CN110772506A - 苯偶酰腙-1-萘甲醛西弗碱的用途 - Google Patents
苯偶酰腙-1-萘甲醛西弗碱的用途 Download PDFInfo
- Publication number
- CN110772506A CN110772506A CN201911099721.1A CN201911099721A CN110772506A CN 110772506 A CN110772506 A CN 110772506A CN 201911099721 A CN201911099721 A CN 201911099721A CN 110772506 A CN110772506 A CN 110772506A
- Authority
- CN
- China
- Prior art keywords
- benzil
- formylnaphthalene
- schiff base
- application
- naphthaldehyde
- 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
- 239000002262 Schiff base Substances 0.000 title abstract description 15
- -1 benzil hydrazone-1-naphthaldehyde Schiff base Chemical class 0.000 title description 2
- 239000013078 crystal Substances 0.000 claims abstract description 28
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 claims abstract description 23
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000002844 melting Methods 0.000 claims abstract description 6
- 230000008018 melting Effects 0.000 claims abstract description 6
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 5
- 241000588724 Escherichia coli Species 0.000 claims abstract description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 5
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 5
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 201000005202 lung cancer Diseases 0.000 claims abstract description 5
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 230000035755 proliferation Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 150000004753 Schiff bases Chemical class 0.000 abstract description 11
- ZWPOAAKGAFHAEX-HBKJEHTGSA-N (e)-[(2e)-2-hydrazinylidene-1,2-diphenylethylidene]hydrazine Chemical compound C=1C=CC=CC=1\C(=N/N)\C(=N\N)\C1=CC=CC=C1 ZWPOAAKGAFHAEX-HBKJEHTGSA-N 0.000 abstract description 6
- 239000008204 material by function Substances 0.000 abstract description 5
- 230000001093 anti-cancer Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000012567 medical material Substances 0.000 abstract description 2
- 229940124350 antibacterial drug Drugs 0.000 abstract 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract 2
