CN111793070A - 一类新型具有荧光特性[1,2,4]-三氮唑并环类化合物及其制备方法和用途 - Google Patents
一类新型具有荧光特性[1,2,4]-三氮唑并环类化合物及其制备方法和用途 Download PDFInfo
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- CN111793070A CN111793070A CN202010601062.3A CN202010601062A CN111793070A CN 111793070 A CN111793070 A CN 111793070A CN 202010601062 A CN202010601062 A CN 202010601062A CN 111793070 A CN111793070 A CN 111793070A
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- compound
- substituted
- aryl
- heterocyclic compound
- triazolo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 9
- 230000004044 response Effects 0.000 claims abstract description 7
- 230000003013 cytotoxicity Effects 0.000 claims abstract description 5
- 231100000135 cytotoxicity Toxicity 0.000 claims abstract description 5
- 150000002739 metals Chemical class 0.000 claims abstract description 4
- 238000012984 biological imaging Methods 0.000 claims abstract description 3
- -1 pyrimidine heterocyclic compound Chemical class 0.000 claims description 42
- 238000001514 detection method Methods 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000523 sample Substances 0.000 claims description 5
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
- 229940125898 compound 5 Drugs 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 229940125904 compound 1 Drugs 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- RWZYAGGXGHYGMB-WGGUOBTBSA-N 2-aminobenzoic acid Chemical class NC1=CC=CC=C1[14C](O)=O RWZYAGGXGHYGMB-WGGUOBTBSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000006492 halo alkyl aryl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910021654 trace metal Inorganic materials 0.000 abstract description 7
- 230000005284 excitation Effects 0.000 abstract description 5
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 15
- 229910001447 ferric ion Inorganic materials 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- 239000007850 fluorescent dye Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 239000003068 molecular probe Substances 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical class 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 229910001431 copper ion Inorganic materials 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 229910001448 ferrous ion Inorganic materials 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 229910001425 magnesium ion Inorganic materials 0.000 description 2
- 229910001437 manganese ion Inorganic materials 0.000 description 2
