A series of acridine-1,2,3-triazole derivatives were designed, synthesized and characterized by NMR. 1-（2-methylacridinyl）-4-（4-methyl phenyl）-1,2,3-triazole（4f）, C_（23）H_（18）N_4, was structurally determined...A series of acridine-1,2,3-triazole derivatives were designed, synthesized and characterized by NMR. 1-（2-methylacridinyl）-4-（4-methyl phenyl）-1,2,3-triazole（4f）, C_（23）H_（18）N_4, was structurally determined by single-crystal X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.585（4）, b = 9.684（4）, c = 11.339（5） A, β = 88.250（7）o, V = 925.3（6）, Z = 2, D_c = 1.258 g/cm^3, F（000） = 368, μ = 0.077 mm^（-1）, the final R = 0.0808 and wR = 0.2218 for 3386 observed reflections（I 〉 2σ（I））. X-ray analysis indicates that the acridine ring is almost vertical to triazole ring with the dihedral angle nearly to be 75°. The crystal packing of the compound is stabilized mainly by π-π interaction. The preliminary biological tests display that some of the title compounds possess a good anti-tumour activity against MGC-803 and T24.展开更多
One new polymer [Co（L）（H2O）2]n（1） was synthesized by 4-（ethoxycarbonyl）-5-methyl-1H-1,2,3-triazole-1-carboxylic acid（Emtc） under the in situ solvent thermal reaction（H2L = 1-（carboxymethyl）-5-methyl-1H-1,...One new polymer [Co（L）（H2O）2]n（1） was synthesized by 4-（ethoxycarbonyl）-5-methyl-1H-1,2,3-triazole-1-carboxylic acid（Emtc） under the in situ solvent thermal reaction（H2L = 1-（carboxymethyl）-5-methyl-1H-1,2,3-triazole-4-carboxylic acid）. The title complex performs a wave-like 2D framework and the ligand H2L demonstrates the coordination mode as μ4-η-2：η-1η-1：η-1. The crystal structure has been established by single-crystal X-ray diffraction, and characterized by FT-IR. Fluorescent property was investigated in this work. Hirshfeld surface analysis has also been carried out on 1, and obvious main intermolecular interactions are observed.展开更多
The novel dinuclear copper complex [Cu2（H20）2（DMF）2（L）2] （1, H2L = 5-phenyl- 2H-1,2,3-triazole-4-carboxylic acid, DMF = N,N-dimethyl-formamide） has been synthesized and characterized by X-ray single-crystal di...The novel dinuclear copper complex [Cu2（H20）2（DMF）2（L）2] （1, H2L = 5-phenyl- 2H-1,2,3-triazole-4-carboxylic acid, DMF = N,N-dimethyl-formamide） has been synthesized and characterized by X-ray single-crystal diffraction. The compound crystallizes in triclinic system, space group P1 with a = 9.591, b = 10.508, c = 15.515A,β = 75.11°, V= 1446.2 A3, Z= 2, Mr = 683.62, Dc = 1.570 g/cm3, μ = 1.531 mm^-1, F（000） = 700, the final R = 0.0404 and wR = 0.1130 for 5327 observed reflections with I 〉 2σ（I）. In each unit of the complex, two Cu2＋ ions coordinated with two triazole ligands to form a dimeric [5,6,5] tricyclic structure. The central Cu atom is five-coordinated, and each copper atom shows a square pyramidal geometry. The crystal structure is stabilized by the inversion-related O-H…O hydrogen bond and C-H…O hydrogen bonding interactions to form a layer structure. Fluorescent spectra show an obvious quenching of fluorescence compared with free 1,2,3-triazole ligand. The results of agarose gel electrophoresis indicate that this complex can cleave the plasmid supercoiled DNA within shorter time in the 50-folds excess of ascorbate under physiological conditions, providing a new example in the research for artificial metal nucleic acid enzyme.展开更多