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 238000010586 diagram Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000003746 solid phase reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- CDQPGWNBSOSEMZ-DTQAZKPQSA-N (2e)-2-hydrazinylidene-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=N/N)\C(=O)C1=CC=CC=C1 CDQPGWNBSOSEMZ-DTQAZKPQSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IDBOAVAEGRJRIZ-UHFFFAOYSA-N methylidenehydrazine Chemical compound NN=C IDBOAVAEGRJRIZ-UHFFFAOYSA-N 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CDQPGWNBSOSEMZ-UHFFFAOYSA-N 2-hydrazinylidene-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=NN)C(=O)C1=CC=CC=C1 CDQPGWNBSOSEMZ-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000003385 bacteriostatic effect Effects 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
- 201000011510 cancer Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及药物化学和功能材料领域，具体为苯偶酰二腙或苯偶酰单腙与1‑萘甲醛反应生成的西弗碱在抗癌、抗菌药物中的用途，也包括其在医药材料、功能材料等领域的用途；苯偶酰二腙‑N,N'‑二(1‑甲酰基萘)外观呈浅黄色梭状晶体，熔点201.0‑203.0℃，分子式C36H26N4；苯偶酰单腙‑N‑1‑甲酰基萘外观呈黄色块状晶体，熔点135.2‑136.7℃，分子式C25H18N2O；二者结构如下：
Description
技术领域
本发明涉及药物化学和功能材料领域，具体为苯偶酰二腙或苯偶酰单腙与1-萘甲醛反应生成的西弗碱在抗癌、抗菌药物中的用途，也包括其在医药材料、功能材料等领域的用途。
背景技术
西弗碱(Schiff base)，是具有核心特性基团亚胺或甲亚胺(-C＝N-)的一类有机化合物，有着许多众所周知的明显的生物活性，例如抗菌、抗真菌、除草、抗结核、抗艾滋病毒、抗癌等，这使得它们在药物化学和功能材料等领域有广泛应用；另外西弗碱可以与元素周期表中的大部分金属离子形成稳定性不同的金属配合物，这些配合物在诸如光学材料、磁性、光谱、动力学和反应机理、化学、生物活性等方面有着广泛的应用；西弗碱及其配合物良好的生物活性激发着大量科学工作者对其进行更深入的研究。
发明内容
本发明的内容是合成了两种西弗碱，均是苯偶酰腙和1-萘甲醛反应产物，苯偶酰二腙和1-萘甲醛反应产物称为苯偶酰二腙-N,N'-二(1-甲酰基萘)，苯偶酰单腙和1-萘甲醛反应产物称为苯偶酰单腙-N-1-甲酰基萘；前者是双西弗碱，外观呈浅黄色梭状晶体，熔点201.0-203.0℃，分子式C36H26N4；后者是单西弗碱，外观呈黄色块状晶体，熔点135.2-136.7℃，分子式C25H18N2O；二者结构如下：
1、结构鉴定。
苯偶酰二腙-N,N'-二(1-甲酰基萘)元素分析表明，其C、H、N的百分含量分别为83.98％(84.02％)、5.10％(5.09％)、10.92％(10.89％)(括号中为理论值)；单晶结构分析表明，其结晶为单斜晶系，C2/c空间群，
β＝115.230°，
Z＝4。1HNMR谱、13CNMR均显示该化合物为对称结构，且谱图特征与单晶结构分析结果完全吻合。有关的1HNMR谱、13CNMR谱分别见附图1和附图2；附图3和附图4分别是该化合物的晶体结构图和晶体结构堆积图。
苯偶酰单腙-N-1-甲酰基萘元素分析表明，其C、H、N的百分含量分别为C 82.18(82.85),H 5.11(5.01),N 7.84％(7.73％)(括号中为理论值)；单晶结构分析表明，其结晶为单斜晶系，P21c空间群，
β＝94.814(7)°，
Z＝4。1HNMR、13CNMR谱图特征与单晶结构分析结果完全吻合。有关的1HNMR谱、13CNMR谱分别见附图5和附图6；附图7和附图8分别是该化合物的晶体结构图和晶体结构堆积图。
苯偶酰二腙-N,N'-二(1-甲酰基萘)有两种合成方法：方法一是以苯偶酰二腙和1-萘甲醛为原料，步骤如下：
1)将苯偶酰二腙溶于合适的有机溶剂后，按照一定的物质的量之比加入1-萘甲醛，在一定温度下搅拌反应一定时间即可完成；若采用固相反应，则不用有机溶剂，二者研磨反应一定时间即可完成。
2)过滤，待滤液自然挥发，析出的浅黄色针状晶体即为目标产物；若采用固相反应，则反应完毕用合适的有机溶剂重结晶即可得目标产物晶体。
方法二是以二苯乙二酮(即苯偶酰)和3-吲哚甲醛腙为原料，在合适的有机溶剂中一步完成，步骤如下：
1)将二苯乙二酮溶于合适的有机溶剂后，按照一定的物质的量之比加入3-吲哚甲醛腙，在一定温度下搅拌反应一定时间即可完成；若采用固相反应，则不用有机溶剂，二者研磨反应一定时间即可完成。