- 229910001453 nickel ion Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- VGDIYIOYCWSUNM-UHFFFAOYSA-N quinoline 1H-1,2,4-triazole Chemical compound C=1N=CNN=1.N1=CC=CC2=CC=CC=C21 VGDIYIOYCWSUNM-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010061481 Renal injury Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 238000000559 atomic spectroscopy Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
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- 238000000295 emission spectrum Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 208000037806 kidney injury Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- HQYNSFAFYFMRLG-UHFFFAOYSA-N tribromo phosphite Chemical compound BrOP(OBr)OBr HQYNSFAFYFMRLG-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
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Abstract
本发明涉及杂环化合物领域,公开了一类[1,2,4]‑三氮唑并环类荧光分子的制备方法及用途,本发明公开的[1,2,4]‑三氮唑并环类杂环化合物的激发波长在200‑800nm之间;发射波长在400‑800nm之间,且细胞毒性低,生物相容性好,连接上不同的金属响应基团,能够选择性的检测对应的微量金属元素。本发明的荧光分子可用于环境、细胞及生物体中痕量金属的检测且在生物成像方面具有良好的应用前景。
Description
技术领域
本发明涉及一类新型荧光分子的制备方法及用途,特别是一类[1,2,4]-三氮唑并环类荧光分子及其制备方法和用途。
背景技术
金属元素与生命体尤其是人体健康的关系已引起人们的广泛关注,至今已知人体内含有的微量元素有铁、锌、铜、锰、钴、钼、铬、钒、镍和锡等。它们都是人体中不可或缺的元素,以铁元素为例,铁元素是生物体中至关重要的,特别是Fe3+,它参与构成了生命体内多种酶和蛋白质,在多种生物的化学反应中起着至关重要的作用。人体Fe3+失衡会引起新陈代谢紊乱,对身体健康产生影响,进而导致贫血、肝肾损伤和心力衰竭等疾病;其它人体必需的微量金属元素同样在生命体的平衡、生长、发育以及代谢活动起着至关重要的作用。另外,非人体必需的重金属元素(如钯、钌、铑、汞等)一旦被生命体摄入,不仅影响其健康甚至危及生命。因此,快速准确的检测食物、饮用水、环境以及生命体内的微量金属元素对自然环境的保护、食品和饮用水安全以及生命科学都具有十分重要的意义。目前,检测微量金属元素的方法主要有分光光度法、原子光谱法、电化学法和质谱法等,这些分析方法通常具有良好的检测范围、灵敏度和重复性,但也存在检测限高、检测时间长、繁琐的样品制备过程、操作复杂、容易受其他离子干扰等缺点。因此,开发一种准确且简单快速地检测诸如Fe3+、钯等微量金属元素的方法是非常必要的,而有机小分子荧光探针就是其中有效的方法之一。常用于荧光检测的有机小分子结构包括香豆素类、萘酰亚胺类、菲咪唑类、苯并噻唑类、罗丹明类、氟硼吡咯类等,这些分子大都具有荧光强度高,检测限低、响应快等特征;但这些分子在生物相容性、金属离子检测的专一性等方面尚有不足,尤其是对铁离子的检测,以上常用的有机荧光探针分子大部分无法有效的区分Fe3+和Fe2+,因此,本发明提供一类新型[1,2,4]-三氮唑类杂环化合物荧光分子及其在金属检测方面的应用,在该荧光分子结构中引入不同的金属响应基团,可以用于不同微量金属元素的检测,尤其在铁离子检测方面,该荧光分子能专一性的识别Fe3+,而不识别Fe2+。
发明内容
有鉴于此,本发明提供一类新型的[1,2,4]-三氮唑并环类杂环化合物荧光分子并将其应用于微量金属元素的检测。
为了实现上述目的,本发明采用以下技术方案:
一类[1,2,4]-三氮唑并环类荧光分子探针,所述[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物的通式(I)和[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II)如下所示:
其中,R1为氨基、(烷基或酰基)取代氨基,烷基、烷氧基;所述烷氧基为-OCH2CH=CH2或-OCOOCH2CH=CH2;对于三价铁离子的检测,R1优选为酰基取代的氨基,对于钯检测,R1优选为OCOOCH2CH=CH2。
R2是烷氧基,苯氧基,烷基,烯基,炔基,环烷基,卤代烷基芳基或杂芳基;每个所述烷基,环烷基,卤代烷基,芳基和杂芳基是未取代或任选一个可取代位置独立取代,各自独立的取代为卤素,氰基,烷氧基,烷基,卤代烷基,卤代烷氧基,芳基,杂芳基,杂环基,环烷基或酰胺基;所述卤代烷基,卤代烷氧基中卤素取代基为氟、氯、溴或碘。作为优选:R2取代基为甲氧基,苯氧基和苯基。
R3是芳基,单环芳基,并环芳基,稠环芳基;所述单环芳基为(取代)苯基,(取代)杂环芳基;所述并环芳基为(取代)苯并呋喃、(取代)苯并噻吩、(取代)苯并咪唑,(取代)苯并噻唑;所述稠环芳基为(取代)萘基,(取代)蒽基或(取代)菲基。其中单环芳基以苯环,噻吩环作为优选;并环芳基以苯并噻吩或苯并噻唑作为优选;稠环芳基以蒽基和菲基作为优选。
本发明还提供了[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)的制备方法如图,
具体包括以下步骤:
(1)[1,2,4]-三氮唑并[1,5-a]嘧啶酮类杂环化合物1的制备方法参考中国专利(CN201611115587.6),将其溶于合适的溶剂中,加入三卤化物,得到7-卤代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2。
(2)7-卤代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2溶于溶剂中,加入芳基硼酸,有机碱或者无机碱和催化剂,得到取代的7-芳基取代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)。
(3)当R1为氨基或氨基的衍生物时,起始原料中的R1为硝基,通式(I)中的硝基经过还原后衍生化得到通式(I)荧光分子。
本发明还提供了[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II)的制备方法如图,
具体包括以下步骤:
(1)取代的2-氨基苯甲酸3经酯化和肼解得到取代的2-氨基酰肼类衍生物4。
(2)将取代的2-氨基酰肼类衍生物溶于合适溶剂中,加入硫氰酸铵,所得混合物加热至一定温度反应,得到化合物5。
(3)将化合物5溶于溶剂中,加入芳香酰氯,加热反应得到取代的[1,2,4]-三氮唑并喹(唑)啉酮类杂环化合物6。
(5)将[1,2,4]-三氮唑并喹(唑)啉酮类杂环化合物6与三卤氧磷反应得到7-卤代-[1,2,4]-三氮唑并喹(唑)啉类杂环化合物7。
(6)将7-溴代-[1,2,4]-三氮唑并喹(唑)啉类杂环化合物7与芳基硼酸衍生物偶联反应得到通式(Π)所示[1,2,4]-三氮唑并喹(唑)啉类杂环化合物目标分子。
(7)如果通式(II)中R1是氨基或取代的氨基衍生物,则起始原料中R1为硝基,化合物7经偶联后还原再衍生化得到通式(II)。
本发明提供了一类[1,2,4]-三氮唑并环类荧光分子,即[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)和[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II)荧光分子,该类荧光分子的激发波长在200-800nm之间;发射波长在400-800nm之间,可用于环境中微量及痕量金属的检测,由于该类化合物细胞毒性低,生物相容性好,因而可用于细胞及生物体内微量金属的检测并在生物成像方面具有良好的应用前景。
附图说明:
图1是荧光探针化合物I-36对Fe3+的选择性荧光发射光谱在450nm处的柱状图
图2是金属阳离子对荧光探针化合物I-36检测Fe3+的干扰图。
图3是荧光探针化合物I-49与不同浓度的Pd0响应后的光谱变化图。
图4是荧光探针化合物I-49对Pd0的选择性荧光发射光谱在440nm处的柱状图。
图5是荧光探针化合物I-36检测Hela细胞中对Fe3+离子的激光共聚焦成像图。
具体实施方式
本发明公开了一类[1,2,4]-三氮唑并环类杂环化合物其制备方法及用途,通式(Ⅰ,Ⅱ)表示的化合物是在本发明中所合成的化合物,通式(Ⅰ,Ⅱ)的激发波长200-800nm之间;发射波长在400-800nm之间,且细胞毒性低,生物相容性好的事实是由本发明首次公开的。
通式(I)表示的化合物所制备的部分化合物结构实例及其激发波长(λex)和发射波长(λ)如下:
通式(Ⅱ)表示的化合物所制备的部分化合物结构实例及其激发波长(λex)和发射波长(λem)如下:
实施例1下面结合附图和实施例对本发明作更加详细的描述,应当理解,此处所描述的优选实施例仅用于说明和解释本发明,并不用于限定本发明。
(1)化合物I-36b的制备
化合物I-36a(1mmol)溶于15mL乙腈中,加入三溴氧磷(4mmol),加热至回流并在该温度下反应5-6小时(TLC跟踪反应),反应完毕后,减压浓缩去除溶剂,所得残留物经二氯甲烷萃取,取有机相溶液,减压浓缩去除溶剂得化合物I-36b纯品,收率为75%。
(2)化合物I-36c的制备
化合物I-36b(0.5mmol)溶于15mL 1,4-二氧六环中,加入苯硼酸(0.6mmol),然后加入碳酸钾(1mmol)和四三苯基膦钯(0.05mmol),无水无氧条件下,回流反应12小时(TLC跟踪反应),反应完毕后,减压浓缩去除溶剂,所得残留物经二氯甲烷萃取,取有机相溶液,减压浓缩去除溶剂得化合物I-36c,收率为80%。
(3)化合物I-36d的制备
化合物I-36c(0.5mmol)溶于10mL甲醇中,加入催化量雷尼镍,常温下氢化反应1-2小时(TLC跟踪反应),反应完毕后,过滤,滤液减压浓缩去除溶剂,得到化合物I-36d。
(4)化合物I-36e的制备
化合物I-36d(0.5mmol)溶于10mL二氯甲烷中,加入苯甲酰氯(0.5mmol),然后加入4-二甲氨基吡啶(0.5mmol),所得混合物常温反应1-2小时(TLC跟踪反应),反应完毕后,加入水,分出有机相,有机相经无水硫酸钠干燥后减压浓缩去除溶剂得化合物I-36e粗品,粗品经柱层析纯化得纯品。1H-NMR:(CD3OD,500MHz):δ8.22(t,J=8.6Hz,4H),8.11(s,1H),7.95(d,J=8.6Hz 2H),7.84-7.79(m,4H),7.69-7.63(m,3H),7.50(t,J=7.3Hz,1H),7.42(t,J=7.4Hz,2H),6.99(d,J=8.7Hz,2H),3.75(s,3H).13C-NMR:(CD3OD,125MHz):δ53.67(2C),108.15,113.53(2C),115.50,118.98(2C),126.30(2C),127.18(2C),127.73(2C),127.90(2C),128.31,128.90(2C),130.75(2C),131.47(2C),131.19,142.45,148.08,149.98,155.90,162.53,162.75,166.17.HRMS(ESI+)m/z calcd for C31H23N5O2(M+H)+498.1930,found 498.1928.
