CN105052936B - The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives - Google Patents

The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives Download PDF

Info

Publication number
CN105052936B
CN105052936B CN201510485923.5A CN201510485923A CN105052936B CN 105052936 B CN105052936 B CN 105052936B CN 201510485923 A CN201510485923 A CN 201510485923A CN 105052936 B CN105052936 B CN 105052936B
Authority
CN
China
Prior art keywords
benzenesulfonyls
acetyl group
compound
bases
methyl indol
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.)
Expired - Fee Related
Application number
CN201510485923.5A
Other languages
Chinese (zh)
Other versions
CN105052936A (en
Inventor
车志平
田月娥
陈根强
陈应武
胡镇杰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henan University of Science and Technology
Original Assignee
Henan University of Science and Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henan University of Science and Technology filed Critical Henan University of Science and Technology
Priority to CN201510485923.5A priority Critical patent/CN105052936B/en
Publication of CN105052936A publication Critical patent/CN105052936A/en
Application granted granted Critical
Publication of CN105052936B publication Critical patent/CN105052936B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Indole Compounds (AREA)

Abstract

The invention discloses a kind of purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives, belong to crop disease technical field of biological control.N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives have significant antibacterial activity, can be used to suppress plant pathogenic fungi, prepare plant pathogenic fungi antiseptic；Its general structure is as follows：In formula：R1Selected from H or Et, R2It is selected from

