CN110922419A - Preparation method of iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex - Google Patents
Preparation method of iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex Download PDFInfo
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- IRUNNPQEOLMMNM-UHFFFAOYSA-N C=NNC(=S)N.BrC1=CC=CC=C1 Chemical compound C=NNC(=S)N.BrC1=CC=CC=C1 IRUNNPQEOLMMNM-UHFFFAOYSA-N 0.000 title claims abstract description 12
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000243 solution Substances 0.000 claims abstract description 16
- 239000012046 mixed solvent Substances 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 claims abstract description 7
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 5
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims abstract description 5
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000011259 mixed solution Substances 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- IWCKHKPTELYTJL-UHFFFAOYSA-N [(2-bromophenyl)methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=CC=C1Br IWCKHKPTELYTJL-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 3
- WRMIJRQJYVDWRZ-UHFFFAOYSA-N (methylideneamino)thiourea Chemical compound NC(=S)NN=C WRMIJRQJYVDWRZ-UHFFFAOYSA-N 0.000 claims description 2
- UITYZVKVKPVDPH-UHFFFAOYSA-N [I].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [I].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UITYZVKVKPVDPH-UHFFFAOYSA-N 0.000 claims description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- ZRKQJQZLZSRFSM-UHFFFAOYSA-N BrC1=C(C=NNC(=S)N)C=CC=C1.IC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu+] Chemical compound BrC1=C(C=NNC(=S)N)C=CC=C1.IC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu+] ZRKQJQZLZSRFSM-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 abstract 5
- 108010046334 Urease Proteins 0.000 description 11
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- -1 iodine triphenylphosphine-2-bromobenzaldehyde thiosemicarbazone Chemical compound 0.000 description 4
- 150000003584 thiosemicarbazones Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000002601 urease inhibitor Substances 0.000 description 2
- 210000003708 urethra Anatomy 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- AJYJUFMKHCYWHJ-UHFFFAOYSA-N BrC1=C(C=NNC(=S)N)C=CC=C1.IC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound BrC1=C(C=NNC(=S)N)C=CC=C1.IC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 AJYJUFMKHCYWHJ-UHFFFAOYSA-N 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 235000010520 Canavalia ensiformis Nutrition 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention discloses a preparation method of a complex of iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I), which comprises the following steps: step 1, dissolving thiosemicarbazide in a hot ethanol/water mixed solvent, and slowly dropwise adding an ethanol solution of 2-bromobenzaldehyde in an equal amount under the condition of vigorous stirring; heating and refluxing for 4h, cooling to room temperature to obtain yellow solid, dissolving the obtained solid in absolute ethyl alcohol, recrystallizing and purifying to obtain yellow powder; step 2, dissolving the yellow powder in a hot ethanol/water mixed solvent, and adding a mixed solution of a 95% ethanol solution of cuprous iodide and an ethanol solution of triphenylphosphine under stirring; stirring and heating to 50-60 ℃, reacting for 4h, cooling, and filtering to obtain yellow clear liquid; after the clear solution was allowed to stand for 8 days, pale yellow block crystals were precipitated.
Description
Technical Field
The invention relates to a preparation method of a complex of iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I), belonging to the field of bio-inorganic chemistry.
Background
Urease is a common enzyme in bacterial infections of the gastrointestinal and urinary tracts. Research shows that urease is an important pathogenic factor of pathogenic bacteria in the urethra and the digestive tract and is closely related to prevention, diagnosis and treatment of diseases of the digestive tract and the urethra. Urease inhibitors play an important role in drug development and have been widely considered as target drugs for treating gastric ulcer.
Thiosemicarbazone compounds are widely used in various fields due to their diverse biological activities, such as antiviral, antifungal, antimalarial, antitubercular, anti-HIV and antiparasitic. In addition, research finds that thiosemicarbazone compounds also have antitumor biological activity, mainly exert the antitumor effect of the thiosemicarbazone compounds by inhibiting ribonucleic acid reductase and regulating the level of ROS, and the donor system of N-N-S and transition metal can form stable coordination compounds and remarkably improve the biological activity, particularly the antitumor activity of the thiosemicarbazone compounds. It is noted that the structural integrity of N1NH (CS) N4H-in thiosemicarbazone is a condition necessary for the thiosemicarbazone to exert the activity, and the difference of the substituents on the positions of N1 and N4 has great influence on the thiosemicarbazone to exert various biological activities such as antitumor, antibacterial and antiviral activities. Therefore, the deep research on the compounds has very important theoretical value and application value.
