CN104402762B - 具抗癌活性的3,5-二氯水杨醛缩2-氨基-2-甲基-1,3-丙二醇希夫碱的合成及应用 - Google Patents
具抗癌活性的3,5-二氯水杨醛缩2-氨基-2-甲基-1,3-丙二醇希夫碱的合成及应用 Download PDFInfo
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- CN104402762B CN104402762B CN201410830039.6A CN201410830039A CN104402762B CN 104402762 B CN104402762 B CN 104402762B CN 201410830039 A CN201410830039 A CN 201410830039A CN 104402762 B CN104402762 B CN 104402762B
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- dichloro
- salicylaldehyde
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- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000002262 Schiff base Substances 0.000 title claims abstract description 37
- -1 AMPD schiff bases Chemical class 0.000 title claims abstract description 32
- 230000001093 anti-cancer Effects 0.000 title claims abstract description 10
- 101150035093 AMPD gene Proteins 0.000 title claims description 8
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000003786 synthesis reaction Methods 0.000 title description 6
- 239000013078 crystal Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960000935 dehydrated alcohol Drugs 0.000 claims abstract description 7
- 238000013461 design Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 238000010189 synthetic method Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 8
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 7
- 239000003005 anticarcinogenic agent Substances 0.000 claims 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 5
- 150000004753 Schiff bases Chemical class 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
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- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000011275 oncology therapy Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N Trimethylene glycol Natural products OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 3
- WSUWZPYQCSWACI-UHFFFAOYSA-N 3,4-dichloro-2-hydroxybenzaldehyde Chemical class OC1=C(Cl)C(Cl)=CC=C1C=O WSUWZPYQCSWACI-UHFFFAOYSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 210000004881 tumor cell Anatomy 0.000 description 6
- 239000012531 culture fluid Substances 0.000 description 4
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- 230000000259 anti-tumor effect Effects 0.000 description 2
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- 201000010881 cervical cancer Diseases 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
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- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound 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](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 201000005112 urinary bladder cancer Diseases 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound 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
- 241000219000 Populus Species 0.000 description 1
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- 230000003110 anti-inflammatory effect Effects 0.000 description 1
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- 230000010261 cell growth Effects 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
37.41±1.53 | 10.39±0.96 | 37.84±1.53 | 43.81±2.39 | 38.03±1.67 |
BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
51.37±0.96 | 349.81±3.99 | 92.37±1.69 | 29.11±0.93 | 80.16±2.21 |
Claims (2)
Priority Applications (1)
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CN201410830039.6A CN104402762B (zh) | 2014-12-26 | 2014-12-26 | 具抗癌活性的3,5-二氯水杨醛缩2-氨基-2-甲基-1,3-丙二醇希夫碱的合成及应用 |
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CN201410830039.6A CN104402762B (zh) | 2014-12-26 | 2014-12-26 | 具抗癌活性的3,5-二氯水杨醛缩2-氨基-2-甲基-1,3-丙二醇希夫碱的合成及应用 |
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CN104402762A CN104402762A (zh) | 2015-03-11 |
CN104402762B true CN104402762B (zh) | 2016-09-28 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880869A (zh) * | 2014-04-05 | 2014-06-25 | 桂林理工大学 | 一种抗癌药物[Cu2(L4)(L6)]及其原位合成方法 |
CN103922992A (zh) * | 2014-04-25 | 2014-07-16 | 温州大学 | 一种抗癌活性吲哚酮衍生物、合成方法及其用途 |
Family Cites Families (2)
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JPS6022337B2 (ja) * | 1976-08-19 | 1985-06-01 | オリエンタル写真工業株式会社 | 熱現像性感光材料 |
WO2008075866A1 (en) * | 2006-12-18 | 2008-06-26 | Yong Jin Park | A composition comprising the processed extract of panax quinquefolium l. for the prevention and treatment of cancer |
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2014
- 2014-12-26 CN CN201410830039.6A patent/CN104402762B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880869A (zh) * | 2014-04-05 | 2014-06-25 | 桂林理工大学 | 一种抗癌药物[Cu2(L4)(L6)]及其原位合成方法 |
CN103922992A (zh) * | 2014-04-25 | 2014-07-16 | 温州大学 | 一种抗癌活性吲哚酮衍生物、合成方法及其用途 |
Non-Patent Citations (2)
Title |
---|
Mixed-ligand Cu(II)evanillin Schiff base complexes;effect of coligands on their DNA binding,DNA cleavage,SOD mimetic and anticancer activity;Sartaj Tabassum等;《European Journal of Medicinal Chemistry》;20120823;第60卷;第216-232页 * |
Schiff Bases of Salicylaldehyde and Their Cobalt(II) Derivatives as Antitumor Agents;Hodnett Ernest M.,Willie Winfred;《Proceedings of the Oklahoma Academy of Science》;19651231;第110页表II * |
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Effective date of registration: 20201215 Address after: 11 / F, Jingang building, south of Lianyungang Road, Sheyang Economic Development Zone, Sheyang County, Yancheng City, Jiangsu Province 224300 Patentee after: Li Zaigao Address before: 541004 the Guangxi Zhuang Autonomous Region Guilin Construction Road No. 12 Patentee before: GUILIN University OF TECHNOLOGY |
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Application publication date: 20150311 Assignee: Yancheng Aipinyue Network Technology Co.,Ltd. Assignor: Li Zaigao Contract record no.: X2023980047070 Denomination of invention: Synthesis and application of 3,5-dichlorosalicylialdehyde 2-amino-2-methyl-1,3-propanediol Schiff base with anticancer activity Granted publication date: 20160928 License type: Common License Record date: 20231120 |
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Assignee: Yancheng Aipinyue Network Technology Co.,Ltd. Assignor: Li Zaigao Contract record no.: X2023980047070 Date of cancellation: 20240416 |