CN108586542A - A kind of ONO types Schiff-base Palladium (II) complex and its preparation method and application containing multiple coordination sites - Google Patents
A kind of ONO types Schiff-base Palladium (II) complex and its preparation method and application containing multiple coordination sites Download PDFInfo
- Publication number
- CN108586542A CN108586542A CN201810587103.0A CN201810587103A CN108586542A CN 108586542 A CN108586542 A CN 108586542A CN 201810587103 A CN201810587103 A CN 201810587103A CN 108586542 A CN108586542 A CN 108586542A
- Authority
- CN
- China
- Prior art keywords
- schiff
- palladium
- complex
- solution
- ligand
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/006—Palladium compounds
- C07F15/0066—Palladium compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
Abstract
The molecular formula of the invention discloses a kind of ONO types Schiff-base Palladium (II) complex and its preparation method and application containing multiple coordination sites, the complex is [Pd (PPh3)(C11H15NO4)]；Wherein, PPh3For triphenylphosphine, C11H15NO4For ligand salicylidene trishydroxymethylaminomethane schiff bases.The present invention is to contain the salicylidene trishydroxymethylaminomethane schiff bases of tri- coordination sites of ONO as main ligand, using triphenylphosphine as Ligands, the metal ion centered on palladium (II), ONO types Schiff-base Palladium (II) complex is prepared by the self-assembling reaction in solution, the complex has stronger inhibiting effect to alpha amylase, inhibiting effect of the ligand to alpha amylase is significantly larger than used alone, it is suitable with common acarbose hypoglycemic effect.This shows that complex of the invention has good blood sugar reducing function, can be effectively used for preparing treatment diabetes medicament, is the innovation treated on diabetes medicament.
Description
Technical field
It ONO types Schiff-base Palladium (II) complex that the present invention relates to a kind of containing multiple coordination sites and preparation method thereof and answers
With belonging to field of medicaments.
Background technology
Diabetes have become the principal disease that is only second to endanger human health after angiocardiopathy, malignant tumour it
One, and there is rejuvenation trend.Currently, the drug for the treatment of diabetes all has different degrees of toxic side effect.Sulfonylurea medicine
Object may lead to hyperinsulinemia, there is the danger of hypoglycemia and weight gain, and primary effect is poor, and easy secondary failure etc. lacks
Point.Biguanides can cause the side effects such as lactic acidosis, vomiting, diarrhea.Acarbose etc. easy tos produce abdominal distension, abdominal pain
Equal gastrointestinal reactions, hypoglycemic effect are weaker and expensive.Glitazone compound is the insulin sensitivity enhancing using PPAR as target spot
Agent improves insulin resistance by activating PPAR γ nuclear receptors, and then is effectively reduced blood glucose.Glitazone compound can carry
High body tissue fundamentally solves insulin resistance to the sensibility of insulin, and then improves β cells, and having prevents disease
The latent effect further developed, but part of compounds shows hepatotoxicity wind agitation.Therefore new antidiabetic medicine tool is continually developed
There is important meaning.
Since cis-platinum comes out, metal complex has boundless application prospect in terms of biological medicine, has drawn
Play the very big concern of researcher.Metal ion is added in drug can not only improve the physicochemical property of drug, and drug is made to be easy
It absorbs, it is often more important that the effect of drug can also be enhanced.Currently, it is domestic the research of antidiabetic medicine is concentrated mainly on it is more
On sugar, flavones, alkaloids plant component and the organic drug of synthesis, the research report of cooperation species hypoglycemic medicine is very few；
Also ground zero, Shindea etc. have found that under insulin existence condition, chromic compound is to Skeletal Muscle Cell glucose for external research
Transhipment has a remarkable effect, Yoshikawa etc. find with a-amino acid and its derivative and picolinic acid and its derivative be with
The Zn complex of body has para-insulin activity, and bio-compatibility is strong, and stability is good, inside and outside blood sugar reducing function is apparent.It grinds
Study carefully and show that schiff base metal complex has a pharmacological actions such as antibacterial, antitumor and antiviral, but schiff base metal complex and
The research of its blood sugar reducing function has not been reported.
Invention content
In view of the deficiencies of the prior art, the ONO type Schiff-base Palladiums containing multiple coordination sites that the object of the present invention is to provide a kind of
(II) complex and its preparation method and application, the complex preparation method is simple, has good blood sugar reducing function.
