CN115197151B - Benzimidazole Schiff base derivative and application thereof - Google Patents
Benzimidazole Schiff base derivative and application thereof Download PDFInfo
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- CN115197151B CN115197151B CN202210603338.0A CN202210603338A CN115197151B CN 115197151 B CN115197151 B CN 115197151B CN 202210603338 A CN202210603338 A CN 202210603338A CN 115197151 B CN115197151 B CN 115197151B
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- -1 Benzimidazole Schiff base Chemical class 0.000 title claims abstract description 41
- 239000002262 Schiff base Substances 0.000 title claims abstract description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 15
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 7
- 150000004700 cobalt complex Chemical class 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 230000001093 anti-cancer Effects 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229940011182 cobalt acetate Drugs 0.000 claims description 5
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000004729 solvothermal method Methods 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 abstract description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000012827 research and development Methods 0.000 description 2
- YWNXHTNWOQHFRL-UHFFFAOYSA-N 2-(1H-benzimidazol-2-yl)aniline Chemical compound NC1=CC=CC=C1C1=NC2=CC=CC=C2N1 YWNXHTNWOQHFRL-UHFFFAOYSA-N 0.000 description 1
- 206010033109 Ototoxicity Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a benzimidazole Schiff base derivative and application thereof, and the structural formula is as followsThe benzimidazole Schiff base derivative has a molecular structure completely different from that of the existing antitumor drugs, provides a new thought for the development of the antitumor drugs, and adopts benzimidazole derivatives, aromatic aldehyde and the like to prepare the benzimidazole Schiff base derivative with high purity and high yield under the conditions of low temperature, absolute ethyl alcohol and other solvents, and has the advantages of simple process, pure product, high yield and convenient post-treatment.
Description
Technical Field
The invention belongs to the technical field of Schiff base derivative application, and particularly relates to a benzimidazole Schiff base derivative and application thereof.
Background
Cancer has become one of the most threatening diseases for modern human health due to its high incidence and mortality, and is also the most common cause of death in humans. Currently, chemotherapy with different classes of anticancer drugs remains an important means of treating cancer.
Cisplatin is used as a first metal antitumor drug and is a chemotherapeutic drug commonly used for treating tumors at present. Because of the characteristics of effective action on various cancer cells, synergistic action with other various antitumor drugs and the like, the composition can be widely applied to clinical treatment of various malignant tumors. In order to solve the serious problems of kidney action and ototoxicity and improve the anticancer effect, although more derived drugs based on platinum are used clinically, the search for new anticancer drugs is still a research hotspot for drug synthesis. Benzimidazole Schiff base metal complex drugs have good anticancer activity, so research and development of anticancer activity of such complexes have great promotion effect on current treatment of cancers.
Disclosure of Invention
The invention aims to provide a benzimidazole Schiff base derivative.
It is another object of the present invention to provide the use of the benzimidazole Schiff base derivatives described above.
The technical scheme of the invention is as follows:
a benzimidazole Schiff base derivative has a structural formula ofWherein R is 1 Is H, OH, alkoxy, unsubstituted alkyl of 1 to 4 carbon atoms or substituted alkyl of 1 to 4 carbon atoms, R 2 Is H, OH, alkoxy, unsubstituted alkyl of 1 to 4 carbon atoms or substituted alkyl of 1 to 4 carbon atoms, R3 is H, OH, alkoxy, unsubstituted alkyl of 1 to 4 carbon atoms or substituted alkyl of 1 to 4 carbon atoms.
In a preferred embodiment of the invention, the structural formula is
The benzimidazole Schiff base derivative comprises the following steps:
(1) Mixing the corresponding benzimidazole derivative with absolute ethyl alcohol, slowly adding absolute ethyl alcohol solution of 5-chlorosalicylaldehyde or the derivative thereof at 58-62 ℃, and carrying out heat preservation and stirring reaction for 5-7h;
(2) And (3) carrying out solid-liquid separation on the material obtained in the step (1), and fully washing the obtained solid with absolute ethyl alcohol to obtain the benzimidazole Schiff base derivative.
Application of the benzimidazole Schiff base derivative in preparing anticancer drugs.
A cobalt complex of benzimidazole Schiff base derivative has the structural formula ofWherein the central ion Co is in a hexacoordinated structure, and the six coordinated atoms are respectively from 4N atoms and 2O atoms of two ligands to form an approximately regular octahedral configuration, R 1 Is H, OH, alkoxy, unsubstituted alkyl of 1 to 4 carbon atoms or substituted alkyl of 1 to 4 carbon atoms, R 2 Is H, OH, alkoxy, unsubstituted alkyl of 1 to 4 carbon atoms or substituted alkyl of 1 to 4 carbon atoms, R 3 H, OH, alkoxy, unsubstituted alkyl of 1 to 4 carbon atoms or substituted alkyl of 1 to 4 carbon atoms.
In a preferred embodiment of the invention, the structural formula isThe crystal belongs to a trigonal system, and the space group is R-3.