Description

The purposes of N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives
Technical field
The present invention relates to a kind of purposes of N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives, category In crop disease technical field of biological control.
Background technology
Benzazole compounds have the multiple biological activities such as anti-inflammatory, antitumor, antibacterial, antiviral, AntiHIV1 RT activity, in recent years Satisfied clinical effectiveness is obtained, and has increasingly been paid attention to by whole world chemical research person, the deep synthesis with research has had A series of compounds with bioactivity.Such as Fan reports N- Benzenesulfonylindole analog derivatives in Anti-HIV-1 Active side Research (Ling-ling Fan, Wu-qing Liu, Hui Xu, the et al.Anti human immunodeficiency in face virus-1(HIV-1)agents 3:Synthesis and in vitro anti-HIV-1 activity of some N- arylsulfonylindoles.Chemical&Pharmaceutical Bulletin.2009,57(8):797-800.)。Ran Etc. report N- benzenesulfonyl -3- acetylindole analog derivatives in terms of Anti-HIV-1 Active research (Jun-qiang Ran, Ning Huang,Hui Xu,et al.Anti HIV-1 agents 5:Synthesis and anti-HIV-1 activity of some N-arylsulfonyl-3-acetylindoles in vitro.Bioorganic&Medicinal Chemistry Letters.2010,20:3534-3536.), etc..
In recent years, 3- acyl indols class compound turns into the focus of researcher's concern because it has real value higher, It has quite varied bioactivity, such as treat gastrointestinal disease, angiocardiopathy, central nervous system disorder etc..Che etc. Report the synthesis of N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives and in terms of Anti-HIV-1 Active Research (Zhi-ping Che, Sheng-ming Liu, Yue-e Tian, et al.Design and synthesis of novel N-arylsulfonyl-3-(2-yl-ethanone)-6-methylindole derivatives as inhibitors of HIV-1replication.Pharmaceuticals.2015,8:221-229.), but it is in antibacterial Research in terms of activity has not been reported.
The content of the invention
It is an object of the invention to provide a kind of N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives Purposes.
In order to realize the above object the technical solution adopted in the present invention is：
The purposes of N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives, specially it is in suppression plant Application in terms of thing disease fungus, or its application in terms of plant pathogenic fungi bacteriostatic agent is prepared；
The general structure of N- benzenesulfonyls -3- (2- bases-the acetyl group) -6- methyl indol analog derivatives is as follows：
In formula：R1Selected from H or Et, R2It is selected fromOr
Preferably, in formula：R1It is H, R2It is selected fromOrOr R1It is Et, R2It is selected fromOr
More excellent, in formula：R1It is Et, R2For
In the bacteriostatic agent N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indols analog derivative be antibacterial activity into Point, its addition is 0.1~99.9wt%.
Can also be included in the bacteriostatic agent can derive with N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indols class The compositions such as excipient, the diluent that thing stabilization coexists.Excipient includes carbohydrate derivative such as lactose, sucrose, glucose, mannose Alcohol and D-sorbite, starch derivatives such as cornstarch, potato starch, dextrin and CMS, cellulose derivative is as tied Crystalline cellulose, hydroxypropyl cellulose, carboxymethylcellulose calcium, calcium carboxymethylcellulose, sodium carboxymethylcellulose, etc..Diluent Including water, ethanol etc..
Beneficial effects of the present invention：
In view of N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol class compounds and its derivative are with stronger Theoretical and application value, and there is indoles skeleton class compound to also tend to show multiple biological activities, add various N- substitutions Benzenesulfonylindole is again the important intermediate of numerous pharmaceutical synthesis.Therefore, N- is replaced benzenesulfonyl -3- acetyl group by the present invention Indole derivatives acetyl position methyl is first single bromo, further with corresponding amine or 5- phenyl -1,3,4- oxadiazole -2- sulphur Alcohol reaction obtains corresponding N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives, and carries out in-vitro antibacterial Activity research, as a result shows, N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives have significant antibacterial Activity, the wherein bacteriostatic activity of compound 7 are higher than commercial antimicrobial agent hymexazol, can be used to suppress plant pathogenic fungi, prepare and plant Thing disease fungus antiseptic.