An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of m...An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of monosubstituted and unsubstituted triazole substrates with various olefins, including vinyl esters, are explored.展开更多
In this work, 1,4-bis(4-phenyl-1,2,3-triazole)benzene, 1,3-bis(4-phenyl-1,2,3-triazole)propane, bis(1-phenyl-1,2,3-triazole)-methylphenylsilane, and 1-ally-4-phenyl-1,2,3-triazole have been designed and synthesized vi...In this work, 1,4-bis(4-phenyl-1,2,3-triazole)benzene, 1,3-bis(4-phenyl-1,2,3-triazole)propane, bis(1-phenyl-1,2,3-triazole)-methylphenylsilane, and 1-ally-4-phenyl-1,2,3-triazole have been designed and synthesized via Click reaction. Fourier transform infrared spectroscopy(FT-IR) and nuclear magnetic resonance spectroscopy(NMR) were used to confirm the compounds' structures. The effect of silicon atom on the optical properties has also been studied. The UV-vis absorption wavelength of silicon-containing compound is about ca. 10 nm red-shifted when compared with that of other three compounds. The fluorescence emission bands of the compounds in CHCl_3 solutions were observed around ca. 440 nm. And the luminescent coordination compound, namely [AgL1?NO_3?3H_2O]n, based on the ligand 1-allyl-4-phenyl-1,2,3-triazole has been prepared. In addition, this complex exhibits a 1 D chain structure. The crystal structure has been determined by single-crystal X-ray diffraction, and the optical properties have been investigated by fluorescence spectrum. In summary, our work may provide new materials with luminescent property which is potentially useful in material fields.展开更多
Seven optimized configurations and their electronic structures of 4-amino-5-nitro- 1,2,3-triazole dimers on their potential energy surface have been obtained by using density functional theory （DPT） method at the B3...Seven optimized configurations and their electronic structures of 4-amino-5-nitro- 1,2,3-triazole dimers on their potential energy surface have been obtained by using density functional theory （DPT） method at the B3LYP/6-311＋＋G＊＊ level. The maximum intermolecular interaction energy is -35.42 kJ/mol via the basis set superposition error-correction （BSSE） and zero point energy-correction （ZPE）. Charge transfers between the two subsystems are small. The vibration analysis of optimized configurations was performed, and the thermodynamic property changes from monomer to dimer have been obtained with the temperature ranging from 200 to 800 K on the basis of statistical thermodynamics. It is found that the hydrogen bonds contribute to the dimers dominantly, and the extent of intermolecular interaction is mainly determined by the hydrogen bonds＇ strength rather than their number. The dimerization processes of Ⅳ, Ⅴand Ⅵ can occur spontaneously at 200 K.展开更多
4-Aryl-5-ethoxycarbonyl-1-H-1,2,3-triazoles have been prepared by treatment of ethyl polystyrylsulfonylacetate with substituted benzaldehydes and then sodium azide.
