CN111961069A - Copper (I) complex based on acetone and salicylaldehyde amino triazole Schiff base and synthesis method thereof - Google Patents
Copper (I) complex based on acetone and salicylaldehyde amino triazole Schiff base and synthesis method thereof Download PDFInfo
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- CN111961069A CN111961069A CN202010989969.1A CN202010989969A CN111961069A CN 111961069 A CN111961069 A CN 111961069A CN 202010989969 A CN202010989969 A CN 202010989969A CN 111961069 A CN111961069 A CN 111961069A
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 30
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000002262 Schiff base Substances 0.000 title claims abstract description 16
- 238000001308 synthesis method Methods 0.000 title abstract description 12
- -1 salicylaldehyde amino triazole Schiff base Chemical class 0.000 title abstract description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N ortho-hydroxybenzaldehyde Natural products OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000011521 glass Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 11
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 6
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000005303 weighing Methods 0.000 claims abstract description 4
- 239000010949 copper Substances 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 230000001093 anti-cancer Effects 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910021645 metal ion Inorganic materials 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 238000011065 in-situ storage Methods 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 8
- MTBSFYGHHCAQIY-UHFFFAOYSA-N O1NC=CC=C1.O1N=NC=C1 Chemical compound O1NC=CC=C1.O1N=NC=C1 MTBSFYGHHCAQIY-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
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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
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
The invention discloses a copper (I) complex based on acetone and salicylaldehyde amino triazole Schiff base and a synthesis method thereof, wherein the synthesis method comprises the following steps: (1) weighing 8-12 mg of salicylaldehyde-shrinkage-3-amino-1, 2, 4-triazole Schiff base, 4-6 mg of CuCl or 6-8 mg of CuBr into a glass tube with one end sealed, adding 1.0-3.0mL of acetone, and shaking to fully mix the materials; then the other end of the glass tube is sealed under the vacuum condition; (2) and (3) placing the sealed glass tube in an oven at the temperature of 110-130 ℃ for reaction, stopping heating after the reaction is carried out for 60-80 hours, and then cooling to room temperature at the temperature of 10 ℃ per hour to obtain colorless long-strip crystals, namely the copper (I) complex product. The 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g ] [1,2,4] triazolo [1,5-c ] [1,3,5] oxadiazoline in the product is a novel polycyclic compound, can be used as an intermediate to be applied to the fields of medicines, pesticides and the like, forms a complex with metal ions, has good antibacterial and anticancer activities, and has important potential application.
Description
Technical Field
The invention relates to a copper complex and an in-situ synthesis method thereof, in particular to a copper (I) complex based on acetone and salicylaldehyde-condensed-3-amino-1, 2, 4-triazole Schiff base and an in-situ synthesis method thereof.
Background
In-situ synthesis technology appeared in recent years is widely applied to the fields of chemistry, chemical engineering, materials and the like. The in-situ synthesis refers to the in-situ generation of one or more novel compounds in a reaction system through chemical reaction under certain conditions. By in-situ synthesis, compounds which are difficult to obtain by other synthetic methods can be obtained.
At present, although in-situ ligand reaction is reported in a few documents, no report is found that salicylidene-3-amino-1, 2, 4-triazole Schiff base (shown as a formula (1)) reacts with solvent acetone to generate 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g ] [1,2,4] triazolo [1,5-c ] [1,3,5] oxadiazolazine (abbreviated as HL, the structure of which is shown as a formula (2)), and further generates a copper (I) complex.
The structural formula of the salicylaldehyde-condensed-3-amino-1, 2, 4-triazole Schiff base is shown as the formula (1):
the structural formula of the 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g ] [1,2,4] triazolo [1,5-c ] [1,3,5] oxadiazolazine (HL) is shown as the formula (2):
disclosure of Invention
To obtain novel 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g ] [1,2,4] triazolo
The invention discloses a [1,5-c ] [1,3,5] oxadiazol oxazine (HL) complex, and discloses two copper (I) complexes prepared from acetone and salicylaldehyde-3-amino-1, 2, 4-triazole Schiff base as raw materials and an in-situ synthesis method of the two copper (I) complexes.
