CN102603561A - Dehydroabietylamine derivatives and application thereof in preparation of antitumor drugs - Google Patents
Dehydroabietylamine derivatives and application thereof in preparation of antitumor drugs Download PDFInfo
- Publication number
- CN102603561A CN102603561A CN2012100358756A CN201210035875A CN102603561A CN 102603561 A CN102603561 A CN 102603561A CN 2012100358756 A CN2012100358756 A CN 2012100358756A CN 201210035875 A CN201210035875 A CN 201210035875A CN 102603561 A CN102603561 A CN 102603561A
- Authority
- CN
- China
- Prior art keywords
- dehydroabietylamine
- application
- preparation
- dehydroabietylamine derivatives
- derivatives
- 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
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses dehydroabietylamine derivatives, which have a structural formula as follow: The dehydroabietylamine derivatives can be used to prepare antitumor drugs.
Description
The application is " dehydroabietylamine derivatives and the application in bactericidal and antineoplastic medicaments thereof " (applying date: on June 18th, 2009; Application number: dividing an application 200910033318.9).
One, technical field
The present invention relates to dehydroabietylamine derivatives Schiff bases compound, and the application in the preparation antitumor drug.
Two, background technology
Extraction or the synthetic different positions on resinous acid C ring and B ring contains the novel compound of different substituents from natural phant; Studying their biological activity can find; Many products have some antibiotic, anticancer, the anti-AIDS that is different from parent compound and other antiviral biological activitys, and this respect has become a research focus at present.From Sequoia sempervirens, separate having obtained the C ring and contain the product that hydroxyl, B ring contain the dehydrogenation fir alkane skeleton of carbonyl, these products have good antitumour activity to lung cancer and mammary cancer; The dehydroabietic acid verivate that contains adjacent diphenol on the C ring is very effective organism free-radical scavengers, has the value of developing new drug; The dehydroabietic acid verivate that two hydroxyls are arranged on C encircles last 11 and 12, finding has good active to fungi and cancer cells.Dehydroabietylamine is the typical composition of rosin Amine D, has optical activity, is a kind of important Forest products, has a wide range of applications at aspects such as papermaking, medicine, agricultural chemicals, chemical industry.Because it is the verivate of sylvic acid, thereby dehydroabietylamine and acetate thereof has certain biological activity, can be used as the anti-algae agent of excellent sterilant, sterilant and mildew-resistant; In addition, owing to have natural chiral carbon in the dehydroabietylamine, thereby it can be used as good optical resolution agent.Dehydroabietylamine also is used as metal inhibitor, crude oil demulsifier, oil dope, tensio-active agent etc.
Three, summary of the invention
Technical problem: the present invention provides one type of dehydroabietylamine derivatives Schiff bases compound, and the application in the preparation antitumor drug.
Technical scheme: dehydroabietylamine derivatives is characterized in that its structural formula representes:
The application of above-mentioned dehydroabietylamine derivatives in the preparation antitumor drug.
Beneficial effect: dehydroabietylamine derivatives Schiff bases compound has extraordinary toxic action to leukemia cell (U-937 and HL-60), ovarian cancer cell (Hey-1B), prostate cancer cell (Pc-3 and Du-145) and small white mouse dermal melanin glucagonoma (B16).
Four, embodiment
Following specific embodiment is to further specify of the present invention, and does not mean that content of the present invention only limits to the scope that is given an actual example.
Embodiment 1
3,5-Dibromosalicylaldehyde 12-glycyl dehydroabietylamine Schiff alkali formula (9) compound that contracts
N
2Protection down; In being furnished with the 250mL four-hole bottle of electronic stirring, tap funnel, reflux condensing tube and TM; Adding 3.42g (10mmol) 12-glycyl dehydroabietylamine is dissolved in the solution of 20mL absolute ethyl alcohol; After being heated to backflow, drip 3.02g (12.2mmol) 3, the 20mL ethanol solution of 5-Dibromosalicylaldehyde.Behind the reaction 3h, cooling suction filtration, oven dry obtain title compound 4.79g, yield 85.9%.Get the sorrel crystal with the absolute ethyl alcohol recrystallization.Fusing point: 231～232 ℃.