2)过滤，待滤液自然挥发，析出的浅黄色梭状晶体即为目标产物；若采用固相反应，则反应完毕用合适的有机溶剂重结晶即可得目标产物晶体。
以上两种制备方法的区别主要在于反应物不同，但反应原料的摩尔比均介于4:1与1:4之间。
苯偶酰单腙-N-1-甲酰基萘的合成是以苯偶酰单腙和1-萘甲醛为原料，其他步骤与苯偶酰二腙-N,N'-二(1-甲酰基萘)的合成方法一相同，反应物的摩尔比介于4:1与1:4之间。
以上两种物质的制备方法中的有机溶剂(反应用溶剂或重结晶用溶剂)选自：甲醇、乙醇、乙腈、二氯甲烷、氯仿、四氢呋喃、丙酮等；固相反应时也可以不用有机溶剂，原料之间直接反应。
优选的,所述反应温度为常温或加热回流，反应方法为搅拌或研磨。
优选的，所述反应时间选自：0.5－10h。
本发明的有益效果是：能够以比较简单的步骤和反应物合成比较复杂的功能分子材料。
3、体外抗肿瘤活性：
将处于对数期生长的肺癌细胞A549或小鼠乳腺癌细胞4T1，用0.25％胰酶消化细胞，使其成为单细胞，用含10％胎牛血清的F12K培养液制成浓度为1.25×107个/L的单细胞悬液，将细胞接种于96孔培养板中，每孔200μL(每孔2.5×103个细胞)。将96孔细胞培养板置于CO2培养箱中，在37℃，5％CO2条件下，培养48h。
当孔内细胞长满(90％满即可)时，按实验分组加入不同剂量的西弗碱溶液(200μL/孔)，使待测化合物的终浓度分别为5μM、10μM、50μM、100μM、150μM，每组设3个复孔，培养96h。
各个孔中分别加入20μL浓度为0.5g/L的MTT，继续培养4h，使MTT还原为甲瓒(Formazan)。吸出全部上清液后，每孔加入200μL的DMSO，震摇15min，使甲瓒充分溶解后，运用酶联免疫检测仪测定490nm处的吸光度(OD值)。然后按照下式进行计算：
细胞抑制率％＝(对照组OD值-实验组OD值)/对照组OD值×100％
测试结果表明，苯偶酰二腙-N,N'-二(1-甲酰基萘)对肺癌细胞A549和小鼠乳腺癌细胞4T1的IC50(药物的半数抑制浓度)分别为130.0和125.0μM；苯偶酰单腙-N-1-甲酰基萘对肺癌细胞A549和小鼠乳腺癌细胞4T1的IC50(药物的半数抑制浓度)分别为150.0和148.0μM；这表明两种西弗碱分子对两种癌细胞均具有一定的抑制效果；二者相比，双西弗碱效果更佳。
4、抑菌活性：
采用滤纸片扩散法测定抑菌效果：将大小相同直径为8mm的圆形滤纸片(每片吸收药液为10微升)浸入浓度为100μg/mL的待测药物的DMSO溶液中，30分钟后取出滤纸片，晾干，每个滤纸片载药量约为1μg，然后将滤纸片放入已经涂布有大肠杆菌或金黄色葡萄球菌的平板中央，在培养皿盖上贴上标签，做好标记，将培养皿放入恒温培养箱中于37℃培养24小时后用游标卡尺测量抑菌圈的直径，并与青霉素钾(浓度为10μg/mL)进行对照。
测试结果表明，苯偶酰二腙-N,N'-二(1-甲酰基萘)对大肠杆菌/金黄色葡萄球菌的抑菌圈直径分别为8.2和8.6mm，苯偶酰单腙-N-1-甲酰基萘对大肠杆菌/金黄色葡萄球菌的抑菌圈直径分别为8.4和8.5mm；二者均比青霉素钾的29.0和28.4mm小，但仍有一定的抑菌活性。
具体实施方式
为了更好的理解本发明内容，下面通过一个具体实施例进一步说明本发明的技术方案：
实施例1
称取0.24g二苯乙二酮双腙于圆底烧瓶内，置于恒温磁力搅拌器上，加入60ml甲醇，搅拌溶解，然后缓慢加入0.32g 1-萘甲醛，溶液为浅黄色澄清液，约半小时后溶液稍有浑浊，继续搅拌5小时，溶液呈浑浊状态；过滤，滤纸上为浅黄色粉末，滤液置于小烧杯中，自然挥发，约12小时后，出现大量浅黄色梭状晶体；滤纸上浅黄色粉末和滤液中析出的梭状晶体均为苯偶酰二腙-N,N'-二(1-甲酰基萘)。
实施例2
将0.224g二苯乙二酮单腙溶解于30ml乙腈中，加入1-萘甲醛0.16g，加热回流3h，待溶剂挥发至剩余约5ml，可得黄色块状晶体，即为苯偶酰单腙-N-1-甲酰基萘，可用乙腈重结晶以得到更纯产物。
附图说明
附图1是苯偶酰二腙-N,N'-二(1-甲酰基萘)的1H NMR谱图(溶剂为DMSO-d6)。
附图2是苯偶酰二腙-N,N'-二(1-甲酰基萘)的13CNMR谱图(溶剂为DMSO-d6)。
附图3是苯偶酰二腙-N,N'-二(1-甲酰基萘)的晶体结构图，椭球概率30％。
附图4是苯偶酰二腙-N,N'-二(1-甲酰基萘)的晶体结构堆积图，椭球概率10％。
附图5是苯偶酰单腙-N-1-甲酰基萘的1H NMR谱图(溶剂为DMSO-d6)。
附图6是苯偶酰单腙-N-1-甲酰基萘的13CNMR谱图(溶剂为DMSO-d6)。
附图7是苯偶酰单腙-N-1-甲酰基萘的晶体结构图，椭球概率30％。
附图8是苯偶酰单腙-N-1-甲酰基萘的晶体结构堆积图，椭球概率10％。
Claims (2)
1.如下式所示两种化合物晶体或其他药物学上可接受的盐在制备预防和/或治疗肿瘤药物中的应用，其特征在于：所述肿瘤为肺癌和乳腺癌；苯偶酰二腙-N,N'-二(1-甲酰基萘)外观呈浅黄色梭状晶体，熔点201.0-203.0℃，分子式C36H26N4；苯偶酰单腙-N-1-甲酰基萘外观呈黄色块状晶体，熔点135.2-136.7℃，分子式C25H18N2O；二者结构如下：