Brief description of the drawings
Fig. 1 is the ESI mass spectrograms of compound 1 in test example；
Fig. 2 is the ESI mass spectrograms of compound 2；
Fig. 3 is the ESI mass spectrograms of compound 3；
Fig. 4 is the ESI mass spectrograms of compound 4；
Fig. 5 is the ESI mass spectrograms of compound 5；
Fig. 6 is the ESI mass spectrograms of compound 6；
Fig. 7 is the ESI mass spectrograms of compound 7.
Specific embodiment
Following embodiments are only described in further detail to the present invention, but do not constitute any limitation of the invention.
Test example
1st, correspondence chooses substituent R in following general structure1、R2, obtain N- benzenesulfonyls -3- (2- bases-acetyl group) - 6- methyl indol classes compound 1~7.
In formula：R1Selected from H or Et, R2It is selected fromOr
N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives are with 6- methyl indols as raw material, first By nitrogen position sulfonylation, N- benzenesulfonyl -3- acetylindole analog derivatives, N- benzene sulphurs further is obtained in C-3 acetylation Acyl group -3- acetylindole analog derivatives acetyl position methyl is first single bromo, further with corresponding amine or 5- phenyl -1,3, 4- oxadiazole -2- thiol reactants are obtained.
The synthetic route of compound 1~6 is as follows：
By N- benzenesulfonyls -3- (the bromo- acetyl group of 2-) -6- methyl indol classes compound (1mmol), amine (1mmol), CuI (0.2mmol) and anhydrous K2CO3(2mmol) is added in DMF (5mL), the lower 80 DEG C of reactions of nitrogen protection, TLC tracing detections to raw material Reaction is complete.Question response liquid is cooled to after room temperature to frozen water (20mL) is poured into reaction solution, is extracted with ethyl acetate (30mL × 3 time) Take, merge organic phase and washed with saturated nacl aqueous solution, anhydrous sodium sulfate drying, filtrate decompression is concentrated and by preparing thin layer Silica gel separates to obtain required sterling.
Reaction expression is as follows：
The amine is selected from morpholinePiperidinesNafoxidineDiisopropylamineOr n-butylamine
The synthetic route of compound 7 is as follows：
By N- benzenesulfonyls -3- (the bromo- acetyl group of 2-) -6- methyl indol classes compound (0.6mmol), 5- phenyl -1,3, 4- oxadiazole -2- mercaptan (0.5mmol) and anhydrous K2CO3(1mmol) adds back flow reaction, TLC tracing detections in acetone (5mL) It is complete to raw material reaction.Question response is filtered while hot after terminating, and filtrate decompression concentrates and separates required by preparing thin layer silica gel Sterling.
Reaction equation is as follows：
5- phenyl -1,3,4- oxadiazoles -2- mercaptan the preparation methods are as follows：
A certain amount of benzoyl hydrazine, appropriate KOH and carbon disulfide are added in the flask of determined volume, and is added appropriate Absolute ethyl alcohol back flow reaction, TLC tracing detections are complete to raw material reaction.Question response liquid is cooled to concentration of reaction solution after room temperature, and Solid being adjusted to watery hydrochloric acid at most, being filtrated to get 5- phenyl -1, the crude product of 3,4- oxadiazole -2- mercaptan, ethyl alcohol recrystallization is obtained To required sterling.
The preparation method of the benzoyl hydrazine is as follows：
It is stirred at room temperature after a certain amount of benzoic acid and appropriate thionyl chloride are added in the flask of determined volume, is turned after stirring Move on in oil bath, the lower 80 DEG C of reactions of argon gas protection, TLC tracing detections, after completion of the reaction air-distillation removes complete two of unreacted Chlorine sulfoxide, adds the methyl alcohol of appropriate chromatographically pure, 60 DEG C of reactions, TLC tracing detections after reaction completely, to remove unreacted complete afterwards Methyl alcohol, obtain methyl benzoate；It is that 80% hydrazine hydrate reacts at 60 DEG C to be subsequently adding quantitative methyl alcohol and appropriate volumetric concentration, TLC tracing detections, after reaction completely, are cooled to room temperature and separate out solid, and suction filtration obtains crude product, needed for filter cake recrystallizing methanol is obtained Sterling.