FT-IR (KBr compressing tablet) v/cm
-1: 3432.24,3256.56,3081.33,2957.03,2929.89,2864.90,1643.55,1617.19,1565.01,1497.81,1441.52,1375.37,1289.23,1157.06,1093.74,972.44,860.64,775.83,687.60;
1HNMR (400MHZ, CDCl
3) δ: 0.99 (s, 3H), 1.24～1.29 (m, 9H), 1.43～1.50 (m, 3H), 1.65 (s, 3H); 1.92～2.09 (m, 5H), 2.33～2.36 (d, J=12Hz, 1H), 2.84～3.14 (m, 3H), 3.29～3.39 (m; 2H), 5.46 (s, 1H), 6.95 (s, 1H), 7.06 (s, 1H), 7.55～7.56 (d; J=4Hz, 1H), 7.77～7.78 (d, J=4Hz, 1H), 8.47 (s, 1H); EI-MS m/z:603.2 (M+1
+), 540.6,512.6,330.5,302.4,274.4,208.2,185.1; Anal.calcd for C
29H
36Br
2N
2O
2: C57.63, H 6.00, and N 4.63; Found:C 57.93, and H 6.43, and N 4.66
Embodiment 2
Formula 9 described novel dehydroabietylamine derivatives Schiff alkali have been done external antitumour activity measured, ovarian cancer cell (Hey-1B) is as the cancer cells that is screened.Concrete experimental technique is following:
Ovarian cancer cell strain Hey-1B cultivates in the DMEM Zooblast culture medium, has added 10% reinforced bovine serum albumin and microbiotic in the substratum, feeds damp atmosphere, controlled temperature 37 ℃, CO
2Content 5%.Non-radioactive cell proliferation detects the cytoactive of confirming Hey-1B with colourimetry (MTT).
Measuring method with reference to manufacturers (Promega, Madison, operation instructions WI), concise and to the point step is following: in each hole of 96 orifice plates, plant 1 * 10
4Individual cell is cultivated and is used sample preparation after one day, and the concentration of treatment gradient is respectively 2.5,5, and 10,20,40,80 μ g/mL cultivated 48 hours.After cultivating end, (be diluted to 40% with 1 * PBS, v/v), 37 ℃ are continued to cultivate 2 hours, use 96 orifice plates to read the plate device at last and detect light absorption ratio OD at the 490nm place in each hole, to add 50 μ L Cell Titer 96Aqueous reagent
490(full wavelength scanner declines and coils analyser Spectra Max 340).The average OD value in each hole of gained is calculated its inhibition rate of tumor cell according to control samples by statistical test.
Experimental result: sample dissolution is in the DMEM Zooblast culture medium, and the cancer cells of growth obviously is suppressed, the Hey-1B apoptosis.
