CN102603561B - 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
- CN102603561B CN102603561B CN201210035875.6A CN201210035875A CN102603561B CN 102603561 B CN102603561 B CN 102603561B CN 201210035875 A CN201210035875 A CN 201210035875A CN 102603561 B CN102603561 B CN 102603561B
- Authority
- CN
- China
- Prior art keywords
- dehydroabietylamine
- application
- dehydroabietylamine derivatives
- derivatives
- preparation
- 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.)
- Expired - Fee Related
Links
- 0 CC(C)c(cc(CCC1C2(C)CCCC1(C)C*)c2c1)c1N=Cc1cc(Br)cc(Br)c1O Chemical compound CC(C)c(cc(CCC1C2(C)CCCC1(C)C*)c2c1)c1N=Cc1cc(Br)cc(Br)c1O 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (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 (applying date: on June 18th, 2009 of the application > > in bactericidal and antineoplastic medicaments thereof; Application number: dividing an application 200910033318.9).
One, technical field
The present invention relates to dehydroabietylamine derivatives Schiff alkaloid compound, and the application in preparing antitumor drug.
Two, background technology
The novel compound that extraction or the synthetic different positions on resinous acid C ring and B ring contains different substituents from natural phant, studying their biological activity can find, many products have some antibacterial, anticancer, the anti-AIDS that is different from parent compound and other antiviral biological activitys, and this respect has become a study hotspot at present.Separatedly from Sequoia sempervirens obtained the product that C ring contains the dehydrogenation fir alkane skeleton that hydroxyl, B ring contain carbonyl, these products have good antitumour activity to lung cancer and mammary cancer; The dehydroabietic acid derivative that contains adjacent diphenol on C ring, is very effective organism free-radical scavengers, has the value of developing new drug; C has the dehydroabietic acid derivative of two hydroxyls on encircling upper 11 and 12, finding has good activity to fungi and cancer cells.Dehydroabietylamine is the typical composition of rosin Amine D, has optical activity, is a kind of important Forest products, at aspects such as papermaking, medicine, agricultural chemicals, chemical industry, has a wide range of applications.Because it is the derivative of sylvic acid, thereby dehydroabietylamine and acetate thereof has certain biological activity, can be used as excellent sterilant, sterilant and mildew-resistant algaecide; In addition, owing to there being natural chiral carbon in dehydroabietylamine, thereby it can be used as good optical resolution agent.Dehydroabietylamine is also used as metal inhibitor, crude oil demulsifier, lubricating oil additive, tensio-active agent etc.
Three, summary of the invention
Technical problem: the invention provides a class dehydroabietylamine derivatives Schiff alkaloid compound, and the application in preparing antitumor drug.
Technical scheme: dehydroabietylamine derivatives, is characterized in that its structural formula represents:
The application of above-mentioned dehydroabietylamine derivatives in preparing antitumor drug.
Beneficial effect: dehydroabietylamine derivatives Schiff alkaloid 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 illustrate of the present invention, and does not mean that content of the present invention only limits to the scope of example.
Embodiment 1
3,5-Dibromosalicylaldehyde contracting 12-glycyl dehydroabietylamine Schiff alkali formula (9) compound
N
2under protection; in being furnished with the 250mL four-hole bottle of electric stirring, dropping funnel, reflux condensing tube and thermometer; add 3.42g (10mmol) 12-glycyl dehydroabietylamine to be dissolved in the solution of 20mL dehydrated alcohol; after being heated to reflux; drip 3.02g (12.2mmol) 3, the 20mL ethanol solution of 5-Dibromosalicylaldehyde.After reaction 3h, cooling suction filtration, oven dry obtain title compound 4.79g, yield 85.9%.With dehydrated alcohol recrystallization, obtain sorrel crystal.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
Novel dehydroabietylamine derivatives Schiff alkali described in formula 9 has been done to Anticancer Activity in vitro mensuration, and ovarian cancer cell (Hey-1B) is as screened cancer cells.Concrete experimental technique is as follows:
Ovarian Cancer Cells Hey-1B cultivates in DMEM Zooblast culture medium, has added 10% reinforced bovine serum albumin and microbiotic in substratum, passes into damp atmosphere, control temperature 37 ℃, CO
2content 5%.Non-radioactive cell proliferation detects the cytoactive of determining Hey-1B with colorimetry (MTT).
Measuring method is with reference to the operation instructions of manufacturers (Promega, Madison, WI), and concise and to the point step is as follows: in each hole of 96 orifice plates, plant into 1 * 10
4individual cell, cultivates and uses sample preparation after one day, and concentration for the treatment of gradient is respectively 2.5,5, and 10,20,40,80 μ g/mL cultivate 48 hours.After cultivation finishes, (with 1 * PBS, be diluted to 40%, v/v), 37 ℃ are continued to cultivate 2 hours, finally use 96 orifice plates to read plate device and at 490nm place, detect light absorption ratio OD 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 sample by statistical test.
Experimental result: sample dissolution is in DMEM Zooblast culture medium, and the cancer cells of growth is obviously suppressed, Hey-1B apoptosis.
