CN104262331B - A kind of acridine acylhydrazone and its production and use - Google Patents
A kind of acridine acylhydrazone and its production and use Download PDFInfo
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- CN104262331B CN104262331B CN201410520603.4A CN201410520603A CN104262331B CN 104262331 B CN104262331 B CN 104262331B CN 201410520603 A CN201410520603 A CN 201410520603A CN 104262331 B CN104262331 B CN 104262331B
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The invention discloses a kind of acridine acylhydrazone and its production and use.The structural formula of this acridine acylhydrazone is:The chemical name of this acridine acylhydrazone is 2-furyl-9-acridine acylhydrazone, and molecular formula is C19H13N3O2, relative molecular weight is 315.33.Method simplicity and the synthetic ratio of preparing this acridine acylhydrazone are high, and this acridine acylhydrazone can be applied in and prepare in antitumor drug, make the antitumor drug being prepared into possess effective prevention and suppress the effect of tumor progression.
Description
Technical field
The present invention relates to technical field of medical chemistry, be specifically related to a kind of acridine acylhydrazone and preparation method thereof, and by acridine acylhydrazone for preparing antitumor drug.
Background technology
Malignant tumor (cancer) is one of disease of society serious harm human health.Statistical data in recent years shows: whole world new cancer patient about 12,000,000, because of cancer mortality 7,600,000 people, there are about 20,000 people every day and dies from cancer.Additionally, the sickness rate of cancer also rises continuing, it is contemplated that the year two thousand twenty whole world new cancer patient will reach 15,000,000.Acridine compounds is the organic synthesis intermediate that a class is important, and its derivant shows important biological activity, and cancerous cell has good inhibitory action, can be applied in new drug research as DNA intercalator and anticancer lead compound etc..People have extracted from natural product or have adopted the method for chemosynthesis to obtain substantial amounts of acridine compound, have studied their pharmacologically active and the mechanism of action.Hydrazone compounds refers to the compounds in molecular structure containing hydrazone group (-CONHN=CH-) functional group, it it is the product of hydrazides and aldehydes or ketones generation necleophilic reaction dehydration, because itself having special biological activity such as anticancer, sterilization etc., the object of people's extensive concern it is always up in fields such as medicine, pesticide, therefore, research and develop novel acylhydrazone, there is boundless prospect and practical significance.
Summary of the invention
It is an object of the present invention to provide a kind of acridine acylhydrazone, this acridine acylhydrazone has anti-tumor activity.Another purpose is to provide a kind of method preparing this acridine acylhydrazone, and this acridine acylhydrazone can be applied in and prepare in antitumor drug, makes the antitumor drug being prepared into possess effective prevention and suppress the effect of tumor progression.
In order to solve above-mentioned technical problem, the invention provides a kind of acridine acylhydrazone and its production and use.
The structural formula of the acridine acylhydrazone of the present invention is:
The chemical name of this acridine acylhydrazone is: 2-furyl-9-acridine acylhydrazone；
The molecular formula of this acridine acylhydrazone is: C19H13N3O2；
The relative molecular weight of this acridine acylhydrazone is: 315.33.
Can preparing this acridine acylhydrazone by the following method, it comprises the steps: simple and feasiblely
1) being added in thionyl chloride by 9-acridine benzoic acid, be heated to reflux 5h, solvent is evaporated under reduced pressure, namely gained thick white shape solid is not separated obtains compound 9-acridine formyl chloride (1)；
2) 9-acridine formyl chloride (1) is dissolved in chloroform, drips hydrazine hydrate, after back flow reaction 2-3h, prepare 9-acridine formylhydrazine (2)；
3) furtural is added after 9-acridine formylhydrazine (2) is dissolved in dehydrated alcohol, it is heated to reflux 1-2h, precipitate out yellow powder, after sucking filtration, after described yellow powder and recrystallized from acetonitrile, namely obtain target product 2-furyl-9-acridine acylhydrazone (3).
This acridine acylhydrazone may be used for preparing antitumor drug, such as makes one or more medicines in antineoplastic injection, tablet, pill, capsule, suspending agent or Emulsion.
