CN104292199A - Preparation method of genistein derivative containing benzylpiperazine and application of genistein derivative for protecting gastric mucosal - Google Patents
Preparation method of genistein derivative containing benzylpiperazine and application of genistein derivative for protecting gastric mucosal Download PDFInfo
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- CN104292199A CN104292199A CN201410496493.2A CN201410496493A CN104292199A CN 104292199 A CN104292199 A CN 104292199A CN 201410496493 A CN201410496493 A CN 201410496493A CN 104292199 A CN104292199 A CN 104292199A
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- China
- Prior art keywords
- target compound
- genistein
- genistein derivative
- benzyl diethylenediamine
- medicine
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- 229930004065 genistein derivative Natural products 0.000 title claims abstract description 22
- 150000002273 genistein derivatives Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 title abstract 4
- 230000002496 gastric effect Effects 0.000 title description 5
- 239000003814 drug Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 35
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 25
- 230000009854 mucosal lesion Effects 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 benzyl diethylenediamine Chemical compound 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 229940045109 genistein Drugs 0.000 claims description 8
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 claims description 8
- 235000006539 genistein Nutrition 0.000 claims description 8
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 4
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims description 4
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 claims description 4
- 229960001701 chloroform Drugs 0.000 claims description 4
- 238000005352 clarification Methods 0.000 claims description 4
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 2
- 238000003760 magnetic stirring Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000013376 functional food Nutrition 0.000 abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract description 2
- 206010061164 Gastric mucosal lesion Diseases 0.000 abstract 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 241000700159 Rattus Species 0.000 description 18
- 230000006378 damage Effects 0.000 description 13
- 230000037396 body weight Effects 0.000 description 9
- 238000003304 gavage Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 229960004756 ethanol Drugs 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000001156 gastric mucosa Anatomy 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 201000005917 gastric ulcer Diseases 0.000 description 2
- 150000002272 genistein Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 208000012895 Gastric disease Diseases 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/38—2,3-Dihydro derivatives, e.g. isoflavanones
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention aims at providing a genistein derivative containing benzylpiperazine, which has antibacterial and anti-inflammatory activity and is used for preparing a functional food or medicine for protecting gastric mucosal lesions. The invention also provides a preparation method of the genistein derivative and use of the genistein derivative. The structural formula of the genistein derivative containing benzylpiperazine disclosed by the invention is as shown in the specification. The genistein derivative containing benzylpiperazine disclosed by the invention has protective activity on gastric mucosal lesions and can be used for preparing the functional food or medicine for protecting the gastric mucosal lesions. The preparation method is simple, feasible and easy to complete.
Description
Technical field
The present invention relates to containing the genistein derivative preparation method of benzyl diethylenediamine and to the functional foodstuff of the prolection of mucosal lesion and the purposes of medicine.
Background technology
Along with the quickening of modern society's rhythm of life, people bear society, the increasing pressure of psychology and work causes greatly that the incidence of gastric mucosa disease is corresponding to be increased.And allegro mode of life, nervous working and learning, and excessive drinking etc. causes the common cause of mucosal lesion.As the worldwide disease of one, no matter in developed country, or in developing country, its sickness rate is all high.It is reported, in Chinese society population, the people more than 10% suffers from stomach ulcer, and the people of about 25% suffers from various gastritis, national patients with gastric disease total number of persons 300,000,000 people nearly.Therefore, find the functional food factor of the mucosal lesion of efficient, low side effect or pharmaceutical cpd and become an important and urgent task.
Genistein and human health closely related, there is many physiological functions, as anti-oxidant, antitumor action, to the protective effect of blood vessel, improve immunizing power and antibacterial and anti-inflammation functions etc.Someone reports that piperazine also has certain antimicrobial antiphlogistic activity in the recent period.Therefore, piperazine is introduced genistein by the present invention, the genistein derivative of preparation containing piperazine.
This analog derivative has prolection to mucosal lesion, and therefore, genistein derivative has the functional foodstuff factor of prolection or the prospect of medicine extremely to merit attention as very potential mucosal lesion.Along with deepening continuously of genistein class drug research; the basis having the mechanism of action of defencive function constantly to understand to its mucosal lesion is carried out effective structure of modification and modification and molecular designing; the functional foodstuff factor or medicine that have the genistein class mucosal lesion provide protection of increasing efficient, low toxicity are used for clinical, promote the well-being of mankind.
Summary of the invention
The object of the present invention is to provide a kind of genistein derivative containing benzyl diethylenediamine and preparation method and purposes.
Technical scheme of the present invention is as follows:
One class, containing the genistein derivative of benzyl diethylenediamine, is characterized in that it has following structural formula:
Prepare a method for the above-mentioned genistein derivative containing benzyl diethylenediamine, it is characterized in that it is made up of the following step:
(1) genistein 270 ㎎ is added in 50ml round-bottomed flask, dehydrated alcohol 25ml, the formalin 0.08ml of 37%;
(2) be heated to 55 ~ 60 DEG C, after reaction solution clarification, add the 1-benzyl diethylenediamine of genistein mol ratio 1 ~ 1.1 times;
(3) in round-bottomed flask, add rotor, sealing, places it in magnetic stirring apparatus and stirs, and reacts at 23 ± 3 DEG C;
(4) react after 72 hours, reaction terminates, and has solid to separate out, filtration, with methyl alcohol: trichloromethane=1: 1 mixing solutions recrystallization, separation and purification obtains target compound.
(5) mixed with Xylo-Mucine by target compound 1, in mixture, target compound mass ratio is 1.42-59%, can be used as functional foodstuff or the medicine of protection mucosal lesion;
(6) be dissolved in by target compound in 0.5-1% carboxymethylcellulose sodium solution, in solution, the concentration of target compound is 0.144-14.4mg/mL, can be used as functional foodstuff or the medicine of protection mucosal lesion.
Target compound 1 reaction process is as follows:
Experimental result shows; the novel genistein derivative containing benzyl diethylenediamine of the present invention has prolection to stomach ulcer mucosa injury; can be used for preparing functional foodstuff or the medicine that mucosal lesion has provide protection, and there is the effect that significant protection gastric mucosa avoids loss.
Embodiment
Further describe the present invention by following examples, but scope of the present invention is not by any restriction of these embodiments.
Embodiment 1: the preparation of the genistein derivative containing benzyl diethylenediamine: 8-((4-benzyl diethylenediamine-1-yl) methyl)-5,7-dihydroxyl-3-(4-hydroxyphenyl) chroman-4-on-(target compound).
Genistein 270mg is added, dehydrated alcohol 25 mL, formalin 0.08 mL of 37% in 50 mL round-bottomed flasks; Be heated to 55 ~ 60 DEG C, after reaction solution clarification, add 1-benzyl diethylenediamine 174 μ L; Sealing, room temperature lower magnetic force stirring reaction 72 hours.After reaction terminates, have solid to separate out, filter, solid is through methyl alcohol: trichloromethane=1: 1 recrystallization, separation and purification obtains target compound.Mixed with Xylo-Mucine by target compound, in mixture, target compound mass ratio is 1.42%, can be used as functional foodstuff or the medicine of protection mucosal lesion; Be dissolved in by target compound in 0.5% carboxymethylcellulose sodium solution, in solution, the concentration of target compound is 0.144mg/mL, can be used as functional foodstuff or the medicine of protection mucosal lesion
Fusing point: 209-209.8 DEG C.
1H?NMR?(300?MHz,?CDCl
3):?3.45?-?3.53?(m,2?H)；3.75?-?3.82?(m,2H)；6.36?-?6.39(m,1H)；6.78?-?6.86(m,2H)；7.23?-7.41?(m,?8H)；8.32-8.35?(m,?1H)?MS(ESI):?458.50?(C
27H
26N
2O
5,?[M+H]+).?Anal.?Calcd?for?C
27H
26N
2O
5:?C:70.72%，H:5.73%，N:?5.32%，O:17.45%。Found:?C:71.1%，H:5.13%，N:?5.92%，O:17.9%。
Embodiment 2: the preparation of the genistein derivative containing benzyl diethylenediamine: 8-((4-benzyl diethylenediamine-1-yl) methyl)-5,7-dihydroxyl-3-(4-hydroxyphenyl) chroman-4-on-(target compound).
