor ligands. The conductivity measurements in PhNO2 solution indicated that the chloro, nitrato, thiocyanato and acetate complexes are essentially non-electrolytes, while the
perchlorate complexes are 1:2 electrolytes. Thermogravimetric studies were performed for some representative complexes and
the decomposition mechanism proposed. Antibacterial and antifungal properties of the ligands and their cobalt(II) complexes
have also been examined and it has been observed that the complexes are more potent bactericides than the ligand. 相似文献
16.
I. V. Voznyi M. S. Novikov A. F. Khlebnikov R. R. Kostikov 《Russian Journal of Organic Chemistry》2006,42(5):689-695
Reactions of N-(5-R-furan-2-ylmethylidene)anilines with difluorocarbene proceeds through intermediate azomethine ylides suffering 1,5-π-cyclization to yield 6,6-difluorocyclopropa[b]furo[2,3-c]pyrrole and/or 4,4,6,6-tetrafluorocyclopropa[b]furo[2,3-c]pyrrole. The heating of these compounds without solvent resulted in high yields of 2,5-disubstituted 7-fluoro-4,5-dihydrofuro[3,2-c]pyridin-4(5H)-ones. 相似文献
17.
Emile Bisagni Alain Civier Jean-Pierre Marquet 《Journal of heterocyclic chemistry》1975,12(3):461-465
Treatment of 4-hydroxy-6-methylpyran-2-one with chloracetalhyde in basic aqueous medium gave 6-methylfuro[3,2-c]pyran-4-one. This compound reacted with ammonium hydroxide and some primary amines to form the corresponding N-substituted furo[3,2-c]pyrid-4-ones which may also be obtained from 4-hydroxy-α-pyridones. Furo[3,2-c]pyran-4-one was acylated at the 2 position and 4-chloro-6-methylfuro[3,2-c]pyridine easily gave 4-substituted derivatives by displacement of the halogen atom. 相似文献
18.
H. Sadaf S. Ahmad S. Sharif I. U. Khan M. Akkurt S. W. Ng M. I. Khan S. A. Bashir M. Mufakkar 《Journal of Structural Chemistry》2012,53(1):151-155
Two mercury(II) cyanide complexes of N-ethylthiourea (Ettu) and N-propylthiourea (Prtu) ligands, [Hg(Ettu)2(CN)2] (1) and [Hg(Prtu)2(CN)2] (2), were prepared and their crystal structures were determined by X-ray crystallography. In both structures, the mercury atom
is coordinated to two sulfur atoms of thioureas and two cyanide carbon atoms in a pseudo-tetrahedral mode with the bond angles
in the range of 90.52(11)–162.2(3)°. The structures are stabilized by N-H—S, N-H—N, and C-H—N intramolecular and intermolecular
hydrogen bonds. 相似文献
19.
Flora Catti Boccuzzi 《Magnetic resonance in chemistry : MRC》1976,8(6):321-323
Significant variations of thiapyrylium chemical shifts, by comparison with their thienohomologues, are shown by 1H n.m.r. spectra of furo[3,2-c]thiapyrylium and furo[2,3-c]thiapyrylium perchlorates. The observed changes can be ascribed to a different distribution of the electron charge (mainly caused by participation of the 3d orbitals of sulphur in the thienohomologues) and to a different contribution of the ring current; this is shown by MO calculations performed by the CNDO/2 and the coupled Hartree–Fock methods, respectively. 相似文献
20.
Sumitava Khan Subhasis Roy Kishalay Bhar Partha Mitra Alexandra M. Z. Slawin Barindra Kumar Ghosh 《Transition Metal Chemistry》2011,36(1):99-106
Two hexacoordinated mononuclear Co(III) compounds of the type cis-[Co(L)(N3)2] X [1, X = ClO4; 2, X = PF6; L = N,N′-(bis(pyridine-2-yl)benzylidine)-1,4-butanediamine] have been synthesized and characterized by physicochemical and spectroscopic
methods. The crystal structures of complexes 1 and 2 both have distorted octahedral geometry with two terminal azides in mutual cis orientations. In the crystalline state, two
mononuclear units of 1 are associated by weak C–H…π interactions to produce a dimeric unit, which packs through C–H…O hydrogen bonds and π…π interactions
leading to a 2-D continuum. The mononuclear units in 2 are engaged in weak cooperative intermolecular C–H…π interactions and multiple C–H…F hydrogen bonds giving rise to a 3-D
network structure. These diamagnetic compounds are redox active and show luminescence in DMF solutions. 相似文献