To achieve the goals above, the technical solution adopted in the present invention is：
The molecular formula of a kind of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites, the complex is [Pd
(PPh3)(C11H15NO4)]；Wherein, PPh3For triphenylphosphine, C11H15NO4For ligand salicylidene trishydroxymethylaminomethane seat
Husband's alkali, molecular structural formula are：
The crystal of Schiff-base Palladium (II) complex belongs to monoclinic system, space group C2/c, and cell parameter is β=114.498 (8) °,
The preparation method of ligand salicylidene trishydroxymethylaminomethane schiff bases, includes the following steps：
(1) it is 1.0~1.2 that molar ratio is added in reaction bulb:1.0~1.2 trishydroxymethylaminomethane and salicylide；
(2) reaction dissolvent is added into the reaction bulb of step (1), (trishydroxymethylaminomethane+salicylide)：Reaction dissolvent
Mass ratio be 1:40~150, in 75~85 DEG C of 4~5h of back flow reaction；
(3) reaction product of step (2) is rotated, obtains bright yellow solid, after drying, then tied again with absolute ethyl alcohol
Crystalline substance to get.
Reaction dissolvent is absolute ethyl alcohol or methanol.
A kind of preparation method of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites, includes the following steps：
(1) palladium is weighed, is dissolved in methanol, palladium salt solution is obtained；
(2) ligand salicylidene trishydroxymethylaminomethane is weighed, is dissolved in methanol, obtains ligand solution, by ligand
Solution is added dropwise in step (1) palladium salt solution, and 5~10min is stirred at room temperature；
(3) triphenylphosphine is weighed, is dissolved in methanol, triphenylphosphine solution is obtained, then is added dropwise to obtained by step (2)
In solution, 5~7h is stirred at room temperature；
(4) step (3) acquired solution is filtered, filtrate stands nature volatilization, until crocus rhabdolith is precipitated, i.e.,
.
Palladium, ligand salicylidene trishydroxymethylaminomethane, triphenylphosphine molar ratio be 1:1:1.
Specifically, the preparation method of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites, includes the following steps：
(1) 0.5mmol palladiums accurately are weighed, is dissolved in 10~15ml methanol, obtains palladium salt solution；
(2) 0.5mmol ligand salicylidene trishydroxymethylaminomethanes accurately are weighed, is dissolved in 4~6ml methanol, obtains
To ligand solution, ligand solution is added dropwise in step (1) palladium salt solution, 5~10min is stirred at room temperature；
(3) 0.5mmol triphenylphosphines accurately are weighed, is dissolved in 4~6ml methanol, obtains triphenylphosphine solution, then dropwise
It is added in step (2) acquired solution, 5~7h is stirred at room temperature；
(4) step (3) acquired solution is filtered, filtrate stands nature volatilization, until crocus rhabdolith is precipitated, i.e.,
.
A kind of application of ONO types Schiff-base Palladium (II) complex in terms of inhibiting alpha-amylase containing multiple coordination sites.
A kind of application of ONO types Schiff-base Palladium (II) complex in terms of preparing hypoglycemic medicine containing multiple coordination sites.
Beneficial effects of the present invention：
1, the present invention is matched using the salicylidene trishydroxymethylaminomethane schiff bases for containing tri- coordination sites of ONO as master
Body, using triphenylphosphine as Ligands, the metal ion centered on palladium (II) is prepared by the self-assembling reaction in solution
ONO types Schiff-base Palladium (II) complex efficiently solves combination problem of the schiff base of salicylaldehyde as ligand, and Metal Palladium.
2, ONO types Schiff-base Palladium (II) complex prepared by the present invention has stronger inhibiting effect, far to alpha-amylase
Far above inhibiting effect of the salicylidene trishydroxymethylaminomethane schiff bases to alpha-amylase is used alone, with common Ah Ka
Wave sugar hypoglycemic effect is suitable.This shows that ONO types Schiff-base Palladium (II) complex of the invention has good blood sugar reducing function, can
Diabetes medicament is treated effective for preparing, is the innovation treated on diabetes medicament.
3, ONO types Schiff-base Palladium (II) complex of the invention synthesizes at normal temperatures and pressures, and required equipment is simple, easily grasps
Make, of low cost, reproducibility is good, and chemical constituent is easy to control, and complex obtained has many advantages, such as that yield is high, can drop
Sugared drug field is used widely.
Description of the drawings
Fig. 1 is complex [Pd (PPh3)(C11H15NO4)] structural unit figure.
Fig. 2 is complex [Pd (PPh3)(C11H15NO4)] accumulation graph.
