CN105461614A - Diaminocarbazole bis-salicylaldehyde derivative and application thereof - Google Patents
Diaminocarbazole bis-salicylaldehyde derivative and application thereof Download PDFInfo
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- CN105461614A CN105461614A CN201510907050.2A CN201510907050A CN105461614A CN 105461614 A CN105461614 A CN 105461614A CN 201510907050 A CN201510907050 A CN 201510907050A CN 105461614 A CN105461614 A CN 105461614A
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- Prior art keywords
- diaminocarbazole
- salicylaldehyde derivative
- bis
- application
- antibacterial
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a diaminocarbazole bis-salicylaldehyde derivative and an application thereof. The molecular structural formula of the diaminocarbazole bis-salicylaldehyde derivative is shown in the formula I. The diaminocarbazole bis-salicylaldehyde derivative is applied to bacterium resistance and has different anti-bacterial effects on staphylococcus aureus, escherichia coli and bacillus subtilis.
Description
Technical field
The present invention relates to a kind of diaminocarbazole salicylaldehyde derivative and the application in antibacterial field thereof.
Background technology
The Schif bases derivative of nitrogenous aromatic heterocycle amine or hydrazine has been widely used at the field tool such as antibacterial, sterilization, antitumor, catalysis, photoelectric material, therefore becomes current study hotspot.
Summary of the invention
The object of the invention is to provide a kind of diaminocarbazole salicylaldehyde derivative and application thereof.
The molecular structural formula of this diaminocarbazole salicylaldehyde derivative is as follows:
Described diaminocarbazole salicylaldehyde derivative is applied to antibacterial.
Diaminocarbazole salicylaldehyde derivative of the present invention all has antibacterial effect in various degree for streptococcus aureus, Escherichia coli and Bacillus subtilis.
Embodiment
Embodiment:
(1) molecular structural formula of diaminocarbazole salicylaldehyde derivative is:
(2) preparation method of diaminocarbazole salicylaldehyde derivative:
In 100ml four-hole boiling flask, taking 5mmol (0.6114g) salicylic aldehyde and adding 30mL dehydrated alcohol makes it dissolve, and installs the reaction units such as agitator, thermometer, reflux condensing tube and dropping funnel.Separately take 2.5mmol (0.5688g) N-ethyl-3,6-diaminocarbazole 20mL dehydrated alcohol heating for dissolving, it is dropwise added dropwise in four-hole boiling flask, after 10min, has yellow flocks to occur, drip and finish, continue back flow reaction 3.5h.After completion of the reaction, suction filtration while hot, product hot ethanol repeatedly washs, and dries, and obtains the two salicylaldehyde derivative 0.7826g of yellow needles body product N-ethyl-3,6-diaminocarbazole.Ultimate analysis w% (experimental value/calculated value): C (77.45/77.60), N (9.81/9.78), H (5.35/5.31).
1HNMR(DMSO，400MHz，TMS)：δ13.62(s，2H，-OH)；δ9.16(s，2H，-N＝C-H)；δ6.98-8.41(m，14H，ph-H)；δ4.50-4.55(m，2H，-CH
2-)；δ1.34-1.37(t，3H，-CH
3)。Meet the molecular structure of target product diaminocarbazole salicylaldehyde derivative.
(3) application of diaminocarbazole salicylaldehyde derivative:
Antibacterial experiment adopts agar diffusion method of the paper to carry out.The two salicylaldehyde derivative of preparation N-ethyl-3,6-diaminocarbazole is respectively the DMF solution of 0.1,0.25,0.5 and 1.0mg/mL tetra-concentration levels.By beef-protein medium sterilizing 20min at 120 DEG C, aseptically be dispensed in culture dish, 6mm is immersed in the solution of above-mentioned each concentration through the circular filter paper sheet of sterilizing, with aseptic nipper, filter paper is placed on the flat board of each bacteria suspension of even spread after fully soaking.Be inverted in 30 DEG C of incubators after cultivating 48h.Adopt right-angled intersection method to measure antibacterial circle diameter, each concentration parallel test of each bacterial classification 3 times, averages.The fungistatic effect of larger this compound of explanation of antibacterial circle diameter is better.Found that the diaminocarbazole salicylaldehyde derivative of the present embodiment all has antibacterial effect in various degree to streptococcus aureus, Escherichia coli and Bacillus subtilis by antibacterial experiment, table 1 is antibacterial experiment result.
According to China " disinfection technology standard) judgement criteria to fungistatic effect in (version in 2002): the antibacterial circle diameter of anti-bacteria is greater than 20mm and represents to have strong fungistatic effect, be moderate antibacterial effect at 10 ~ 20mm, and to be less than 10mm be weak fungistatic effect.From the antibacterial data of table 1, in the present embodiment, the two salicylaldehyde derivative of N-ethyl-3, the 6-diaminocarbazole of different concns has different antibacterial effects to streptococcus aureus, Escherichia coli and Bacillus subtilis, and the higher antibacterial effect of concentration is more remarkable.To above-mentioned bacterial classification, all there is more significant antibacterial effect higher than during 0.50mg/mL in concentration.
The chemical reagent purity used in embodiment is analytical pure or the above reagent of analytical pure.
Table 1 antibacterial experiment effect (antibacterial circle diameter, mm)
Claims (2)
1. a diaminocarbazole salicylaldehyde derivative, is characterized in that the molecular structural formula of this compound is:
2. the application of diaminocarbazole salicylaldehyde derivative according to claim 1, is characterized in that this diaminocarbazole salicylaldehyde derivative is for antibacterial.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510907050.2A CN105461614A (en) | 2015-12-08 | 2015-12-08 | Diaminocarbazole bis-salicylaldehyde derivative and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510907050.2A CN105461614A (en) | 2015-12-08 | 2015-12-08 | Diaminocarbazole bis-salicylaldehyde derivative and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105461614A true CN105461614A (en) | 2016-04-06 |
Family
ID=55599832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510907050.2A Pending CN105461614A (en) | 2015-12-08 | 2015-12-08 | Diaminocarbazole bis-salicylaldehyde derivative and application thereof |
Country Status (1)
| Country | Link |
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| CN (1) | CN105461614A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0145466B2 (en) * | 1982-05-08 | 1989-10-03 | Kyowa Hatsuko Kogyo Kk | |
| CN105294539A (en) * | 2015-11-20 | 2016-02-03 | 齐鲁工业大学 | Aluminum ion fluorescent probe compound and preparation method thereof |
-
2015
- 2015-12-08 CN CN201510907050.2A patent/CN105461614A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0145466B2 (en) * | 1982-05-08 | 1989-10-03 | Kyowa Hatsuko Kogyo Kk | |
| CN105294539A (en) * | 2015-11-20 | 2016-02-03 | 齐鲁工业大学 | Aluminum ion fluorescent probe compound and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| BRUNO LISBOA TIMM，等: "In Vitro and In Vivo Biological Effects of Novel Arylimidamide Derivatives against Trypanosoma cruzi", 《ANTIMICROBIAL AGENTS AND CHEMOTHERAPY》 * |
| ZUBI SADIQ，等: "SYNTHESIS AND ANTIMICROBIAL ASSESSMENT OF EFFICACIOUS CARBAZOLE DERIVATIVES", 《INT J PHARM BIO SCI》 * |
| 杨莲莲: "新型咔唑基席夫碱衍生物的合成及离子识别性能研究", 《中国优秀硕士学位论文全文数据库（电子期刊）》 * |
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Application publication date: 20160406 |
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