CN101235019B - 3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 - Google Patents
3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 Download PDFInfo
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- CN101235019B CN101235019B CN2008100204342A CN200810020434A CN101235019B CN 101235019 B CN101235019 B CN 101235019B CN 2008100204342 A CN2008100204342 A CN 2008100204342A CN 200810020434 A CN200810020434 A CN 200810020434A CN 101235019 B CN101235019 B CN 101235019B
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- Prior art keywords
- diiodo
- morpholine
- salicylidene
- omega
- metal complexes
- 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.)
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 title claims description 25
- 239000002184 metal Substances 0.000 title claims description 25
- 241000588697 Enterobacter cloacae Species 0.000 claims abstract description 11
- 241000194032 Enterococcus faecalis Species 0.000 claims abstract description 11
- 229910052793 cadmium Inorganic materials 0.000 claims abstract description 3
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 3
- 229910052753 mercury Inorganic materials 0.000 claims abstract description 3
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 3
- -1 morpholine metal complex Chemical class 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 claims description 5
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 5
- 241000191967 Staphylococcus aureus Species 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229940032049 enterococcus faecalis Drugs 0.000 claims description 5
- 230000000968 intestinal effect Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 abstract description 6
- 241000588724 Escherichia coli Species 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 229940124350 antibacterial drug Drugs 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 28
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 20
- ZYLSJJCXONXHPE-UHFFFAOYSA-N C1C(N(C(C(=CC2=CC=CC=C2O)O1)I)CCCN)I Chemical compound C1C(N(C(C(=CC2=CC=CC=C2O)O1)I)CCCN)I ZYLSJJCXONXHPE-UHFFFAOYSA-N 0.000 description 10
- HBLLIFMOTXEWMN-UHFFFAOYSA-N C1C(N(C(C(=CC2=CC=CC=C2O)O1)I)CCN)I Chemical compound C1C(N(C(C(=CC2=CC=CC=C2O)O1)I)CCN)I HBLLIFMOTXEWMN-UHFFFAOYSA-N 0.000 description 10
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 10
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 10
- 239000011701 zinc Substances 0.000 description 9
- 239000010949 copper Substances 0.000 description 8
- 239000011572 manganese Substances 0.000 description 7
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 244000063299 Bacillus subtilis Species 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- QLUROEONRHAJHT-UHFFFAOYSA-N (2-formylphenyl) hypoiodite Chemical compound IOC1=CC=CC=C1C=O QLUROEONRHAJHT-UHFFFAOYSA-N 0.000 description 3
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000000452 restraining effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 150000001412 amines Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- ZLWLTDZLUVBSRJ-UHFFFAOYSA-K chembl2360149 Chemical compound [Na+].[Na+].[Na+].O=C1C(N=NC=2C=CC(=CC=2)S([O-])(=O)=O)=C(C(=O)[O-])NN1C1=CC=C(S([O-])(=O)=O)C=C1 ZLWLTDZLUVBSRJ-UHFFFAOYSA-K 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000013643 reference control Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
Classifications
-
- 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
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
序号 | 金属盐 | 配合物 | 性状 | 产率(%) |
12345678 | Zn(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCu(CH<sub>3</sub>COO)<sub>2</sub>·H<sub>2</sub>ONi(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OCo(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCd(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OMn(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OFeSO<sub>4</sub>·7H<sub>2</sub>OHg(CH<sub>3</sub>COO)<sub>2</sub> | (C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Zn(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cu(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Ni(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Co(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cd(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Mn(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Fe(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Hg | 黄色晶体,Mp:249-250℃墨绿色晶体,Mp:221-223℃淡绿色晶体,Mp:217-220℃浅棕色晶体,Mp:193-195℃黄色晶体,Mp:248-250℃黑色晶体,Mp:153-156℃黑色晶体,Mp:>300℃亮黄色晶体,Mp:192-194℃ | 7072666471656572 |
序号 | 金属盐 | 配合物 | 性状 | 产率(%) |