We report here a solid-phase synthesis of 1, 4-disubstituted 1, 2, 3-triazole using polystyrene-supported selenium resin. The resin used here not only works as a simple linker, but also assists the crucial α-alkylati...We report here a solid-phase synthesis of 1, 4-disubstituted 1, 2, 3-triazole using polystyrene-supported selenium resin. The resin used here not only works as a simple linker, but also assists the crucial α-alkylation reaction and selenoxide syn-elimimation, which ensures the purity of the products.展开更多
The title compound2-p-methyloxyphenyl-3a-（2-phenyl-1,2,3-triazole-4-yl）-3,4- dihydro-1,2,4-oxa-diazolo[4,5-d][1,5] benzothiazepine （C31H25N5O2S, Mr = 531.63） has been synthesized and its structure was determined b...The title compound2-p-methyloxyphenyl-3a-（2-phenyl-1,2,3-triazole-4-yl）-3,4- dihydro-1,2,4-oxa-diazolo[4,5-d][1,5] benzothiazepine （C31H25N5O2S, Mr = 531.63） has been synthesized and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P1^- with a = 10.888（2）, b = 15.115（3）, c = 16.702（3）A, α = 99.90（3）, β = 95.21（3）, γ = 100.41（3）°, V = 2642.1（9） nm^3, Dc = 1.336 g/cm^3, Z = 4, F（000） = 1112, μ = 0.162 mm^-1 ,λ（MoKα） = 0.071073 nm, R = 0.0357 and wR = 0.1126 for 10620 observed reflections with I 〉 2σ（I）. X-ray analysis reveals that the molecular backbone consists of a tricyclic system with the central seven- membered ring in a twisted boat-like conformation.展开更多
According to the superposition principle of reinforcement of biological activities, 24 novel 1,4- disubstituted phenyl-5-（halo-2-hydroxyphenyl）imino-l,2,3-triazoles was synthesized and characterized by 1H NMR, ^13C ...According to the superposition principle of reinforcement of biological activities, 24 novel 1,4- disubstituted phenyl-5-（halo-2-hydroxyphenyl）imino-l,2,3-triazoles was synthesized and characterized by 1H NMR, ^13C NMR, elemental analysis and IR. All the target compounds were screened for their antibacterial potential in vitro against Monilia albican, Escherichia coli and Staphylococcus aureus. It was shown that all the compounds possessed efficient antibacterial activities at a concentration of 0.1 mg/mL, even at a concentration of 0.01 mg/mL, some of the compounds still exhibited antibacterial activities against Escherichia coli and Monilia albican. At last, the struc- ture-activity relationship was discussed based on the antibacterial results.展开更多
Gas-phase thermolysis of 1-ethoxycarbonyl-benzotriazole under static, FVP and microwaves condition yielded N^1 and NZ-ethylbenzotriazole, 2-ethoxy-1,3-benzooxazole, biphenylene and oxazolidin-2-one. On the other hand,...Gas-phase thermolysis of 1-ethoxycarbonyl-benzotriazole under static, FVP and microwaves condition yielded N^1 and NZ-ethylbenzotriazole, 2-ethoxy-1,3-benzooxazole, biphenylene and oxazolidin-2-one. On the other hand, direct condensation and pyrolysis of naphtho[1,8-de][1,2,3]triazine with ethylisocyanate, phenylisocyanate and their isothiocayanates, benzoylisothiocyanate and thiourea at 150-160 ℃ or under microwaves irradiation produced the corresponding naphthopyrimidin-2-one derivatives.展开更多
Fifteen 1-（4-substituted phenyl）-4-（4-bromophenyl）-5-（halo-o-hydroxyphenyl）imino-1,2,3-triazoles were designed and synthe- sized based on rational combination of 1,2,3-triazoles and （halo）o-hydroxyphenyl group...Fifteen 1-（4-substituted phenyl）-4-（4-bromophenyl）-5-（halo-o-hydroxyphenyl）imino-1,2,3-triazoles were designed and synthe- sized based on rational combination of 1,2,3-triazoles and （halo）o-hydroxyphenyl group according to the superposition principle of reinforcement of biological activities. All the compounds were tested to an in vitro antimicrobial screening against M.a. and E.c.. Compounds IIe-IIo exhibited more potent antimicrobial activities against M.a. and E.c. than triclosan and fluconazole, which provided valuable information to further study of novel antimicrobial research.展开更多
