CN106220559A - N‑3‑吡啶酰基‑脱氢枞胺衍生物及其制备方法和应用 - Google Patents
N‑3‑吡啶酰基‑脱氢枞胺衍生物及其制备方法和应用 Download PDFInfo
- Publication number
- CN106220559A CN106220559A CN201610597221.0A CN201610597221A CN106220559A CN 106220559 A CN106220559 A CN 106220559A CN 201610597221 A CN201610597221 A CN 201610597221A CN 106220559 A CN106220559 A CN 106220559A
- Authority
- CN
- China
- Prior art keywords
- dehydroabietylamine
- ethyl acetate
- reaction
- preparation
- 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
- 238000002360 preparation method Methods 0.000 title abstract description 9
- -1 3 pyridine acyl dehydroabietylamine derivatives Chemical class 0.000 title abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 64
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 9
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims abstract description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 5
- 238000004090 dissolution Methods 0.000 claims abstract description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 3
- 239000012265 solid product Substances 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 7
- 239000000047 product Substances 0.000 abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 abstract description 6
- 230000004071 biological effect Effects 0.000 abstract description 4
- 235000002639 sodium chloride Nutrition 0.000 abstract description 4
- 239000011780 sodium chloride Substances 0.000 abstract description 4
- 231100000614 poison Toxicity 0.000 abstract description 2
- 230000007096 poisonous effect Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical class CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002814 niacins Chemical class 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 230000001629 suppression Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 238000011160 research Methods 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 241001597008 Nomeidae Species 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000012531 culture fluid Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 238000005554 pickling Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 description 1
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000222727 Leishmania donovani Species 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 241000222481 Schizophyllum commune Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- WREBNDYJJMUWAO-LWYYNNOASA-N [(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 WREBNDYJJMUWAO-LWYYNNOASA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 description 1
- 229940118781 dehydroabietic acid Drugs 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
化合物 | IC50/μmol/L |
1 | 11.69 |
2 | 10.87 |
3 | 15.87 |
化合物 | IC50/μmol/L |
1 | 28.45 |
2 | 8.52 |
3 | 11.97 |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610597221.0A CN106220559B (zh) | 2016-07-26 | 2016-07-26 | N-3-吡啶酰基-脱氢枞胺衍生物及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610597221.0A CN106220559B (zh) | 2016-07-26 | 2016-07-26 | N-3-吡啶酰基-脱氢枞胺衍生物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106220559A true CN106220559A (zh) | 2016-12-14 |
CN106220559B CN106220559B (zh) | 2019-07-30 |
Family
ID=57533374
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610597221.0A Expired - Fee Related CN106220559B (zh) | 2016-07-26 | 2016-07-26 | N-3-吡啶酰基-脱氢枞胺衍生物及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106220559B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113773288A (zh) * | 2021-09-30 | 2021-12-10 | 南京林业大学 | 一类含杂环的脱氢枞基甲酰胺类化合物及其制备方法和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101580477A (zh) * | 2009-06-18 | 2009-11-18 | 南京林业大学 | 脱氢枞胺衍生物及其在杀菌抗肿瘤药物中的应用 |
WO2012078667A2 (en) * | 2010-12-06 | 2012-06-14 | The Penn State Research Foundation | Compositions and methods relating to proliferative diseases |
CN102603561A (zh) * | 2009-06-18 | 2012-07-25 | 南京林业大学 | 脱氢枞胺衍生物及其在制备抗肿瘤药物中的应用 |
CN102807495A (zh) * | 2012-08-22 | 2012-12-05 | 中国林业科学研究院林产化学工业研究所 | 3-氯-2-羟丙基二甲基脱氢枞基氯化铵及其制备方法 |
CN103922961A (zh) * | 2014-04-09 | 2014-07-16 | 南京林业大学 | 烷基二醇二苯醚脱氢枞胺双希夫碱化合物及其合成方法 |
-
2016
- 2016-07-26 CN CN201610597221.0A patent/CN106220559B/zh not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101580477A (zh) * | 2009-06-18 | 2009-11-18 | 南京林业大学 | 脱氢枞胺衍生物及其在杀菌抗肿瘤药物中的应用 |
CN102603561A (zh) * | 2009-06-18 | 2012-07-25 | 南京林业大学 | 脱氢枞胺衍生物及其在制备抗肿瘤药物中的应用 |
WO2012078667A2 (en) * | 2010-12-06 | 2012-06-14 | The Penn State Research Foundation | Compositions and methods relating to proliferative diseases |