Claims (2)
1. dehydroabietylamine derivatives is characterized in that its structural formula representes:
2. the application of the described dehydroabietylamine derivatives of claim 1 in the preparation antitumor drug.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210035875.6A CN102603561B (en) | 2009-06-18 | 2009-06-18 | Dehydroabietylamine derivatives and application thereof in preparation of antitumor drugs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210035875.6A CN102603561B (en) | 2009-06-18 | 2009-06-18 | Dehydroabietylamine derivatives and application thereof in preparation of antitumor drugs |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910033318A Division CN101580477B (en) | 2009-06-18 | 2009-06-18 | Dehydroabietylamine derivatives and application thereof in bactericidal and antineoplastic medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102603561A true CN102603561A (en) | 2012-07-25 |
| CN102603561B CN102603561B (en) | 2014-03-26 |
Family
ID=46521411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210035875.6A Expired - Fee Related CN102603561B (en) | 2009-06-18 | 2009-06-18 | Dehydroabietylamine derivatives and application thereof in preparation of antitumor drugs |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102603561B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113368A (en) * | 2013-02-04 | 2013-05-22 | 南京林业大学 | Hexahydro-phenanthro tetrahydroindolizine compounds, and preparation method and application thereof |
| CN104961673A (en) * | 2015-06-26 | 2015-10-07 | 南京林业大学 | Dipyridyl dehydroabietylamine Schiff base compound and preparing method thereof |
| CN106220570A (en) * | 2016-07-26 | 2016-12-14 | 南京林业大学 | Imidazoles dehydroabietylamine amides compound and its preparation method and application |
| CN106220559A (en) * | 2016-07-26 | 2016-12-14 | 南京林业大学 | N 3 pyridine acyl dehydroabietylamine derivatives and its preparation method and application |
| CN106220558A (en) * | 2016-07-26 | 2016-12-14 | 南京林业大学 | N 4 pyridine acyl dehydroabietylamine derivatives and its preparation method and application |
| CN106316939A (en) * | 2016-07-26 | 2017-01-11 | 南京林业大学 | N-2-pyridine-acyl-dehydroabietylamine, preparation method and application thereof |
| CN108299330A (en) * | 2018-02-06 | 2018-07-20 | 桂林医学院 | Dehydrogenation Cong Suan oxazolidinone derivatives and its preparation method and application |
| CN109251154A (en) * | 2018-10-25 | 2019-01-22 | 广西民族大学 | A kind of dehydroabietic acid sulfonyl urea compound and the preparation method and application thereof |
| CN115819268A (en) * | 2022-08-22 | 2023-03-21 | 浙江工业大学 | C-14 amide substituted dehydroabietic acid derivatives, and preparation method and application thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1669347A1 (en) * | 2004-12-10 | 2006-06-14 | Helm AG | Process for the preparation of 3-¬(4-fluorophenyl) sulfonyl|-2-hydroxy-2-methyl propionic acid |
| CN101003548B (en) * | 2006-12-12 | 2010-09-08 | 中国林业科学研究院林产化学工业研究所 | Rosinyl diterpene modified alpha - phosphoramidate, preparation method, and application for anti tumors |
| CN101219949B (en) * | 2007-11-30 | 2010-11-03 | 中国林业科学研究院林产化学工业研究所 | Process for producing abietic acid |
-
2009
- 2009-06-18 CN CN201210035875.6A patent/CN102603561B/en not_active Expired - Fee Related
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113368A (en) * | 2013-02-04 | 2013-05-22 | 南京林业大学 | Hexahydro-phenanthro tetrahydroindolizine compounds, and preparation method and application thereof |
| CN104961673A (en) * | 2015-06-26 | 2015-10-07 | 南京林业大学 | Dipyridyl dehydroabietylamine Schiff base compound and preparing method thereof |
| CN106316939B (en) * | 2016-07-26 | 2019-07-30 | 南京林业大学 | N-2- pyridine acyl-dehydroabietylamine and its preparation method and application |
| CN106220559A (en) * | 2016-07-26 | 2016-12-14 | 南京林业大学 | N 3 pyridine acyl dehydroabietylamine derivatives and its preparation method and application |
| CN106220558A (en) * | 2016-07-26 | 2016-12-14 | 南京林业大学 | N 4 pyridine acyl dehydroabietylamine derivatives and its preparation method and application |
| CN106316939A (en) * | 2016-07-26 | 2017-01-11 | 南京林业大学 | N-2-pyridine-acyl-dehydroabietylamine, preparation method and application thereof |
| CN106220570B (en) * | 2016-07-26 | 2019-07-30 | 南京林业大学 | Imidazoles dehydroabietylamine amides compound and its preparation method and application |
| CN106220570A (en) * | 2016-07-26 | 2016-12-14 | 南京林业大学 | Imidazoles dehydroabietylamine amides compound and its preparation method and application |