Two calix[4]arene derivatives containing 1,2,3-triazole moiety were synthesized via K2CO3-catalyzed1,3-dipolar cycloaddition reaction between calix[4]arene-based azide and active methylene compounds in good yields.The...Two calix[4]arene derivatives containing 1,2,3-triazole moiety were synthesized via K2CO3-catalyzed1,3-dipolar cycloaddition reaction between calix[4]arene-based azide and active methylene compounds in good yields.The structures of the two compounds synthesized herein were fully confirmed by 1HNMR,,（13）C NMR,and MS（ESI）.The thermal analysis showed that the mass losses of the synthesized compounds 4 and 5 containing 1,2,3-triazole groups are similar to each other.展开更多
1-Substituted 1,2,3-triazoles represents‘privileged’structural scaffolds of many clinical pharmaceuticals.However,the traditional methods for their preparation mainly rely on thermal[3+2]cycloaddition of potentially...1-Substituted 1,2,3-triazoles represents‘privileged’structural scaffolds of many clinical pharmaceuticals.However,the traditional methods for their preparation mainly rely on thermal[3+2]cycloaddition of potentially dangerous acetylene and azides.Here we report a base-mediated[4+1]annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones(DFHZ-Ts)with amines under relatively mild conditions.This azide-and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner.This transformation has great functional group tolerance and can suit a broad substrate scope.Furthermore,the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality,practicability and applicability.展开更多
A highly selective iron ions fluorescent probe based on the benz(c)acridine-1,2,3-triazole derivatives was produced by multi-step reactions. 1-(7-Benz[c]acridinyl)-4-(4-methylphenyl)-1,2,3-triazole(4 a), C_(26)H_(18)N...A highly selective iron ions fluorescent probe based on the benz(c)acridine-1,2,3-triazole derivatives was produced by multi-step reactions. 1-(7-Benz[c]acridinyl)-4-(4-methylphenyl)-1,2,3-triazole(4 a), C_(26)H_(18)N_(4), was structurally determined by single-crystal X-ray diffraction. It crystallizes in the trigonal system, space group R-3 with a = 36.230(10), b = 36.230(10), c = 7.993(3)Å, β = 90°, V = 9086(6)Å^(3), Z = 18, D_(c)= 1.271 g/cm^(3), F(000) = 3636, μ = 0.602 mm^(-1), the final R = 0.0865 and wR = 0.1619 for 3951 observed reflections(I > 2σ(I)). X-ray analysis indicated that all four rings of benz(c)acridine are in the same plane, and the 1,2,3-triazole ring and the corresponding linked benzene(C(1)–C(6)–C(7)–C(8)–C(9)–N(1)) are approximately perpendicular with a dihedral angle of 106.5°. The crystal packing of the compound was stabilized by two weak interactions between C(11)–H(10)…N(4) and C(18)–H(18)…N(1). In fluorescence spectra studies, compound 4 c was exhibited good selectivity and sensitivity towards iron ions in DMSO: mops buffer solution. Furthermore, 4 c was successfully used for imaging iron ions in living He La cervical cancer cells.展开更多
基金Supported by the National Natural Science Foundation of China(No.51263002)Natural Science Foundation of Guangxi Province(No.2014GXNSFBA118182)+3 种基金the Scientific Research Fund of Guangxi Provincial Education Department(No.YB2014181)the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources(Guangxi Normal University)Ministry of Education of China(CMEMR2015-B04)the Scientific Research Fund of Guangxi University of Chinese Medicine(No.QN14017,2015MS003)
文摘A series of acridine-1,2,3-triazole derivatives were designed, synthesized and characterized by NMR. 1-（2-methylacridinyl）-4-（4-methyl phenyl）-1,2,3-triazole（4f）, C_（23）H_（18）N_4, was structurally determined by single-crystal X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.585（4）, b = 9.684（4）, c = 11.339（5） A, β = 88.250（7）o, V = 925.3（6）, Z = 2, D_c = 1.258 g/cm^3, F（000） = 368, μ = 0.077 mm^（-1）, the final R = 0.0808 and wR = 0.2218 for 3386 observed reflections（I 〉 2σ（I））. X-ray analysis indicates that the acridine ring is almost vertical to triazole ring with the dihedral angle nearly to be 75°. The crystal packing of the compound is stabilized mainly by π-π interaction. The preliminary biological tests display that some of the title compounds possess a good anti-tumour activity against MGC-803 and T24.
