CN105601670B - A kind of chromium (III) complex and its preparation method and application - Google Patents
A kind of chromium (III) complex and its preparation method and application Download PDFInfo
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- CN105601670B CN105601670B CN201610146067.5A CN201610146067A CN105601670B CN 105601670 B CN105601670 B CN 105601670B CN 201610146067 A CN201610146067 A CN 201610146067A CN 105601670 B CN105601670 B CN 105601670B
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- chromium
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- 0 C[C@](CCN1CCN2CCC=C3C)Cl123(O1)[U]c2c([C-]*)cccc2C1=[U] Chemical compound C[C@](CCN1CCN2CCC=C3C)Cl123(O1)[U]c2c([C-]*)cccc2C1=[U] 0.000 description 1
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
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic System
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic System compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
Abstract
The present invention provides a kind of chromium (III) complex and its preparation method and application, the chromium (III) complex molecule formula is CrC14H26N4O4Cl, molecular weight 402, crystal structure category anorthic system, space group be P 1, a=7.8880 (6), b=9.8380 (7),α=70.4550 (10), β=85.729 (2), γ=82.0880 (10) °, Z=2.Preparation method：Chromic salts (III) and 3 cresotinic acids are dissolved with organic solvent, a little zinc granule is put into, is heated to reflux, then instill triethylene tetramine, continue reflux a period of time, stops reaction, cooling, filtering, gained filtrate is stood, room temperature volatilizees naturally, obtains aubergine crystal after a few days.Complex of the present invention can be applied in preparing hypoglycemic medicine.
Description
Technical field：
The present invention relates to metal complexs, specially a kind of to be matched for mixture based on 3- methoxy-salicylics acid and triethylene tetramine
Chromium (III) complex of body and its preparation method and application.
Background technology：
Chromium is the essential trace elements of the human body.Trivalent chromium is the element beneficial to human body, still, the physiological function of chromium be with
The substances of other control metabolism coordinates works together, as hormone, insulin, various enzymes, cell genetic stew (DNA with
RNA) etc..Studies have shown that diabetic's chromium obviously lowers, chromium level and blood glucose are negatively correlated.Chromium (III) content in human body
It is gradually decreased with the increase at age, lacking chromium (III) can make tissue reduce the sensibility of insulin, be susceptible to suffer from diabetes and artery
Atherosis.The effect of insulin can be enhanced by supplementing appropriate chromium (III) to diabetes patient, and the impaired glucose of sustained release human body is resistance to
Amount reduces blood glucose level and serum cholesterol levels.Currently, chromium supplementing agent available on the market have nicotinate chromium, amino acid chromium and
The commodity such as chromium picolinate, wherein chromium picolinate are current the most salable nutrition chromium supplementing agents.But related document report in the recent period：
Chromium picolinate may cause chromosome damage, DNA mutation and cancer, and intestinal absorption rate it is low (<3%), its use by
Gradually cause the query of people.Therefore, find more effective chromium picolinate substitute become research hotspot, synthesizing efficient, easily
It absorbs, novel Organic Chromium (III) complex of low toxicity is of great significance.
Invention content：
The preparation method of the purpose of the present invention is to provide a kind of chromium (III) complex with hypoglycemic weight losing function and
Application of the complex in preparing hypoglycemic slimming medicine.
A kind of chromium (III) complex provided by the invention, molecular structural formula are：
A kind of preparation method of chromium (III) complex provided by the invention, reaction equation：
Preparation process includes：
1) chromic salts and 3- methoxy-salicylics acid are dissolved with organic solvent, puts into zinc granule, be heated to reflux 1~3 hour, then
Triethylene tetramine is instilled, reflux at least 1~2 hour is continued, stops reaction, cooling, filtering；
2) obtained filtrate is stood, volatilizees naturally under room temperature, aubergine crystal is obtained after three days.
Chromic salts described in step 1) is chromium chloride, chromic nitrate or chromium sulfate.
The amount ratio of the substance of chromic salts, 3- methoxy-salicylics acid and zinc granule described in step 1) is 1: 1: 0.5~1.65.
The amount ratio of the substance of chromic salts and triethylene tetramine described in step 1) is 1: 50~100.
Zinc granule described in step 1) is the arsenic-free zinc granule of 20~50 mesh.