Disclosure of Invention
The invention aims to provide a preparation method for synthesizing an iodo-triphenylphosphine-2-bromobenzaldehyde thiosemicarbazone cuprous (I) complex.
The technical scheme of the invention is as follows:
a preparation method of an iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex comprises the following steps:
step 1, dissolving thiosemicarbazide in a hot ethanol/water mixed solvent, and slowly dropwise adding an ethanol solution of 2-bromobenzaldehyde in an equal amount under the condition of vigorous stirring; heating and refluxing for 4h, cooling to room temperature, washing with ethanol and water respectively, filtering under reduced pressure to obtain yellow solid, dissolving the obtained solid in absolute ethanol, recrystallizing and purifying to obtain yellow powder, namely 2-bromobenzene formaldehyde thiosemicarbazone;
step 2, dissolving the yellow powder obtained in the step 1 in a hot ethanol/water mixed solvent, and adding a mixed solution of a 95% ethanol solution of cuprous iodide and an ethanol solution of triphenylphosphine under stirring; stirring and heating to 50-60 ℃, reacting for 4h, cooling, and filtering to obtain yellow clear liquid; standing the clear solution for 8 days to separate out a light yellow blocky crystal, namely an iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex;
wherein the iodine triphenylphosphine.2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex has a structure shown as a formula 1:
in the above production method, the solution for culturing the single crystal is a mixed solvent of ethanol and water.
In the preparation method, in the step 1, the volume ratio of ethanol to water in the ethanol/water mixed solvent is 1: 1.
According to the preparation method, in the step 2, the mass ratio of the 2-bromobenzaldehyde thiosemicarbazone, the triphenylphosphine and the cuprous iodide is 1:1: 1.
Through research, the iodine triphenylphosphine-2-bromobenzaldehyde thiosemicarbazone cuprous (I) complex has an obvious inhibiting effect on urease, and therefore, the iodine-triphenylphosphine-2-bromobenzaldehyde thiosemicarbazone cuprous (I) complex can be used for preparing urease inhibitors.
Drawings
FIG. 1 shows a ligand H of the iodine triphenylphosphine 2-bromobenzaldehyde thiosemicarbazone cuprous (I) complex2Crystal structure of L;
FIG. 2 is a crystal structure diagram of the iodine triphenylphosphine 2-bromobenzaldehyde thiosemicarbazone cuprous (I) complex of the present invention.
Detailed Description
The first embodiment is as follows: preparation of iodine, triphenylphosphine and 2-bromobenzaldehyde thiosemicarbazone cuprous (I) complex
1. In a 100mL round-bottomed flask, thiosemicarbazide (0.91g,10.0mmol) was dissolved in 50mL of a hot ethanol/water mixed solvent (the temperature of the ethanol/water mixed solvent is such that thiosemicarbazide can be dissolved), and an ethanol solution of 2-bromobenzaldehyde in an amount equivalent to that of the above was slowly added dropwise with vigorous stirring. Heating and refluxing for 4 hr, cooling to room temperature, filtering under reduced pressure, washing with ethanol and water respectively to obtain yellowish solid, dissolving the solid in anhydrous ethanolRecrystallizing and purifying to obtain yellow powder. Yield 65%, melting point 211-52H46Br2Cu2I2N6OP2S2:C,37.4； H,2.7；N,16.3.Found:C,37.2；H,2.6；N,16.6％.IR(KBr,cm-1) 3412,3245,3152,1603,1516, 1462,1372,1288,1230,1189,1109,945,868, 819,750,645,614,492,446. analysis by X-ray diffraction shows C8H7BrN3S。
2. 2-bromobenzaldehyde thiosemicarbazone H2L (0.13g,0.5mmol) was dissolved in 80ml of a hot ethanol/water mixed solvent, and a mixed solution of CuI (0.096g,0.5mmol) in 95% ethanol (20ml) and triphenylphosphine (0.13g,0.5mmol) in absolute ethanol (5ml) was added under nitrogen. Stirring and heating to 50-60 ℃, reacting for 4h, cooling and filtering to obtain yellow clear liquid. Standing the clear solution for 8 days to precipitate light yellow crystals with the yield of 56 percent, mp 190-52H46Br2Cu2I2N6OP2S2:C,43.44,H,3.22,N,5.85；Found:C,43.12,H,3.46,N,5.69.IR (KBr,cm-1) 3473(s),1579(s),1518(s),750(m), 1116(s). The result of X-ray single crystal diffraction analysis was C52H46Br2Cu2I2N6OP2S2。
The iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex has a structure shown in a formula 1:
ligand H2The crystal structures of L and its copper (I) complex are shown in FIG. 1 and FIG. 2, respectively, the crystallographic data are shown in Table 1, and the main bond lengths and bond angles are shown in Table 2.