The synthetic route of N- benzenesulfonyls -3- (the bromo- acetyl group of the 2-) -6- methyl indol class compounds is as follows：
N- benzenesulfonyls -3- acetyl group -6- methyl indol classes compound (1mmol) is added into CCl under nitrogen protection4 Backflow is completely dissolved it in (5mL), and NBS (1.1mmol) and AIBN (8mg) is added afterwards, continues back flow reaction 20min.Now AIBN (4mg) is added, continues back flow reaction, and it is complete to raw material reaction with TLC tracing detections.After question response liquid is cooled to room temperature The succinimide that reaction is produced is filtered to remove, concentration filtrate obtains transition intermediate.Because of N- benzenesulfonyls -3- (the bromo- acetyl of 2- Base) -6- methyl indol class compounds are unstable on silica gel, so the product being concentrated to give processes directly carry out down without isolation Single step reaction.
Reaction expression is as follows：
The synthetic route of the N- benzenesulfonyls -3- acetyl group -6- methyl indol class compounds is as follows：
Weigh AlCl3(3mmol) adds dichloromethane (5mL) in 50mL flasks, and (28 DEG C) are slowly added dropwise second at room temperature Acyl chlorides (1.5mmol) is in reaction solution.(i.e. reaction solution become clarification) is slowly added dropwise the N- of dichloromethane dissolving and takes after reaction 15min For Benzenesulfonylindole, room temperature reaction 2h, TLC tracing detection are complete to reaction after drop finishes, and add water (10mL) terminating reaction.With two Chloromethanes (20mL × 3 time) is extracted, and merges organic phase, and organic phase uses saturated sodium bicarbonate solution (30mL) and saturation chlorination successively Sodium solution (30mL) is washed, anhydrous sodium sulfate drying, is concentrated under reduced pressure, and thin-layer chromatography separates required sterling.
Reaction expression is as follows：
The physicochemical property of N- benzenesulfonyl -3- acetyl group -6- methyl indols is as follows：
1) white solid, 220~222 DEG C of fusing point, yield is 93%.
2) compound nuclear magnetic resonance map (1HNMR, 300MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.16 (d, J=8.4Hz, 1H), 8.14 (s, 1H), 7.93 (d, J=7.5Hz, 2H), 7.73 (s, 1H), 7.58-7.63 (m, 1H), 7.48-7.53 (m, 2H), 7.15 (d, J=8.1Hz, 1H), 2.56 (s, 3H, COCH3),2.47(s,3H,CH3)。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 314.
The physicochemical property of N- (p- ethyls) benzenesulfonyl -3- acetyl group -6- methyl indols is as follows：
1) white solid, 118~119 DEG C of fusing point, yield is 88%.
2) compound nuclear magnetic resonance map (1HNMR, 400MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.17 (d, J=8.4Hz, 1H), 8.14 (s, 1H), 7.84 (d, J=8.0Hz, 2H), 7.74 (s, 1H), 7.30 (d, J=8.0Hz, 2H), 7.15 (d, J= 8.0Hz, 1H), 2.66 (q, J=7.6Hz, 2H, CH 2CH3),2.55(s,3H,COCH3),2.48(s,3H,CH3),1.18(t,J =8.0Hz, 3H, CH2CH 3)。
3) EI sources mass spectrum (MS) figure feature of the compound：Its [M+] peak be 341.
The synthetic route of the N- benzenesulfonyls -6- methyl indol class compounds is as follows：
Weigh 6- methyl indols (1mmol), substituted phenylsulfonyl chloride (1.2mmol), NaOH (1.8mmol) and TEBA (0.1mmol) adds dichloromethane (5mL) in 50mL flasks, and room temperature reaction 1~2h, TLC tracing detection are complete to reaction, Add water (10mL) terminating reaction.Extracted with dichloromethane (20mL × 3 time), merge organic phase, organic phase is molten with saturated sodium-chloride Liquid (10mL) is washed, anhydrous sodium sulfate drying, is concentrated under reduced pressure, and thin-layer chromatography separates to obtain required sterling.
Reaction expression is as follows：
The physicochemical property of N- benzenesulfonyl -6- methyl indols is as follows：
1) white solid, 70~71 DEG C of fusing point, yield is 96%.
2) compound nuclear magnetic resonance map (1HNMR, 300MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:7.81-7.88(m,3H),7.41- 7.49 (m, 5H), 7.04 (d, J=6.9Hz, 1H), 6.61 (s, 1H), 2.47 (s, 3H).
3) EI sources mass spectrum (MS) figure feature of the compound：Its [M+] peak be 271.
The physicochemical property of N- (p- ethyls) benzenesulfonyl -6- methyl indols is as follows：
1) white solid, 84~85 DEG C of fusing point, yield is 94%.
2) compound nuclear magnetic resonance map (1HNMR, 300MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:7.76-7.81(m,3H),7.49 (s, 1H), 7.38 (d, J=7.8Hz, 1H), 7.03-7.25 (m, 3H), 6.59 (s, 1H), 2.61 (q, J=7.2Hz, 2H), 2.47 (s, 3H), 1.17 (t, J=7.2Hz, 3H).
3) EI sources mass spectrum (MS) figure feature of the compound：Its [M+] peak be 299.