The first of the present invention, based on acetone and salicylaldehyde-Copper (I) complex of 3-amino-1, 2, 4-triazole Schiff base with chemical formula of [ Cu (HL)2Cl]Wherein HL = 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g] [1,2,4]Triazolo [1,5-c] [1,3,5]The oxadiazoline, the complex crystal belongs to an orthorhombic system,P21212space group, unit cell parameters are:a=28.317(13) Å，b = 5.714(3)Å ，c =7.326(3)Å，α= 90.00º，β=90.00º，γ= 90.00º，V = 1185.4 (10) Å3；
the structural formula of the complex is shown as the formula (3):
the second copper (I) complex based on acetone and salicylaldehyde-condensed-3-amino-1, 2, 4-triazole Schiff base has a chemical formula of [ Cu (HL)2Br]Wherein HL = 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g] [1,2,4]Triazolo [1,5-c] [1,3,5]The oxadiazoline, the complex crystal belongs to an orthorhombic system,P21212space group, unit cell parameters are:a=28.63(2) Å，b = 5.659(5)Å ，c =7.502(6)Å，α= 90.00º，β=90.00º，γ= 90.00º，V = 1215.5 (17) Å3；
the structural formula of the complex is shown as the formula (4):
the synthetic routes of the two complexes are as follows:
X=Cl, Br。
said first complex [ Cu (HL)2Cl]The in-situ synthesis method comprises the following steps:
(1) weighing 8-12 mg of salicylaldehyde-shrinkage-3-amino-1, 2, 4-triazole Schiff base and 4-6 mg of CuCl into a glass tube with one end sealed, adding 1.0-3.0mL of acetone, and shaking to mix the mixture fully; then the other end of the glass tube is sealed under the vacuum condition;
(2) placing the sealed glass tube in an oven at the temperature of 110-130 ℃ for reaction, stopping heating after the reaction is carried out for 60-80 hours, and then cooling to room temperature at the temperature of 10 ℃ per hour to obtain colorless long-strip crystals, namely [ Cu (HL)2Cl]And (3) obtaining the product.
Said second complex [ Cu (HL)2Br]The in-situ synthesis method of (1) substituting CuBr 6-8 mg for the first complex [ Cu (HL)2Cl]CuCl in the synthesis method is not changed under other conditions, and colorless long-strip crystal is also obtained, namely [ Cu (HL) ]2Br]And (3) obtaining the product.
The synthetic routes of the two complexes show that the solvent acetone and the salicylaldehyde-condensed-3-amino-1, 2, 4-triazole Schiff base undergo addition reaction, and then one molecule of water H is removed2O to 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g] [1,2,4]Triazolo [1,5-c] [1,3,5]Oxadiazolazine (HL), in turn, coordinates with metallic copper (I).
The 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g ] [1,2,4] triazolo [1,5-c ] [1,3,5] oxadiazoline in the product is a novel polycyclic compound, can be used as an intermediate to be applied to the fields of medicines, pesticides and the like, forms a complex with metal ions, has good antibacterial and anticancer activities, and has important potential application.
The in-situ synthesis method of the two copper complexes has the advantages of easily obtained raw materials, low cost, simple process and the like. In addition, the IC of partial cell strains of the two copper complexes of the invention is preliminarily determined by an MTT colorimetric method50The results show that the two complexes have certain antitumor activity.
Drawings
FIG. 1 shows the complex [ Cu (HL) of example 12Cl]Molecular structure diagram (hydrogen atom omitted);
FIG. 2 shows the complex [ Cu (HL) of example 22Br]Molecular structure of (2) (hydrogen atom is omitted).
Detailed Description
The present invention will be further described with reference to the following examples, but the present invention is not limited thereto.
Example 1
Complex [ Cu (HL)2Cl]The in-situ synthesis method comprises the following steps:
(1) respectively weighing 9.4 mg (0.05 mmol) of salicylaldehyde-condensed-3-amino-1, 2, 4-triazole Schiff base and 5.0 mg (0.05 mmol) of CuCl into a glass tube which is about 19 cm long and 1.0 cm in inner diameter and is sealed at one end, adding 2.0 mL of acetone, and oscillating to fully mix the materials; then the other end of the glass tube is sealed under the vacuum condition;
(2) placing the sealed glass tube in a 120 ℃ oven for reaction, stopping heating after the reaction is carried out for 72 hours, and then cooling to room temperature at 10 ℃ per hour to obtain colorless long-strip crystal, namely [ Cu (HL) ]2Cl]The product, yield 53.2%.
Referring to FIG. 1, it can be seen that the smallest unit of the complex of example 1 has only one crystallographically independent Cu (I) ion, which is coordinated by 1 Cl atom and 1N atom from each of two ligands (HL) to form a complex of the formula [ Cu (HL) ]2Cl]The complex of (1). The minimum structural unit of the complex forms a three-dimensional crystal structure through weak bond interaction.