Fig. 3 is complex [Pd (PPh3)(C11H15NO4)] infrared results figure.
Specific implementation mode
The specific implementation mode of the present invention is described in further detail with reference to embodiments.
Embodiment 1
The preparation method of ligand salicylidene trishydroxymethylaminomethane schiff bases of the present invention, includes the following steps：
(1) it is 1.0 that molar ratio is added in reaction bulb:1.0 trishydroxymethylaminomethane and salicylide；
(2) absolute ethyl alcohol is added into the reaction bulb of step (1), (trishydroxymethylaminomethane+salicylide)：Absolute ethyl alcohol
Mass ratio be 1:50, in 80 DEG C of back flow reaction 5h；
(3) reaction product of step (2) is rotated, obtains bright yellow solid, after drying, then tied again with absolute ethyl alcohol
Crystalline substance obtains bright yellow solid, as salicylidene trishydroxymethylaminomethane schiff bases, yield 83.4%.
Prepared ligand salicylidene trishydroxymethylaminomethane schiff bases nuclear-magnetism1H NMR(500MHz,DMSO)δ
14.51 (s, 1H, ArOH), 8.56 (s, 1H ,-CH=), 7.40 (dd, J=7.6,1.4Hz, 1H, ArH), 7.31-7.24 (m,
1H, ArH), 6.79 (t, J=8.2Hz, 2H, ArH), 4.72 (t, J=5.3Hz, 3H ,-OH), 3.61 (d, J=5.2Hz, 6H ,-
CH2=)；Infrared spectrum (cm-1, KBr)：3319(s),1672(s),1636(s),1605(m),1586(w),1535(s),1486
(s),1453(m),1396(s),1320(s),1290(s),1178(s),1153(s),1100(s),1059(s),1026(s),
981(m),919(m),893(m),870(m),799(w),764(m),729(w),715(s),685(w),664(w),647(w),
628(w),567(w),541(m),476(w),441(w)。
Embodiment 2
A kind of preparation method of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites, includes the following steps：
(1) 0.5mmol palladiums accurately are weighed, is dissolved in 10mL methanol, obtains palladium salt solution；
(2) 0.5mmol ligand salicylidene trishydroxymethylaminomethanes accurately are weighed, is dissolved in 5mL methanol, is matched
Ligand solution is added dropwise in step (1) palladium salt solution, 10min is stirred at room temperature by liquid solution；
(3) 0.5mmol triphenylphosphines accurately are weighed, be dissolved in 5mL methanol, obtain triphenylphosphine solution, then add dropwise
Enter into step (2) acquired solution, 5h is stirred at room temperature；
(4) step (3) acquired solution is filtered, filtrate stands nature volatilization and obtained until crocus rhabdolith is precipitated
Schiff-base Palladium (II) complex, yield 70%.
The experiment condition and result of the X-ray single crystal diffraction structure of complex of the present invention are as follows：
Single crystal structural data is in the Xcalibur with graphite monochromator, Eos, is measured on Gemini diffractometers.Selection is closed
Suitable size (0.30 × 0.13 × 0.09mm3) crystal be fixed on glass fiber and collect crystal data.Using CuK alpha rays With ω scan modes, 3.428<θ<11485 point diffractions are collected within the scope of 67.072 °, wherein independently spreading out
Exit point number is 5462 (Rint=0.033).Empirical absorption correction uses SADABS programs.The molecular structure of compound is by direct
Method solves, with SHELXTL complete matrix least square method refine.All non-hydrogen atoms use anisotropy thermal parameter refine, most
The position of hydrogen atom is determined with theoretical hydrogenation method afterwards.
The monocrystalline of prepared ONO type Schiff-base Palladium complexs, detailed axonometry data are shown in Table 1, important bond distance
2 are shown in Table with bond angle data, crystal structure is shown in Fig. 1 and Fig. 2, which belongs to monoclinic system, crystallizes in C2/c space groups.In
Heart Pd atoms use four-coordination, respectively with the N atoms in schiff base ligand C=N double bonds, the O atom on two hydroxyls and
P atom chelating ligands on triphenylphosphine, form the plane quadrilateral coordination configuration of distortion.Cell parameter is β=114.498 (8) °,Infrared spectrum (cm-1,
KBr):3405.85 (br), 1673 (s), 1620 (m), 1602 (m), 1585 (w), 1507 (m), 1484 (s), 1452 (m), 1398
(s),1320(s),1290(s),1177(s),1099(s),1072(s),1025(s),933(m),800(w),750(w),728
(w), 715 (s), 691 (m), 664 (w), 616 (w), 531 (s) (Fig. 3).