The preparation method to ethyl benzene sulfonyl chloride is as follows：
Its reaction solution is cooled to -10 DEG C in ice salt bath after a certain amount of ethylo benzene appropriate volume chloroform is dissolved Left and right, the rear appropriate chlorosulfonic acid of fast drop, stirring reaction 20min removes ice salt bath, continues that 30min, TLC is stirred at room temperature Tracing detection is complete to raw material reaction.Reaction solution is poured slowly into appropriate trash ice water and obtains two phase liquid.Separate organic phase, water phase Extracted three times with appropriate chloroform.Merge organic phase, be washed once with saturated aqueous common salt, anhydrous sodium sulfate drying.Filter, be concentrated to give To faint yellow oily solution.
Compound 1
The physicochemical property of the compound is as follows：
1) yellow solid, 132~134 DEG C of fusing point, yield is 73%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 400MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.23 (d, J=8.4Hz, 1H), 8.18(s,1H),7.95-7.97(m,2H),7.91(s,1H),7.58-7.60(m,1H),7.47-7.51(m,2H),7.31(d, J=8.4Hz, 1H), 3.59 (s, 2H), 2.57 (s, 3H), 2.34 (s, 4H), 1.55-1.60 (m, 4H), 1.43-1.44 (m, 2H)；δ:193.4,137.5,137.0,135.1,134.5,132.0,129.5,127.1,126.4,126.3,122.5, 121.8,113.3,63.7,54.3,27.8,26.0,24.3。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 397 (see Fig. 1).
4) reaction equation is：
The physicochemical property of the compound is as follows：
1) white solid, 174~176 DEG C of fusing point, yield is 66%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 500MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.25 (d, J=8.0Hz, 1H), 8.19 (s, 1H), 7.94-7.96 (m, 2H), 7.90 (s, 1H), 7.62 (t, J=7.5Hz, 1H), 7.48-7.51 (m, 2H), 7.33 (dd, J=8.0Hz, 1.0Hz, 1H), 3.71 (t, J=4.5Hz, 4H), 3.61 (s, 2H), 2.57 (s, 3H), 2.41 (t, J =4.0Hz, 4H)；δ:193.4,137.5,136.2,135.1,134.5,132.1,129.5,127.1,126.7,126.2, 122.8,121.7,113.3,67.0,63.3,53.4,27.8。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 399 (see Fig. 2).
4) reaction equation is：
The physicochemical property of the compound is as follows：
1) yellow solid, 124~126 DEG C of fusing point, yield is 57%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 500MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.24 (d, J=8.5Hz, 1H), 8.18(s,1H),7.95-7.97(m,2H),7.91(s,1H),7.58-7.61(m,1H),7.47-7.50(m,2H),7.33- 7.35(m,1H),3.75(s,2H),2.56(s,3H),2.49(s,4H),1.78-1.80(m,4H)；δ:193.3,137.5, 135.1,134.5,132.0,129.5,127.1,126.5,126.1,122.7,121.8,113.2,60.5,53.8,27.7, 23.5。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 383 (see Fig. 3).
4) reaction equation is：
The physicochemical property of the compound is as follows：
1) brown liquid, yield is 49%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 500MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.17-8.19(m,2H),8.02 (s, 1H), 7.97 (d, J=8.0Hz, 2H), 7.57-7.60 (m, 1H), 7.46-7.49 (m, 2H), 7.32 (d, J=8.0Hz, 1H), 3.74 (s, 2H), 2.99-3.04 (m, 2H), 2.56 (s, 3H), 1.03 (d, J=6.5Hz, 12H)；δ:193.4,142.0, 137.6,135.3,134.4,131.6,129.5,127.2,126.0,124.9,122.2,121.8,112.1,49.0,48.0, 27.7,20.8。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 413 (see Fig. 4).
4) reaction equation is：
The physicochemical property of the compound is as follows：
1) yellow liquid, yield is 51%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 500MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.26 (d, J=8.5Hz, 1H), 8.18(s,1H),7.95-7.97(m,2H),7.90(s,1H),7.59-7.62(m,1H),7.48-7.51(m,2H),7.31- 7.33(m,1H),3.91(s,2H),2.75(s,1H),2.58-2.61(m,2H),2.56(s,3H),1.48-1.51(m,2H), 1.32-1.36(m,2H),0.89-0.92(m,3H)；δ:193.4,138.7,137.6,135.2,134.5,132.0,129.6, 127.0,126.4,125.4,122.9,121.8,112.4,53.9,48.8,32.1,27.7,20.4,14.0。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 385 (see Fig. 5).
4) reaction equation is：
The physicochemical property of the compound is as follows：
1) white solid, 108~110 DEG C of fusing point, yield is 37%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 500MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.25 (d, J=8.5Hz, 1H), 8.19 (s, 1H), 7.92 (s, 1H), 7.87 (d, J=8.0Hz, 2H), 7.29-7.33 (m, 3H), 3.71 (s, 4H), 3.62 (s, 2H), 2.68 (q, J=7.5Hz, 2H), 2.56 (s, 3H), 2.42 (s, 4H), 1.21 (t, J=7.5Hz, 3H)；δ:193.4, 151.9,135.1,134.7,132.2,129.0,127.3,126.7,126.2,122.8,121.5,113.4,67.0,63.3, 53.4,28.8,27.7,14.8。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 427 (see Fig. 6).
4) reaction equation is：
The physicochemical property of the compound is as follows：
1) white solid, 122~124 DEG C of fusing point, yield is 36%.
2) compound nuclear magnetic resonance map (1H NMR and13C NMR, 500MHz and 125MHz) feature：
With deuterated CDCl3It is solvent, TMS is internal standard compound, wherein each peak is attributed to：δ:8.29 (d, J=8.0Hz, 1H), 8.18 (s, 1H), 8.15 (s, 1H), 7.98-8.00 (m, 2H), 7.90 (d, J=8.5Hz, 2H), 7.49-7.52 (m, 3H), 7.43 (d, J=7.5Hz, 1H), 7.29-7.41 (m, 2H), 4.64 (s, 2H), 2.58-2.59 (m, 2H), 2.54 (s, 3H), 1.13 (t, J=7.5Hz, 3H)；δ:193.2,165.8,163.6,151.9,134.9,134.4,133.7,132.5,131.7, 129.2,129.1,129.0,127.3,127.2,126.6,125.9,123.6,123.4,121.4,114.0,37.0,28.8, 27.7,14.6。
3) ESI-TRAP sources mass spectrum (MS) figure feature of the compound：Its [M+H]+Peak is 518 (see Fig. 7).
4) reaction equation is as above.
2nd, biological activity determination experiment
(1) test sample and reagent：Positive control hymexazol (commercial antimicrobial agent), the compound 1~7 of above-mentioned preparation, third Ketone (analysis is pure).
(2) test plant disease fungus (totally 14 kinds)：Exserohilum turcicum [Exserohilum turcicum (Pass.) Leonard et Suggs], southern corn leaf blight [Helminthosporium maydis Nisik＆Miy], Curvularia leaf Pinta bacterium [Currularia lunata (Boed) Wakker], fusarium graminearum [Fusarium graminearum Schw.], Cochliobolus sativus [Bipolaris sorokiniana (Sacc.) Shoem], wheat stalk Phyllostachys pubescens [Fusarium pseudograminearum, Fpg], rice blast fungus [Pyricularia oryzae Cav.], Sclerotina Sclerotiorum in Winter Rape Core germ [Sclerotinia sclerotiorum (Lib.) de Bary], Phytophthora nicotianae germ [Phytophora Nicotianae Breda de Haan Tuker], tobacco brown spot pathogen [Alternaria alternata Keissler], Botrytis cinerea [Botrytis cinerea Pers.], Alternaria brassicae [Alternaria brassicae Sacc.], cotton-wilt fusarium [Fusarium oxysporium f.sp.Vasinfectum synder et Hansen], Huang Cucurbit wilt bacterium [Fusarium oxysporium f.sp cucumerinum Owen], by forestry institute of University Of Science and Technology Of He'nan Plant protection system laboratory provides.
(3) sod cultivation (using mycelial growth rate method)：
Culture medium：(its proportioning is V8 culture mediums：V-8 vegetable juice 160mL, agar 15g, distilled water 1500mL) and PDA trainings (its proportioning is to support base：Peeled potatoes 200g, glucose 20g, agar 20g, distilled water are settled to 1000mL).
Determine N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol class chemical combination respectively using mycelial growth rate method 14 kinds of indoor virulences of frequently seen plants disease fungus of thing 1~7 pair, using hymexazol as positive control.By compound 1~7 and evil Mould spirit acetone solution, it is subject to sterilization after culture medium mix with compound 1~7 and hymexazol respectively when being cooled to 65 DEG C, fully It is mixed evenly to prepare containing 100ppm (100 μ g/mL) band medicine culture mediums, with not adding medicine is blank, and each treatment sets three Individual repetition.After culture medium is sufficiently cool, inoculation growth vigor is consistent, and diameter 5mm's supplies examination pathogen bacterium piece, in 28 ± 1 DEG C Investigated after incubated 4d.During investigation, colony diameter is measured with crossing method, and each sample pair is calculated with following formula The growth inhibition ratio of surveyed pathogen, as a result see the table below 1, table 2.
(4) result of the test
The fungistatic effect of the compound 1~7 of table 1 and hymexazol to strains tested
The fungistatic effect of the compound 1~7 of table 2 and hymexazol to strains tested
Result shows, N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol class chemical combination prepared by above-described embodiment Thing 1~7 pair surveys 14 kinds of plant pathogenic fungis and shows preferable bacteriostatic activity, wherein 7 pairs of all strains testeds of compound Bacteriostatic activity all be higher than commercial antimicrobial agent hymexazol；Additionally, 1~7 pair of Sclerotinia sclerotiorum of compound and botrytis cinerea Bacteriostatic activity exceed hymexazol, its inhibiting rate is above 75%.
Embodiment 1
Application of the compound 7 in terms of plant pathogenic fungi bacteriostatic agent is prepared, specially：Compound 7 and filler are formed sediment Powder is according to 10wt%:The ratio of 90wt% is well mixed, packaging, obtains final product.
In other embodiments of the invention, compound 4,5 etc. is also can use for preparing plant pathogenic fungi bacteriostatic agent.