Genistein 270mg is added, dehydrated alcohol 25 mL, formalin 0.08 mL of 37% in 50 mL round-bottomed flasks; Be heated to 55 ~ 60 DEG C, after reaction solution clarification, add 1-benzyl diethylenediamine 191 μ L; Sealing, room temperature lower magnetic force stirring reaction 72 hours.After reaction terminates, have solid to separate out, filter, solid is through methyl alcohol: trichloromethane=1: 1 recrystallization, separation and purification obtains target compound.Mixed with Xylo-Mucine by target compound, in mixture, target compound mass ratio is 59%, can be used as functional foodstuff or the medicine of protection mucosal lesion; Target compound is dissolved in 1% carboxymethylcellulose sodium solution, the concentration 14.4mg/mL of target compound in solution, can be used as functional foodstuff or the medicine of protection mucosal lesion.
Embodiment 3: containing the genistein derivative of benzyl diethylenediamine to protection mucosal lesion activity research
1. experiment material and method
1.1 medicines and reagent
70% ethanol, CMC(Xylo-Mucine) etc. be analytical reagent, Ranitidine HCL purchased from Hong Rentang pharmacy.The target compound of synthesis.
1.2 animal
SD rat 100-200g, male, resist purchased from Shandong, animal productiong license licensed licenser licence SCXK (Shandong) 20130001.
1.3 experimental technique
1.3.1 animal grouping and model preparation
Animal is divided into six groups at random, often organizes 8 rats, 25 DEG C, 70% humidity.
Treatment group and experimental protocol are as follows in detail:
(1) reagent controls group.0,24,48,49 hours gavage 0.5%CMC 1mL, kill rat in 50 hours.
(2) ethanol group.0,24,48 hours gavage 0.5%CMC 1mL, 49 hours gavage 70% ethanol, dosage is 2mL/1000g rat body weight.Within 50 hours, kill rat.
(3) positive drug group.0,24,48 hours gavage Ranitidine HCLs (50 mg/1000g rat body weight), 49 hours gavage 70% ethanol, dosage is 2mL/1000g rat body weight.Within 50 hours, kill rat.
(4) target compound low dose group.0,24,48 hours gavage target compounds once, and dosage is 0.45 mg/1000g rat body weight, 49 hours oral 70% ethanol, and dosage is 2 mL/1000g rat body weights, within 50 hours, kills rat.
(5) dosage group in target compound.0,24,48 hours gavage target compounds once, and dosage is 4.5 mg/1000g rat body weights, 49 hours oral 70% ethanol, and dosage is 2 mL/1000g rat body weights, within 50 hours, kills rat.
(6) target compound high dose group.0,24,48 hours gavage target compounds once, and dosage is 45 mg/1000g rat body weights, 49 hours oral 70% ethanol, and dosage is 2 mL/1000g rat body weights, within 50 hours, kills rat.
1.3.2 gastric mucosal damage index and mucosal lesion inhibiting rate calculate
Put to death rat and get gastric mucosa tissue, with the naked eye observe the degree of impairment of gastric mucosa with magnifying glass, with reference to Guth standards of grading, calculate gastric mucosal damage index, it is 1 point that point-like damage or damage are less than 1 mm, wire damage length 1 ~ 2 mm is 2 points, wire damage length 2 ~ 3 mm is 3 points, wire damage length 3 ~ 4 mm is 4 points, by that analogy, wherein damage width to be greater than 2 mm score values and to double, all score sums are gastric mucosal damage index, mucosal lesion inhibiting rate=(model group damage index-administration group damage index)/model group damage index × 100%
2. experimental result
Listed by table 1 the present invention, target compound is to mucosal lesion inhibiting rate
| Sample | Mucosal lesion inhibiting rate (%) |
| Positive drug group | 72.5±2.6 |
| Target compound low dose group | 80.4±3.4 |
| Dosage group in target compound | 86.3±2.8 |
| Target compound high dose group | 98.0±4.1 |
From table 1, when target compound dosage is respectively 0.9%, 9% and 90% of control drug group dosage, inhibiting rate is respectively 111%, 119% and 135% of control drug group.Visible, the effect of target compound is more effective than positive drug.