基金Supported by the financial support of Fundamental Research Funds for the Central Universities(3207045420)Jiangsu Ainaji Neoenergy Science&Technology Co.,Ltd.(8507040091)
文摘One new polymer [Co（L）（H2O）2]n（1） was synthesized by 4-（ethoxycarbonyl）-5-methyl-1H-1,2,3-triazole-1-carboxylic acid（Emtc） under the in situ solvent thermal reaction（H2L = 1-（carboxymethyl）-5-methyl-1H-1,2,3-triazole-4-carboxylic acid）. The title complex performs a wave-like 2D framework and the ligand H2L demonstrates the coordination mode as μ4-η-2：η-1η-1：η-1. The crystal structure has been established by single-crystal X-ray diffraction, and characterized by FT-IR. Fluorescent property was investigated in this work. Hirshfeld surface analysis has also been carried out on 1, and obvious main intermolecular interactions are observed.
基金supported by the National Natural Science Foundation of China(No.21002076)Wuhan Youth Chenguang Program of Science and Technology(No.201271031374)
文摘The novel dinuclear copper complex [Cu2（H20）2（DMF）2（L）2] （1, H2L = 5-phenyl- 2H-1,2,3-triazole-4-carboxylic acid, DMF = N,N-dimethyl-formamide） has been synthesized and characterized by X-ray single-crystal diffraction. The compound crystallizes in triclinic system, space group P1 with a = 9.591, b = 10.508, c = 15.515A,β = 75.11°, V= 1446.2 A3, Z= 2, Mr = 683.62, Dc = 1.570 g/cm3, μ = 1.531 mm^-1, F（000） = 700, the final R = 0.0404 and wR = 0.1130 for 5327 observed reflections with I 〉 2σ（I）. In each unit of the complex, two Cu2＋ ions coordinated with two triazole ligands to form a dimeric [5,6,5] tricyclic structure. The central Cu atom is five-coordinated, and each copper atom shows a square pyramidal geometry. The crystal structure is stabilized by the inversion-related O-H…O hydrogen bond and C-H…O hydrogen bonding interactions to form a layer structure. Fluorescent spectra show an obvious quenching of fluorescence compared with free 1,2,3-triazole ligand. The results of agarose gel electrophoresis indicate that this complex can cleave the plasmid supercoiled DNA within shorter time in the 50-folds excess of ascorbate under physiological conditions, providing a new example in the research for artificial metal nucleic acid enzyme.
基金supported by the National Natural Science Foundation of China (21272268 and 21472237)~~
文摘An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of monosubstituted and unsubstituted triazole substrates with various olefins, including vinyl esters, are explored.
基金supported by the National Natural Science Foundation of China(No.21274080)
文摘In this work, 1,4-bis(4-phenyl-1,2,3-triazole)benzene, 1,3-bis(4-phenyl-1,2,3-triazole)propane, bis(1-phenyl-1,2,3-triazole)-methylphenylsilane, and 1-ally-4-phenyl-1,2,3-triazole have been designed and synthesized via Click reaction. Fourier transform infrared spectroscopy(FT-IR) and nuclear magnetic resonance spectroscopy(NMR) were used to confirm the compounds' structures. The effect of silicon atom on the optical properties has also been studied. The UV-vis absorption wavelength of silicon-containing compound is about ca. 10 nm red-shifted when compared with that of other three compounds. The fluorescence emission bands of the compounds in CHCl_3 solutions were observed around ca. 440 nm. And the luminescent coordination compound, namely [AgL1?NO_3?3H_2O]n, based on the ligand 1-allyl-4-phenyl-1,2,3-triazole has been prepared. In addition, this complex exhibits a 1 D chain structure. The crystal structure has been determined by single-crystal X-ray diffraction, and the optical properties have been investigated by fluorescence spectrum. In summary, our work may provide new materials with luminescent property which is potentially useful in material fields.