Claims (7)

  1. The purposes of 1.N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives, it is characterised in that：It is suppressing Application in terms of plant pathogenic fungi；
    The general structure of N- benzenesulfonyls -3- (2- bases-the acetyl group) -6- methyl indol analog derivatives is as follows：
    In formula：R1Selected from H or Et, R2It is selected from
    The plant pathogenic fungi is Exserohilum turcicum, southern corn leaf blight, Maize Curvularia, wheat scab Bacterium, Cochliobolus sativus, wheat stalk Phyllostachys pubescens, rice blast fungus, Sclerotinia sclerotiorum, Phytophthora nicotianae germ, tobacco are red Star germ, botrytis cinerea, Alternaria brassicae, cotton-wilt fusarium, cucumber fusarium axysporum.
  2. 2. purposes according to claim 1, it is characterised in that：R1It is H, R2It is selected from Or R1It is Et, R2It is selected from
  3. 3. purposes according to claim 2, it is characterised in that：R1It is Et, R2For
  4. The purposes of 4.N- benzenesulfonyls -3- (2- bases-acetyl group) -6- methyl indol analog derivatives, it is characterised in that：It is being prepared Application in terms of plant pathogenic fungi bacteriostatic agent；
    The general structure of N- benzenesulfonyls -3- (2- bases-the acetyl group) -6- methyl indol analog derivatives is as follows：
    In formula：R1Selected from H or Et, R2It is selected from
    The plant pathogenic fungi is Exserohilum turcicum, southern corn leaf blight, Maize Curvularia, wheat scab Bacterium, Cochliobolus sativus, wheat stalk Phyllostachys pubescens, rice blast fungus, Sclerotinia sclerotiorum, Phytophthora nicotianae germ, tobacco are red Star germ, botrytis cinerea, Alternaria brassicae, cotton-wilt fusarium, cucumber fusarium axysporum.
  5. 5. purposes according to claim 4, it is characterised in that：R1It is H, R2It is selected from Or R1It is Et, R2It is selected from
  6. 6. purposes according to claim 5, it is characterised in that：R1It is Et, R2For
  7. 7. the purposes according to any one of claim 4~6, it is characterised in that：N- benzenesulfonyls -3- in the bacteriostatic agent (2- bases-acetyl group) -6- methyl indols analog derivative is Antibacterial Constituents, and its addition is 0.1~99.9wt%.
CN201510485923.5A 2015-08-10 2015-08-10 The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives Expired - Fee Related CN105052936B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510485923.5A CN105052936B (en) 2015-08-10 2015-08-10 The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510485923.5A CN105052936B (en) 2015-08-10 2015-08-10 The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives

Publications (2)

Publication Number Publication Date
CN105052936A CN105052936A (en) 2015-11-18
CN105052936B true CN105052936B (en) 2017-07-07

Family

ID=54482672

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510485923.5A Expired - Fee Related CN105052936B (en) 2015-08-10 2015-08-10 The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives

Country Status (1)

Country Link
CN (1) CN105052936B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011025805A1 (en) * 2009-08-25 2011-03-03 The Ohio State University Research Foundation Alkyl indole-3-carbinol-derived antitumor agents
CN102321009A (en) * 2011-07-11 2012-01-18 西北农林科技大学 Arylhydrazone derivate, preparation method thereof and application in preparing anti-HIV-1 medicines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011025805A1 (en) * 2009-08-25 2011-03-03 The Ohio State University Research Foundation Alkyl indole-3-carbinol-derived antitumor agents
CN102321009A (en) * 2011-07-11 2012-01-18 西北农林科技大学 Arylhydrazone derivate, preparation method thereof and application in preparing anti-HIV-1 medicines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Antifungal Agents. Part 3: Synthesis and Antifungal Activities of 3-Acylindole Analogs against Phytopathogenic Fungi In Vitro;Hui Xu,et,al.;《Chem Biol Drug Des》;20110915;第78卷;第864-868页 *

Also Published As

Publication number Publication date
CN105052936A (en) 2015-11-18

Similar Documents

Publication Publication Date Title
Khan et al. Synthesis and biological evaluation of novel angularly fused polycyclic coumarins
CN105753814A (en) Substituted nitrogen heterocyclic derivative and application thereof
CN109942546B (en) Quinolone pyrimidine compound and preparation method and application thereof
CN107711855A (en) Application of the peaceful alkali A derivatives of camel in the medicine of preventing and treating or anti-plant disease is prepared
CN109232545A (en) A kind of myricetin derivative, preparation method and the usage containing quinoxaline
CN107721924A (en) Gatifloxacin derivative and its production and use
CN110372692A (en) Dihydroquinazoline ketone antiport process blocking agent, preparation method and the usage
CN105052936B (en) The purposes of N benzenesulfonyls 3 (2 base acetyl group) 6 methyl indol analog derivatives
CN108929353B (en) A kind of rhamnose or the berberine salt derivative and its preparation method and application of ribose modification
CN110372588A (en) A kind of 4- amido quinoline compound and its preparation method and application
CN104974108B (en) Series connection double thiazole class compound of one kind 2,2 ' and its production and use
CN103864765B (en) Benzazepine analog derivative containing five-membered ring, Preparation Method And The Use
CN101974016A (en) Amide compound and preparation method and applications thereof
CN113185505B (en) Quinolone oxazolidinone compound and preparation method and application thereof
CN109422734A (en) Nortopsentin Alkaloid derivative and its preparation and the application in prevention and treatment pest and disease damage
CN107494553A (en) Disinfectant use in agriculture and purposes derived from a kind of gallic acid
CN113698378A (en) Naphthoquinone compounds and preparation and acaricidal and bactericidal application thereof
CN106565744B (en) The crystal form and preparation method thereof of PA-824 compound
CN104798808B (en) Application of 2-quinazoline diselenide derivatives in preparing phytopathogen resisting medicine
CN106083746B (en) A kind of synthetic method of benzamide derivatives
CN105061287B (en) N- substitution benzenesulfonyl -3- propionos indole derivatives, preparation method and application
Liu et al. Bioinspired total synthesis and biological activity of Pegaharine A
CN105198869B (en) Oxazole oxazoline derivates, preparation method and its application in terms of plant pathogenic fungi antiseptic is prepared
CN107954898A (en) Salicylaldoxime ester type compound and preparation method thereof, purposes
CN104230786B (en) Indole-structure-containing compound with anti-tumor activity and synthesis method thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170707

Termination date: 20180810

CF01 Termination of patent right due to non-payment of annual fee