Organosulfur materials are a sustainable alternative to the present-day layered oxide cathodes in lithium-based batteries.One such organosulfur material that was intensely explored from the 1990s to early 2010s is 2,5...Organosulfur materials are a sustainable alternative to the present-day layered oxide cathodes in lithium-based batteries.One such organosulfur material that was intensely explored from the 1990s to early 2010s is 2,5-dimercapto-1,3,4-thiadiazole(DMCT).However,research interest declined as the electrode reactions with DMCT were assumed to be too sluggish to be practical.Armed with the advances in metal-sulfur batteries,we revisit DMCT-based materials in the form of poly[tetrathio-2,5-(1,3,4-thiadiazole)],referred to as pDMCT-S.With an appropriate choice of electrode design and electrolyte,pDMCT-S cathode paired with a Li-metal anode shows a capacity of 715 mA h g^(-1)and a Coulombic efficiency of 97.7%at a C/10 rate,thus quelling the concerns of sluggish reactions.Surprisingly,pDMCT-S shows significantly improved long-term cyclability compared to a sulfur cathode.Investigations into the origin of the stability reveals that the discharge product Li-DMCT in its mesomeric form can strongly bind to polysulfides,preventing their dissolution into the electrolyte and shuttling.This unique mechanism solves a critical problem faced by sulfur cathodes.Encouragingly,this mechanism results in a stable performance of pDMCT-S with Na-metal cells as well.This study opens the potential for exploring other organic materials that have inherent polysulfide sequestering capabilities,enabling long-life metal-sulfur batteries.展开更多
The title compound N-(2,6-difluorobenzoyl)-N'-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]urea(C17H9F5N4O2S,Mr = 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-1,3,...The title compound N-(2,6-difluorobenzoyl)-N'-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]urea(C17H9F5N4O2S,Mr = 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-1,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate,and its crystal structure was determined by single-crystal X-ray diffraction.The crystal belongs to monoclinic,space group P21/n with a = 10.7316(13),b = 10.5617(13),c = 16.037(2) ,β = 106.408(2)°,V = 1743.6(4) 3,Z = 4,Dc = 1.632 g/cm3,μ = 0.260 mm-1,F(000) = 864,the final R = 0.0599 and wR = 0.1420 for 3467 observed reflections with I〉 2σ(I).The urea group,which adopts a planar configuration mediated by the intramolecular N-H...O hydrogen bond,is nearly coplanar with the thiadiazole and 4-trifluoromethylbenzene rings.The title compound was found to exhibit good fungicidal activity against Rhizoctonia solani and Botrytis cinerea.展开更多
The title compound N-[5-(benzylthio)-1,3,4-thiadiazol-2-yl]-4-chlorobenzamide(C(16)H(12)ClN3OS2, Mr = 361.86) was designed and synthesized as anticancer agent, and its crystal structure was determined by singl...The title compound N-[5-(benzylthio)-1,3,4-thiadiazol-2-yl]-4-chlorobenzamide(C(16)H(12)ClN3OS2, Mr = 361.86) was designed and synthesized as anticancer agent, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P1 with a = 5.7417(10), b = 9.8057(17), c = 14.330(3) A, a = 91.987(3), b = 97.154(3), γ = 93.402(3)°, V = 798.4(2) A3, Z = 2, Dc = 1.505 g/cm^3, μ = 0.507 mm-1) F(000) = 372, the final R = 0.0481 and wR = 0.1290 for 2064 observed reflections with I 〉 2s(I). In the crystal packing, the molecules form stacks by a three-dimensional framework, which results from intermolecular N(1)-H(1)···N(2) and C(5)-H(5)···N(3) hydrogen bonds together with π-π stacking interactions between the thiadiazole and chlorobenzene rings. The title compound was found to exhibit more potent in vitro antitumor activities against the four tested cancer cell lines than sorafenib.展开更多
An environmental benign procedure for synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles has been developed by reaction of 2-amino-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with formic acid in PEG-400.The...An environmental benign procedure for synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles has been developed by reaction of 2-amino-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with formic acid in PEG-400.The key advantages of this protocol are the shorter reaction time,higher yields,lower cost,simple workup,and environment-friendly compared to conventional organic solvent reaction.The present method does not involve any hazardous organic solvent or catalyst.展开更多