基金Project of National Natural Science Foundation of China (No. 10576030, 20173028)
文摘Seven optimized configurations and their electronic structures of 4-amino-5-nitro- 1,2,3-triazole dimers on their potential energy surface have been obtained by using density functional theory （DPT） method at the B3LYP/6-311＋＋G＊＊ level. The maximum intermolecular interaction energy is -35.42 kJ/mol via the basis set superposition error-correction （BSSE） and zero point energy-correction （ZPE）. Charge transfers between the two subsystems are small. The vibration analysis of optimized configurations was performed, and the thermodynamic property changes from monomer to dimer have been obtained with the temperature ranging from 200 to 800 K on the basis of statistical thermodynamics. It is found that the hydrogen bonds contribute to the dimers dominantly, and the extent of intermolecular interaction is mainly determined by the hydrogen bonds＇ strength rather than their number. The dimerization processes of Ⅳ, Ⅴand Ⅵ can occur spontaneously at 200 K.
文摘4-Aryl-5-ethoxycarbonyl-1-H-1,2,3-triazoles have been prepared by treatment of ethyl polystyrylsulfonylacetate with substituted benzaldehydes and then sodium azide.
基金the National Natural Science Foundation of China(No.20332060)the Natural Science Foundation of Zhejiang Province(No.Y405407).
文摘We report here a solid-phase synthesis of 1, 4-disubstituted 1, 2, 3-triazole using polystyrene-supported selenium resin. The resin used here not only works as a simple linker, but also assists the crucial α-alkylation reaction and selenoxide syn-elimimation, which ensures the purity of the products.
基金This work was supported by the National Natural Science Foundation of China (No. 29702007 and 20162004)
文摘The title compound2-p-methyloxyphenyl-3a-（2-phenyl-1,2,3-triazole-4-yl）-3,4- dihydro-1,2,4-oxa-diazolo[4,5-d][1,5] benzothiazepine （C31H25N5O2S, Mr = 531.63） has been synthesized and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P1^- with a = 10.888（2）, b = 15.115（3）, c = 16.702（3）A, α = 99.90（3）, β = 95.21（3）, γ = 100.41（3）°, V = 2642.1（9） nm^3, Dc = 1.336 g/cm^3, Z = 4, F（000） = 1112, μ = 0.162 mm^-1 ,λ（MoKα） = 0.071073 nm, R = 0.0357 and wR = 0.1126 for 10620 observed reflections with I 〉 2σ（I）. X-ray analysis reveals that the molecular backbone consists of a tricyclic system with the central seven- membered ring in a twisted boat-like conformation.
基金Supported by the National Natural Science Foundation of China(Nos.20976135,21176194)
文摘According to the superposition principle of reinforcement of biological activities, 24 novel 1,4- disubstituted phenyl-5-（halo-2-hydroxyphenyl）imino-l,2,3-triazoles was synthesized and characterized by 1H NMR, ^13C NMR, elemental analysis and IR. All the target compounds were screened for their antibacterial potential in vitro against Monilia albican, Escherichia coli and Staphylococcus aureus. It was shown that all the compounds possessed efficient antibacterial activities at a concentration of 0.1 mg/mL, even at a concentration of 0.01 mg/mL, some of the compounds still exhibited antibacterial activities against Escherichia coli and Monilia albican. At last, the struc- ture-activity relationship was discussed based on the antibacterial results.
文摘Gas-phase thermolysis of 1-ethoxycarbonyl-benzotriazole under static, FVP and microwaves condition yielded N^1 and NZ-ethylbenzotriazole, 2-ethoxy-1,3-benzooxazole, biphenylene and oxazolidin-2-one. On the other hand, direct condensation and pyrolysis of naphtho[1,8-de][1,2,3]triazine with ethylisocyanate, phenylisocyanate and their isothiocayanates, benzoylisothiocyanate and thiourea at 150-160 ℃ or under microwaves irradiation produced the corresponding naphthopyrimidin-2-one derivatives.