The preparation method of the benzimidazole Schiff base derivative cobalt complex comprises the following steps:
(1) Uniformly stirring the benzimidazole Schiff base derivative, absolute ethyl alcohol, triethylamine and cobalt acetate according to claim 1 or 2 at room temperature, then carrying out solvothermal reaction at 58-62 ℃ for 70-75h, and naturally cooling to room temperature;
(2) And (3) carrying out solid-liquid separation on the material obtained in the step (1), and fully washing the obtained solid with absolute ethyl alcohol to obtain the benzimidazole derivative cobalt complex.
In a preferred embodiment of the present invention, the benzimidazole Schiff base derivative, absolute ethanol, triethylamine and cobalt acetate are present in a ratio of 0.030g:20mL:0.22mL:0.014g.
Application of the benzimidazole Schiff base derivative cobalt complex in preparing anticancer drugs.
An anticancer drug contains the benzimidazole Schiff base derivative cobalt complex as an active ingredient.
The beneficial effects of the invention are as follows:
1. the benzimidazole Schiff base derivative has a molecular structure completely different from that of the existing antitumor drugs, and provides a new idea for the research and development of the antitumor drugs.
2. The benzimidazole Schiff base derivative cobalt complex of the invention shows good anticancer activity, which is of great significance for effectively developing and utilizing series of anticancer drugs.
3. The preparation method of the benzimidazole Schiff base derivative adopts the benzimidazole derivative, aromatic aldehyde and the like to prepare the benzimidazole Schiff base derivative with high purity and high yield under the conditions of low temperature, absolute ethyl alcohol and other solvents, and has the advantages of simple process, pure product, high yield and convenient post-treatment.
4. The preparation method of the benzimidazole Schiff base derivative cobalt complex adopts a solvothermal preparation method, and has the characteristics of pure product, higher yield and convenient post-treatment.
Drawings
FIG. 1 is a molecular structure diagram of a benzimidazole Schiff base derivative cobalt complex prepared in example 2 of the present invention.
FIG. 2 is a graph showing the experimental results of example 3 of the present invention.
Detailed Description
The technical scheme of the invention is further illustrated and described below by the specific embodiments in combination with the accompanying drawings.
Example 1
The reaction formula of this example is:
the method specifically comprises the following steps: 2.0g (0.00955 mol) of 2- (2-aminophenyl) benzimidazole and 50mL of absolute ethyl alcohol are added into a reactor provided with a stirrer and a temperature control device, the temperature is controlled at 60 ℃, 50mL of 5-chlorosalicylaldehyde absolute ethyl alcohol solution with the total amount of 2.3807g (0.00955 mol) is slowly added in batches, the reaction is kept uniformly mixed, the stirring is continued for 6 hours, the filtration and the absolute ethyl alcohol washing are carried out to obtain a white benzimidazole Schiff base derivative Y1 powder product with the purity of 99.5 percent and the yield of 84.34 percent.
The benzimidazole Schiff base derivative Y1 1 H NMR(400MHz，d 6 -DMSO) nuclear magnetic consequences: δ10.49 (s, 1H), 7.96 (dd, j=7.76 hz, j=1.56 hz, 1H), 7.67 (d, j=7.96 hz, 1H), 7.34 (d, j=1.96 hz, 1H), 7.26-7.09 (m, 6H), 6.93-6.80 (m, 3H), 6.64 (d, j=2.68 hz, 1H); y1 13 C NMR(101MHz，d 6 -DMSO) nuclear magnetic consequences: delta 153.9, 147.6, 144.3, 143.6, 133.2, 132.1, 130.2, 128.5, 126.4, 125.1, 123.0, 122.8, 122.6, 119.2, 118.5, 118.2, 111.9, 110.6, 63.4.
Example 2
The reaction formula of this example is:
the method specifically comprises the following steps: the reaction flask was charged with 0.030g of 5-chlorosalicylaldehyde Schiff base, 20mL of absolute ethanol, 0.22mL of triethylamine and 0.0014g of cobalt acetate, and the solution was stirred and mixed at room temperature. Transferring the solution into a polytetrafluoroethylene liner in a 25mL high-pressure reaction kettle, performing solvothermal reaction for 72h at 60 ℃ with the filling degree of 80%, and naturally cooling to room temperature to obtain reddish brown crystals. After solid-liquid separation, washing 3 times by absolute ethyl alcohol, and obtaining the 5-chlorosalicylaldehyde 2- (2-aminophenyl) benzimidazole Schiff base cobalt complex (Y2 cobalt complex) crystal shown in the figure 1.