The title compound, [HgI2(C12H8N4S)], has been synthesized and characterized by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 14.086(2), b = 6.0365(6), c = ...The title compound, [HgI2(C12H8N4S)], has been synthesized and characterized by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 14.086(2), b = 6.0365(6), c = 20.286(2)°A,β= 108.818(5)°, V = 1632.7(3)°A^3, Mr = 694.67, Z = 4, D, = 2.826 g/cm^3,μ= 13.331 mm^-1, F(000) = 1240, S = 1.108, the final R = 0.0438 and wR = 0.0934 for 3085 observed reflections (I〉 2σ(I)). The Hg(Ⅱ) atom is coordinated by two 2,5-bis(4-pyridyl)-1,3,4-thiadiazole (L) molecules and two iodine anions in a distorted tetrahedral coordination geometry. Mercury atoms are linked by the organic ligands to form a one-dimensional zigzag chain. It is noteworthy that such 1D zigzag chains are extended into a two-dimensional double layer framework through I…I interactions展开更多
The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction...The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.452(4), b = 12.335(4), c = 13.017(5) A, α = 90.624(5), β = 110.541(5), γ =104.879(4)°, Dc = 1.561 g/cm3, Z = 2, V = 1364.9(9) A3, F(000) = 656, the final R = 0.0300 and w R = 0.0635 for 4206 observed reflections with I 】 2σ(I). The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici(Enjoji) Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory activities to be 9.82%, 44.44% and 20.00%, respectively.展开更多
A series of new 1-(alkenoyl/hydroxyalkenoyl)-4-benzoyl-thiosemicarbazides 2a-d and 2-benzamide-5-alkenyl/hydroxyalk- enyl-1,3,4-thiadiazoles 3a-d were synthesized from fatty acid hydrazides. Structure of all these c...A series of new 1-(alkenoyl/hydroxyalkenoyl)-4-benzoyl-thiosemicarbazides 2a-d and 2-benzamide-5-alkenyl/hydroxyalk- enyl-1,3,4-thiadiazoles 3a-d were synthesized from fatty acid hydrazides. Structure of all these compounds was confirmed by IR, IH NMR, Sac NMR, mass spectra and elemental analysis. The bioassay results indicate that some compounds 2e, 2d, 3e and 3d have good antibacterial activity.展开更多
A new series of N^1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives were designed and synthesized. These compounds have not been reported in literature, and their structure chemical wer...A new series of N^1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives were designed and synthesized. These compounds have not been reported in literature, and their structure chemical were confirmed by IR, ^1H NMR and MS (HRMS). The results of antitumor inhibitory activity test showed that some compounds possess more potent antitumor inhibitory activity than 5-fluorouracil.展开更多
The crystal structure of the title compound, 2-isobutyl-6-(2?4?dichlorophenyl)- imidazo[2,1-b]-1,3,4-thiadiazole (C14H13Cl2N3S, Mr = 326.23), has been synthesized by the treatment of 2-amino-5-isobutyl-1,3,4-thiadiazo...The crystal structure of the title compound, 2-isobutyl-6-(2?4?dichlorophenyl)- imidazo[2,1-b]-1,3,4-thiadiazole (C14H13Cl2N3S, Mr = 326.23), has been synthesized by the treatment of 2-amino-5-isobutyl-1,3,4-thiadiazole with a-chloroaceto-2,4-dichlorophenone and determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 12.483(7), b = 8.420(4), c = 14.998(8) ? b = 105.770(10)? V = 1517.0(14) 3, Z = 4, Dc = 1.428 g/cm3, S = 0.902, m(MoKa) = 0.558 mm-1, F (000) = 672, R = 0.0579 and wR = 0.1186. The X-ray analytic results showed that all ring atoms in the imidazothiadiazole moiety are almost coplanar. The dihedral angel between the phenyl group and hetero-cycle is 16.8(0.2)?展开更多