Organic solvent described in step 1) is methanol or ethyl alcohol.
Chromium (III) complex good water solubility prepared by the present invention, stability is moderate, and takes full advantage of 3- methoxy-salicylics
The blood sugar reducing function of sour itself distinctive bioactivity and chromic salts, plays the collaboration biological effect of biological hypoglycemic.Animal hypoglycemic
Anti-obesity activity experiment shows that compared with nutritional agents chromium picolinate, the complex has aobvious in control animal blood glucose lipid aspects
Works is used, and is hopeful to apply in preparing hypoglycemic slimming medicine.
Description of the drawings
The crystal x-ray diffraction pattern of Fig. 1 chromium of the present invention (III) complex
The uv-visible absorption spectra of Fig. 2 chromium of the present invention (III) complex
Fluorescence spectrum (the λ of Fig. 3 chromium of the present invention (III) complexex=300nm)
Specific implementation mode：
Embodiment 1：The preparation of chromium (III) complex and structural characterization
Weigh 2.67g (10.0mmol) CrCl3·6H2O and 1.52g (10.0mmol) 3- methoxy-salicylic acid (3-CH3-
SA), it is placed in 100mL round-bottomed flasks, the dissolving of 50mL methanol is added, adds 0.30g without arsenic Zn, is heated to reflux 1 hour,
0.5mL triethylene tetramines (Trientine) are then slowly added into, waits for that the color of solution slowly becomes red from green, continues anti-
It answers 1 hour, it is cooling, it filters, filtrate room temperature volatilizees naturally, and red crystals, yield 60% are obtained after three days.
Determination of elemental analysis is as a result, by molecular formula CrC14H26N4O4Cl theoretical values (%)：C, 41.79；H, 6.47；N,
13.93；Experiment value (%)：C, 41.55；H, 6.69；N, 13.88.
Crystal structure determination result (see attached drawing 1)：Complex molecule formula is CrC14H26N4O4Cl, molecular weight 402, three tiltedly
Crystallographic system, space group P-1, a=7.8880 (6), b=9.8380 (7),α=70.4550 (10), β
=85.729 (2), γ=82.0880 (10) °,Z=2.The interior boundary of complex is by chromium ion, 1 3-
Methoxy-salicylic acid group and 1 triethylene tetramine constitute hexa-coordinate octahedral structure；The external world is by 1 chlorion and 1 hydrone structure
At.Complex part bond distanceIt is shown in Table 1 with bond angle (°).
1 complex part bond distance of tableWith bond angle (°)
Uv-visible absorption spectra (see attached drawing 2)：Ligand have at 239 and 308nm characteristic absorption peak (curve a), with
Cr3+π-the π of its phenyl ring after coordination*Absorption peak distinguishes red shift, and to 285 and 338nm, (curve b) illustrates the electronics in pi-conjugated system
Cloud is to Cr3+Empty d tracks shift；The absorption peak that complex occurs in 549nm is attributed to Cr in complex3+D-d transition
Peak.
Fluorescence spectrum (see attached drawing 3)：Ligand has strong fluorescence (curve a), when itself and Cr near 420nm3+Formation is matched
(curve b) is seriously quenched in fluorescence after conjunction object near 420nm.
Embodiment 2：The preparation of chromium (III) complex
Weigh 2.67g (10.0mmol) CrCl3·6H2O and 1.52g (10.0mmol) 3- methoxy-salicylic acid are placed in 100mL
In round-bottomed flask, 50mL ethyl alcohol is added, adds 1.0g arsenic-free zinc granules, agitating and heating flows back 2 hours, is slowly added to 1mL tri-
The color of ethylene tetramine, solution slowly becomes red from green, continues about 2 hours of agitating and heating back flow reaction, cooling, often
Temperature is volatilized naturally, and red crystals, yield 75% are obtained after 3 days.