910111213141516 | Zn(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCu(CH<sub>3</sub>COO)<sub>2</sub>·H<sub>2</sub>ONi(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OCo(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCd(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OMn(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OFeSO<sub>4</sub>·7H<sub>2</sub>OHg(CH<sub>3</sub>COO)<sub>2</sub> | (C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Zn(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cu(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Ni(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Co(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cd(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Mn(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Fe(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Hg | 黄色晶体,Mp:165-167℃墨绿色晶体,Mp:170-172℃黄绿色晶体,Mp:251-253℃棕色晶体,Mp:230-232℃黄色晶体,Mp:254-256℃黑色晶体,Mp:145-148℃褐色晶体,Mp:198-201℃亮黄色晶体,Mp:183-185℃ | 6267666070626472 |
配合物 | 最小半数抑制浓度MICs(μg/mL) | |||||
革兰氏(染色)阳性(Gram positive) | 革兰氏(染色)阴性(Gram negative) | |||||
B.subtilis | S.aureus | S.faecalis | P.aeruginosa | E.coli | E.cloacae | |
1 | 0.781 | >50 | 1.562 | 3.125 | 0.781 | 12.5 |
配合物 | 最小半数抑制浓度MICs(μg/mL) | |||||
2 | 12.5 | 25 | 1.562 | 0.781 | >50 | 0.781 |
3 | 1.562 | 6.25 | 0.781 | 0.781 | >50 | 1.56 |
4 | 0.781 | 12.5 | 6.25 | 3.125 | 50 | 12.5 |
5 | 0.781 | 12.5 | 12.5 | 0.781 | 0.781 | 1.562 |
6 | 0.781 | 25 | 1.562 | 50 | >50 | 6.25 |
7 | 0.781 | 12.5 | 3.125 | 0.781 | >50 | 12.5 |
8 | 0.781 | 12.5 | 6.25 | 3.125 | 3.125 | 6.25 |
9 | 6.25 | >50 | 1.562 | 6.25 | 1.562 | 12.5 |
10 | 25 | >50 | 0.781 | 6.25 | >50 | 6.25 |
11 | 0.781 | 12.5 | 1.562 | 0.781 | >50 | 6.25 |
12 | >50 | 12.5 | 1.562 | 6.25 | 50 | 0.781 |
13 | 3.125 | 12.5 | 12.5 | 6.25 | 3.125 | 6.25 |
14 | 3.125 | 50 | 3.125 | 12.5 | 50 | 6.25 |
15 | 0.781 | 6.25 | 1.562 | 6.25 | 12.5 | 6.25 |
16 | 1.562 | 6.25 | 1.562 | 3.125 | 3.125 | 1.562 |
Penicillin | 1.562 | 1.562 | 1.562 | 6.25 | 6.25 | 3.125 |
Kanamycin | 0.39 | 1.562 | 3.125 | 3.125 | 3.125 | 1.562 |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN2008100204342A CN101235019B (zh) | 2008-03-06 | 2008-03-06 | 3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 |
Applications Claiming Priority (1)
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CN2008100204342A CN101235019B (zh) | 2008-03-06 | 2008-03-06 | 3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 |
Publications (2)
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CN101235019A CN101235019A (zh) | 2008-08-06 |
CN101235019B true CN101235019B (zh) | 2010-11-24 |
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CN2008100204342A Expired - Fee Related CN101235019B (zh) | 2008-03-06 | 2008-03-06 | 3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 |
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CN (1) | CN101235019B (zh) |
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CN104370855A (zh) * | 2014-09-22 | 2015-02-25 | 山东理工大学 | 双-(对氟苯基)甲基哌嗪缩乙酸配合物及制备方法 |
CN105753908A (zh) * | 2016-03-23 | 2016-07-13 | 桂林理工大学 | 具抗癌活性的Co(mtyp)2的合成及应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1075582A (en) * | 1964-02-18 | 1967-07-12 | Pechiney Progil Sa | Salicylaldimino derivatives and their use as fungicides |
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2008
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1075582A (en) * | 1964-02-18 | 1967-07-12 | Pechiney Progil Sa | Salicylaldimino derivatives and their use as fungicides |
Non-Patent Citations (6)
Title |
---|
Cara Evans, et al.New Schiff base zinc(II) complexes exhibiting secondharmonic generation.J. Chem. Soc., Dalton Trans..2002,83-86. * |
Da-Hua Shi, et al.Synthesis, crystal structure and urease inhibitory activities ofSchiff base metal complexes.Inorganic Chemistry Communications10.2007,10404-406. * |
Kui Cheng, et al.New Method for the Synthesis of a Mononucleating CyclicPeptide Ligand, Crystal Structures of its Ni, Zn, Cu, and CoComplexes, and Their Inhibitory Bioactivity Against Urease.Aust. J. Chem.60.2007,60375-379. * |
Yu-Guang Li, et al.Transition metal complexes (M = Cu, Ni and Mn) ofSchiff-base ligands: Syntheses, crystal structures, andinhibitory bioactivities against urease and xanthine oxidase.Inorganica Chimica Acta360.2007,3602881-2889. * |
赵全芹,等.3 5-二溴水杨醛Schiff碱及其铜(II)配合物的合成和抑菌活性.化学试剂23 1.2001 |
赵全芹等.3,5-二溴水杨醛Schiff碱及其铜(II)配合物的合成和抑菌活性.化学试剂23 1.2001,23(1),30-31. * |
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Free format text: CORRECT: ADDRESS; FROM: 221116 COLLEGE OF CHEMISTRY AND CHEMICAL ENGINEERING, XUZHOU NORMAL UNIVERSITY, NO. 101, SHANGHAI ROAD, TONGSHAN NEW DISTRICT, XUZHOU CITY, JIANGSU PROVINCE TO: 221116 NO. 101, SHANGHAI ROAD, TONGSHAN NEW DISTRICT, XUZHOU CITY, JIANGSU PROVINCE |
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Effective date of registration: 20110607 Address after: 221116 Shanghai Road, Copper Mt. New District, Jiangsu, No. 101, No. Patentee after: Xuzhou Normal University Address before: 221116 School of chemistry and chemical engineering, Xuzhou Normal University, 101 Shanghai Road, Copper Mt. New District, Xuzhou, Jiangsu Patentee before: Xu Suoping |
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Granted publication date: 20101124 Termination date: 20120306 |