以下为探针分子的应用实例,分别以检测铁和钯为例说明:
实施例2荧光分子I-36对Fe3+离子的检测
2.1检测限的测定
向1×10-5μmol/L的I-36溶液中,分别加入0、20、40、60、80、100、120、140、160μmol/L的Fe3+离子,检测荧光强度的变化。440nm处的荧光强度不断降低,直至荧光消失,可计算出其检测限为0.8×10-6mol/L。
2.2荧光分子探针I-36对Fe3+离子的选择性
向1×10-5μmol/L的I-36溶液中,分别加入160μmol/L的三价铁离子、二价铁离子、锂离子、镁离子、铝离子、钙离子、锌离子、铜离子、镍离子、锰离子,快速检测荧光强度的变化。测试结果如图1所示,该探针与其他离子几乎没有响应,三价铁离子导致明显的荧光淬灭,该荧光分子突出的特性是对三价铁离子响应而二价铁离子不响应。
2.3荧光分子I-36检测Fe3+离子的抗干扰性
向1×10-5μmol/L的I-36溶液中,分别加入160μmol/L的二价铁离子、锂离子、镁离子、铝离子、钙离子、锌离子、铜离子、镍离子、锰离子后再加入相同浓度的三价铁离子,检测荧光强度的变化。测试结果如图2所示,该探针对Fe3+的响应中,不受其他金属离子的干扰,显示了荧光探针化合物检测Fe3+的优越性。
2.4荧光分子探针I-36的细胞成像
荧光化合物I-36在Hela细胞中的荧光成像研究如图5所示,发现该荧光分子可很好的在细胞内成像。
实施例3荧光分子I-49对金属钯的检测
采用类似的手段,如图3和图4,荧光探针化合物I-49对金属钯具有良好的选择性,检测限同样低至微摩尔级别。
实施例4部分代表性化合物的细胞毒性
以Hela细胞为例,其在10μg/mL 20μg/mL 30μg/mL浓度下的细胞存活率如下表所示:
Claims (5)
1.一类新型具有荧光特性[1,2,4]-三氮唑并环类化合物,其特征在于,包括[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)和[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II):
其中,R1为氨基、(烷基或酰基)取代氨基、烷基、烷氧基;所述烷氧基为-OCH2CH=CH2或-OCOOCH2CH=CH2;
R2是烷氧基,苯氧基,烷基,烯基,炔基,环烷基,卤代烷基芳基或杂芳基;每个所述烷基,环烷基,卤代烷基,芳基和杂芳基是未取代或任选一个可取代位置独立取代,各自独立的取代为卤素,氰基,烷氧基,烷基,卤代烷基,卤代烷氧基,芳基,杂芳基,杂环基,环烷基或酰胺基;所述卤代烷基,卤代烷氧基中卤素取代基为氟、氯、溴或碘;
R3是芳基,单环芳基,并环芳基,稠环芳基;所述单环芳烃为(取代)苯基,(取代)杂环芳基;所述并环芳基为(取代)苯并呋喃、(取代)苯并噻吩、(取代)苯并咪唑,(取代)苯并噻唑;所述稠环芳基为(取代)萘基,(取代)蒽基或(取代)菲基。
2.根据权利要求1所述的化合物,其特征在于,所述通式(I)所示[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物和通式(II)所示[1,2,4]-三氮唑并喹(唑)啉类杂环化合物能在200-800nm的波长下被激发并能发射400-800nm波长的荧光。
3.根据权利要求3所述的化合物,其特征在于,在所述化合物分子结构中引入不同的金属元素响应基团,可应用于不同金属离子的检测;可用于环境、细胞及生物体中痕量金属的检测,该类分子细胞毒性低,生物相容性好,在生物成像方面有潜在的应用。
4.根据权利要求1所述的化合物,其特征在于,所述通式(I)所示的化合物的制备方法如下:
(1)[1,2,4]-三氮唑并[1,5-a]嘧啶酮类杂环化合物1的制备方法如下,将化合物1溶于合适的溶剂中,加入三卤氧磷,得到7-卤代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2;
(2)7-卤代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2溶于溶剂中,加入芳基硼酸,然后加入有机碱或者无机碱,加入催化剂,得到取代的7-芳基取代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式I;
(3)当R1为氨基或含氨基的衍生物时,则起始原料中R1为硝基,化合物2经偶联后还原再衍生化得到通式(I)的荧光分子。
5.根据权利要求1所述的化合物,其特征在于,所述通式(II)化合物的制备方法如下,
具体包括以下步骤:
(1)取代的2-氨基苯甲酸3经酯化和肼解得到取代的2-氨基酰肼类衍生物4;
(2)将取代的2-氨基酰肼类衍生物溶于合适溶剂中,加入硫氰酸铵,所得混合物加热至一定温度反应,得到化合物5;
(3)将化合物5溶于溶剂中,加入芳香酰氯,加热反应得到取代的[1,2,4]-三氮唑并喹(唑)啉酮类杂环化合物6;
(5)将[1,2,4]-三氮唑并喹(唑)啉酮类杂环化合物6与三卤氧磷反应得到7-卤代-[1,2,4]-三氮唑并喹(唑)啉类杂环化合物7;
(6)将7-溴代-[1,2,4]-三氮唑并喹(唑)啉类杂环化合物7与芳基硼酸衍生物偶联反应得到通式(Π)所示[1,2,4]-三氮唑并喹(唑)啉类杂环化合物目标分子。
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