CN102807495A (zh) * | 2012-08-22 | 2012-12-05 | 中国林业科学研究院林产化学工业研究所 | 3-氯-2-羟丙基二甲基脱氢枞基氯化铵及其制备方法 |
CN103922961A (zh) * | 2014-04-09 | 2014-07-16 | 南京林业大学 | 烷基二醇二苯醚脱氢枞胺双希夫碱化合物及其合成方法 |
Non-Patent Citations (9)
Title |
---|
CHAO-XIANG LIU等: "Antitumor and scavenging radicals activities of some polyphenols related to dehydroabietylamine derivatives", 《JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH》 * |
LING-YING LIN等: "N-Benzoyl-12-nitrodehydroabietylamine-7-one, a novel dehydroabietylamine derivative, induces apoptosis and inhibits proliferation in HepG2 cells", 《CHEMICO-BIOLOGICAL INTERACTIONS》 * |
M. MZLFTIC M. D: "ESSAY ON ANTIBIOTIC PROPERTIES OF ABIETYL COMPOUNDS", 《QUARTERLY JOURNAL OF CRUDE DRUG RESEARCH》 * |
TAOTAO LING等: "(+)-Dehydroabietylamine derivatives target triple-negative breast cancer", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
YONG CHEN等: "Synthesis and antitumour activities of a novel class of dehydroabietylamine derivatives", 《NATURAL PRODUCT RESEARCH》 * |
王哲清: "实用高效的酰胺键形成试剂", 《中国医药工业杂志》 * |
田伟生,等: "《有机合成中的副反应-成功合成设计指南》", 31 March 2006 * |
谢建翔,等: "脱氢枞胺衍生物DHAA-urea对人肝癌HepG2细胞糖代谢的抑制作用", 《中国药科大学学报》 * |
马宇衡: "《有机合成反应速查手册》", 30 April 2009 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113773288A (zh) * | 2021-09-30 | 2021-12-10 | 南京林业大学 | 一类含杂环的脱氢枞基甲酰胺类化合物及其制备方法和应用 |
CN113773288B (zh) * | 2021-09-30 | 2023-09-29 | 南京林业大学 | 一类含杂环的脱氢枞基甲酰胺类化合物及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN106220559B (zh) | 2019-07-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Jarrahpour et al. | Synthesis of novel β-lactams bearing an anthraquinone moiety, and evaluation of their antimalarial activities | |
KR20020063277A (ko) | 살균제로서의 트리플루오로메틸피롤카복사미드 및트리플루오로메틸피롤티오아미드 | |
EP3075729B1 (en) | Pyrazole amide compound and application thereof | |
CN103071423A (zh) | 吡啶氨基甲酰季铵盐表面活性剂及其制备方法 | |
Xu et al. | Natural products-based insecticidal agents 5. Design, semisynthesis and insecticidal activity of novel 4′-substituted benzenesulfonate derivatives of 4-deoxypodophyllotoxin against Mythimna separata Walker in vivo | |
CN106220570B (zh) | 咪唑脱氢枞胺酰胺类化合物及其制备方法和应用 | |
CN106220558B (zh) | N-4-吡啶酰基-脱氢枞胺衍生物及其制备方法和应用 | |
CN104961781B (zh) | 2‑脱氧‑2‑异硫氰酸酯‑1,3,4,6‑四‑O‑苄基‑β‑D‑吡喃葡萄糖及合成方法与用途 | |
CN104447782A (zh) | 溴代去甲斑蝥素单酸苄酯及其合成方法和应用 | |
CN111642504A (zh) | 一种喹啉4-位羟基吡啶甲酸酯类化合物及其防治水稻稻瘟病菌的用途 | |
CN106045938B (zh) | 一种去氢枞酸基b环并噻唑‑硫脲化合物的合成方法 | |
CN106316939B (zh) | N-2-吡啶酰基-脱氢枞胺及其制备方法和应用 | |
CN106220559A (zh) | N‑3‑吡啶酰基‑脱氢枞胺衍生物及其制备方法和应用 | |
Iniama et al. | Antimicrobial activities of synthesized Zinc (II) mixed ligand complexes derived from 2-acetylpyridine-4-phenylsemicarbazone and nitrogensulphurmonodentate ligands | |
CN106397254A (zh) | 手性8‑羟基升补身烷倍半萜酰胺类化合物及作为农用杀菌剂的用途 | |
CN105669559A (zh) | 蒎烷基吡唑类化合物及其合成方法与应用 | |
CN102718731A (zh) | 4/5-甲基-1,2,3-噻二唑甲酸衍生物及制备方法 | |
CN107459490A (zh) | 吩嗪‑1‑甲酰胺类化合物及其应用 | |
CN103626748A (zh) | 一种含吡啶的噁二唑类化合物及其制备与应用 | |
CN102850341B (zh) | 一种噻二唑类化合物及其制备与应用 | |
CN107721956B (zh) | 苯并丁内酯类衍生物、合成方法及其制备杀菌剂的应用 | |
CN103030608B (zh) | 一种n-(5-脱氢枞基-[1,3,4]噻二唑-2-基)-芳酰胺衍生物、其制备方法及其应用 | |
CN105859618B (zh) | 含环烷基腈基团的异喹啉‑1,3(2h,4h)‑二酮及其制法和用途 | |
CN112624973B (zh) | 一种羧酸酯类化合物及其应用 | |
Zhang et al. | Synthesis and biological activity of novel anthranilic diamides containing N-substituted arylmethylene moieties |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20161214 Assignee: SPECTRUM DETECTION (SUZHOU) Co.,Ltd. Assignor: Nanjing Forestry University Contract record no.: X2019320000186 Denomination of invention: N-3-pyridine acyl-dehydroabietylamine derivative as well as preparation method and application thereof Granted publication date: 20190730 License type: Common License Record date: 20191029 |
|
EC01 | Cancellation of recordation of patent licensing contract |
Assignee: SPECTRUM DETECTION (SUZHOU) Co.,Ltd. Assignor: NANJING FORESTRY University Contract record no.: X2019320000186 Date of cancellation: 20201223 |
|
EC01 | Cancellation of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20161214 Assignee: SPECTRUM DETECTION (SUZHOU) Co.,Ltd. Assignor: NANJING FORESTRY University Contract record no.: X2020320000405 Denomination of invention: N-3-pyridyl-dehydroabietylamine derivatives and their preparation and Application Granted publication date: 20190730 License type: Common License Record date: 20201228 |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190730 Termination date: 20210726 |
|
CF01 | Termination of patent right due to non-payment of annual fee |