The title compound 1-(4-chlorophenyl)-3-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]urea (C14H10CIN5OS, Mr = 331.79) has been synthesized by the reaction of 2-amino-5-(pyrid-4-yl)- 1,3,4-thiadiazole with 4-chloroben...The title compound 1-(4-chlorophenyl)-3-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]urea (C14H10CIN5OS, Mr = 331.79) has been synthesized by the reaction of 2-amino-5-(pyrid-4-yl)- 1,3,4-thiadiazole with 4-chlorobenzoyl azide, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic system, space group PI with a = 5.8550(8), b = 7.5668(10), c = 16.416(2)A, α= 78.364(2), β= 81.204(2), γ= 84.749(2)°, V= 702.58(16)A^3, Z= 2, Dc = 1.568 g/cm^3, p = 0.429 mm ^-1, F(000) = 340, the final R = 0.0442 and wR = 0.1092 for 2001 observed reflections (1 〉 2σ(I)). X-ray diffraction analysis reveals that the title molecule is nearly planar. In the crystal structure, the molecules are linked by strong intermolecular N-H…N hydrogen bonds together with weak nonclassical intennolccular (C-H…Y, Y = N, O and CI) hydrogen bonds and stacked through π-π interactions. The preliminary bioassay shows that the title compound exhibits good fungicidal activities against Rhizoctonia solani, Botrytis cinerea and Dothiorella gregaria.展开更多
The potassium dithiocarbazate 2 was obtained through condensation of 5-pyrazole hydrazide 1 with carbon disulfide in ethanolic potassium hydroxide. and its cyclization gave 5-pyrazolyl-1,3,4-thiadiazole-2-thione 3 in ...The potassium dithiocarbazate 2 was obtained through condensation of 5-pyrazole hydrazide 1 with carbon disulfide in ethanolic potassium hydroxide. and its cyclization gave 5-pyrazolyl-1,3,4-thiadiazole-2-thione 3 in concentrated sulfuric acid. Alkylation of 3 yielded 2-alkylthio-5-pyrazolyl-1,3,4-thiadiazole 4. The preliminary bioassay tests indicated that compounds 3 and 4 have fungicidal activity.展开更多
Six new 1,3,4-thiadiazole Schiff base derivatives were synthesized and characterized by IR spectroscopy and ~1H NMR spectrometry, and their anti-corrosion properties and thermal stability were investigated via thermog...Six new 1,3,4-thiadiazole Schiff base derivatives were synthesized and characterized by IR spectroscopy and ~1H NMR spectrometry, and their anti-corrosion properties and thermal stability were investigated via thermogravimetric analysis(TGA) and copper strip corrosion test. The tribological behavior of the said Schiff base derivatives was evaluated on an Optimol SRV~?4 oscillating reciprocating friction and wear tester. The worn surfaces of the steel discs were investigated using a scanning electron microscope(SEM) and energy dispersive X-ray spectrometer(EDS). The test results indicated that these thiadiazole Schiff base derivatives possessed favourable thermal stability, corrosion inhibiting ability and the capability of improving the tribological characteristic of the base oil effectively. It is assumed that the adsorbed additives probably reacted with the steel surfaces during the friction process, resulting in the formation of a protective film composed of sulphates, sulphides and organic nitrogen compounds.展开更多
A facile one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles was achieved by ultrasonic irradiation of a mixture of 1-naphthylacetyl chloride, NH4CNS, CH2Cl2 and PEG-400 for 1.5 h at 10–20 °C and subsequen...A facile one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles was achieved by ultrasonic irradiation of a mixture of 1-naphthylacetyl chloride, NH4CNS, CH2Cl2 and PEG-400 for 1.5 h at 10–20 °C and subsequent irradiation for 1.5 h in the presence of N-arylglycine hydrazides. This method requires short time and gives thiadiazoles in high yields.展开更多
In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l...In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l,3,4-thiadiazol-2-yl}carba- mothioyl)-2/3/4-substitutedbenzamide were designed, synthesized and evaluated for their anticonvulsant activity. The findings of the present studies confirmed that the pharmacophore model with four binding sites is crucial for anticonvulsant activity. Structure-activity relationships among synthesized compounds were also established.展开更多
Two novel cobalt(Ⅱ) compounds were obtained and characterized by X-ray sing- le-crystal diffraction, IR, 1H NMR and elemental analysis. Compound 1 crystallizes in monoclinic, space group P21/n, with a = 18.046(4)...Two novel cobalt(Ⅱ) compounds were obtained and characterized by X-ray sing- le-crystal diffraction, IR, 1H NMR and elemental analysis. Compound 1 crystallizes in monoclinic, space group P21/n, with a = 18.046(4), b = 11.335(3), c = 19.157(5)A, β = 92.707(3)°, Z = 4, V = 3914.4(16) A3, Mr = 968.56, Dc = 1.644 g/cm3, μ = 1.378 mm^-1, F(000) = 1960, the final R = 0.0367 and wR = 0.0895. The crystal of compound 2 is of monoclinic, space group P211c with a = 8.7253(10), b = 10.9031(13), c = 18.235(2)A,β = 93.2210(10)°, Z = 4, V = 1732.0(3)A3, Mr = 464.21, Dc = 1.780 g/cm3,μ = 1.560 mm-1, F(000) = 932, the final R = 0.0322 and wR = 0.0743.展开更多