Beneficial effects of the present invention: the acridine acylhydrazone of the present invention is with acridine for parent nucleus, synthesize target product 2-furyl-9-acridine acylhydrazone, this structure had both had the precursor structure of acridine, again containing acylhydrazone base active structure, the anti-tumor activity of its parent nucleus itself can be strengthened, make the acridine acylhydrazone being prepared into have very strong anti-tumor activity.And the preparation method synthetic ratio of the present invention is high, and side-product is few, can effectively be applied to and prepare in antitumor drug, and gastric carcinoma cells, hepatoma cell strain, human lung carcinoma cell, human bladder cancer cell's strain etc. can be produced very high inhibition effect.
Accompanying drawing explanation
Fig. 1 is the method route schematic diagram that the present invention prepares described acridine acylhydrazone；
Fig. 2 is acridine acylhydrazone of the present invention and other antitumor drug medium effective concentration comparison diagram to tumor cell line.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, to make those skilled in the art can implement according to this with reference to description word.
Embodiment 1
Fig. 1 is the method route schematic diagram that the present invention prepares described acridine acylhydrazone.In conjunction with Fig. 1, the preparation method of acridine acylhydrazone of the present invention comprises the following specific steps that:
1) being added in 30ml thionyl chloride by 2.23g or 10mmol9-acridine benzoic acid, be heated to reflux 5h, solvent is evaporated under reduced pressure, namely gained thick white shape solid is not separated obtains compound 9-acridine formyl chloride (1), and its gained productivity is 100%；
2) 2.24g or 10mmol compound 9-acridine formyl chloride (1) is dissolved in the chloroform that 30ml Non-aqueous processing is crossed, dropping 3ml hydrazine hydrate, back flow reaction 2h, material after cooling removal solvent obtains white solid with dehydrated alcohol recrystallization, i.e. 9-acridine formylhydrazine (2), its gained productivity is 80%；
3) 0.1g or 1mmol furtural is added after 0.24g or 1mmol9-acridine formylhydrazine (2) is dissolved in 15ml dehydrated alcohol, it is heated to reflux 1h, precipitate out yellow powder, namely obtaining target product 2-furyl-9-acridine acylhydrazone (3) after described yellow powder and recrystallized from acetonitrile after sucking filtration, its gained productivity is 78%.
Embodiment 2
Fig. 1 is the method route schematic diagram that the present invention prepares described acridine acylhydrazone.In conjunction with Fig. 1, the preparation method of acridine acylhydrazone of the present invention comprises the following specific steps that:
1) with 22g9-acridine formic acid for raw material, 300mlSOCl2As solvent, Hybrid Heating backflow 5h does acylation reaction, and solvent is then evaporated under reduced pressure, and namely gained thick white shape solid is not separated obtains compound 9-acridine formyl chloride (1), and its gained productivity is 98.2%；
2) being dissolved in 300ml chloroform by 22g9-acridine formyl chloride (1), drip 30ml hydrazine hydrate, prepare 9-acridine formylhydrazine (2) after back flow reaction 3h, its gained productivity is 85%；
3) 1g furtural is added after 2.9g9-acridine formylhydrazine (2) is dissolved in 150ml dehydrated alcohol, it is heated to reflux 2h, precipitate out yellow powder, namely obtaining target product 2-furyl-9-acridine acylhydrazone (3) after described yellow powder and recrystallized from acetonitrile after sucking filtration, its gained productivity is 82%.
The structural formula of the acridine acylhydrazone that above-described embodiment 1 and 2 is prepared into is:
The chemical name of this acridine acylhydrazone is 2-furyl-9-acridine acylhydrazone, and molecular formula is C19H13N3O2, relative molecular weight is 315.33.Obtaining its physicochemical property through physico-chemical analysis instrument is: yellow crystals, FAB-MSm/z:316 ([M+H]+),1HNMR(DMSO-d6, 400MHz), δ: 9.26 (s, 1H ,=CH), 8.41 (br, s, 1H ,-NH), 8.15～8.20 (m, 3H, ArH), 7.63 (s, 2H, ArH), 7.57 (s, 1H, ArH), 7.33 (s, 1H, ArH), 7.40 (d, 2H, J=8.40Hz, furan nucleus), 6.30 (m, 1H, furan nucleus), 6.26 (d, 1H, J=8.40Hz, furan nucleuss).