Claims (6)
1., containing a genistein derivative for benzyl diethylenediamine, it is characterized in that it has following structural formula:
。
2. a method for the genistein derivative containing benzyl diethylenediamine according to claim 1, is characterized in that comprising the following steps:
(1) genistein 270 ㎎ is added in 50ml round-bottomed flask, dehydrated alcohol 25ml, the formalin 0.08ml of 37%;
(2) be heated to 55 ~ 60 DEG C, after reaction solution clarification, add the 1-benzyl diethylenediamine of genistein mol ratio 1 ~ 1.1 times;
(3) in round-bottomed flask, add rotor, sealing, places it in magnetic stirring apparatus and stirs, and reacts at 23 ± 3 DEG C;
(4) react after 72 hours, reaction terminates, and has solid to separate out, filtration, with methyl alcohol: trichloromethane=1: 1 mixing solutions recrystallization, separation and purification obtains target compound.
3. for the preparation of functional foodstuff or the medicine of auxiliary protection mucosal lesion.
4. the purposes of the genistein derivative containing benzyl diethylenediamine according to claim 3; it is characterized in that: target compound is mixed with Xylo-Mucine; in mixture, target compound mass ratio is 1.42-59%, can be used as functional foodstuff or the medicine of protection mucosal lesion.
5. the purposes of the genistein derivative containing benzyl diethylenediamine according to claim 3; it is characterized in that: target compound is dissolved in 0.5-1% carboxymethylcellulose sodium solution; in solution, the concentration of target compound is 0.144-14.4mg/mL, can be used as functional foodstuff or the medicine of protection mucosal lesion.
6. target compound reaction process is as follows:
。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410496493.2A CN104292199B (en) | 2014-09-25 | 2014-09-25 | Genistein derivative preparation method containing benzyl diethylenediamine and its to gastric mucosal protection application |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410496493.2A CN104292199B (en) | 2014-09-25 | 2014-09-25 | Genistein derivative preparation method containing benzyl diethylenediamine and its to gastric mucosal protection application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104292199A true CN104292199A (en) | 2015-01-21 |
| CN104292199B CN104292199B (en) | 2019-03-26 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106074204A (en) * | 2016-04-18 | 2016-11-09 | 山东理工大学 | The application in whitening field of a kind of genistein derivant |
| CN113549044A (en) * | 2021-07-23 | 2021-10-26 | 中国药科大学 | 8-azacyclo-substituted chromone derivative and preparation method and pharmaceutical application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL2031294B1 (en) * | 2021-12-30 | 2023-07-05 | Univ Shandong Technology | Preparation method and application of genistein derivative containing benzylpiperazine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102293936A (en) * | 2011-09-14 | 2011-12-28 | 四川万安石斛产业开发有限公司 | Medicinal composition or health food composition for protecting gastric mucosa, and preparation method thereof |
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2014
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102293936A (en) * | 2011-09-14 | 2011-12-28 | 四川万安石斛产业开发有限公司 | Medicinal composition or health food composition for protecting gastric mucosa, and preparation method thereof |
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| 任杰等: "木犀草素Mannich碱衍生物的合成及其抗癌活性", 《中国新药杂志》 * |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106074204A (en) * | 2016-04-18 | 2016-11-09 | 山东理工大学 | The application in whitening field of a kind of genistein derivant |
| CN106074204B (en) * | 2016-04-18 | 2018-10-23 | 山东理工大学 | A kind of application of genistein derivative in whitening field |
| CN113549044A (en) * | 2021-07-23 | 2021-10-26 | 中国药科大学 | 8-azacyclo-substituted chromone derivative and preparation method and pharmaceutical application thereof |
| CN113549044B (en) * | 2021-07-23 | 2024-01-23 | 中国药科大学 | 8-azacyclo-substituted chromone derivative and preparation method and pharmaceutical application thereof |
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| CN104292199B (en) | 2019-03-26 |
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