CN104352519A - Manganese-containing compound for treating diabetes and preparation method thereof - Google Patents
Manganese-containing compound for treating diabetes and preparation method thereof Download PDFInfo
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- CN104352519A CN104352519A CN201410652421.2A CN201410652421A CN104352519A CN 104352519 A CN104352519 A CN 104352519A CN 201410652421 A CN201410652421 A CN 201410652421A CN 104352519 A CN104352519 A CN 104352519A
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- 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 29
- 239000011572 manganese Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052748 manganese Inorganic materials 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 7
- IWFHBRFJOHTIPU-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Cl)C=C1N IWFHBRFJOHTIPU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 150000002697 manganese compounds Chemical class 0.000 claims description 14
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 239000008280 blood Substances 0.000 abstract description 19
- 210000004369 blood Anatomy 0.000 abstract description 19
- 238000002156 mixing Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 235000001727 glucose Nutrition 0.000 abstract 1
- 150000002304 glucoses Chemical class 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000000967 suction filtration Methods 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 14
- 239000008103 glucose Substances 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
- 208000007241 Experimental Diabetes Mellitus Diseases 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 4
- 108090001061 Insulin Proteins 0.000 description 4
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
- 229940125396 insulin Drugs 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin hydrochloride Natural products CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 2
- 230000023852 carbohydrate metabolic process Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000037356 lipid metabolism Effects 0.000 description 2
- 206010025482 malaise Diseases 0.000 description 2
- 229960003105 metformin Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000007410 oral glucose tolerance test Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 230000025938 carbohydrate utilization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229960004329 metformin hydrochloride Drugs 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- 238000003032 molecular docking Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a manganese-containing compound for treating diabetes and a preparation method thereof. The preparation method comprises the following steps: (1) dissolving a suitable amount of 4,5-dichloro o-phenylendiamine into an ethanol solution, so that a solution I is obtained; and dissolving a suitable amount of salicylaldehyde into an ethanol solution, so that a solution II is obtained; (2) dropwise adding the solution II into the solution I in a water bath or oil bath at a constant temperature of 60 DEG C, uniformly mixing the two, and carrying out reaction and reflux on the obtained mixture for 4 h, so that a yellow flocculent precipitate is precipitated out; cooling, carrying out suction filtration, and recrystallizing in ethanol, so that a precipitate is obtained; and drying the precipitate, so that a ligand is obtained; and (3) dissolving the synthesized ligand in CH2Cl2, dissolving Mn(CH3COO)2.4H2O in CH3OH, mixing and stirring the two for 30 minutes, and 14 d later, precipitating out yellow massive complex crystals, so that the compound disclosed by the invention is obtained. The compound can be used for effectively reducing blood glucoses, and is simple in preparation method, easy to operate, and low in production cost.
Description
Technical field
The present invention relates to medicine technology field, particularly relate to a kind of be used for the treatment of diabetes containing manganese compound and preparation method thereof.
Background technology
Along with the development of society and the raising of people's living standard, operating pressure is also increasing, and the exercise of health is fewer and feweri, and the sickness rate of diabetes is more and more higher, and the diabetics of higher proportion has caused complication, even result in life danger.Diabetes are a kind of diseases being feature with the elevated blood glucose levels continued.The cardinal symptom of diabetes is carbohydrate metabolism exception and Abnormal Lipid Metabolism, and the reduction of the blood flow obstructions caused due to elevated blood glucose levels and sugar utilization can make the systematic complication of diabetes more and more serious.These diabetic symptoms cause due to the insufficient insulin or insulin resistant controlling carbohydrate and lipid metabolism.Due to cannot excreting insulin and the diabetes caused are called as " type i diabetes "; And the diabetes caused due to insulin resistant are called as " type 2 diabetes mellitus ".
The data of WHO shows, in world wide, the sickness rate of diabetes is 3%-5%, and total number of persons is about between 1.7-2.0 hundred million, estimates that the year two thousand thirty will reach about 3.5 hundred million.China is that current diabetes mellitus patient increases one of the fastest country, and age of onset is tending towards rejuvenation especially.
Summary of the invention
The object of the present invention is to provide a kind of be used for the treatment of diabetes containing manganese compound and preparation method thereof.
That treats diabetes contains a manganese compound, has following chemical structural formula:
Treat the preparation method containing manganese compound of diabetes, comprise the following steps:
(1) get appropriate 4,5-dichloro o-phenylenediamines to be dissolved in alcoholic solution and to obtain solution I; Get salicylide to be dissolved in alcoholic solution in right amount and to obtain solution II;
(2) in 60 DEG C of waters bath with thermostatic control or oil bath, dropwise solution II is instilled solution I, by the two mix homogeneously, reaction backflow 4h, have yellow flocculent deposit to separate out, cooling, sucking filtration, carries out recrystallization in ethanol, is precipitated, and oven dry, obtains part;
(3) part of above-mentioned synthesis is dissolved in CH
2cl
2in, by Mn (CH
3cOO)
24H
2o is dissolved in CH
3in OH, then incite somebody to action both mix and blends 30 minutes, separate out yellow block complex crystal after 14d, namely obtain the compounds of this invention.