Embodiment 3
The acridine acylhydrazone that above-described embodiment 1 and 2 prepares is carried out anti tumor activity in vitro experiment:
Adopt MTT method, carry out vitro cytotoxicity mensuration.Target product 2-furyl-9-acridine acylhydrazone embodiment 1 and 2 obtained distinguishes 24 hours action time with urinary bladder carcinoma T24 cell line strain, people's gastric cancer cell line MGC-803, hepatocarcinoma BEL-7404 cell strain, pulmonary carcinoma NCI-H460 cell, the medium effective concentration of tumor cell line is carried out contrast experiment when identical tumor cell line and identical action time by the acridine acylhydrazone of the present invention and other antitumor drug, and result is as shown in Figure 2.
From the result of embodiment 3 it can be seen that the acridine acylhydrazone of the present invention shows through anticancer experiment in vitro, this compound has strong anti-tumor activity.2-furyl-9-acridine the acylhydrazone of the present invention can make one or more medicines in antineoplastic injection, tablet, pill, capsule, suspending agent or Emulsion.Gastric carcinoma cells, hepatoma cell strain, human lung carcinoma cell, human bladder cancer cell's strain etc. can be produced very high inhibition effect by the acridine acylhydrazone of the present invention and the medicine prepared thereof.Can obtaining from the correction data of Fig. 2, it is the most obvious to the inhibitory action of urinary bladder carcinoma T24 cell line strain, treats bladder cancer better effects if, and the present invention researchs and develops new antitumor drug to provide new thinking.
Although embodiment of the present invention are disclosed as above, but listed utilization that it is not restricted in description and embodiment, it can be applied to various applicable the field of the invention completely, for those skilled in the art, it is easily achieved other amendment, therefore, under the general concept limited without departing substantially from claim and equivalency range, the present invention is not limited to specific details.
Claims (3)
1. an acridine acylhydrazone, it is characterised in that the structural formula of described acridine acylhydrazone is:
The chemical name of described acridine acylhydrazone is: 2-furyl-9-acridine acylhydrazone；
The molecular formula of described acridine acylhydrazone is: C19H13N3O2；
The relative molecular weight of described acridine acylhydrazone is: 315.33.
2. the preparation method of an acridine acylhydrazone as claimed in claim 1, it is characterised in that comprise the steps:
1) being added in thionyl chloride by 9-acridine benzoic acid, be heated to reflux 5h, solvent is evaporated under reduced pressure, namely gained thick white shape solid is not separated obtains compound 9-acridine formyl chloride (1)；
2) 9-acridine formyl chloride (1) is dissolved in chloroform, drips hydrazine hydrate, after back flow reaction 2-3h, prepare 9-acridine formylhydrazine (2)；
3) furtural is added after 9-acridine formylhydrazine (2) is dissolved in dehydrated alcohol, it is heated to reflux 1-2h, precipitate out yellow powder, after sucking filtration, after described yellow powder and recrystallized from acetonitrile, namely obtain target product 2-furyl-9-acridine acylhydrazone (3).
3. the purposes of an acridine acylhydrazone as claimed in claim 1, it is characterized in that, described acridine acylhydrazone is as the purposes preparing anti-bladder cancer T24 cell strain, gastric cancer cell line MGC-803, hepatocarcinoma BEL-7404 cell strain or pulmonary carcinoma NCI-H460 cell drug.
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Effective date of registration: 20201224 Address after: 344700 service center of Nancheng Industrial Park, Fuzhou City, Jiangxi Province Patentee after: Nancheng county industry and Technology Innovation Investment Development Co.,Ltd. Address before: Room 503, building 3, No. 133, development avenue, Tongxiang Economic Development Zone, Tongxiang City, Jiaxing City, Zhejiang Province Patentee before: ZHEJIANG MAIZHI NETWORK TECHNOLOGY Co.,Ltd. |
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