Example 2
Complex [ Cu (HL)2Br]By substituting CuBr 7.2 mg (0.05 mmol) for CuCl in example 1 under otherwise unchanged conditions, a colorless elongated crystal was obtained [ Cu (HL) ]2Br]The product, with a yield of 55.3%, has a molecular structure as shown in FIG. 2, which differs from FIG. 1 only in the substitution of the Cl atoms by Br atoms.
Example 3
Determination of IC of two complexes of the examples on partial cell lines by means of MTT colorimetry50As shown in Table 1, HL-7702 was a human normal liver cell line, A549 was a human lung cancer cell line, T-24 was a human bladder cancer cell line, and MGC80-3 was a human gastric cancer cell line.
TABLE 1 IC of the example complexes on different cell lines50Value (μ M)
The results in Table 1 show that the two complexes of the examples have a certain antitumor activity.
Claims (4)
1. Copper (I) complex based on acetone and salicylaldehyde-3-amino-1, 2, 4-triazole Schiff base, and is characterized in that:
the copper (I) complex has the chemical formula [ Cu (HL)2Cl]Wherein HL = 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g] [1,2,4]Triazolo [1,5-c] [1,3,5]The oxadiazoline, the complex crystal belongs to an orthorhombic system,P21212space group, unit cell parameters are:a =28.317(13) Å，b = 5.714(3)Å ，c =7.326(3)Å，α= 90.00º，β=90.00º，
γ= 90.00º，V = 1185.4 (10) Å3；
the molecular structural formula of the complex is as follows:
2. copper (I) complex based on acetone and salicylaldehyde-3-amino-1, 2, 4-triazole Schiff base, and is characterized in that: has a chemical formula of [ Cu (HL)2Br]Wherein HL = 5-methyl-3, 11-dihydro-5H-5, 11-methylbenzo [ g] [1,2,4]Triazolo [1,5-c] [1,3,5]The oxadiazoline, the complex crystal belongs to an orthorhombic system,P21212space group, unit cell parameters are:a =28.63(2) Å，b = 5.659(5)Å ，c =7.502(6)Å，α= 90.00º，β=90.00º，γ= 90.00º，V = 1215.5 (17) Å3；
the molecular structural formula of the complex is as follows:
3. the process for the synthesis of copper (i) complexes according to any one of claims 1 to 2, characterized in that the synthesis route of the complex is:
X=Cl，Br 。
4. the method of synthesizing a copper (i) complex according to claim 3, wherein the method of synthesizing comprises the steps of:
(1) weighing 8-12 mg of salicylaldehyde-shrinkage-3-amino-1, 2, 4-triazole Schiff base, 4-6 mg of CuCl or 6-8 mg of CuBr into a glass tube with one end sealed, adding 1.0-3.0mL of acetone, and shaking to fully mix the materials; then the other end of the glass tube is sealed under the vacuum condition;
(2) and (3) placing the sealed glass tube in an oven at the temperature of 110-130 ℃ for reaction, stopping heating after the reaction is carried out for 60-80 hours, and then cooling to room temperature at the temperature of 10 ℃ per hour to obtain colorless long-strip crystals, namely the copper (I) complex product.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100204467A1 (en) * | 2007-07-18 | 2010-08-12 | Cis Bio International | Lanthanide (iii) ion complexing compounds, luminescent lanthanide (iii) ion complexes and use thereof as fluorescent labels |
| CN106397461A (en) * | 2016-09-13 | 2017-02-15 | 桂林理工大学 | Magnetic material salicylaldehyde derivative Schiff base copper complex [Cu4(emdo)4].H2O and synthesis method |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100204467A1 (en) * | 2007-07-18 | 2010-08-12 | Cis Bio International | Lanthanide (iii) ion complexing compounds, luminescent lanthanide (iii) ion complexes and use thereof as fluorescent labels |
| CN106397461A (en) * | 2016-09-13 | 2017-02-15 | 桂林理工大学 | Magnetic material salicylaldehyde derivative Schiff base copper complex [Cu4(emdo)4].H2O and synthesis method |
Non-Patent Citations (2)
| Title |
|---|
| NIKOLAY YU. GOROBETS等: "Unexpected alternative direction of a Biginelli-like multicomponent reaction with 3-amino-1,2,4-triazole as the urea component", 《TETRAHEDRON LETTERS》 * |
| 高霞等: "1,5-双(苯并三氮唑)戊烷钬配合物的抑菌性研究", 《化学工程与装备》 * |
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