In recent years, fused heterocycles have been reported to possess important properties in synthesis and pharmacology. Especially, s-triazolo, 3,4-thiadiazole derivatives have been attracting much attention for chemist...In recent years, fused heterocycles have been reported to possess important properties in synthesis and pharmacology. Especially, s-triazolo, 3,4-thiadiazole derivatives have been attracting much attention for chemists and pharmacologists because they show broad spectra of biological activities, such as antifungal, antibacterial, hy-展开更多
Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H3...Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H31FN4S) was structurally determined by single-crystal X-ray diffraction.The crystal belongs to the orthorhombic system,space group P212121 with a=6.0153(14),b=12.2577(19),c=34.055(3)A,V=2511.0(7)A^3,Z=4,Mr=474.63,Dc=1.255Mg/m^3,λ=0.71073 A,μ(MoKα)=0.160 mm^-1,F(000)=1008,the final R=0.0555 and wR=0.1248 for 3094 observed reflections with I〉2σ(I).There are six rings in the crystal structure of the title compound.The dihedral angle between 1,2,4-triazole and 1,3,4-thiadiaole rings is 1.4o,and that between 1,2,4-triazole and benzene ring D 25.5o.展开更多
N-(5-Aryl-1,3,4-thiadiazol-2-yl)-N?-((E)-styryl)ureas 4 a~4 i were designed and synthesized as antitumor agents, and their structures were characterized by IR, 1 H NMR, 13 C NMR,MS and elemental analysis. The single ...N-(5-Aryl-1,3,4-thiadiazol-2-yl)-N?-((E)-styryl)ureas 4 a~4 i were designed and synthesized as antitumor agents, and their structures were characterized by IR, 1 H NMR, 13 C NMR,MS and elemental analysis. The single crystal of compound 4 a, C17 H13 FN4 OS, was also determined by X-ray crystallography. Crystal data: monoclinic, space group P21/n, a = 4.9401(8), b= 8.7100(15), c = 36.604(6) ?, β = 93.320(3)°, V = 1572.4(5) ?3, Z = 4, F(000) = 704, Dc = 1.438 g/cm3, μ = 0.228 mm-1, R = 0.0600 and wR = 0.1448 for 2743 independent reflections(Rint =0.0418) and 2174 observed ones(I > 2σ(I)). The in vitro antitumor activities of compounds 4 a~4 i were preliminarily evaluated by the standard MTT assay.展开更多
By ring-closure of 1-nicotinyl-4-arylthiosemicarbazides under the catalysis of concentrated sulfuric acid or mercuric acetate, a series of 2-(3-pyridyl)-5-arylarnino-1,3,4-thiadiazoles and 2-(3-pyridyl)-5-ary-lamino-1...By ring-closure of 1-nicotinyl-4-arylthiosemicarbazides under the catalysis of concentrated sulfuric acid or mercuric acetate, a series of 2-(3-pyridyl)-5-arylarnino-1,3,4-thiadiazoles and 2-(3-pyridyl)-5-ary-lamino-1,3,4-oxadiazoles were synthesized, respectively. All the products were subjected to testing of biological activity. Furthermore, the IR, 1H NMR and MS spectral properties of these new compounds were studied in details and some significant conclusions were drawn.展开更多
The title compound N1-(1,3,4-thiadiazole-2-yl)-N3-m-chlorobenzoyl-urea (C9HTN4OSC1, Mr = 254.70) was prepared by the reaction of m-chlorophenyl isocyanate with 2-amino-1,3,4- thiadiazole in dry acetonitrile. The e...The title compound N1-(1,3,4-thiadiazole-2-yl)-N3-m-chlorobenzoyl-urea (C9HTN4OSC1, Mr = 254.70) was prepared by the reaction of m-chlorophenyl isocyanate with 2-amino-1,3,4- thiadiazole in dry acetonitrile. The effect of the title compound on tumor metastasis was analyzed by Lewis-lung-carcinoma model. The bioassay showed that the title compound significantly reduced the number of lung metastasis. The crystal structure has been determined by X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 11.565(2), b = 9.5616(19), c = 10.221(2) A, β = 111.75(3)°, Z = 4, V= 1049.8(4) A3, De = 1.612 Mg/m3, F(000) = 520, g(MoKa) = 0.544 mm^-1, R = 0.0468 and wR = 0.0922 for 1236 observed reflections (I〉 2σ(I).展开更多
基金supported by the U.S.Department of Energy,Office of Basic Energy Sciences,Division of Materials Science and Engineering under award number DE-SC0005397.