2.如权利要求1中所述的两种化合物在抗菌药物或抗菌材料中的应用，其特征在于，可以有效抑制大肠杆菌和金黄色葡萄球菌的繁殖。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911099721.1A CN110772506B (zh) | 2019-11-12 | 2019-11-12 | 苯偶酰腙-1-萘甲醛西弗碱的用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911099721.1A CN110772506B (zh) | 2019-11-12 | 2019-11-12 | 苯偶酰腙-1-萘甲醛西弗碱的用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110772506A true CN110772506A (zh) | 2020-02-11 |
| CN110772506B CN110772506B (zh) | 2022-07-22 |
Family
ID=69390463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911099721.1A Active CN110772506B (zh) | 2019-11-12 | 2019-11-12 | 苯偶酰腙-1-萘甲醛西弗碱的用途 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110772506B (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113577071A (zh) * | 2021-09-17 | 2021-11-02 | 齐鲁工业大学 | 双吡啶酮腙-2-吲哚甲醛西弗碱的用途 |
| CN113730406A (zh) * | 2021-09-18 | 2021-12-03 | 齐鲁工业大学 | 双吡啶酮腙-6-吲哚甲醛西弗碱的用途 |
| CN113730405A (zh) * | 2021-09-18 | 2021-12-03 | 齐鲁工业大学 | 双吡啶酮腙-4-吲哚甲醛西弗碱的用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104193650A (zh) * | 2014-08-12 | 2014-12-10 | 齐鲁工业大学 | 苯偶酰二腙-n,n’-二(1-甲酰基萘)的结构、制备和用途 |
| CN104945302A (zh) * | 2015-06-12 | 2015-09-30 | 齐鲁工业大学 | 苯偶酰二腙-3-吲哚甲醛双西弗碱的结构、制备和用途 |
| CN105348146A (zh) * | 2015-06-11 | 2016-02-24 | 齐鲁工业大学 | 二苯乙二酮腙-氯代苯甲醛双席夫碱的结构、制备和用途 |
| CN105367445A (zh) * | 2015-06-15 | 2016-03-02 | 齐鲁工业大学 | 苯偶酰二腙-n-单-（2-羟基-4-二乙氨基-1-甲酰基苯）的制备、结构和用途 |
-
2019
- 2019-11-12 CN CN201911099721.1A patent/CN110772506B/zh active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104193650A (zh) * | 2014-08-12 | 2014-12-10 | 齐鲁工业大学 | 苯偶酰二腙-n,n’-二(1-甲酰基萘)的结构、制备和用途 |
| CN105348146A (zh) * | 2015-06-11 | 2016-02-24 | 齐鲁工业大学 | 二苯乙二酮腙-氯代苯甲醛双席夫碱的结构、制备和用途 |
| CN104945302A (zh) * | 2015-06-12 | 2015-09-30 | 齐鲁工业大学 | 苯偶酰二腙-3-吲哚甲醛双西弗碱的结构、制备和用途 |
| CN105367445A (zh) * | 2015-06-15 | 2016-03-02 | 齐鲁工业大学 | 苯偶酰二腙-n-单-（2-羟基-4-二乙氨基-1-甲酰基苯）的制备、结构和用途 |
Non-Patent Citations (2)
| Title |
|---|
| REGISTRY: "473245-06-6", 《STN》 * |
| REGISTRY: "473245-06-6", 《STN》, 12 November 2002 (2002-11-12), pages 1 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113577071A (zh) * | 2021-09-17 | 2021-11-02 | 齐鲁工业大学 | 双吡啶酮腙-2-吲哚甲醛西弗碱的用途 |
| CN113730406A (zh) * | 2021-09-18 | 2021-12-03 | 齐鲁工业大学 | 双吡啶酮腙-6-吲哚甲醛西弗碱的用途 |
| CN113730405A (zh) * | 2021-09-18 | 2021-12-03 | 齐鲁工业大学 | 双吡啶酮腙-4-吲哚甲醛西弗碱的用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110772506B (zh) | 2022-07-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110772506B (zh) | 苯偶酰腙-1-萘甲醛西弗碱的用途 | |