Further, the preparation method containing manganese compound for the treatment of diabetes as above, in step 1, the mol ratio of described 4,5-dichloro o-phenylenediamines and salicylide is: 1:3.
Further, the preparation method containing manganese compound for the treatment of diabetes as above, in step 2, part and Mn (CH
3cOO)
24H
2the mol ratio of O is 1:1.
Treatment diabetes provided by the invention containing manganese compound, effectively can reduce blood glucose, and its preparation method is simple, easy to operate, production cost is low.
Detailed description of the invention
For making the object, technical solutions and advantages of the present invention clearly, below technical scheme in the present invention be clearly and completely described, obviously, described embodiment is the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art, not making the every other embodiment obtained under creative work prerequisite, belong to the scope of protection of the invention.
Reaction equation of the present invention is:
Embodiment:
(1) getting 4,5-dichloro o-phenylenediamine (3mmol, 0.51g) is dissolved in 30mL alcoholic solution, get salicylide (9mmol, 1.05g) be dissolved in 15mL alcoholic solution, dropwise salicylide solution instilled in 60 DEG C of water bath with thermostatic control/oil baths, both mixing.Reaction backflow 4h, has yellow flocculent deposit to separate out, cooling, sucking filtration.Carry out recrystallization in ethanol, be precipitated, dry, obtain part;
(2) the above-mentioned part (1mmol, 0.383g) that obtains is dissolved in 6mL CH
2cl
2, Mn (CH
3cOO)
24H
2o (1mmol, 0.245g) is dissolved in 20mL CH
3stir 30 minutes in OH, after 14d, separate out yellow block complex crystal, be applicable to X-ray single crystal diffraction.Productive rate is 80%.
The chemical characteristic parameter of the block complex crystal of above-mentioned obtained yellow is:
Elementary analysis Anal.Calcd.for C
22h
15cl
2mnN
2o
4: C, 53.10; H, 3.02; N, 5.63, Found:C, 53.15; H, 3.06; N, 5.61; Infrared spectrum IR (KBrdisk): ν (cm
-1)=1601,1491 (ν
c=N), 1686,1601,1458, (ν
c=c); Its molecular formula C
22h
15cl
2mnN
2o
4, its molecular weight FW=497.2.
Experimental example:
Healthy ICR mice (♂), adaptability feeds 3 days, and the mice choosing body weight > 24g carries out modeling.Modeling method: tail vein injection alloxan after mice fasting 6h, dosage 65mg/kg, administration volume 10ml/kg.After injection alloxan, blood is got in docking in the 4th day, and measure blood glucose with Glucose estimation kit, the mice choosing blood glucose value >=11.1mmol/L is diabetic mice, by blood glucose value and body weight random packet, often organizes 10.Normal group then injects equal-volume normal saline (NS).Test mice is divided into normal group, diabetic groups, diabetes+manganese compound group at random by blood glucose.Grouping situation is as follows:
1. diabetic model group: 0.5%CMC-Na (containing 0.9%NaCl);
2. positive group: metformin hydrochloride tablet dosage 250mg/kg, a slice is dissolved in 10ml 0.5%CMC-Na;
3. [Mn (C
22h
15n
2o
4cl
2)] group: dosage 77mg/kg, weigh 0.077g and be dissolved in 10ml 0.5%CMC-Na.
All samples is 3 days configuration amount, 4 DEG C of preservations.Every day gastric infusion once, weekly after gastric infusion 1 hour measure blood glucose, fasting 2.5 hours before blood sugar detection.
Experimental result carries out statistical disposition, and result is as shown in table 1:
The coordination compound administration impact on alloxan diabetes mouse blood sugar in 3 weeks
Table 1 coordination compound [Mn (C
22h
15n
2o
4cl
2)] the administration impact on alloxan diabetes mouse blood sugar in 3 weeks
Note: compared with model group, * P < 0.05, * * P < 0.01
From table 1, administration first week coordination compound [Mn (C
22h
15n
2o
4cl
2)] fasting blood glucose level of administration group mice is starkly lower than model group (P < 0.05), effect lasts 3 weeks.The coordination compound administration impact on the glucose tolerance of alloxan diabetes Mouse oral in 2 weeks
Two weeks carries out oral glucose tolerance (OGTT) experiment, and the results are shown in Table 2, gavage gives glucose (2g/kg), and the blood glucose till of diabetic mice raises, to peak after 60min.Metformin administration group blood sugar level ascensional range is less than model group, and during 120min, metformin administration group blood sugar level is starkly lower than model group (P < 0.05).
Coordination compound [Mn (C
22h
15n
2o
4cl
2)] in alloxan diabetes mice administration 120min, blood sugar level obviously reduces (with model group ratio, P < 0.05).This shows, coordination compound [Mn (C
22h
15n
2o
4cl
2)] removing of blood sugar level can be accelerated, the carbohydrate tolerance of alloxan diabetes mice can be improved.
Table 2 coordination compound [Mn (C
22h
15n
2o
4cl
2)] the administration impact on alloxan diabetes mice OGTT in 2 weeks
Note: compared with model group, * P < 0.05, * * P < 0.01
Visible, rare Buddhist alkali manganese compound of the present invention is used for the treatment of in the experiment of diabetes, proves that there is obvious hypoglycemic activity.
Last it is noted that above embodiment is only in order to illustrate technical scheme of the present invention, be not intended to limit; Although with reference to previous embodiment to invention has been detailed description, those of ordinary skill in the art is to be understood that: it still can be modified to the technical scheme described in foregoing embodiments, or carries out equivalent replacement to wherein portion of techniques feature; And these amendments or replacement, do not make the essence of appropriate technical solution depart from the spirit and scope of various embodiments of the present invention technical scheme.
Claims (4)
1. what be used for the treatment of diabetes contains a manganese compound, it is characterized in that having following chemical structural formula:
2. what be used for the treatment of diabetes contains a manganese compound preparation method, it is characterized in that, comprises the following steps:
(1) get appropriate 4,5-dichloro o-phenylenediamines to be dissolved in alcoholic solution and to obtain solution I; Get salicylide to be dissolved in alcoholic solution in right amount and to obtain solution II;
(2) in 60 DEG C of waters bath with thermostatic control or oil bath, dropwise solution II is instilled solution I, by the two mix homogeneously, reaction backflow 4h, have yellow flocculent deposit to separate out, cooling, sucking filtration, carries out recrystallization in ethanol, is precipitated, and oven dry, obtains part;
(3) part of above-mentioned synthesis is dissolved in CH
2cl
2in, by Mn (CH
3cOO)
24H
2o is dissolved in CH
3in OH, then incite somebody to action both mix and blends 30 minutes, separate out yellow block complex crystal after 14d, namely obtain the compounds of this invention.
3. according to claim 2 be used for the treatment of diabetes containing manganese compound preparation method, it is characterized in that, in step 1, the mol ratio of described 4,5-dichloro o-phenylenediamines and salicylide is: 1:3.
4. according to claim 2 be used for the treatment of diabetes containing manganese compound preparation method, it is characterized in that, in step 2, part and Mn (CH
3cOO)
24H
2the mol ratio of O is 1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410652421.2A CN104352519A (en) | 2014-11-17 | 2014-11-17 | Manganese-containing compound for treating diabetes and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410652421.2A CN104352519A (en) | 2014-11-17 | 2014-11-17 | Manganese-containing compound for treating diabetes and preparation method thereof |
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| Publication Number | Publication Date |
|---|---|
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Family
ID=52519892
Family Applications (1)
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|---|---|---|---|
| CN201410652421.2A Pending CN104352519A (en) | 2014-11-17 | 2014-11-17 | Manganese-containing compound for treating diabetes and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104352519A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111227A (en) * | 2015-08-13 | 2015-12-02 | 云南大学 | Schiff base dinuclear cadmium complex and preparation method therefor |
| CN117551596A (en) * | 2024-01-11 | 2024-02-13 | 云南大学 | Method for relieving bacteriostatic action of soil on biocontrol fungi |
-
2014
- 2014-11-17 CN CN201410652421.2A patent/CN104352519A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 祝明蓉: "酶抑制剂的席夫碱金属配合物的合成、结构及其生物活性研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111227A (en) * | 2015-08-13 | 2015-12-02 | 云南大学 | Schiff base dinuclear cadmium complex and preparation method therefor |
| CN105111227B (en) * | 2015-08-13 | 2017-04-26 | 云南大学 | Schiff base dinuclear cadmium complex and preparation method therefor |
| CN117551596A (en) * | 2024-01-11 | 2024-02-13 | 云南大学 | Method for relieving bacteriostatic action of soil on biocontrol fungi |
| CN117551596B (en) * | 2024-01-11 | 2024-03-29 | 云南大学 | Method for relieving bacteriostatic action of soil on biocontrol fungi |
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