CN106316939B - N-2-吡啶酰基-脱氢枞胺及其制备方法和应用 - Google Patents
N-2-吡啶酰基-脱氢枞胺及其制备方法和应用 Download PDFInfo
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- CN106316939B CN106316939B CN201610597298.8A CN201610597298A CN106316939B CN 106316939 B CN106316939 B CN 106316939B CN 201610597298 A CN201610597298 A CN 201610597298A CN 106316939 B CN106316939 B CN 106316939B
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- Prior art keywords
- dehydroabietylamine
- ethyl acetate
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- pyridine
- pyridine acyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 48
- 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 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 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
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 6
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 3
- 239000012265 solid product Substances 0.000 claims abstract description 3
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims 1
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- 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
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- 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
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- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
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CN201610597298.8A CN106316939B (zh) | 2016-07-26 | 2016-07-26 | N-2-吡啶酰基-脱氢枞胺及其制备方法和应用 |
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CN201610597298.8A CN106316939B (zh) | 2016-07-26 | 2016-07-26 | N-2-吡啶酰基-脱氢枞胺及其制备方法和应用 |
Publications (2)
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CN106316939A CN106316939A (zh) | 2017-01-11 |
CN106316939B true CN106316939B (zh) | 2019-07-30 |
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Families Citing this family (1)
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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 |
Citations (3)
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 |
-
2016
- 2016-07-26 CN CN201610597298.8A patent/CN106316939B/zh not_active Expired - Fee Related
Patent Citations (3)
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 |
Non-Patent Citations (3)
Title |
---|
(+)-Dehydroabietylamine derivatives target triple-negative breast cancer;Taotao Ling等;《European Journal of Medicinal Chemistry》;20150723;第102卷(第18期);第9-13页 |
N-Benzoyl-12-nitrodehydroabietylamine-7-one, a novel dehydroabietylamine derivative, induces apoptosis and inhibits proliferation in HepG2 cells;Ling-Ying Lin等;《Chemico-Biological Interactions》;20120625;第199卷(第2期);第67页图2,补充数据表S2化合物63 |
实用高效的酰胺键形成试剂;王哲清;《中国医药工业杂志》;20061231;第37卷(第12期);第855-858页 |
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