TABLE 1 copper (I) complexes of the invention and their ligand H2Crystallographic data of L
TABLE 2 copper (I) complexes of the invention and their ligand H2Important bond length of L
Angle of harmony key (°)
Example two: research on in-vitro urease activity inhibition of iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex
Inhibition of Urease (Urease) activity assay: megastigma (jack bean) urease was purchased from Sigma-Aldrich (St. Louis, Mo, USA) and various concentrations of test compounds were prepared using a mixed solvent of DMSO and water (v/v, 1: 1). The mixture will contain urease (25. mu.L, 10 kU. L)-1) And various concentrations of the test compound (25. mu.L) were placed in an assay plate (96-well) and pre-incubated at 37 ℃ for 1 h. Further, a Hepes buffer solution (0.2ml, 100 mM; pH 6.8) containing urease (500mM) and a phenol red indicator at a concentration of 0.002% were added, and the culture was performed at 37 ℃. The reaction time was measured by a microplate reader (570nm) and sufficient ammonium carbonate was formed to raise the pH of the Hepes buffer solution from 6.8 to 7.7, the end point of the test being dependent on the color change of the phenol red indicator.
Median Inhibitory Concentration (IC)50) Defined as the concentration of drug at which the inhibition rate is 50%, the IC measured50See table 3.
TABLE 3 copper (I) complexes of the invention and their ligand H2Inhibition of megastigma urease of L IC50Value (μ M)
aMeaning that the inhibition of urease is low.
Claims (5)
1. A preparation method of an iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex is characterized by comprising the following steps:
step 1, dissolving thiosemicarbazide in a hot ethanol/water mixed solvent, and slowly dropwise adding an ethanol solution of 2-bromobenzaldehyde in an equal amount under the condition of vigorous stirring; heating and refluxing for 4h, cooling to room temperature, washing with ethanol and water respectively, filtering under reduced pressure to obtain yellow solid, dissolving the obtained solid in absolute ethanol, recrystallizing and purifying to obtain yellow powder, namely 2-bromobenzene formaldehyde thiosemicarbazone;
step 2, dissolving the yellow powder obtained in the step 1 in a hot ethanol/water mixed solvent, and adding a mixed solution of a 95% ethanol solution of cuprous iodide and an ethanol solution of triphenylphosphine under stirring; stirring and heating to 50-60 ℃, reacting for 4h, cooling, and filtering to obtain yellow clear liquid; standing the clear solution for 8 days to separate out a light yellow blocky crystal, namely an iodine, triphenylphosphine and 2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex;
wherein the iodine triphenylphosphine.2-bromobenzene formaldehyde thiosemicarbazone cuprous (I) complex has a structure shown as a formula 1:
2. the method according to claim 1, wherein the solution for growing the single crystal is a mixed solvent of ethanol and water.
3. The method according to claim 1, wherein the volume ratio of ethanol to water in the ethanol/water mixed solvent in step 1 is 1: 1.
4. The method according to claim 1, wherein in step 2, the ratio of the amounts of the 2-bromobenzaldehyde thiosemicarbazone, triphenylphosphine and cuprous iodide is 1:1: 1.
5. The preparation method as claimed in claim, wherein the copper (I) iodotriphenylphosphine-2-bromobenzaldehyde thiosemicarbazone is a megastigmaurase inhibitor.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911191A (en) * | 2012-10-26 | 2013-02-06 | 商丘师范学院 | Preparation method for ethanol 2-hydroxyl naphthaldehyde thiosemicarbazone o-phenanthroline metal complex |
| CN108395453A (en) * | 2018-05-23 | 2018-08-14 | 河南城建学院 | Quinoline thiosemicarbazones-pyridine copper complex and the preparation method and application thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911191A (en) * | 2012-10-26 | 2013-02-06 | 商丘师范学院 | Preparation method for ethanol 2-hydroxyl naphthaldehyde thiosemicarbazone o-phenanthroline metal complex |
| CN108395453A (en) * | 2018-05-23 | 2018-08-14 | 河南城建学院 | Quinoline thiosemicarbazones-pyridine copper complex and the preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| TARLOK S. LOBANA 等: "Bonding Trends of Thiosemicarbazones in Mononuclear and Dinuclear Copper(I) Complexes: Syntheses, Structures, and Theoretical Aspects", 《INORGANIC CHEMISTRY》 * |
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