CN103880701B - O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗人宫颈鳞状癌药物中的应用 - Google Patents
O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗人宫颈鳞状癌药物中的应用 Download PDFInfo
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- CN103880701B CN103880701B CN201410095084.1A CN201410095084A CN103880701B CN 103880701 B CN103880701 B CN 103880701B CN 201410095084 A CN201410095084 A CN 201410095084A CN 103880701 B CN103880701 B CN 103880701B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 229960000581 salicylamide Drugs 0.000 title claims abstract description 22
- 239000003814 drug Substances 0.000 title claims abstract description 13
- 206010041823 squamous cell carcinoma Diseases 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 substituted-phenyl Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000000259 anti-tumor effect Effects 0.000 abstract description 5
- 239000002246 antineoplastic agent Substances 0.000 abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 238000011160 research Methods 0.000 abstract description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 31
- 239000011737 fluorine Substances 0.000 description 27
- 229910052731 fluorine Inorganic materials 0.000 description 27
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000012937 correction Methods 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 150000001263 acyl chlorides Chemical class 0.000 description 12
- 235000015097 nutrients Nutrition 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 240000000203 Salix gracilistyla Species 0.000 description 7
- 229960000616 diflunisal Drugs 0.000 description 7
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- NQBWNECTZUOWID-QSYVVUFSSA-N cinnamyl cinnamate Chemical compound C=1C=CC=CC=1\C=C/C(=O)OC\C=C\C1=CC=CC=C1 NQBWNECTZUOWID-QSYVVUFSSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 0 Cc(cc1)ccc1NC(C(C(*[C@@](C=Cc1ccccc1)O)CC1)=CCC1c(ccc(F)c1)c1F)=O Chemical compound Cc(cc1)ccc1NC(C(C(*[C@@](C=Cc1ccccc1)O)CC1)=CCC1c(ccc(F)c1)c1F)=O 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 108010019160 Pancreatin Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229940059260 amidate Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 238000006482 condensation reaction Methods 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
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- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
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- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
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- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
化合物 | R | Q1 | Q2 | Q3 | Q4 | Q5 |
Ⅰ-1 | / | H | H | H | H | H |
Ⅰ-2 | / | CH3 | H | H | H | H |
Ⅰ-3 | / | H | CH3 | H | H | H |
Ⅰ-4 | / | H | H | CH3 | H | H |
Ⅰ-5 | / | H | H | F | H | H |
Ⅰ-6 | / | Cl | H | H | H | H |
Ⅰ-7 | / | H | Cl | H | H | H |
Ⅰ-8 | / | H | H | Cl | H | H |
Ⅰ-9 | / | H | NO2 | H | H | H |
Ⅰ-10 | / | OCH3 | H | H | H | H |
Ⅰ-11 | / | OC2H5 | H | H | H | H |
Ⅰ-12 | / | F | H | F | H | H |
Ⅰ-13 | CH2C6H5 | / | / | / | / | / |
实施例 | 化合物 | IC50mg/L | 评价 |
15 | Ⅰ-1 | 9.18 | 有效 |
16 | Ⅰ-2 | 11.70 | 弱效 |
17 | Ⅰ-3 | 20.31 | 弱效 |
18 | Ⅰ-4 | 18.37 | 弱效 |
19 | Ⅰ-5 | 5.75 | 有效 |
20 | Ⅰ-6 | 9.40 | 有效 |
21 | Ⅰ-7 | 8.34 | 有效 |
22 | Ⅰ-8 | 5.22 | 有效 |
23 | Ⅰ-9 | 9.01 | 有效 |
24 | Ⅰ-10 | 27.53 | 弱效 |
25 | Ⅰ-11 | 21.34 | 弱效 |
26 | Ⅰ-12 | 15.45 | 弱效 |
27 | Ⅰ-13 | 23.43 | 弱效 |
Claims (2)
Priority Applications (1)
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CN201410095084.1A CN103880701B (zh) | 2014-03-14 | 2014-03-14 | O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗人宫颈鳞状癌药物中的应用 |
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CN201410095084.1A CN103880701B (zh) | 2014-03-14 | 2014-03-14 | O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗人宫颈鳞状癌药物中的应用 |
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CN103880701A CN103880701A (zh) | 2014-06-25 |
CN103880701B true CN103880701B (zh) | 2016-04-13 |
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CN201410095084.1A Active CN103880701B (zh) | 2014-03-14 | 2014-03-14 | O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗人宫颈鳞状癌药物中的应用 |
Country Status (1)
Country | Link |
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CN (1) | CN103880701B (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999066925A1 (en) * | 1998-06-24 | 1999-12-29 | Smithkline Beecham Corporation | Protease inhibitors |
CN102614197A (zh) * | 2012-03-05 | 2012-08-01 | 浙江工业大学 | 苯乙酰氟苯水杨酰胺类化合物在制备抗宫颈癌药物中的应用 |
CN102702071A (zh) * | 2012-06-12 | 2012-10-03 | 大连市食品药品检验所 | 一种天仙子中新化合物和制备方法及应用 |
-
2014
- 2014-03-14 CN CN201410095084.1A patent/CN103880701B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999066925A1 (en) * | 1998-06-24 | 1999-12-29 | Smithkline Beecham Corporation | Protease inhibitors |
CN102614197A (zh) * | 2012-03-05 | 2012-08-01 | 浙江工业大学 | 苯乙酰氟苯水杨酰胺类化合物在制备抗宫颈癌药物中的应用 |
CN102702071A (zh) * | 2012-06-12 | 2012-10-03 | 大连市食品药品检验所 | 一种天仙子中新化合物和制备方法及应用 |
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Denomination of invention: O-cinnamoyl-fluorobenzsalicylamide compounds and their application in the preparation of anti-human cervical squamous cell carcinoma drugs Granted publication date: 20160413 Pledgee: Anhui Linquan rural commercial bank Limited by Share Ltd. Pledgor: ANHUI YONGSHENGTANG PHARMACEUTICAL Co.,Ltd. Registration number: Y2024980019892 |