Claims (2)
1. dehydroabietylamine derivatives, is characterized in that its structural formula represents:
2. the application of dehydroabietylamine derivatives claimed in claim 1 in preparing 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 CN102603561A (en) | 2012-07-25 |
| CN102603561B true 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) |
Families Citing this family (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 |
| CN106220570B (en) * | 2016-07-26 | 2019-07-30 | 南京林业大学 | Imidazoles dehydroabietylamine amides compound 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 |
| 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 |
| 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 |
| CN108299330B (en) * | 2018-02-06 | 2021-02-12 | 桂林医学院 | Dehydroabietic acid oxazolidinone derivative and preparation method and application thereof |
| CN109251154B (en) * | 2018-10-25 | 2021-01-05 | 广西民族大学 | Dehydroabietic acid sulfonylurea compound and preparation method and application thereof |
| CN115819268B (en) * | 2022-08-22 | 2024-11-01 | 浙江工业大学 | C-14 amide substituted dehydroabietic acid derivative, and preparation method and application thereof |
Citations (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 |
| CN101003548A (en) * | 2006-12-12 | 2007-07-25 | 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 |
| CN101219949A (en) * | 2007-11-30 | 2008-07-16 | 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
Patent Citations (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 |
| CN101003548A (en) * | 2006-12-12 | 2007-07-25 | 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 |
| CN101219949A (en) * | 2007-11-30 | 2008-07-16 | 中国林业科学研究院林产化学工业研究所 | Process for producing abietic acid |
Non-Patent Citations (6)
| Title |
|---|
| A.G.Tolstikov等.The povarov reaction of cyclopentadiene with imines from methyl 12-amino-dehydroabietate.《Heteroatom Chemistry》.2005,第16卷(第7期),605-612. |
| Synthesis and biological activity of Schiff bases derived from dehydroabietylamine and benzaldehyde derivatives;Xiaoping Zhao等;《Organic synthesis》;20071231;第80卷(第8期);1373-1375 * |
| The povarov reaction of cyclopentadiene with imines from methyl 12-amino-dehydroabietate;A.G.Tolstikov等;《Heteroatom Chemistry》;20051231;第16卷(第7期);605-612 * |
| Xiaoping Zhao等.Synthesis and biological activity of Schiff bases derived from dehydroabietylamine and benzaldehyde derivatives.《Organic synthesis》.2007,第80卷(第8期),1373-1375. |
| 含氟脱氢枞胺Schiff碱的合成及抑菌活性;饶小平等;《林产化学与工业》;20070430;第27卷(第2期);97-99 * |
| 饶小平等.含氟脱氢枞胺Schiff碱的合成及抑菌活性.《林产化学与工业》.2007,第27卷(第2期),97-99. |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102603561A (en) | 2012-07-25 |
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 | |
| Xu et al. | Synthesis and antitumor activity of novel 2-substituted indoline imidazolium salt derivatives | |
| Zainab et al. | Novel polyhydroquinoline-hydrazide-linked Schiff’s base derivatives: multistep synthesis, antimicrobial, and calcium-channel-blocking activities | |
| Li et al. | Design, synthesis, and anticancer evaluation of novel indole derivatives of ursolic acid as potential topoisomerase II inhibitors | |
| US9211333B2 (en) | Anti-cancer agents synthesized based on miliusane compounds | |
| Sisto et al. | Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. pylori strains and AGS cell proliferation | |
| CN101967135B (en) | 4-aryl coumarin compound and preparation method and application thereof | |
| 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 | |
| CN103058960A (en) | Cabazitaxel polymorphic form and preparation method thereof | |
| Li et al. | Synthesis and anticancer activities of glycyrrhetinic acid derivatives | |
| Meza-Morales et al. | A new family of homoleptic copper complexes of curcuminoids: Synthesis, characterization and biological properties | |
| Oniciuc et al. | Benzoquinoline derivatives: an attractive approach to newly small molecules with anticancer activity | |
| CN108299398B (en) | Carbazole-containing quinazoline derivative with anti-tumor activity and pharmaceutical application thereof | |
| 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 | |
| Li et al. | Synthesis and biological evaluation of strictosamide derivatives with improved antiviral and antiproliferative activities | |
| Pathan et al. | An efficient one pot I2/DMSO mediated synthesis and molecular modeling of novel fused pyrimidine‐chromone hybrids bearing potential antibacterial and antifungal pharmacophores sites | |
| US9822071B2 (en) | Anticancer miliusane lactams | |
| Sondhi et al. | Synthesis, anti‐inflammatory, and anticancer activity evaluation of some heterocyclic amidine and bis‐amidine derivatives | |
| CN103396437B (en) | Two (Tricyclohexyltin) dicarboxylic esters and preparation method and application | |
| CN107494553B (en) | Agricultural bactericide derived from gallic acid and application | |
| CN107698648B (en) | Naphthylimide derivative containing cholesterol and synthesis and application thereof | |
| Aiello et al. | Synthesis and antioxidative properties of 1, 2, 3, 4-tetrahydropyridine derivatives with different substituents in 4-position | |
| CN111039844A (en) | Polysubstituted arylpyrrole compounds |
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 |