The Y2 cobalt complex crystal belongs to a trigonal system,the space group is R-3, the central ion Co is in a six-coordination structure, and six coordination atoms are respectively from 4N atoms and 2O atoms of two ligands to form an approximate octahedral configuration. The unit cell parameters are as follows:α＝90°，β＝90°，γ＝120°，/>D c ＝1.233g·cm -3 。
example 3 anticancer Performance test and evaluation based on Schiff base ligand Metal complexes
The MTT colorimetric method is adopted: taking 96-well plate, adding 100 μl of PBS (phosphate buffered saline) to each well around the plate, sealing edge, adding 100 μl of cell suspension to 5 lines in the middle, and concentrating at 4×10 4 About one/mL. The first row was blank, the same volume of complete medium was added, the second row was negative control with 1% dmso, and 100 μl of cell suspension was added. Culturing was continued in an incubator for 24 hours with 100. Mu.L of each well. After 72h, 10. Mu.L of 0.5mg/mL MTT solution was added to each well, and after further incubation for 4h, purple crystalline formazan was produced, 150. Mu.L of DMSO was added to each well, and shaking was performed at 37℃for 10min, and the OD was measured at 490nm using an microplate reader until formazan crystals were completely dissolved. The inhibition was calculated by repeating 5 wells per sample concentration and taking the average.
As shown in Table 1 and FIG. 2, the results of experiments show that the Y2 cobalt complex has a certain inhibition effect on four different cancer cells by using the MTT method to screen cytotoxicity of the compounds, and the Table 1 shows that the Y2 cobalt complex has strong anticancer activity on MAD-MB-231, CNE-2Z, A549 and SMMC-7721 cells, wherein the IC50 of the Y2 cobalt complex is lower than that of cisplatin, and has wide anticancer activity, which is related to the specific molecular structure of the benzimidazole Schiff base cobalt complex. The Y2 cobalt complex has stronger inhibition effect on four cancer cells than cisplatin, and has strong anticancer effect with IC50 value lower than 10 mu M. These results indicate that the benzimidazole Schiff base derivatives of the present invention have anticancer potential, and the anticancer activity can be increased by forming a metal complex of a specific structure through the coordination with different metal ions.
Anticancer Activity of the Compounds of Table 1 against MAD-MB-231, CNE-2Z, A549 and SMMC-7721 cells (IC 50)
The foregoing description is only illustrative of the preferred embodiments of the present invention and is not to be construed as limiting the scope of the invention, i.e., the invention is not to be limited to the details of the invention.
Claims (5)
1. A benzimidazole schiff base derivative cobalt complex, characterized in that: the structure is as followsThe crystal belongs to a trigonal system, and the space group is R-3.
2. A process for the preparation of a benzimidazole schiff base derivative cobalt complex according to claim 1, characterised in that: the method comprises the following steps:
(1) Uniformly stirring benzimidazole Schiff base derivatives, absolute ethyl alcohol, triethylamine and cobalt acetate at room temperature, then carrying out solvothermal reaction at 58-62 ℃ for 70-75h, and naturally cooling to room temperature; the structural formula of the benzimidazole Schiff base derivative is
(2) And (3) carrying out solid-liquid separation on the material obtained in the step (1), and fully washing the obtained solid with absolute ethyl alcohol to obtain the benzimidazole derivative cobalt complex.
3. The method of manufacturing as claimed in claim 2, wherein: the proportion of the benzimidazole Schiff base derivative, the absolute ethyl alcohol, the triethylamine and the cobalt acetate is 0.030g, 20mL, 0.22mL and 0.014g.
4. Use of the cobalt complex of benzimidazole schiff base derivative according to claim 1 for the preparation of an anticancer drug having anticancer activity against MAD-MB-231, CNE-2Z, A549 and SMMC-7721 cells.
5. An anticancer drug, characterized in that: the active ingredient of the composition comprises the benzimidazole Schiff base derivative cobalt complex of claim 1.
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| CN202210603338.0A CN115197151B (en) | 2022-05-27 | 2022-05-27 | Benzimidazole Schiff base derivative and application thereof |
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| CN202210603338.0A CN115197151B (en) | 2022-05-27 | 2022-05-27 | Benzimidazole Schiff base derivative and application thereof |
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| CN115197151A CN115197151A (en) | 2022-10-18 |
| CN115197151B true CN115197151B (en) | 2024-03-22 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151454A (en) * | 2014-07-25 | 2014-11-19 | 浙江大学 | Cobalt catalyst and application thereof in polymerization reaction of 1, 3-butadiene |
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- 2022-05-27 CN CN202210603338.0A patent/CN115197151B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151454A (en) * | 2014-07-25 | 2014-11-19 | 浙江大学 | Cobalt catalyst and application thereof in polymerization reaction of 1, 3-butadiene |
Non-Patent Citations (3)
| Title |
|---|
| Potential apoptosis inducing agents based on a new benzimidazole schiff base ligand and its dicopper(II) complex;Anup Paul et al.;RSC Adv;第4卷;第41228-41236页 * |
| Synthesis, DNA binding, cellular DNA lesion and cytotoxicity of a series of new benzimidazole-based Schiff base copper(II) complexes;Anup Paul et al.;Dalton Trans;第44卷;第19983-19996页 * |
| Synthesis¸ structural characterization, molecular modelling and antimicrobial studies of transition metal complexes of schiff base ligand derived from 5-chlorosalicylaldehyde and 2-(2-aminophenyl) 1H-benzimidazole;Matangi. Sunitha et al.;Journal of Chemical and Pharmaceutical Research;第4卷(第3期);第1553-1561页 * |
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