The crystal structural data of complex prepared by table 1
aR1=Σ | | Fo|-|Fc||/Σ|Fo|.bwR2=[Σ w (Fo 2-Fc 2)2/Σw(Fo 2)2]1/2
The main bond distance of complex prepared by table 2 and bond angle data
Embodiment 3
The present invention is used for the inhibiting effect to alpha-amylase, and inhibiting rate assay method is：
1, the preparation of reagent
The preparation of terminator DNS reagents：3,5- dinitrosalicylic acid 1.6250g are weighed with assay balance precision, are added
2mol/L sodium hydroxide solution 81.25mL, glycerine 11.25g shake up, and distilled water is added to be settled to 250mL, and ultrasonic dissolution assisting waits for complete
It after portion dissolves and clarifies, is cooled to room temperature, sets spare in brown reagent bottle.
The preparation of PBS buffer solution (0.2mol/L, pH6.5)：First prepare 0.2mol/L sodium dihydrogen phosphates, 0.2mol/L phosphoric acid
Disodium hydrogen measures sodium dihydrogen phosphate 68.50mL, the disodium hydrogen phosphate 31.5mL mixings of preparation respectively, adjusts pH to 6.5.
The preparation of 2mg/mL cornstarch：Cornstarch 0.2g is weighed in beaker, is dissolved with boiling water, is transferred to 100mL
Volumetric flask, boiling water is settled to scale can be (with before needing to shake up).
The preparation of alphalise starch enzyme solution：Alpha-amylase 0.0600g is weighed with assay balance, with the PBS of 0.2mol/L pH 6.5
Buffer solution is settled to 100mL, and ultrasonic dissolution assisting filters to get (reagent is preferably now with the current).
The preparation of ligand test liquid：Precision weighing ligand salicylidene trishydroxymethylaminomethane 0.005g, is placed in beaker,
It is dissolved with absolute ethyl alcohol, is transferred to 10mL volumetric flasks, constant volume, compound concentration is the solution of 0.5mg/mL.
The preparation of complex test liquid：Precision weighing Schiff-base Palladium (II) complex 0.005g, is placed in beaker, with anhydrous second
Alcohol dissolves, and is transferred to 10mL volumetric flasks, constant volume, and compound concentration is the solution of 0.5mg/mL.
The preparation of acarbose test liquid：It takes acarbose tablet a piece of (contain acarbose 50mg), tablet is ground as powder,
It is settled to 100mL with distilled water, is filtered, compound concentration is 0.5mg/mL acarbose test liquid solution.
2, complex is tested
Sequentially add the alphalise starch enzyme solution 1mL of 600 μ g/mL in 25mL has plug cillin bottle, ligand test liquid (or complex
Test liquid, acarbose test liquid) 1mL, 2mg/mL corn starch solution 1mL react in 37 DEG C of water-baths after mixing
20min (exact timing) is added DNS reagents 5mL and terminates reaction, develops the color, be cooled to then at boiling water bath 5min immediately after
After room temperature, absorbance value is measured at 540nm.
The calculation formula of inhibiting rate is：
In formula：Emin is to replace test liquid and alphalise starch enzyme solution with water, and Emax is, instead of test liquid, background radix is with water
Corn starch solution is replaced with water.
The inhibitory activity of the alpha-amylase of complex of the present invention is shown in Table 3：
Inhibiting rate of the different compounds of table 3 to alpha-amylase
From the point of view of the measurement result that external hypoglycemic activity is tested, ligand salicylidene trishydroxymethylaminomethane schiff bases pair
The inhibiting effect of alpha-amylase is weaker, under concentration, the suppression of ONO types Schiff-base Palladium (II) complex of the invention to alpha-amylase
It makes of being better than ligand, it is suitable with the preferable drug acarbose inhibiting effect of diabetes curative effect is treated in the market.This shows this
ONO types Schiff-base Palladium (II) complex prepared by invention is expected to further study pharmacology and physiological activity.