文摘Organosulfur materials are a sustainable alternative to the present-day layered oxide cathodes in lithium-based batteries.One such organosulfur material that was intensely explored from the 1990s to early 2010s is 2,5-dimercapto-1,3,4-thiadiazole(DMCT).However,research interest declined as the electrode reactions with DMCT were assumed to be too sluggish to be practical.Armed with the advances in metal-sulfur batteries,we revisit DMCT-based materials in the form of poly[tetrathio-2,5-(1,3,4-thiadiazole)],referred to as pDMCT-S.With an appropriate choice of electrode design and electrolyte,pDMCT-S cathode paired with a Li-metal anode shows a capacity of 715 mA h g^(-1)and a Coulombic efficiency of 97.7%at a C/10 rate,thus quelling the concerns of sluggish reactions.Surprisingly,pDMCT-S shows significantly improved long-term cyclability compared to a sulfur cathode.Investigations into the origin of the stability reveals that the discharge product Li-DMCT in its mesomeric form can strongly bind to polysulfides,preventing their dissolution into the electrolyte and shuttling.This unique mechanism solves a critical problem faced by sulfur cathodes.Encouragingly,this mechanism results in a stable performance of pDMCT-S with Na-metal cells as well.This study opens the potential for exploring other organic materials that have inherent polysulfide sequestering capabilities,enabling long-life metal-sulfur batteries.
基金supported by the Natural Science Foundation of Hubei Province (No. 2008CDB016)the Research Project for Innovative Research Team of Hubei University for Nationalities
文摘The title compound N-(2,6-difluorobenzoyl)-N'-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]urea(C17H9F5N4O2S,Mr = 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-1,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate,and its crystal structure was determined by single-crystal X-ray diffraction.The crystal belongs to monoclinic,space group P21/n with a = 10.7316(13),b = 10.5617(13),c = 16.037(2) ,β = 106.408(2)°,V = 1743.6(4) 3,Z = 4,Dc = 1.632 g/cm3,μ = 0.260 mm-1,F(000) = 864,the final R = 0.0599 and wR = 0.1420 for 3467 observed reflections with I〉 2σ(I).The urea group,which adopts a planar configuration mediated by the intramolecular N-H...O hydrogen bond,is nearly coplanar with the thiadiazole and 4-trifluoromethylbenzene rings.The title compound was found to exhibit good fungicidal activity against Rhizoctonia solani and Botrytis cinerea.
基金supported by the National Natural Science Foundation of China(No.21262012)the Natural Science Foundation of Hubei Province(No.2016CFB400)the State Undergraduate Innovative Training Program(No.201410517002)
文摘The title compound N-[5-(benzylthio)-1,3,4-thiadiazol-2-yl]-4-chlorobenzamide(C(16)H(12)ClN3OS2, Mr = 361.86) was designed and synthesized as anticancer agent, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P1 with a = 5.7417(10), b = 9.8057(17), c = 14.330(3) A, a = 91.987(3), b = 97.154(3), γ = 93.402(3)°, V = 798.4(2) A3, Z = 2, Dc = 1.505 g/cm^3, μ = 0.507 mm-1) F(000) = 372, the final R = 0.0481 and wR = 0.1290 for 2064 observed reflections with I 〉 2s(I). In the crystal packing, the molecules form stacks by a three-dimensional framework, which results from intermolecular N(1)-H(1)···N(2) and C(5)-H(5)···N(3) hydrogen bonds together with π-π stacking interactions between the thiadiazole and chlorobenzene rings. The title compound was found to exhibit more potent in vitro antitumor activities against the four tested cancer cell lines than sorafenib.
基金support from the Natural Science Foundation of Gansu Province(No.3ZS061- A25-019)the Scientific Research fund of Gansu Provincial Education Department(No.0601-25)
文摘An environmental benign procedure for synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles has been developed by reaction of 2-amino-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with formic acid in PEG-400.The key advantages of this protocol are the shorter reaction time,higher yields,lower cost,simple workup,and environment-friendly compared to conventional organic solvent reaction.The present method does not involve any hazardous organic solvent or catalyst.
基金This work was supported by the 973 Program of the MOST (001CB108906) and the Natural Science Foundation of Fujian Province (2005HZ01-1)
文摘The title compound, [HgI2(C12H8N4S)], has been synthesized and characterized by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 14.086(2), b = 6.0365(6), c = 20.286(2)°A,β= 108.818(5)°, V = 1632.7(3)°A^3, Mr = 694.67, Z = 4, D, = 2.826 g/cm^3,μ= 13.331 mm^-1, F(000) = 1240, S = 1.108, the final R = 0.0438 and wR = 0.0934 for 3085 observed reflections (I〉 2σ(I)). The Hg(Ⅱ) atom is coordinated by two 2,5-bis(4-pyridyl)-1,3,4-thiadiazole (L) molecules and two iodine anions in a distorted tetrahedral coordination geometry. Mercury atoms are linked by the organic ligands to form a one-dimensional zigzag chain. It is noteworthy that such 1D zigzag chains are extended into a two-dimensional double layer framework through I…I interactions
基金funded by the National Natural Science Foundation of China(No.21002090)the Key Innovation Team of Science and Technology in Zhejiang Province(2010R50018-06)the National Key Technologies R&D Program(2011BAE06B03-01)
文摘The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.452(4), b = 12.335(4), c = 13.017(5) A, α = 90.624(5), β = 110.541(5), γ =104.879(4)°, Dc = 1.561 g/cm3, Z = 2, V = 1364.9(9) A3, F(000) = 656, the final R = 0.0300 and w R = 0.0635 for 4206 observed reflections with I 】 2σ(I). The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici(Enjoji) Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory activities to be 9.82%, 44.44% and 20.00%, respectively.
文摘A series of new 1-(alkenoyl/hydroxyalkenoyl)-4-benzoyl-thiosemicarbazides 2a-d and 2-benzamide-5-alkenyl/hydroxyalk- enyl-1,3,4-thiadiazoles 3a-d were synthesized from fatty acid hydrazides. Structure of all these compounds was confirmed by IR, IH NMR, Sac NMR, mass spectra and elemental analysis. The bioassay results indicate that some compounds 2e, 2d, 3e and 3d have good antibacterial activity.
文摘A new series of N^1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives were designed and synthesized. These compounds have not been reported in literature, and their structure chemical were confirmed by IR, ^1H NMR and MS (HRMS). The results of antitumor inhibitory activity test showed that some compounds possess more potent antitumor inhibitory activity than 5-fluorouracil.
基金The project was supported by NNSFC (20172031 29832050) the NSF of shandong province (Y2003B01) and the Fund for the Doctoral Program of Higher Education
文摘The crystal structure of the title compound, 2-isobutyl-6-(2?4?dichlorophenyl)- imidazo[2,1-b]-1,3,4-thiadiazole (C14H13Cl2N3S, Mr = 326.23), has been synthesized by the treatment of 2-amino-5-isobutyl-1,3,4-thiadiazole with a-chloroaceto-2,4-dichlorophenone and determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 12.483(7), b = 8.420(4), c = 14.998(8) ? b = 105.770(10)? V = 1517.0(14) 3, Z = 4, Dc = 1.428 g/cm3, S = 0.902, m(MoKa) = 0.558 mm-1, F (000) = 672, R = 0.0579 and wR = 0.1186. The X-ray analytic results showed that all ring atoms in the imidazothiadiazole moiety are almost coplanar. The dihedral angel between the phenyl group and hetero-cycle is 16.8(0.2)?
基金This work was supported by the National Natural Science Foundation of China (No. 20072009) the Research Project from Hubei Provincial Department of Education (No. Q200529003)
文摘The title compound 1-(4-chlorophenyl)-3-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]urea (C14H10CIN5OS, Mr = 331.79) has been synthesized by the reaction of 2-amino-5-(pyrid-4-yl)- 1,3,4-thiadiazole with 4-chlorobenzoyl azide, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic system, space group PI with a = 5.8550(8), b = 7.5668(10), c = 16.416(2)A, α= 78.364(2), β= 81.204(2), γ= 84.749(2)°, V= 702.58(16)A^3, Z= 2, Dc = 1.568 g/cm^3, p = 0.429 mm ^-1, F(000) = 340, the final R = 0.0442 and wR = 0.1092 for 2001 observed reflections (1 〉 2σ(I)). X-ray diffraction analysis reveals that the title molecule is nearly planar. In the crystal structure, the molecules are linked by strong intermolecular N-H…N hydrogen bonds together with weak nonclassical intennolccular (C-H…Y, Y = N, O and CI) hydrogen bonds and stacked through π-π interactions. The preliminary bioassay shows that the title compound exhibits good fungicidal activities against Rhizoctonia solani, Botrytis cinerea and Dothiorella gregaria.
文摘The potassium dithiocarbazate 2 was obtained through condensation of 5-pyrazole hydrazide 1 with carbon disulfide in ethanolic potassium hydroxide. and its cyclization gave 5-pyrazolyl-1,3,4-thiadiazole-2-thione 3 in concentrated sulfuric acid. Alkylation of 3 yielded 2-alkylthio-5-pyrazolyl-1,3,4-thiadiazole 4. The preliminary bioassay tests indicated that compounds 3 and 4 have fungicidal activity.
文摘Six new 1,3,4-thiadiazole Schiff base derivatives were synthesized and characterized by IR spectroscopy and ~1H NMR spectrometry, and their anti-corrosion properties and thermal stability were investigated via thermogravimetric analysis(TGA) and copper strip corrosion test. The tribological behavior of the said Schiff base derivatives was evaluated on an Optimol SRV~?4 oscillating reciprocating friction and wear tester. The worn surfaces of the steel discs were investigated using a scanning electron microscope(SEM) and energy dispersive X-ray spectrometer(EDS). The test results indicated that these thiadiazole Schiff base derivatives possessed favourable thermal stability, corrosion inhibiting ability and the capability of improving the tribological characteristic of the base oil effectively. It is assumed that the adsorbed additives probably reacted with the steel surfaces during the friction process, resulting in the formation of a protective film composed of sulphates, sulphides and organic nitrogen compounds.
文摘A facile one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles was achieved by ultrasonic irradiation of a mixture of 1-naphthylacetyl chloride, NH4CNS, CH2Cl2 and PEG-400 for 1.5 h at 10–20 °C and subsequent irradiation for 1.5 h in the presence of N-arylglycine hydrazides. This method requires short time and gives thiadiazoles in high yields.
文摘In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l,3,4-thiadiazol-2-yl}carba- mothioyl)-2/3/4-substitutedbenzamide were designed, synthesized and evaluated for their anticonvulsant activity. The findings of the present studies confirmed that the pharmacophore model with four binding sites is crucial for anticonvulsant activity. Structure-activity relationships among synthesized compounds were also established.
文摘Two novel cobalt(Ⅱ) compounds were obtained and characterized by X-ray sing- le-crystal diffraction, IR, 1H NMR and elemental analysis. Compound 1 crystallizes in monoclinic, space group P21/n, with a = 18.046(4), b = 11.335(3), c = 19.157(5)A, β = 92.707(3)°, Z = 4, V = 3914.4(16) A3, Mr = 968.56, Dc = 1.644 g/cm3, μ = 1.378 mm^-1, F(000) = 1960, the final R = 0.0367 and wR = 0.0895. The crystal of compound 2 is of monoclinic, space group P211c with a = 8.7253(10), b = 10.9031(13), c = 18.235(2)A,β = 93.2210(10)°, Z = 4, V = 1732.0(3)A3, Mr = 464.21, Dc = 1.780 g/cm3,μ = 1.560 mm-1, F(000) = 932, the final R = 0.0322 and wR = 0.0743.
文摘In recent years, fused heterocycles have been reported to possess important properties in synthesis and pharmacology. Especially, s-triazolo, 3,4-thiadiazole derivatives have been attracting much attention for chemists and pharmacologists because they show broad spectra of biological activities, such as antifungal, antibacterial, hy-
基金Supported by the Foundation of 100 Young and Middle-aged Discipline Leaders of Guangxi Province in the 21st century (No 2004219)the Natural Science Foundation of Guangxi Province (No 0731054)
文摘Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H31FN4S) was structurally determined by single-crystal X-ray diffraction.The crystal belongs to the orthorhombic system,space group P212121 with a=6.0153(14),b=12.2577(19),c=34.055(3)A,V=2511.0(7)A^3,Z=4,Mr=474.63,Dc=1.255Mg/m^3,λ=0.71073 A,μ(MoKα)=0.160 mm^-1,F(000)=1008,the final R=0.0555 and wR=0.1248 for 3094 observed reflections with I〉2σ(I).There are six rings in the crystal structure of the title compound.The dihedral angle between 1,2,4-triazole and 1,3,4-thiadiaole rings is 1.4o,and that between 1,2,4-triazole and benzene ring D 25.5o.
基金supported by the National Natural Science Foundation of China(No.21262012)the Natural Science Foundation of Hubei Province(No.2016CFB400)
文摘N-(5-Aryl-1,3,4-thiadiazol-2-yl)-N?-((E)-styryl)ureas 4 a~4 i were designed and synthesized as antitumor agents, and their structures were characterized by IR, 1 H NMR, 13 C NMR,MS and elemental analysis. The single crystal of compound 4 a, C17 H13 FN4 OS, was also determined by X-ray crystallography. Crystal data: monoclinic, space group P21/n, a = 4.9401(8), b= 8.7100(15), c = 36.604(6) ?, β = 93.320(3)°, V = 1572.4(5) ?3, Z = 4, F(000) = 704, Dc = 1.438 g/cm3, μ = 0.228 mm-1, R = 0.0600 and wR = 0.1448 for 2743 independent reflections(Rint =0.0418) and 2174 observed ones(I > 2σ(I)). The in vitro antitumor activities of compounds 4 a~4 i were preliminarily evaluated by the standard MTT assay.
文摘By ring-closure of 1-nicotinyl-4-arylthiosemicarbazides under the catalysis of concentrated sulfuric acid or mercuric acetate, a series of 2-(3-pyridyl)-5-arylarnino-1,3,4-thiadiazoles and 2-(3-pyridyl)-5-ary-lamino-1,3,4-oxadiazoles were synthesized, respectively. All the products were subjected to testing of biological activity. Furthermore, the IR, 1H NMR and MS spectral properties of these new compounds were studied in details and some significant conclusions were drawn.
基金supported by 863 high technology program (No.2001AA23561)
文摘The title compound N1-(1,3,4-thiadiazole-2-yl)-N3-m-chlorobenzoyl-urea (C9HTN4OSC1, Mr = 254.70) was prepared by the reaction of m-chlorophenyl isocyanate with 2-amino-1,3,4- thiadiazole in dry acetonitrile. The effect of the title compound on tumor metastasis was analyzed by Lewis-lung-carcinoma model. The bioassay showed that the title compound significantly reduced the number of lung metastasis. The crystal structure has been determined by X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 11.565(2), b = 9.5616(19), c = 10.221(2) A, β = 111.75(3)°, Z = 4, V= 1049.8(4) A3, De = 1.612 Mg/m3, F(000) = 520, g(MoKa) = 0.544 mm^-1, R = 0.0468 and wR = 0.0922 for 1236 observed reflections (I〉 2σ(I).