Embodiment 3：The hypoglycemic anti-obesity activity application of chromium (III) complex
It is tested by feeding small white mouse to verify the hypoglycemic anti-obesity activity of chromium (III) complex.Experiment small white mouse used by
Shanxi Institute of Traditional Chinese Medicine's Experimental Animal Center provides.We choose Kunming mouse 48, wherein male fifty-fifty, weight model
Enclose 12~15g；15~25 DEG C of room temperature condition, relative humidity 30%~40%, natural lighting allow feed food and water freely.It is general
Logical feed is provided by Beijing Suo Laibao Science and Technology Ltd.High lipid food formula：It is general food 66.5%, sucrose 20%, lard 10%,
Cholesterol 2.5% and sodium taurocholate 1%.Mouse is randomly divided into 4 groups by weight, wherein normally group 12, model group 12 is positive
Control group 12, administration group 12.At the beginning from experiment, normal group mouse normal diet is given, the equal feeding of remaining each group is high in fat
Feed lasts 50 days, modeling success.Then start to be administered, wherein normal group and model group use physiological saline as a contrast, sun
Property control group use Cr (Pic)3Aqueous solution, Cr (Pic)3Dosage is 50mg/kg, and administration group uses the aqueous solution of the chromic compound,
Dosage is 60mg/kg, every morning 9:00 gavage 1 time, Therapy lasted 9 weeks.There is individual animal damage in experimentation, finally
Every group of unification chooses 10 to count.After experiment, make mouse fasting 20 hours, claims its weight respectively, taken from orbital vein
Blood measures every biochemical indicator using related kit.Each group of data is for statistical analysis using SPSS17.0, and all data are equal
WithIt indicates, group difference uses one-way analysis of variance, with P<0.05 is significant difference.Specific experiment result counts
Referring to table 2.
The every physiological and biochemical index of table 2 (N=10)
Compared with normal group, ▲ P<0.05, ▲ ▲ p<0.01；Compared with model group, * P ﹤ 0.05, * * P ﹤ 0.01
From table 2：
(1) indices normally organized, there are significant difference, it is small to illustrate that high confectionery object high in fat causes compared with model group
Mouse blood pressure and blood lipoid concentration is significantly raised, and ldl concn improves, and high-density lipoprotein concentration reduces, weight gain；
(2) compared with model group, positive controls Cr (Pic)3Fat-reducing effect it is unsatisfactory.In addition to weight slightly lowers
Outside, all there were significant differences for remaining index；
(3) and compared with model group, the blood glucose of administration group reduces, and total cholesterol and triglycerides are substantially reduced, highly dense
It spends lipoprotein to increase, weight significantly reduces.
Cr(Pic)3It is general hypoglycemic slimming medicine in the world at present.In this experiment, it compares and positive controls
Close object Cr (Pic)3For, synthesized novel chromic compound [Cr (3-CH3-SA)(Trientine)]Cl·H2O has preferable
Physiology hypoglycemic anti-obesity activity.This may be due to：1) chemically from the point of view of key bond distance, the sum of boundary bond distance compares Cr in the complex
(Pic)3To grow, illustrate the complexes stability compared with Cr (Pic)3It is weak, it is easy to dissociate in metabolic process, chromium ion is easy quilt
Internal chromium transport protein transhipment so that bioavailability is high；2) the 3- methoxy-salicylic acid structures in the complex molecule are similar to
Aspirin has the function of inhibiting platelet aggregation etc.；3) complex is NaCl types, good water solubility, bio-absorbable utilization
Rate is high.
Claims (4)
1. a kind of chromium (III) complex with hypoglycemic weight losing function, which is characterized in that structural formula is：
2. a kind of preparation method of chromium (III) complex as described in claim 1, which is characterized in that include the following steps：
1) chromic salts and 3- methoxy-salicylics acid are dissolved with organic solvent, puts into zinc granule, is heated to reflux 1~3 hour, then instills
Triethylene tetramine continues reflux at least 1~2 hour, stops reaction, cooling, filtering；
2) obtained filtrate is stood, volatilizees naturally under room temperature, aubergine crystal is obtained after three days；
Chromic salts described in step 1) is chromium chloride, chromic nitrate or chromium sulfate, the chromic salts, 3- methoxy-salicylics acid and zinc granule
The amount ratio of substance is 1: 1: 0.5~1.65, and the amount ratio of the substance of the chromic salts and triethylene tetramine is 1:50~100, it is described
Zinc granule be 20~50 mesh arsenic-free zinc granule, the organic solvent be methanol or ethyl alcohol.
3. application of chromium (III) complex as described in claim 1 in preparing hypoglycemic medicine.
4. application of chromium (III) complex as described in claim 1 in preparing slimming medicine.
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