Claims (9)
1. a kind of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites, which is characterized in that the molecular formula of the complex
For [Pd (PPh3)(C11H15NO4)]；Wherein, PPh3For triphenylphosphine, C11H15NO4For ligand salicylidene trihydroxy methyl amino first
Alkane schiff bases, molecular structural formula are：
2. ONO types Schiff-base Palladium (II) complex according to claim 1 containing multiple coordination sites, which is characterized in that seat
The crystal of husband's alkali palladium (II) complex belongs to monoclinic system, space group C2/c, and cell parameter is β=114.498 (8) °,
3. ONO types Schiff-base Palladium (II) complex according to claim 1 containing multiple coordination sites, which is characterized in that match
The preparation method of body salicylidene trishydroxymethylaminomethane schiff bases, includes the following steps：
(1) it is 1.0~1.2 that molar ratio is added in reaction bulb:1.0~1.2 trishydroxymethylaminomethane and salicylide；
(2) reaction dissolvent is added into the reaction bulb of step (1), (trishydroxymethylaminomethane+salicylide)：The matter of reaction dissolvent
Amount is than being 1:40~150, in 75~85 DEG C of 4~5h of back flow reaction；
(3) reaction product of step (2) is rotated, obtains bright yellow solid, after drying, then recrystallized with absolute ethyl alcohol,
To obtain the final product.
4. ONO types Schiff-base Palladium (II) complex according to claim 3 containing multiple coordination sites, which is characterized in that anti-
It is absolute ethyl alcohol or methanol to answer solvent.
5. a kind of system of ONO types Schiff-base Palladium (II) complex according to any one of claims 1-4 containing multiple coordination sites
Preparation Method, which is characterized in that include the following steps：
(1) palladium is weighed, is dissolved in methanol, palladium salt solution is obtained；
(2) ligand salicylidene trishydroxymethylaminomethane is weighed, is dissolved in methanol, obtains ligand solution, by ligand solution
It is added dropwise in step (1) palladium salt solution, 5~10min is stirred at room temperature；
(3) triphenylphosphine is weighed, is dissolved in methanol, triphenylphosphine solution is obtained, then is added dropwise to step (2) acquired solution
In, 5~7h is stirred at room temperature；
(4) by step (3) acquired solution filter, filtrate stand nature volatilization, until be precipitated crocus rhabdolith to get.
6. the preparation method of ONO types Schiff-base Palladium (II) complex according to claim 5 containing multiple coordination sites, special
Sign is, palladium, ligand salicylidene trishydroxymethylaminomethane, triphenylphosphine molar ratio be 1:1:1.
7. the preparation method of ONO types Schiff-base Palladium (II) complex according to claim 5 containing multiple coordination sites, special
Sign is, includes the following steps：
(1) 0.5mmol palladiums accurately are weighed, is dissolved in 10~15mL methanol, obtains palladium salt solution；
(2) 0.5mmol ligand salicylidene trishydroxymethylaminomethanes accurately are weighed, is dissolved in 4~6mL methanol, is matched
Ligand solution is added dropwise in step (1) palladium salt solution, 5~10min is stirred at room temperature by liquid solution；
(3) 0.5mmol triphenylphosphines accurately are weighed, is dissolved in 4~6mL methanol, obtains triphenylphosphine solution, then be added dropwise
Into step (2) acquired solution, 5~7h is stirred at room temperature；
(4) by step (3) acquired solution filter, filtrate stand nature volatilization, until be precipitated crocus rhabdolith to get.
8. a kind of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites as described in claim 1 is inhibiting alphalise starch
Application in terms of enzyme.