| CN110790695B (zh) | 苯偶酰腙-n-甲基-3-吲哚甲醛的合成及用途 | |
| CN110606843B (zh) | 双吡啶酮腙-2-乙酰基吡嗪的结构、制备和用途 | |
| CN111205311A (zh) | 新型高抗肿瘤活性白叶藤碱锌(ii)配合物及其合成方法和应用 | |
| CN110698383B (zh) | 苯偶酰腙-3-乙酰基吲哚的结构、合成及用途 | |
| CN107043345A (zh) | 联苯乙酮腙‑吲哚啉‑2,3‑二酮西弗碱的制备、结构和用途 | |
| CN107501303B (zh) | 一种布洛芬与喹啉-8-甲醛席夫碱构筑的铜(ii)配合物及其合成方法和应用 | |
| CN110698382B (zh) | 苯偶酰腙-3-吲哚甲醛西弗碱的用途 | |
| CN113735781B (zh) | 一种铜配合物及其制备方法和应用 | |
| CN109912491B (zh) | 4-羟基二苯甲酮腙-靛红席夫碱的制备和用途 | |
| CN109824572B (zh) | 4-羟基二苯甲酮腙-1-甲基-3吲哚甲醛席夫碱的结构、制备和用途 | |
| CN110590765B (zh) | 2-噻唑甲醛-糠醛席夫碱的结构、制备和用途 | |
| CN110172075B (zh) | 一种新型香豆素-喹啉-铂(ii)配合物及其合成方法和应用 | |
| CN113577071A (zh) | 双吡啶酮腙-2-吲哚甲醛西弗碱的用途 | |
| CN113730405A (zh) | 双吡啶酮腙-4-吲哚甲醛西弗碱的用途 | |
| CN113694064A (zh) | 双吡啶酮腙-3-吲哚甲醛西弗碱的用途 | |
| CN110590763B (zh) | 2-噻唑甲醛-噻吩席夫碱的结构、制备和用途 | |
| CN109824541B (zh) | (1z，2z)-1,2-双((2-氟苯基)(4-氟苯基)亚甲基)肼的制备和用途 | |
| CN109912517B (zh) | 4-羟基二苯甲酮腙-2-乙酰基吡嗪席夫碱的制备和用途 | |
| CN110577521B (zh) | 2-噻唑甲醛-2-吡啶席夫碱的结构、制备和用途 | |
| CN110563716B (zh) | 2-噻唑甲醛-6-吲哚席夫碱的结构、制备和用途 | |
| CN109912451B (zh) | 4-羟基二苯甲酮腙-水杨醛席夫碱的制备和用途 | |
| CN110590764B (zh) | 2-噻唑甲醛-4-吡啶席夫碱的结构、制备和用途 | |
| CN113730406A (zh) | 双吡啶酮腙-6-吲哚甲醛西弗碱的用途 | |
| CN110563667B (zh) | 2-噻唑甲醛-1-萘席夫碱的结构、制备和用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | 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 | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20221221 Address after: 250306 Room 3115, No. 135, Ward Avenue, Ping'an Street, Changqing District, Jinan City, Shandong Province Patentee after: Shandong Jiqing Technology Service Co.,Ltd. Address before: 250353 Qilu University of technology, Changqing University Town, Jinan City, Shandong Province Patentee before: Qilu University of Technology |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20240717 Address after: 250353 University Road, Changqing District, Ji'nan, Shandong Province, No. 3501 Patentee after: Qilu University of Technology (Shandong Academy of Sciences) Country or region after: China Address before: 250306 Room 3115, No. 135, Ward Avenue, Ping'an Street, Changqing District, Jinan City, Shandong Province Patentee before: Shandong Jiqing Technology Service Co.,Ltd. Country or region before: China |