基金supported by the National Natural Science Foundation of China (No. 20976135)
文摘Fifteen 1-（4-substituted phenyl）-4-（4-bromophenyl）-5-（halo-o-hydroxyphenyl）imino-1,2,3-triazoles were designed and synthe- sized based on rational combination of 1,2,3-triazoles and （halo）o-hydroxyphenyl group according to the superposition principle of reinforcement of biological activities. All the compounds were tested to an in vitro antimicrobial screening against M.a. and E.c.. Compounds IIe-IIo exhibited more potent antimicrobial activities against M.a. and E.c. than triclosan and fluconazole, which provided valuable information to further study of novel antimicrobial research.
基金the financial supports of the National Natural Science Foundation of China(No.21102003)Scientific Research Foundation for the Introduction of Talent and Young Teachers Scientific Research Foundation of Anhui University of Science & Technology(Nos.11214,2012QNY27)
文摘Two calix[4]arene derivatives containing 1,2,3-triazole moiety were synthesized via K2CO3-catalyzed1,3-dipolar cycloaddition reaction between calix[4]arene-based azide and active methylene compounds in good yields.The structures of the two compounds synthesized herein were fully confirmed by 1HNMR,,（13）C NMR,and MS（ESI）.The thermal analysis showed that the mass losses of the synthesized compounds 4 and 5 containing 1,2,3-triazole groups are similar to each other.
基金supported by the National Natural Science Foundation of China(NSFC,Nos.21871043,21961130376)Department of Science and Technology of Jilin Province(Nos.20180101185JC,20190701012GH,20200801065GH)the Fundamental Research Funds for the Central Universities(Nos.2412019ZD001,2412020ZD003)。
文摘1-Substituted 1,2,3-triazoles represents‘privileged’structural scaffolds of many clinical pharmaceuticals.However,the traditional methods for their preparation mainly rely on thermal[3+2]cycloaddition of potentially dangerous acetylene and azides.Here we report a base-mediated[4+1]annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones(DFHZ-Ts)with amines under relatively mild conditions.This azide-and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner.This transformation has great functional group tolerance and can suit a broad substrate scope.Furthermore,the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality,practicability and applicability.
基金Supported by the National Natural Science Foundation of China(No.22067001)Natural Science Foundation of Guangxi Province(No.2018GXNSFAA281189)+4 种基金Graduate Education Innovation Project of Guangxi University of Chinese Medicine(No.YCSY20190027)the Guangxi Key Laboratory of Zhuang and Yao Ethnic Medicine((2013)No.20)Collaborative Innovation Center of Zhuang and Yao Ethnic Medicine((2014)No.32)Guangxi Key Discipline Zhuang Pharmacology((2013)No.16)First-class Discipline in Guangxi of traditional Chinese Pharmacology(Direction of Ethnic Medicine)((2018)No.12)。
文摘A highly selective iron ions fluorescent probe based on the benz(c)acridine-1,2,3-triazole derivatives was produced by multi-step reactions. 1-(7-Benz[c]acridinyl)-4-(4-methylphenyl)-1,2,3-triazole(4 a), C_(26)H_(18)N_(4), was structurally determined by single-crystal X-ray diffraction. It crystallizes in the trigonal system, space group R-3 with a = 36.230(10), b = 36.230(10), c = 7.993(3)Å, β = 90°, V = 9086(6)Å^(3), Z = 18, D_(c)= 1.271 g/cm^(3), F(000) = 3636, μ = 0.602 mm^(-1), the final R = 0.0865 and wR = 0.1619 for 3951 observed reflections(I > 2σ(I)). X-ray analysis indicated that all four rings of benz(c)acridine are in the same plane, and the 1,2,3-triazole ring and the corresponding linked benzene(C(1)–C(6)–C(7)–C(8)–C(9)–N(1)) are approximately perpendicular with a dihedral angle of 106.5°. The crystal packing of the compound was stabilized by two weak interactions between C(11)–H(10)…N(4) and C(18)–H(18)…N(1). In fluorescence spectra studies, compound 4 c was exhibited good selectivity and sensitivity towards iron ions in DMSO: mops buffer solution. Furthermore, 4 c was successfully used for imaging iron ions in living He La cervical cancer cells.