| CN106220559B (en) * | 2016-07-26 | 2019-07-30 | 南京林业大学 | N-3- pyridine acyl-dehydroabietylamine derivatives and its preparation method and application |
| CN106220558B (en) * | 2016-07-26 | 2019-10-18 | 南京林业大学 | N-4- pyridine acyl-dehydroabietylamine derivatives and its preparation method and application |
| CN108299330A (en) * | 2018-02-06 | 2018-07-20 | 桂林医学院 | Dehydrogenation Cong Suan oxazolidinone derivatives and its preparation method and application |
| CN108299330B (en) * | 2018-02-06 | 2021-02-12 | 桂林医学院 | Dehydroabietic acid oxazolidinone derivative and preparation method and application thereof |
| CN109251154A (en) * | 2018-10-25 | 2019-01-22 | 广西民族大学 | A kind of dehydroabietic acid sulfonyl urea compound and the preparation method and application thereof |
| CN115819268A (en) * | 2022-08-22 | 2023-03-21 | 浙江工业大学 | C-14 amide substituted dehydroabietic acid derivatives, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102603561B (en) | 2014-03-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102603561B (en) | Dehydroabietylamine derivatives and application thereof in preparation of antitumor drugs | |
| CN101580477B (en) | Dehydroabietylamine derivatives and application thereof in bactericidal and antineoplastic medicaments | |
| Li et al. | Design, synthesis, and anticancer evaluation of novel indole derivatives of ursolic acid as potential topoisomerase II inhibitors | |
| Almansour et al. | Facile, regio-and diastereoselective synthesis of spiro-pyrrolidine and pyrrolizine derivatives and evaluation of their antiproliferative activities | |
| Pertino et al. | Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid | |
| Sisto et al. | Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. pylori strains and AGS cell proliferation | |
| Ouyang et al. | Mollicellins O–R, four new depsidones isolated from the endophytic fungus Chaetomium sp. Eef-10 | |
| Cao et al. | Synthesis, characterization, and biological evaluations of 1, 3, 5-triazine derivatives of metformin cyclization with berberine and magnolol in the presence of sodium methylate | |
| Bu et al. | Synthesis of ergosterol peroxide conjugates as mitochondria targeting probes for enhanced anticancer activity | |
| Glamočlija et al. | Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone | |
| Mungara et al. | Synthesis and antiproliferative activity of novel α-aminophosphonates | |
| CN107266348A (en) | Preparation, structure and the purposes of the indolecarboxaldehyde Schiff base of 4-acetylbiphenyl hydrazone 3 | |
| He et al. | Synthesis, characterization and cytotoxicity of new rotundic acid derivatives | |
| Oniciuc et al. | Benzoquinoline derivatives: an attractive approach to newly small molecules with anticancer activity | |
| Grigoropoulou et al. | Synthesis and antiproliferative activity of novel dehydroabietic acid-chalcone hybrids | |
| Cai et al. | Design, synthesis, and SAR of novel 2-glycinamide cyclohexyl sulfonamide derivatives against Botrytis cinerea | |
| Kretschmer et al. | Synthesis and pharmacological in vitro investigations of novel shikonin derivatives with a special focus on cyclopropane bearing derivatives | |
| Escarcena et al. | Diterpenes synthesized from the natural serrulatane leubethanol and their in vitro activities against mycobacterium tuberculosis | |
| Assiri et al. | Synthesis and anticancer activity of some novel diethyl {(chromonyl/pyrazolyl)[(4-oxo-2-phenyl-quinazolin-3 (4 H)-yl) amino] methyl} phosphonates | |
| Karcev et al. | Selective and reversible 1, 3-dipolar cycloaddition of 2-(2-oxoindoline-3-ylidene) acetates with nitrones in the synthesis of functionalized spiroisoxazolidines | |
| Lou et al. | Natural antioxidants, tyrosinase and acetylcholinesterase inhibitors from Cercis glabra leaves | |
| CN107827914A (en) | A kind of copper schiff bases complex and its preparation method and application | |
| Liang et al. | Novel Indole-Containing Hybrids Derived from Millepachine: Synthesis, Biological Evaluation and Antitumor Mechanism Study | |
| US9822071B2 (en) | Anticancer miliusane lactams | |
| Song et al. | Synthesis, biomacromolecular interactions, photodynamic NO releasing and cellular imaging of two [RuCl (qn)(Lbpy)(NO)] X complexes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into 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: 20140326 Termination date: 20150618 |
|
| EXPY | Termination of patent right or utility model |