9. a kind of ONO types Schiff-base Palladium (II) complex containing multiple coordination sites as described in claim 1 is preparing antidiabetic drug
The application in object space face.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810587103.0A CN108586542B (en) | 2018-06-08 | 2018-06-08 | ONO type Schiff base palladium (II) complex containing multiple coordination sites as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810587103.0A CN108586542B (en) | 2018-06-08 | 2018-06-08 | ONO type Schiff base palladium (II) complex containing multiple coordination sites as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108586542A true CN108586542A (en) | 2018-09-28 |
| CN108586542B CN108586542B (en) | 2020-06-02 |
Family
ID=63623297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810587103.0A Expired - Fee Related CN108586542B (en) | 2018-06-08 | 2018-06-08 | ONO type Schiff base palladium (II) complex containing multiple coordination sites as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108586542B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2709512C1 (en) * | 2019-02-14 | 2019-12-18 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Water-soluble cis-s, s-complex diacetate [di-1,6- (3,5-dimethylisoxazol-4-yl) -2,5-dithiahexane] palladium (ii), having inhibitory activity on the enzyme α-amylase |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968127A (en) * | 2016-07-14 | 2016-09-28 | 河南中医学院 | Azacyclic transition metal zinc complex containing multiple coordination sites, and preparation method and application of azacyclic transition metal zinc complex |
| CN106188103A (en) * | 2016-07-14 | 2016-12-07 | 河南中医学院 | A kind of azacyclo-transition metal copper complex containing multiple coordination sites, preparation method and application |
-
2018
- 2018-06-08 CN CN201810587103.0A patent/CN108586542B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968127A (en) * | 2016-07-14 | 2016-09-28 | 河南中医学院 | Azacyclic transition metal zinc complex containing multiple coordination sites, and preparation method and application of azacyclic transition metal zinc complex |
| CN106188103A (en) * | 2016-07-14 | 2016-12-07 | 河南中医学院 | A kind of azacyclo-transition metal copper complex containing multiple coordination sites, preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| E.HALEVAS ET AL.,: "Design, synthesis and characterization of novel binary V(V)-Schiff base materials linked with insulin-mimetic vanadium-induced differentiation of 3T3-L1 fibroblasts to adipocytes. Structure–function correlations at the molecular level", 《JOURNAL OF INORGANIC BIOCHEMISTRY》 * |
| MISHTU DEY ET AL.,: "Four-, Five- and Six-Coordinated ZnII Complexes of OH-Containing Ligands: Syntheses, Structure and Reactivity", 《EUR.J.INORG.CHEM.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2709512C1 (en) * | 2019-02-14 | 2019-12-18 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Water-soluble cis-s, s-complex diacetate [di-1,6- (3,5-dimethylisoxazol-4-yl) -2,5-dithiahexane] palladium (ii), having inhibitory activity on the enzyme α-amylase |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108586542B (en) | 2020-06-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106188103B (en) | A kind of azacyclo- transition metal copper complex containing multiple coordination sites, preparation method and application | |
| CN105968127B (en) | A kind of azacyclo- transition metal Zn complex containing multiple coordination sites, preparation method and application | |
| CA2914999C (en) | Stable crystal form of tipiracil hydrochloride and crystallization method for the same | |
| CN102020679B (en) | Method for preparing lobaplatin trihydrate by usingoxalate | |
| CN105175422B (en) | A kind of phosphoric acid Xi Gelieting crystal and its preparation method and application | |
| CN108912149A (en) | It is a kind of using 2- acetyl group -3- ethyl pyrazine thiosemicarbazones as the copper compound of ligand and its synthetic method and application | |
| CN111377975B (en) | Novel mitochondrion-targeted iridium complex and preparation method and application thereof | |
| CN106632043A (en) | Licochalcone A pyrazoline derivatives with antitumor activity and synthesis method thereof | |
| CN108586542A (en) | A kind of ONO types Schiff-base Palladium (II) complex and its preparation method and application containing multiple coordination sites | |
| CN102070657B (en) | Bis-o-vanillin ethylene diamine schiff base and transitional metal coordination compound and preparation method thereof | |
| CN103724374A (en) | Benfotiamine compound, preparation method and pharmaceutical composition containing benfotiamine compound | |
| CN104844632B (en) | A kind of copper metal complex and its compound with human serum albumins and their synthetic method and application | |
| CN105294641B (en) | Brefeldin A selenium ester derivant and its preparation and application | |
| CN106966986B (en) | N- benzyl heterocyclic nitro ketene semiamine analog derivative and synthetic method and antitumor application thereof | |
| CN106883251A (en) | A kind of many pyridine copper complexes of amino acid and its preparation method and application | |
| CN107417678B (en) | Nitric oxide donor type dihydromyricetin derivative and preparation and application thereof | |
| CN106632455A (en) | Vanadium complex with anti-diabetic effect as well as preparation method and application of vanadium complex | |
| CN108148080B (en) | Organic golden (III) complex of metal and its synthetic method and application | |
| CN105481944B (en) | A kind of two peptide copper complex of benzimidizole derivatives and its preparation method and application | |
| CN104230997B (en) | A kind of platinum (II) coordination compound, its preparation method, pharmaceutical composition and application | |
| CN104370805B (en) | Torasemide compound | |
| CN102552309A (en) | Application and preparation method of gold hyaluronic acid | |
| CN106008545B (en) | The compound salt derivative of Norcantharidin and its antitumor application thereof | |
| Athimoolam et al. | Synthesis, Characterization, Molecular Docking, and in Vitro Antidiabetic Activity Studies of New and Highly Selective Methoxy-Substituted Benzimidazole | |
| CN114014893A (en) | Selenium-containing iron group metal complex and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200602 Termination date: 20210608 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |