CN102391207A - N-(2-(substituted benzo- thiazole-2- amino formacyl) -phenyl group) - benzamide, as well as preparation method and usages thereof - Google Patents

N-(2-(substituted benzo- thiazole-2- amino formacyl) -phenyl group) - benzamide, as well as preparation method and usages thereof Download PDF

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CN102391207A
CN102391207A CN2011102102010A CN201110210201A CN102391207A CN 102391207 A CN102391207 A CN 102391207A CN 2011102102010 A CN2011102102010 A CN 2011102102010A CN 201110210201 A CN201110210201 A CN 201110210201A CN 102391207 A CN102391207 A CN 102391207A
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compound
formamyl
phenyl
thiazole
benzo
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CN102391207B (en
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薛伟
何勇
陈前进
韩菲菲
丁晓燕
熊壮
郑玉国
魏学
杨松
李海畅
祁慧雪
范会涛
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Guizhou Qian Hong Agriculture Development Co., Ltd.
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Guizhou University
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Abstract

The invention discloses N-(2-(substituted benzo- thiazole -2- amino formacyl) -phenyl group) - benzamide with an effect of plant virus resistance, and a preparation method thereof. The chemical structure is expressed by a general formula (1). The invention introduces a benzothiazole ring benzoyl aminobenzene methanamide compound containing substituted benzoic acid, which adopts raw materials of substituted benzoic acid, substituted anthranllic acid, substituted benzothiazole amine, thionyl chloride and acetic oxide and is synthesized through four steps of chlorination, acidylation, cyclization and ring opening, and the compound has plant virus resisting activity and anticancer activity.

Description

N-(2-(replacing benzothiazole-2-formamyl)-phenyl)-BM
Technical field
What the present invention relates to have the Antiphytoviral effect contains the synthetic and preparation method thereof of benzothiazole ring o-benzoyl aminobenzoyl aminated compounds.
Background technology
O-benzoyl aminobenzoyl aminated compounds is one type and has the active Ryanicide receptor analogs of good biological, is that to carry out structural modification be that new field has been opened up in the initiative of novel pesticide to parent with the Ryanicide acceptor.At present, existing several commercial products occur, the synthetic pesticide Flubendiamide of the Ryanicide receptor structure of two wide spectrums finding like Japanese agricultural chemicals company, Beyer Co., Ltd and E.I.Du Pont Company and chlorine insect amide etc.O-benzoyl aminobenzoyl aminated compounds has identical action characteristic with Ryanicide alkali, not only insect is had excellent insecticidal activity, and to mammalian safe.
(Lahm, G.P. such as Lahm in 2005; Selby, T.P.; Freudenberger, J.H.; Stevenson, T.M.; Myers, B.J.; Seburyamo, G.; Smith, B.K.; Flexner, L.; Clark, C.E.; Cordova; D.Insecticidal anthranilic diamides:A new class of potent ryanodine receptor activators [J] .Bioorganic&Medicinal Chemistry Letters; 2005; 25 (22); 4898-4906.) with trifluoroacetic ethyl acetoacetate, substituted phenylhydrazines, replacement anthranilic acid, 3-(trifluoromethyl)-1H-pyrazoles, 2; The 3-dichloropyridine is the O-formammidotiazol-benzamide compounds of the synthetic a series of novelties of raw material, and wherein the part of compounds release that can suppress intracellular Ca2+ has caused the Ryanicide acceptor, and lepidoptera pest fall army worm (Spodoptera frugiperda), Heliothis virescens (HeliothisVirescens), small cabbage moth (Plutella xylostella) are had excellent insecticidal activity.
2006, (Masanori, T. such as Masanori; Hayami, N.; Kazuyuki, S.; Shinsuke, F.; Hideo, K.; Eiji, K.; Tateki, N; Takashi, F.; Toshiaki, S.; Akira; S.Phthalic acid diamide derivatives; Agricultural and horticultural insecticides and a method for application of the insecticides [P] .EP 1700844 (A1); 2006.) reported that has an insecticidal activity phthalic acid bisamide derivatives preferably, 500 * 10 -6Majority of compounds has better activity to agricultural and gardening pest insect under the concentration.
2006, (Jeanguenat, A. such as Jeanguenat; Osullivan; A.C.Anthranilamide derivatives as insecticides [P] .WO 2006061200; 2006 [Chem.Abstr.2006,145,62886] .) reported one type of ortho position formamido group benzamide compound; In concentration is 400mg/L, compound to lethality rates such as cigarette aphid, bean aphid, small cabbage moth, cigarette aphid noctuid, prodenia lituras more than 80%.
2006, (Richards, M.L. such as Richards; Lio, S.C.; Sinha, A.; Banie, H.; Thomas, R.J.; Major, M.; Tanji, M.; Sircar, J.C.Substituted 2-phenyl-benzimidazole derivativesL:novel compounds that suppress key markers of allergy [J] .Tetrahedron,
2007, Lu, (Lu, D. such as Ding; Vince; R.Discovery of potent HIV-1 protease inhibitors incorporating sultoximine functionality [J] .Bioorganic&Medicinal Chemistry Letters; 2007; 17 (20), 5614-5619.) a series of bisamide compounds that contain the sulfoximide structure have been synthesized in design, and active testing shows that this compounds has good inhibitory effect to HIV-1 proteolytic enzyme.Active best compound reaches 87%, anti-HIV-1 proteolytic enzyme IC at 10 μ M to the inhibiting rate of HIV-1 proteolytic enzyme 50IC for 2.5nM, anti-HIV-1 50Be 408nM.
2007, (Loiseleur, O. such as Loiseleur; Durieux, P.; Trah, S.; Edmunds, A.; Jeanguenat, A; Stoller, A.; Hughes, D.J.Preparation of pyrazole derivatives as pesticides [P] .WO 2007093402,2007 [Chem.Abstr.2007,147,55334] .) reported one type of bisamide compounds that contains pyrazoles, be 400 * 10 in concentration -6, this compound to the lethality rate of Heliothis virescens (Heliothis virescens), small cabbage moth (Plutella xvlostella), corn root aphid fly (Diabrotica balteata) all more than 80%.
2008; (Li Bin, Yang Wen brightness .1-substituted pyridyl-pyrazol acid amide compounds and application [P] .CN 101333213,2008 [Chem.Abstr.2008 thereof such as Li Bin; 150; 168341] .) reported the pyrazole amide compounds, be 10mg/L in concentration, compound to the lethality rate of beet armyworm more than 90%.
2008, (David, C.A. such as David; Lahm, G.P.; Smith, B.K.; Barry, J.D.; Clagg; D.G.Synthesis of insecticidal fluorinated anthranilic diamides [J] .Bioorganic&Medicinal Chemistry, 2008,16 (6); 3163-3170.) be guide with the chlorine insect amide; The fluorine-containing o-amino benzoyl acid diamine insecticides of a series of high reactivity has been synthesized in design, and biological activity test shows: this compounds is higher to the inhibition activity of black peach aphid and cotten aphid, and wherein part of compounds is 100% under 250 * 10-6 concentration.
2008, Scott, (Scott, D.A. such as D.A.; Aquila, B.M.; Bebernitz, G.A.; Cook, D.J.; Deegan, T.L.; Hattersley, M.M.; Ioannidis, S.; Lyne, P.D.; Omer, C.A.; Ye, M.; Zheng; X.L.Pyridyl and thiazolyl bisamides CSF-1R inhibitors for the treatment of cancer [J] .Bioorganic&Medicinal Chemistry Letters; 200818 (17); 4794-4797.) synthesized heterocyclic bisamide compounds such as containing thiazole, pyridine with gavaculine, substituted benzoic acid for raw material design; Be somebody's turn to do compound acceptor network propylhomoserin kinases is had better inhibited activity, structure activity relationship shows that thiazole derivative IC50 generally is superior to pyridine compounds and their.
Benzothiazole compound also comes to light and has better antibacterial activity; Since U.S.'s Beckman company development sixties in 20th century benthiozole (benthiazole) sterilant, the molecular designing of this compounds is the focus of agricultural chemicals initiative with synthetic and bioactivity research.
2002, (El-Gaby, M.A. such as El-Gaby; Micky, J.; Tahol, N.Antimicrobial activity of some novel thiourea, hydrazine; Fused pyrimidine and 2-(4-substituted) aniline benzoazole derivatives containing sulfonamide moieties [J] .Journal of Chinese Chemical Society, 2002,49; 407-414.) synthesized the lsothiocyanates that contains benzsulfamide with 4-aminobenzene sulfonamide and thio phosgene reaction; This lsothiocyanates again with N, refluxed in dinethylformamide and the triethylamine several hours, synthesized benzo benzo thiazole derivative with fungicidal activity; Adopt growth rate method; This compounds is carried out the fungicidal activity test, and active testing shows: under the concentration of 1.0mg/ml, this compounds has higher inhibition active to Bacillus proteus; Wherein a compound has medium inhibition active to streptococcus aureus (Staphylococcus aureus), penicillium mould (Penicillium); Another compound to the inhibition activity of Bacterium prodigiosum, bent U.S. mould a little less than.
2006, (Hou Xuetai, Wang Min such as Hou Taixue; The river rears people. the synthetic and bioactivity research [J] of diazosulfide class and benzothiazole compound. and agricultural chemicals, 2006,45 (12); 812-817.)) reported that at benzothiazole be on the basis of precursor structure, be raw material with the gavaculine, synthesized a series of benzothiazole compounds through over-churning, closed loop, amidation; Biological activity test shows: under isolated condition; Part of compounds 1.0mg/L to the inhibiting rate of gray mold of cucumber (Botrytis cinereapers) about 60%, under middle isolated condition, part of compounds does not have restraining effect to gray mold of cucumber under the concentration of 1.0mg/mL; Under condition of living body, also higher to the inhibiting rate of gray mold of cucumber.
Can know from background technology; Bisamide compounds such as chlorine insect amide have insecticidal activity preferably; To mammalian safe, benzothiazole compound such as benzene metsulfovax have better antibacterial activity, and rice sheath blight disease is had excellent preventive effect; Still nobody synthesized but the pyrazol acid amide that contains benzothiazole gets the bisamide compound, and the pyrazol acid amide that contains benzothiazole gets the bisamide compound and is used in the research of plant virus more nobody studied.
Summary of the invention
The object of the invention is to design the o-benzoyl aminobenzoyl amino derivative that has synthesized a series of novel structures; This compounds had both had biamide structure; Also contain the benzothiazole structure, and this series compound has been carried out the novel pesticide initiative of compound method and resisting tobacco mosaic virus sick (TMV) and anti-cucumber blossom disease viral disease (CMV) and studies as cancer therapy drug.Its general structure (I) is as follows:
R wherein 1Be (1) hydrogen; (2) neighbour,, contraposition is single to be replaced or polysubstituted halogen atom; (3) C1-6 alkyl; (4) C1-6 alkoxyl group;
R 2Be (1) halogen atom; (2) C1-6 alkyl; (3) C1-6 alkoxyl group;
R 3Be (1) hydrogen; (2) single halogen atom that replaces; (3) C1-6 alkyl; (4) C1-6 alkoxyl group.
In the content of the present invention, the C1-6 alkyl can be methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, tert-pentyl, neo-pentyl, n-hexyl, isohexyl, uncle's hexyl, new hexyl; Halogen atom can be fluorine, chlorine, bromine or iodine.
In the content of the present invention, the purposes of compound is as the plant virus suppressor factor, particularly tobacco mosaic virus disease (TMV) and cucumber mosaic virus (CMV) is had good active.
In the content of the present invention, the purposes of compound is as anti-tumor agent, particularly human breast cancer cell (Bcap-37) is had good active.
The preparation method of general formula of the present invention (I) compound be with substituted benzoic acid, to replace anthranilic acid, replace benzothiazole ammonia, thionyl chloride and acetic anhydride be raw material, synthetic through perchlorizing, acidylate, cyclisation and open loop four-step reaction, synthetic route is following:
Figure BSA00000544564400041
The first step: the preparation of substituted benzoyl chloride
Get a certain amount of substituted benzoic acid (band TM, drying tube and device for absorbing tail gas) in the there-necked flask of 100ml, then to wherein adding thionyl chloride, reflux number hour; React completely, TLC follows the tracks of, and reacts completely; Steam excessive thionyl chloride, get product;
Second step: the preparation of 2-substituted benzamide yl benzoic acid
Get a certain amount of 2-amino-substituted benzoic acid in the there-necked flask of 250ml, in reaction flask, add methylene dichloride then, to wherein adding triethylamine solution, clarify then up to solution; The acyl chlorides that will prepare then dropwise splashes in the reaction solution with after the methylene dichloride dilution, and stirring at normal temperature is separated out a large amount of solids in the reaction system; TLC follows the tracks of, and reacts completely, and suction filtration gets solid; Washing, methylene dichloride is washed, and the precipitation of will filtrating then gets solid; The washing, suction filtration gets solid, with two parts of solids merge product;
The preparation of the 3rd step: benzoxazinone
Get a certain amount of amido acid in the there-necked flask of 100ml, to wherein adding an amount of acetic anhydride in there-necked flask, reflux number hour leaves standstill, and solid is separated out in cooling, suction filtration, washing, product;
The 4th step: the preparation of 2-substituted benzene formyl amido N-(benzo [d] thiazole-2 base) substituted benzamide
In the there-necked flask of 100ml, add an amount of replacement benzoxazinone,, stir and make its dissolving then to wherein adding acetonitrile; In reaction system, add salt of wormwood (oven dry) and benzothiazole ammonia then, reflux, TLC follows the tracks of; React completely, filter precipitation; DMF and water recrystallization, suction filtration gets product;
This step is applicable to all above-mentioned target compound N-(replace benzothiazole-2-formamyl)-phenyl)-substituted benzamide synthetic.
Embodiment
Embodiment one, compound N-(2-(6-ethoxyl benzo thiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide (compound number is a) synthetic:
(1) 2,4 dichlorobenzyl chloride is synthetic
Get the 2,4 dichloro benzene formic acid (band TM, drying tube and device for absorbing tail gas) in the there-necked flask of 100ml of 14.32g (0.075mol), then to wherein adding the 20ml thionyl chloride; Reflux 10 hours, TLC follows the tracks of, and reacts completely; Steam excessive thionyl chloride, get 10.99g liquid;
(2) 2-(2,4 dichloro benzene formamido-) is benzoic synthetic
The anthranilic acid of getting 8.83g (0.064mol) adds the methylene dichloride of 30ml then in reaction flask in the there-necked flask of 250ml, to wherein adding the 3ml triethylamine solution, be brown clarification up to solution then; After the methylene dichloride dilution of the acyl chlorides that will prepare then with 30ml, dropwise splash in the reaction solution, stirring at normal temperature is separated out a large amount of white solids in the 1h afterreaction system; 10h reacts completely, and suction filtration gets white solid, washing, and methylene dichloride is washed; The precipitation of will filtrating then gets solid, the washing, suction filtration gets solid, with two parts of solids merge product; The absolute ethyl alcohol recrystallization gets little yellow crystals, productive rate: 65%, and mp:214-216 ℃;
(3) 2-(2,4 dichloro benzene base)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Get 4.48g2-(2,4 dichloro benzene formamido-) phenylformic acid (0.014mol) in the there-necked flask of 50ml, to the acetic anhydride that wherein adds 15ml in there-necked flask; Reflux 5h leaves standstill, and white solid is separated out in cooling; Washing, oven dry, acetone recrystallization; Get product, productive rate: 78%, mp:197-198 ℃;
(4) N-(2-(6-ethoxyl benzo thiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide is synthetic
2-(2,4 dichloro benzene base)-4H-benzo [d] [the synthesizing of 1,3] oxazine-4-ketone that in the there-necked flask of 100ml, adds 0.61g (0.002mol); To the acetonitrile that wherein adds 30ml, stir and make its dissolving then, in reaction system, add the salt of wormwood (oven dry) of 0.27g (0.002mol) and 2-amino-6-ethoxyl benzo thiazole of 0.35g (0.002mol) then; Reflux 8h reacts completely, and filters; Precipitation with DMF and water recrystallization or silica gel column chromatography separating purification, gets yellow solid; Productive rate: 47%, mp:＞250 ℃.
Synthesizing of embodiment two, compound N-(2-(6-methylbenzothiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide (compound number is b)
(1) 2,4 dichlorobenzyl chloride is synthetic
Synthetic like embodiment one (1) condition and method;
(2) 2-(2,4 dichloro benzene formamido-) is benzoic synthetic
Synthetic like embodiment one (2) condition and method;
(3) 2-(2,4 dichloro benzene base)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like embodiment one (3) condition and method;
(4) N-(2-(6-methylbenzothiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide is synthetic
Synthetic like embodiment one (4) condition and method, difference is to add 0.33g2-amino-6-methylbenzothiazole, and reaction times 6h gets faint yellow solid, productive rate: 40%, and mp:228-229 ℃.
Synthesizing of embodiment three, compound N-(2-(6-chloro benzothiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide (compound number is c)
(1) 2,4 dichlorobenzyl chloride is synthetic
Synthetic like embodiment one (1) condition and method;
(2) 2-(2,4 dichloro benzene formamido-) is benzoic synthetic
Synthetic like embodiment one (2) condition and method;
(3) 2-(2,4 dichloro benzene base)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like embodiment one (3) condition and method;
(4) N-(2-(6-chloro benzothiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide is synthetic
Synthetic like embodiment one (4) condition and method, difference is to add 0.37g2-amino-6-chloro benzothiazole, and reaction times 9h gets white solid, productive rate: 37%, and mp:＞250 ℃.
Synthesizing of embodiment four, compound N-(2-(6-methoxyl group benzo thiazole-2-formamyl)-6-aminomethyl phenyl)-2,4 dichloro benzene methane amide (compound number is d)
(1) 2,4 dichlorobenzyl chloride is synthetic
Synthetic like embodiment one (1) condition and method;
(2) 2-(2,4 dichloro benzene formamido-)-3-tolyl acid is synthetic
Synthetic like embodiment one (2) condition and method, difference is to add 2-amino-3-tolyl acid;
(3) 8-methyl-2-(2,4 dichloro benzene base)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like embodiment one (3) condition and method, difference is to add 2-(2,4 dichloro benzene formamido-)-3-tolyl acid;
(4) N-(2-(6-methoxyl group benzo thiazole-2-formamyl)-6-aminomethyl phenyl)-2,4 dichloro benzene methane amide is synthetic
Synthetic like embodiment one (4) condition and method, difference is to add 0.36g2-amino-6-methoxyl group benzo thiazole, and reaction times 5h gets faint yellow solid, productive rate: 34%, and mp:218-220 ℃.
Synthesizing of embodiment five, compound N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-3-chlorobenzamide (compound number is e)
(1) the 3-chloro-benzoyl chloride is synthetic
Synthetic like embodiment one (1) condition and method, difference is to add the 3-chloro-benzoic acid;
(2) 2-(3-chloro-benzoyl amino) is benzoic synthetic
Synthetic like embodiment one (2) condition and method, difference is to add the 3-chloro-benzoyl chloride;
(3) 2-(3-chloro-phenyl-)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like embodiment one (3) condition and method, difference is to add 2-(3-chloro-benzoyl amino) phenylformic acid;
(4) N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-3-chlorobenzamide is synthetic
Synthetic like embodiment one (4) condition and method, difference is to add 0.33g (0.002ml) 2-amino-4-methylbenzothiazole, and reaction times 10h gets white solid, productive rate: 36%, and mp:192-194 ℃.
Synthesizing of embodiment six, compound N-(2-(6-methylbenzothiazole-2-formamyl)-4-aminomethyl phenyl)-3-chlorobenzamide (compound number is f)
(1) the 3-chloro-benzoyl chloride is synthetic
Synthetic like embodiment five (1) conditions and method;
(2) 2-(3-chloro-benzoyl amino) is benzoic synthetic
Synthetic like embodiment five (2) conditions and method;
(3) 2-(3-chloro-phenyl-)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like embodiment five (3) conditions and method;
(4) N-(2-(6-methylbenzothiazole-2-formamyl)-4-aminomethyl phenyl)-3-chlorobenzamide is synthetic
Synthetic like embodiment five (4) conditions and method, difference is to add 0.33g2-amino-4-methylbenzothiazole, and reaction times: 6h gets pale yellow powder, productive rate: 41%, and fusing point: 236-238 ℃.
Embodiment seven, compound N-(2-(6-ethoxyl benzo thiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM (compound number is g) synthetic
Synthesizing of (1) 3,4-dimethoxy-benzoyl chloride
Synthetic like embodiment one (1) condition and method, difference is to add 3, the 4-dimethoxybenzoic acid;
(2) 2-(3,4-dimethoxy benzoylamino) is benzoic synthetic
Synthetic like embodiment one (2) condition and method, difference is to add 3, the 4-dimethoxy-benzoyl chloride;
(3) 2-(3, the 4-Dimethoxyphenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like embodiment one (3) condition and method, difference is to add 2-(3,4-dimethoxy benzoylamino) phenylformic acid;
(4) N-(2-(6-ethoxyl benzo thiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM synthetic
Synthetic like embodiment one (4) condition and method, difference is to add 0.39g2-amino-6-ethoxyl benzo thiazole, and reaction times: 7h gets faint yellow solid, productive rate: 33%, and mp:＞250 ℃.
Embodiment eight, compound N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM (compound number is h) synthetic
Synthesizing of (1) 3,4-dimethoxy-benzoyl chloride
Synthetic like instance seven (1) conditions and method;
(2) 2-(3,4-dimethoxy BM) is benzoic synthetic
Synthetic like instance seven (2) conditions and method;
(3) 2-(3, the 4-Dimethoxyphenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance seven (3) conditions and method;
(4) N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM synthetic
Synthetic like instance seven (4) conditions and method, difference is to add 2-amino-4-methylbenzothiazole of 0.33g (0.002mol), and reaction times 15h gets faint yellow solid, productive rate: 33%, and mp:＞250 ℃.
Synthesizing of embodiment nine, compound N-(2-(6-ethoxyl benzo thiazole-2-formamyl)-phenyl)-2-methoxy benzamide (compound number is i)
(1) the 2-methoxy benzoyl chloride is synthetic
Synthetic like instance eight (1) conditions and method, difference is to add O-Anisic Acid;
(2) 2-(2-methoxy benzamide) is benzoic synthetic
Synthetic like instance eight (2) conditions and method, difference is to add the 2-methoxy benzoyl chloride;
(3) 2-(2-p-methoxy-phenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance eight (3) conditions and method, difference is to add 2-(2-methoxy benzamide) phenylformic acid;
(4) N-(2-(6-ethoxyl benzo thiazole-2-formamyl)-phenyl)-2-methoxy benzamide is synthetic
Synthetic like instance eight (4) conditions and method, difference is to add amino-6 ethoxyl benzo thiazoles of 2-of 0.39g, and reaction times 10h gets faint yellow solid, productive rate: 33%, and mp:241-242 ℃.
Synthesizing of embodiment ten, compound N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-2-methoxy benzamide (compound number is j)
(1) the 2-methoxy benzoyl chloride is synthetic
Synthetic like instance nine (1) conditions and method;
(2) 2-(2-methoxy benzamide) is benzoic synthetic
Synthetic like instance nine (2) conditions and method;
(3) 2-(2-p-methoxy-phenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance nine (3) conditions and method;
(4) N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-2-methoxy benzamide is synthetic
Synthetic like instance nine (4) conditions and method, difference is to add 2-amino-4-methylbenzothiazole of 0.33g, and reaction times 8h gets faint yellow solid, productive rate: 40.5%, and mp:＞250 ℃.
Synthesizing of embodiment 11, compound N-(2-(6-methoxyl group benzo thiazole-2-formamyl)-phenyl)-2-methoxy benzamide (compound number is k)
(1) the 2-methyl benzoyl chloride is synthetic
Synthetic like instance nine (1) conditions and method;
(2) 2-(2-methoxy benzamide) is benzoic synthetic
Synthetic like instance nine (2) conditions and method;
(3) 2-(2-p-methoxy-phenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance nine (3) conditions and method;
(4) N-(2-(6-methoxyl group benzo thiazole-2-formamyl)-phenyl)-2-methoxy benzamide is synthetic
Synthetic like instance eight (4) conditions and method, difference is to add 2-amino-6-methoxyl group benzo thiazole of 0.36g, reaction times 7.5h, and productive rate: 37%, mp:218-219 ℃.
Synthesizing of embodiment 12, compound N-(2-(6-methylbenzothiazole-2-formamyl)-phenyl)-4-fluorobenzamide (compound number is 1)
(1) the 4-fluorobenzoyl chloride is synthetic
Synthetic like instance one (1) condition and method, difference is to add the 4-fluorobenzoic acid;
(2) 2-(4-fluorobenzamide) is benzoic synthetic
Synthetic like instance one (2) condition and method, difference is to add the 4-fluorobenzoyl chloride;
(3) 2-(4-fluorophenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance one (3) condition and method, difference is to add 2-(4-fluorobenzamide) phenylformic acid;
(4) N-(2-(6-methylbenzothiazole-2-formamyl)-phenyl)-4-fluorobenzamide is synthetic
Synthetic like instance one (4) condition and method, difference is to add 2-amino-6-methylbenzothiazole of 0.33g, and reaction times 11h gets faint yellow solid, productive rate: 47%, and mp:＞250 ℃.
Synthesizing of embodiment 13, compound N-(2-(6-fluoro benzothiazole-2-formamyl)-phenyl)-4-fluorobenzamide (compound number is m)
(1) the 4-fluorobenzoyl chloride is synthetic
Synthetic like instance ten two (1) conditions and method;
(2) 2-(4-fluorobenzamide) is benzoic synthetic
Synthetic like instance ten two (2) conditions and method;
(3) 2-(4-fluorophenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance ten two (3) conditions and method;
(4) N-(2-(6-fluoro benzothiazole-2-formamyl)-phenyl)-4-fluorobenzoyl is synthetic
Synthetic like instance ten two (4) conditions and method, difference is to add 2-amino-6-fluoro benzothiazole of 0.34g, and reaction times 15h gets white solid, productive rate: 31%, and fusing point: 234-236 ℃.
Synthesizing of embodiment 14, compound N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-4-fluorobenzamide (compound number is n)
(1) the 4-fluorobenzoyl chloride is synthetic
Synthetic like instance ten two (1) conditions and method;
(2) 2-(4-fluorobenzamide) is benzoic synthetic
Synthetic like instance ten two (2) conditions and method;
(3) 2-(4-fluorophenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance ten two (3) conditions and method;
(4) N-(2-(4-methylbenzothiazole-2-formamyl)-phenyl)-4-fluorobenzamide is synthetic
Synthetic like instance eight (4) conditions and method, difference is to add 2-amino-4-methylbenzothiazole of 0.33g, and reaction times 13h gets micro-yellow powder, productive rate: 33%, and fusing point: 205-207 ℃.
Synthesizing of embodiment 15, compound N-(2-(4-methylbenzothiazole-2-formamyl)-4-aminomethyl phenyl)-4-fluorobenzamide (compound number is o)
(1) the 4-fluorobenzoyl chloride is synthetic
Synthetic like instance one (1) condition and method;
(2) 2-(4-fluorobenzamide)-3-tolyl acid is synthetic
Synthetic like instance one (2) condition and method, difference is to add 2-amino-3-tolyl acid;
(3) 8-methyl-2-(4-fluorophenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance one (3) condition and method, difference is to add 2-(4-fluorobenzamide)-3-tolyl acid;
(4) N-(2-(4-methylbenzothiazole-2-formamyl)-4-aminomethyl phenyl)-4-fluorobenzamide is synthetic
Synthetic like instance one condition and method, difference is to add 2-amino-4-methylbenzothiazole of 0.33g, and reaction times 13h gets micro-yellow powder, gets yellow powder, productive rate: 44%, and fusing point: 210-211 ℃.
Synthesizing of embodiment 16, compound N-(2-(6-chloro benzothiazole-2-formamyl)-phenyl)-2,4 difluorobenzene methane amide (compound number is p)
(1) the 2,4 difluorobenzene formyl chloride is synthetic
Synthetic like instance one (1) condition and method, difference is to add 2,4 difluorobenzene formic acid;
(2) 2-(2, the 4-fluorobenzamide) is benzoic synthetic
Synthetic like instance one (2) condition and method, difference is to add the 2,4 difluorobenzene formyl chloride;
(3) 2-(2,4 difluorobenzene base)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance one (3) condition and method, difference is to add 2-(2, the 4-fluorobenzamide) phenylformic acid;
(4) N-(2-(6-chloro benzothiazole-2-formamyl)-phenyl)-2,4 difluorobenzene methane amide is synthetic
Synthetic like instance one (4) condition and method, difference is to add 2-amino-6-chloro benzothiazole of 0.37g, and reaction times 13h gets yellow powder, productive rate: 45%, and fusing point: 214-216 ℃.
Synthesizing of embodiment 17, compound N-(2-(6-fluoro benzothiazole-2-formamyl)-phenyl)-2,4 difluorobenzene methane amide (compound number is q)
(1) the 2,4 difluorobenzene formyl chloride is synthetic
Synthetic like instance ten six (1) conditions and method;
(2) 2-(2,4 difluorobenzene methane amide) is benzoic synthetic
Synthetic like instance ten six (2) conditions and method;
(3) 2-(2,4 difluorobenzene base)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance ten six (3) conditions and method;
(4) N-(2-(6-fluoro benzothiazole-2-formamyl)-phenyl)-2,4 difluorobenzene methane amide is synthetic
Synthetic like instance ten six (4) conditions and method, difference is to add 2-amino-6-fluoro benzothiazole of 0.34g, and reaction times 13h gets micro-yellow powder, productive rate: 47%, and fusing point: 124-126 ℃.
Synthesizing of embodiment 18, compound N-(2-(6-chloro benzothiazole-2-formamyl)-phenyl)-2-methyl benzamide (compound number is r)
(1) the 2-methyl benzoyl chloride is synthetic
Synthetic like instance one (1) condition and method, difference is the 2-tolyl acid;
(2) 2-(2-methyl benzamide) is benzoic synthetic
Synthetic like instance one (2) condition and method, difference is to add the 2-methyl benzoyl chloride;
(3) 2-(2-aminomethyl phenyl)-4H-benzo [d] [synthesizing of 1,3] oxazine-4-ketone
Synthetic like instance one (3) condition and method, difference is to add 2-(2-methyl benzamide) phenylformic acid;
(4) N-(2-(6-chloro benzothiazole-2-formamyl)-phenyl)-2-methyl benzamide is synthetic
Synthetic like instance one (4) condition and method, difference is to add 2-amino-6-chloro benzothiazole of 0.37g, and reaction times 13h gets light yellow crystal, productive rate: 39%, and fusing point: 210-212 ℃.
(2-(replacing benzo [d] thiazole-2-formamyl)-phenyl)-the benzamide derivatives spectral data is following for the N-of partial synthesis:
Compound a: N-(2-(6-oxyethyl group benzo [d] thiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide yellow solid, yield 47%, fusing point: 268-270 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.72 (s, 1H, NH), 8.15 (s, 1H, Ph-H), 7.99 (d, J=7.5Hz, 1H; Ph-H), 7.82 (d, J=8.1Hz, 1H, Ph-H), 7.76 (s, 1H, Ph-H), 7.55-7.62 (m; 3H, Ph-H), 7.47 (s, 1H, Ph-H), 7.28 (t, 1H, Ph-H), 6.98 (dd; J=2.3,2.3Hz, 1H, Ph-H), 4.05 (q, J=6.9Hz, 2H, OCH 2), 1.34 (t, J=6.9Hz, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 168.4,164.2,155.5,142.8,138.1,135.8,135.6,133.5,132.3,132.1,131.2,130.2,130.1,128.2,125.9,124.5,122.5,120.7,115.3,105.9,64.1,15.2; IR (KBr) v:3419,2978,2868,1674,1587,1496,1448,1429,1313,1217,1109,1066,918,813,758.Anal.calcd for C 23H 17C L2N 3O 3S:C, 56.80; H, 3.52; N, 8.64; Found C, 56.35; H, 3.36; N, 8.59.
Compound b: N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide faint yellow solid, yield 40%, fusing point 228-229 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.87 (s, 1H, NH), 10.98 (s, 1H, NH), 7.95 (s, 1H, Ph-H), 7.91 (s, 1H; Ph-H), 7.76 (s, 2H, Ph-H), 7.72 (d, J=8.6Hz, 1H, Ph-H), 7.63 (q, 3H, Ph-H); 7.35 (t, 1H, Ph-H), 7.27 (d, J=8.0Hz, 1H, Ph-H), 2.42 (s, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 165.1,156.3,135.2,136.4,132.0,131.9,131.3,129.5,128.6,125.1,115.7,105.0,19.1; IR (KBr) v:3223,3057,2914,1645,1587,1543,1496,1448,1423,1342,1301,1234,1103,1047,918,754.Anal.calcd for C 22H 15Cl 2N 3O 2S:C, 57.90; H, 3.31; N, 9.21; Found C, 57.49; H, 3.54; N, 9.05.
Compound c: N-(2-(the 6-chlorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2,4 dichloro benzene methane amide white solid, yield 37%, fusing point 283-284 ℃; 1HNMR (500MHz, DMSO-d 6) δ: 8.63 (s, 1H, Ph-H), 8.26 (d, J=7.5Hz, 1H, Ph-H), 8.05 (d, J=8.6Hz, 1H; Ph-H), 7.80 (d, J=9.2Hz, 2H, Ph-H), 7.64 (d, J=8.0Hz, 1H, Ph-H), 7.47 (q; 2H, Ph-H), 7.27 (d, J=8.6Hz, 1H, Ph-H), 7.17 (t, 1H, Ph-H); 13CNMR (125MHz, DMSO-d 6) δ: 170.7,167.7,163.8,135.7,135.6,132.5,131.6,131.4,130.9,130.4,128.4,125.4,125.3,123.2,120.8,120.5; IR (KBr) v:3213,3169,3078,3062,1668,1651,1585,1494,1444,1427,1373,1342,1288,1259,1103,1049,912,845,810,682.Anal.calcd for C 21H 12Cl 3N 3O 2S:C, 52.90; H, 2.54; N, 8.81; Found C, 52.73; H, 2.44; N, 8.57.
Compound d: N-(2-(6-methoxyl group benzo [d] thiazole-2-formamyl)-6-aminomethyl phenyl)-2,4 dichloro benzene methane amide
Faint yellow solid, yield 34%, fusing point 218-220 ℃; 1HNMR (500MHz, DMSO-d 6) 12.65 (s, 1H, NH), 10.22 (s, 1H, NH), 7.72 (s, 1H, Ph-H), 7.67 (d, J=8.0Hz; 1H, Ph-H), 7.59 (s, 3H, Ph-H), 7.52 (dd, J=6.9,7.5Hz, 2H, Ph-H); 7.36 (q, 2H, Ph-H), 7.04 (d, J=8.6Hz, 1H, Ph-H), 3.82 (s, 3H, OCH 3), 2.36 (s, 3H, OCH 3); 13CNMR (125MHz, DMSO-d 6) δ: 167.0,164.8,156.9,156.7,143.3,136.2,136.1,135.3,133.8,133.6,132.5,131.6,130.6,129.7,127.9,127.0,121.7,115.4,105.2,56.2,18.5; IR (KBr) v:3443,3419,2991,1666,1647,1602,1541,1533,1469,1296,1261,1244,1220,1147,1101,1058,1028,958,827,738,648.Anal.calcd for C 23H 17Cl 2N 3O 3S:C, 56.80; H, 3.52; N, 8.64; Found C, 56.48; H, 3.68; N, 8.31.
Verbindung: N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-3-chlorobenzamide
White solid, yield 36%, fusing point: 192-194 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.90 (s, 1H, NH), 10.96 (s, 1H, NH), 8.19-8.15 (m, 1H, Ph-H), 7.99-7.92 (m; 2H, Ph-H), 7.87 (d, J=5.7Hz, 1H, Ph-H), 7.80 (d, J=7.5Hz, 1H, Ph-H); 7.77-7.75 (m, 1H, Ph-H), 7.69-7.62 (m, 2H, Ph-H), 7.33 (t, 1H, Ph-H), 7.26 (d; J=6.9Hz, 1H, Ph-H), 7.22 (d, J=7.5Hz, 1H, Ph-H), 2.73 (s, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 164.3,162.8,159.2,155.7,146.5,137.5,132.9,131.6,129.5,128.7,127.9,127.7,127.6,126.9,40.0,36.3,31.3,18.6; IR (KBr) v:3072,2920,2850,1759,1647,1600,1525,1473,1319,1246,1220,1057,1036,1004,923,798,767,688.Anal.calcd for C 22H 16ClN 3O 2S:C, 62.63; H, 3.82; N, 9.96; Found C, 62.74; H, 3.91; N, 9.49.
Compound f:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-3-chlorobenzamide
Pale yellow powder, yield 41%, fusing point: 236-238 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.88 (s, 1H, NH), 11.42 (s, 1H, NH), 8.06 (s, 1H, Ph-H), 8.00 (s; 2H, Ph-H), 7.87 (d, J=6.9Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.68 (d; J=6.9Hz, 1H, Ph-H), 7.59 (t, 1H, Ph-H), 7.61 (t, 1H, Ph-H), 7.43 (d; J=8.6Hz, 1H, Ph-H), 7.25 (d, J=8.0Hz, 1H, Ph-H), 2.42 (s, 3H, CH 3), 2.38 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 164.0,137.3,134.0,133.7,133.4,132.2,131.2,130.6,127.9,127.8,126.6,124.7,121.9,119.7,21.5,20.9; IR (KBr) v:3334,3145,2916,1647,1606,1550,1518,1456,1313,1290,1267,1199,952,898,858,810,771,740,700; Anal.calcd for C 23H 18ClN 3O 2S:C, 63.37; H, 4.16; N, 9.64; Found C, 63.01; H, 3.75; N, 9.66.
Compound g:N-(2-(6-oxyethyl group benzo [d] thiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM
Faint yellow solid, yield 33%, fusing point: 273-274 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.81 (s, 1H, NH), 11.23 (s, 1H, NH), 8.41 (s, 1H, Ph-H), 8.12 (s, 1H, Ph-H), 7.61-7.50 (m, 5H, Ph-H), 7.10 (t, 3H, Ph-H), 4.05 (s, 2H, OCH 2), 3.82 (s, 6H, OCH 3), 1.33 (s, 3H, CH 3). 13C NMR (125MHz, DMSO-d 6) δ: 164.9,156.1,149.1,133.5,127.2,123.7,122.3,121.0,116.0,111.8,111.0,106.0,64.2,56.3,56.1,15.2; IR (KBr) v:3153,3126,2972,2929,1660,1647,1600,1392,1346,1217,1176,1138,945,908,864,752; Anal.calcd for C 25H 23N 3O 5S:C, 62.88; H, 4.85; N, 8.80; Found C, 62.67; H, 5.02; N, 8.60.
Compound h:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM
Faint yellow solid, yield are 33%, fusing point＞300 ℃. 1H?NMR(500MHz，DMSO-d 6)δ：12.97(s，1H，NH)，11.25(s，1H，NH)，8.20(s，1H，Ph-H)，7.81(m，4H，Ph-H)，7.25(m，5H，Ph-H)，3.82(s，6H，OCH 3)，2.47(s，3H，CH 3). 13C?NMR(125MHz，DMSO-d 6)δ：164.9，152.4，149.1，133.5，130.2，127.2，123.6，122.5，121.0，119.6，111.8，111.0，56.2，56.0，18.6；IR(KBr)v：3286，3259，3134，2987，2931，1662，1643，1604，1446，1328，1219，1128，1024，945，912，854，823，767，750；Anal.calcd?for?C 24H 21N 3O 4S：C，64.41；H，4.73；N，9.39；Found?C，64.85；H，4.71；N，9.12.
Compound i: N-(2-(6-oxyethyl group benzo [d] thiazole-2-formamyl)-phenyl)-2-methoxy benzamide
Faint yellow solid, yield 33%, fusing point: 241-242 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.91 (s, 1H, NH), 11.76 (s, 1H, NH), 8.60 (d, J=8.6Hz, 1H, Ph-H), 8.01 (s, 2H, Ph-H), 7.56 (t, 4H, Ph-H), 7.23 (d, J=7.5Hz, 4H, Ph-H), 4.10-3.31 (m, 5H, OCH 3+ OCH 2), 1.34 (t, 3H, J=6.9Hz, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 163.7,157.8,156.1,139.0,134.3,133.3,132.1,130.0,123.6,122.5,121.8,121.4,116.1,112.8,112.7,105.8,64.1,56.6,15.2; IR (KBr) v:3020,2976,2926,2879,1658,1639,1597,1550,1510,1458,1440,1269,1215,1022,948,918,869,799,750; Anal.calcd for C 24H 21N 3O 4S:C 64.41, and H 4.73, and N 9.39; Found C, 64.45, H 5.03, and N 8.94
Compound j:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-2-methoxy benzamide
Faint yellow solid, yield 40.5%, fusing point＞300 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 13.08 (s, 1H, NH), 11.70 (s, 1H, NH), 8.58 (d, 1H, J=7.5Hz, Ph-H), 8.01 (s, 2H, Ph-H), 7.56 (d, J=17.8Hz, 2H, Ph-H), 7.23 (m, 5H, Ph-H), 4.12 (s, 3H, OCH 3), 2.52 (s, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 167.8,163.7,157.8,148.1,134.3,133.4,132.1,130.2,127.3,124.3,123.6,122.6,121.8,121.4,119.7,112.8,56.6,18.6; IR (KBr) v:3251,3172,2943,2918,1670,1645,1598,1583,1446,1406,1296,1267,1242,1228,1159,1072,1016,918,891,856,744; Anal.calcd for C 23H 19N 3O 3S:C, 66.17; H, 4.59; N, 10.07; Found C, 66.22; H, 4.92; N, 10.21.
Compound k:N-(2-(6-methoxyl group benzo [d] thiazole-2-formamyl)-phenyl)-2-methoxy benzamide
Faint yellow solid, yield are 37%, fusing point 218-219 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.91 (s, 1H, NH), 11.74 (s, 1H, NH), 8.60 (d, J=8.1Hz, 1H, Ph-H), 8.01 (s, 2H, Ph-H), 7.59 (t, J=17.7Hz, 2H, Ph-H), 7.23 (m, 4H, Ph-H), 4.12 (s, 3H, OCH 3), 3.31 (s, 3H, OCH 3); 13C NMR (125MHz, DMSO-d 6) δ: 163.7,157.8,156.9,139.0,134.3,133.3,132.2,130.1,123.6,122.5,122.1,115.8,112.8,105.2,56.6,56.2; IR (KBr) v:3250,3099,2935,2833,1734,1654,1639,1550,1315,1296,1219,1126,1076,1022,948,920,837,808,752,684; Anal.calcd for C 23H 19N 3O 4S:C, 63.73; H, 4.42; N, 9.69; Found C, 63.56; H, 4.53; N, 9.38.
Compound l:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-fluorobenzamide
Faint yellow solid, yield 47%, fusing point: 266-268 ℃; 1HNMR (500MHz, DMSO-d 6) δ: 8.87 (d, J=8.1Hz, 1H, Ph-H), 8.80 (q, 2H, Ph-H), 8.28 (dd, J=1.8,1.8Hz; 1H, Ph-H), 7.61 (d, J=8.0Hz, 1H, Ph-H), 7.56 (s, 1H, Ph-H); 7.46-7.41 (m, 3H, Ph-H), 7.15 (t, 2H, Ph-H), 2.40 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 170.0,167.4,165.8,163.9,163.7,149.0,140.9,133.7,131.9,131.7,131.6,131.1,131.0,130.4,126.4,125.7,122.5,121.2,119.5,116.0,115.9,21.6; IR (KBr) v:3115,3070,3051,2918,1666,1602,1585,1506,1454,1382,1319,1298,1242,1134,1111,925,885,844,812,756; Anal.calcd for C 22H 16FN 3O 2S:C, 65.17; H, 3.98; N, 10.36; Found C, 64.73; H, 3.67; N, 10.38.
Compound m:N-(2-(the 6-fluorobenzene is [d] thiazole-2-formamyl also)-phenyl)-4-fluorobenzamide
White powder, yield 31%, fusing point 234-236 ℃; 1HNMR (500MHz, DMSO-d 6) δ: 13.00 (s, 1H, NH), 11.83 (s, 1H, NH), 8.50 (d, J=8.6Hz, 1H, Ph-H), 8.04-7.63 (m, 6H, Ph-H), 7.43-7.32 (m, 3H, Ph-H), 7.14 (t, 1H, Ph-H); 13CNMR (125MHz, DMSO-d 6) δ: 167.8,164.5,163.9,163.8,162.8,160.1,158.2,133.2,130.7,130.6,129.9,129.8,124.0,121.6,116.3,116.2,116.1,116.0,114.9,114.7,114.6; IR (KBr) v:3442,3419,3300,3230,3177,1647,1600,1558,1505,1437,1342,1286,1253,1234,1195,1163,852,758,692; Anal.calcd for C 21H 13FN 3O 2S:C, 61.61; H, 3.20; N, 10.26; Found C, 61.99; H, 3.09; N, 10.14.
Compound n:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-fluorobenzamide
Micro-yellow powder, yield 33%, fusing point: 205-207 ℃; 1HNMR (500MHz, DMSO-d 6) δ: 12.98 (s, 1H, NH), 11.83 (s, 1H, NH), 8.48 (d, J=8.0Hz, 1H, Ph-H), 8.05 (s, 1H, Ph-H), 7.80 (s, 1H, Ph-H), 7.70-7.62 (m, 2H, Ph-H), 7.34-7.12 (m, 6H, Ph-H), 2.60 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 167.8,165.8,164.5,164.0,163.8,162.8,133.2,130.7,130.6,129.9,129.8,124.0,116.3,116.2,116.1,18.6; IR (KBr) v:3479,3471,3462,1651,1604,1585,1531,1506,1449,1427,1327,1290,1265,1230,1161,920,846,744; Anal.calcd for C 22H 16FN 3O 2S:C, 65.17; H, 3.98; N, 10.36; Found C, 64.96; H, 4.16; N, 10.21.
Compound o:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-4-fluorobenzamide
Yellow powder, yield 44%, fusing point: 210-211 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.88 (s, 1H, NH), 11.02 (s, 1H, NH), 8.01 (s, 3H, Ph-H), 7.80 (s, 2H, Ph-H), 7.45 (s, 1H, Ph-H), 7.41 (s, 2H, Ph-H), 7.28 (s, 1H, Ph-H), 7.22 (s, 1H, Ph-H), 2.61 (s, 3H, CH 3), 2.38 (s, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 168.0,165.7,164.3,163.8,158.0,148.1,133.8,131.6,130.5,130.4,124.2,123.2,116.3,116.2,60.3,20.8,18.5; IR (KBr) v:3296,3109,2916,1680,1653,1602,1589,1521,1506,1473,1404,1317,1282,1259,1232,1201,1159,1074,948,875,842,746; Anal.calcd for C 22H 18FN 3O 2S:C, 65.86; H, 4.33; N, 10.02; Found C, 65.78; H, 4.27; N, 10.16.
Compound p:N-(2-(the 6-chlorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2,4 difluorobenzene methane amide
Yellow powder, yield 45%, fusing point: 214-216 ℃; 1HNMR (500MHz, DMSO-d 6) δ: 13.10 (s, 1H, NH), 11.11 (s, 1H, NH), 8.18 (s, 3H, Ph-H), 7.78 (d, J=8.0Hz, 1H, Ph-H), 7.67 (t, 1H, Ph-H), 7.49 (t, 3H, Ph-H), 7.36 (t, 1H, Ph-H), 7.33 (t, 1H, Ph-H); 13CNMR (125MHz, DMSO-d 6) δ: 165.5,162.8,161.6,161.4,137.9,133.4,133.2,133.1,130.0,128.3,126.9,124.7,123.8,123.1,122.0,120.3,120.2,112.9,112.7,105.7,105.5,105.2; IR (KBr) v:3454,3442,3331,1685,1651,1597,1556,1442,1315,1265,1139,1101,966,918,856,808,759; Anal.calcd for C 21H 12ClF 2N 3O 2S:C, 56.83; H, 2.73; N, 9.47; Found C, 56.37; H, 3.25; N, 9.90.
Compound q:N-(2-(the 6-fluorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2,4 difluorobenzene methane amide
Micro-yellow powder, yield 47%, fusing point: 124-126 ℃; 1HNMR (500MHz, DMSO-d 6) δ: 13.05 (s, 1H, NH), 11.15 (s, 1H, NH), 8.21 (s, 1H, Ph-H), 7.96 (q, 2H, Ph-H), 7.80-7.64 (m, 3H, Ph-H), 7.51 (t, 1H, Ph-H), 7.35-7.24 (m, 3H, Ph-H); 13CNMR (125MHz, DMSO-d 6) δ: 161.6,161.5,160.2,159.6,158.3,133.3,133.2,133.1,130.1,124.6,123.7,115.0,114.8,113.0,112.8,105.7,105.5; IR (KBr) v:3442,3419,3336,1680,1614,1587,1556,1525,1463,14421288,1253,1197,1072,972,850,827,806; Anal.calcd for C 21H 12F 3N 5O 2S:C, 59.01; H, 2.83; N, 9.83; Found C, 58.67; H, 3.21; N, 9.44.
Compound r:N-(2-(the 6-chlorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2-methyl benzamide
Light yellow crystal, yield 39%, fusing point 210-212 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.95 (s, 1H, NH), 11.51 (s, 1H, NH), 8.06 (s, 2H, Ph-H), 7.95 (d, J=6.9Hz, 1H, Ph-H), 7.71-7.57 (m, 3H, Ph-H), 7.43-7.27 (m, 5H, Ph-H), 2.43 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 168.0,136.7,136.5,132.6,131.4,130.6,130.0,127.9,126.7,125.4,121.8,20.1; IR (KBr) v:3251,3207,3061,2958,1651,1587,1523,1446,1367,1273,1103,921,852,812,748,686; Anal.calcd for C 22H 16ClN 3O 2S:C, 62.63; H, 3.82; N, 9.96; Found C, 62.41; H, 4.13; N, 9.56.
Compound s:N-(2-(benzo [d] thiazole-2-formamyl)-6-aminomethyl phenyl)-2-methyl benzamide
The white roll body, yield 31%, fusing point: 214-216 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.74 (s, 1H, NH), 9.96 (s, 1H, NH), 8.01 (d, J=8.0Hz, 1H, Ph-H), 7.77 (d; J=8.0Hz, 1H, Ph-H), 7.50 (m, 3H, Ph-H), 7.45 (t, 1H, Ph-H), 730 (q, 3H; Ph-H), 7.28-7.23 (m, 2H, Ph-H), 2.37 (s, 3H, CH3), 2.34 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 168.5,167.4,159.0,149.2,137.3,136.2,136.1,134.6,133.6,132.5,132.1,130.9,130.0,127.8,127.0,126.7,126.0,124.0,122.2,121.0,19.8,18.6; IR (KBr) v:3273,3178,3064,1662,1597,1541,1300,1099,1012,960,867,744; Anal.calcd forC 23H 19N 3O 2S:C, 68.81; H, 4.77; N, 10.47; Found C, 68.46; H, 4.67; N, 10.13.
Compound t:N-(2-(benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-2-methyl benzamide
Yellow solid, yield 37%, fusing point: 180-181 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.76 (s, 1H, NH), 10.70 (s, 1H, NH), 7.98 (d, J=8.0Hz, 1H; Ph-H), 7.78 (s, 1H, Ph-H), 7.74 (d, J=8.1Hz, 1H, Ph-H); 7.58 (d, J=7.5Hz, 1H, Ph-H), 7.47-7.43 (m, 2H, Ph-H), 7.40 (t; 1H, Ph-H), 7.32 (q, 3H, Ph-H), 2.40 (s, 3H, CH 3), 2.38 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 167.9,137.0,136.4,133.7,133.4,131.4,130.5,130.3,127.7,126.8,126.3,124.2,122.4,20.9,20.0; IR (KBr) v:3252,3238,3057,2920,1683,1653,1591,1525,1440,1317,1271,1226,1195,950,829,752,719; Anal.calcd for C 23H 19N 3O 2S:C, 68.81; H, 4.77; N, 10.47; Found C, 68.73; H, 4.54; N, 10.35..
Compound u:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-chlorobenzamide
Clear crystal, yield 45%, fusing point＞300 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 8.85 (d, J=8.0Hz, 1H, Ph-H), 8.74 (d, J=8.6Hz, 2H, Ph-H), 8.26 (dd, J=1.7; 1.8Hz, 1H, Ph-H), 7.68 (d, J=5.0Hz, 2H, Ph-H), 7.56 (t, 2H, Ph-H); 7.42 (t, 1H, Ph-H), 7.14-7.11 (m, 2H, Ph-H), 3.81 (s, 3H, OCH 3); 13C NMR (125MHz, DMSO-d 6) δ: 170.0,163.7,140.7,137.0,134.2,131.2,131.0,126.5,125.6,121.2,119.7,119.4,21.6; IR (KBr) v:3163,3120,3101,1653,1591,1552,1506,1491,1456,1381,1334,1249,1113,918,815,756; Anal.calcd for C 22H 16ClN 3O 2S:C, 62.63; H, 3.82; N, 9.96; Found C, 62.76; H, 3.72; N, 9.70.
Compound v:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-chlorobenzamide clear crystal, yield 34%, fusing point＞300 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 8.85 (d, J=8.0Hz, 1H, Ph-H), 8.64 (d, J=8.6Hz, 2H, Ph-H), 8.27 (dd; J=1.7,1.2Hz, 1H, Ph-H), 7.68 (d, J=8.6Hz, 2H, Ph-H); 7.56 (d, J=7.5Hz, 1H, Ph-H), 7.42 (t, 1H, Ph-H), 7.13 (q; 2H, Ph-H), 6.99 (t, 1H, Ph-H), 2.70 (s, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 172.1,163.2,140.2,136.8,134.0,131.2,131.6,126.9,125.6,121.9,119.1,118.7,21.1; IR (KBr) v:3051,3032,1666,1585,1508,1467,1444,1381,1319,1255,1113,1009,921,839,756; Anal.calcd for C 22H 16ClN 3O 2S:C, 62.63; H, 3.82; N, 9.96; Found C, 62.63; H, 3.82; N, 9.96.
Compound w:N-(2-(the 6-fluorobenzene is [d] thiazole-2-formamyl also)-phenyl)-4-chlorobenzamide
Clear crystal, yield 34%, fusing point＞300 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 13.06 (s, 1H, NH), 8.10-7.96 (m, 4H, Ph-H), 7.77 (s, 1H, Ph-H), 7.64 (d, J=8.0Hz, 4H, Ph-H), 7.34-7.30 (m, 2H, Ph-H); 13C NMR (125MHz, DMSO-d 6) δ: 164.6,160.2,158.3,137.3,133.8,133.1,130.1,129.8,129.3,124.6,114.9,114.7,108.9,108.6; IR (KBr) v:3523,3448,3419,3169,3149,3115,3064,1654,1593,1552,1506,1489,1437,1348,1253,1196,752; Anal.calcd for C 21H 13ClFN 3O 2S:C, 59.23; H, 3.08; N, 9.87; Found C, 59.50; H, 3.01; N, 9.67.
Compound x:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-4-chlorobenzamide
Faint yellow solid, yield 38%, fusing point: 237-238 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.77 (s, 1H, NH), 11.19 (s, 1H, NH), 8.07 (s, 1H, Ph-H); 7.95 (d, J=7.5Hz, 2H, Ph-H), 7.87 (s, 1H, Ph-H), 7.77 (s, 1H; Ph-H), 7.64 (d, J=8.1Hz, 3H, Ph-H), 7.45 (d, J=8.0Hz, 1H; Ph-H), 7.27 (d, J=8.1Hz, 1H, Ph-H), 2.42 (s, 3H, CH 3), 2.37 (s, 3H, CH 3); 13CNMR (125MHz, DMSO-d 6) δ: 174.7,166.4,31.4,24.8; IR (KBr) v:3155,3076,2920,1653,1595,1504,1454,1419,1338,1193,1116,1093,1010,939,896,844,806,742; Anal.calcd for C 23H 18ClN 3O 2S:C, 63.37; H, 4.16; N, 9.64; Found C, 63.32; H, 3.92; N, 9.55.
Compound y:N-(2-(benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-4-chlorobenzamide
Yellow powder, yield 42%, fusing point: 242-244 ℃; 1H NMR (500MHz, DMSO-d 6) δ: 12.91 (s, 1H, NH), 11.25 (s, 1H, NH), 8.08 (s, 1H, Ph-H); 7.98 (d, J=6.0Hz, 2H, Ph-H), 7.88 (s, 1H, Ph-H), 7.74 (s, 1H; Ph-H), 7.64 (d, J=8.6Hz, 2H, Ph-H), 7.45 (d, J=9.7Hz, 3H; Ph-H), 7.32 (d, J=6.9Hz, 1H, Ph-H), 2.38 (s, 3H, CH 3); 13C NMR (125MHz, DMSO-d 6) δ: 164.4,133.7,130.6,129.7,129.3,126.8,124.2,122.4,20.9; IR (KBr) v:3066,2920,1654,1595,1570,1539,1506,1496,1462,1450,1400,1338,1309,1284,1249,1220,1197,825,742,677; Anal.calcd for C 22H 16ClN 3O 2S:C, 62.63; H, 3.82; N, 9.96; Found C, 62.46; H, 3.79; N, 10.08.
Embodiment 15, the compound inhibition activity test TP sick to cucumber mosaic virus (CMV)
(1) TP
Chenopodium amaranticolor (Chenopodium amaranticolor) so that growing way is consistent is cooked withered spot host, with writing brush with the artificial frictional inoculation of virus on the of the right age blade that spreads silicon carbide, with clear water blade is cleaned up illumination cultivation 1.5h behind the 0.5h.Accurately take by weighing an amount of test compound in weighing bottle, add solvent DMF 30 μ L it is fully dissolved, if the insoluble 50 μ L that add to use the redistilled water that contains 1%Tween20 to be made into the compound solution of 500mg/L.Other gets 125 μ L2% Ningnanmycin aquas, adds solvent DMF 30 μ L, contains the redistilled water 5mL of 1%Tween20, is made into the Ningnanmycin solution of 500mg/L.Spread 500mg/L test compound and Ningnanmycin respectively at Zuo Banye, right half leaf is contrast with the solvent.Every chemicals treatment 3 strains, 6 leaves of every strain.The cultivation of in illumination box, preserving moisture subsequently, 28 ± 1 ℃ of controlled temperature, illumination 10000Lux observes behind 6～7d and record produces the number of withered spot.Withered spot inhibiting rate calculation formula:
X％＝(CK-T)/CK×100％
X: relative inhibition (%), CK: control group (right half leaf) withered spot number (individual)
T: compound treatment group (Zuo Banye) withered spot number (individual)
(2) test-results
Adopt aforesaid method; When drug concentration is 500 μ g/mL, part of compounds having been carried out cucumber mosaic virus (CMV) live body therapeutic activity measures; The result sees that table 1. is through test; Compound i, j, k, s, u are that 500 μ g/mL are respectively 44.4,52.3,45.1,47.3,45.6% to the live body treatment inhibiting rate that CMV infects in concentration, show certain anti-phytoviral activity.
Table 1 bisamide compound is active to the inhibition of CMV
Figure BSA00000544564400151
Figure BSA00000544564400161
Embodiment 16, the compound inhibition activity test TP sick to tobacco mosaic virus(TMV) (TMV)
Select the consistent Nicotiana glutinosa of growing way; With phosphoric acid buffer the TMV crude extract is diluted to suitable concentration; With the artificial frictional inoculation of writing brush (full leaf virus inoculation on the of the right age blade that spreads silicon carbide; Every blade manual work is smeared virus once gently, about the half leaf dynamics of smearing accomplish evenly as far as possible), use flushing with clean water after the inoculation.Treat the dried back of blade (being generally 2h), spread compound solution at Zuo Banye, the solvent that right half leaf spreads matched doses compares.The cultivation of in illumination box, preserving moisture subsequently, 23 ± 1 ℃ of controlled temperature, illumination 10000Lux observes behind 3～4d and record produces the number of withered spot.Every chemicals treatment is established 3 strains, 3～4 leaves of every strain.Every as stated above medicament carries out 3 times to be repeated.
On half leaf of blank, present obvious withered spot, just can investigate behind the 3-4d about test, write down respectively every leaf about the withered spot number of half leaf, be calculated as follows out the inhibiting rate of test compound, promptly relative effect to plant virus.
Expression mode: Y=(C-A)/C * 100
Wherein: Y is the inhibiting rate of compound to plant virus,
C is control group (right half a leaf) withered spot number, unit: individual
A is compound treatment group (Zuo Banye) withered spot number, unit: individual
Wherein control group (right half leaf) withered spot number and compound treatment group (Zuo Banye) withered spot number can be joined with each group multiple mean number or respectively organized the withered spot sum of multiple.Each handle all be with oneself second half as contrast, the processing that one group of commodity Ningnanmycin is set again is as a comparison.
Tested the live body therapeutic activity of target compound to tobacco mosaic virus(TMV), the result sees table 2.The result is illustrated in compound d, l, n, u, w under the 500 μ g/mL concentration and shows higher resisting tobacco mosaic virus and suppress active, and inhibiting rate is respectively 44.3,47.7,45.7,44.3,49.0%.
Table 2 part bisamide is to the inhibition effect (500 μ g/mL) of TMV
Figure BSA00000544564400162
Figure BSA00000544564400171
Embodiment 17, compound suppress activity test method to the in-vitro multiplication to two kinds of cancer cells
The uplink and downlink of 96 orifice plates are used sterilization secondary water seal limit, every hole 200 μ L.The cell in vegetative period of taking the logarithm after the conventional digestion, is resuspended among the RPMI 1640 or DMDM substratum that contains 10%FBS, with 2 * 10 4The final concentration of individual/mL is inoculated in 96 well culture plates, every hole 100 μ L, and the rightmost side one is classified the blank group as, adds acellular serum RPMI 1640 substratum that have.Place 37 ℃, 5%CO 2The saturated humidity incubator in cultivate 24h and make cell attachment.Sop up substratum, add the blood serum medium that has that contains different pharmaceutical concentration, every hole 200 μ L notice that the DMSO final concentration can not surpass 0.1% in the substratum, and the every hole of blank group adds 200 μ L perfect mediums.Handle the requirement of experiment time respectively, remove supernatant, add the MTT of 100 μ L/well concentration 0.5mg/mL.Cultivate 10% the SDS that adds 100 μ Lwell behind the 4h again.37 ℃ of following 10h make crystallisate fully dissolve the back and take out, and 5min is swung in microseism, places 30min under the room temperature, at A 595Wavelength is surveyed the OD value down, and calculates cytoactive, inhibiting rate and P value.
With drug level or treatment time be transverse axis, OD value or inhibiting rate are the longitudinal axis, curve plotting.Every concentration of specimens repeats six holes, and each tests triplicate, averages to be net result.
Experimental result is carried out variance analysis with SPSS software, and p＜0.05 o'clock is a significant difference, and p＜0.01 o'clock is that difference is extremely remarkable.The inhibiting rate calculation formula of cell proliferation is following:
Figure BSA00000544564400172
Table 3 bisamide compound is to the inhibiting rate to PC3 and BGC-823 tumour cell
Figure BSA00000544564400173
Can find out from table 3; Compound h, m, n, x, y are respectively 74.2,73.2,76.2,70.8,76.3% to the inhibiting rate of prostate cancer cell when concentration is 10 μ M; Inhibiting rate to breast cancer cell is respectively 77.8,68.1,62.2,62.0,72.8%, and above-claimed cpd has good inhibitory effect to prostate cancer cell and breast cancer cell.
The embodiment of the invention is aided with explanation technical scheme of the present invention, but the content of embodiment is not limited thereto.

Claims (5)

  1. (1.N-2-(replacing benzothiazole-2-formamyl)-phenyl)-benzamide compound, its general structure is following:
    Figure FSA00000544564300011
    R wherein 1Be hydrogen, neighbour,, contraposition is single to be replaced or polysubstituted halogen atom, C1-6 alkyl or C1-6 alkoxyl group;
    R 2Be hydrogen, single halogen atom, C1-6 alkyl or C1-6 alkoxyl group of replacing;
    R 3Be hydrogen, single halogen atom, C1-6 alkyl or C1-6 alkoxyl group of replacing.
  2. 2. compound according to claim 1 is characterized in that said compound is as follows:
    Compound a: N-(2-(6-oxyethyl group benzo [d] thiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide
    Compound b: N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-phenyl)-2,4 dichloro benzene methane amide (
    Compound c: N-(2-(the 6-chlorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2,4 dichloro benzene methane amide (
    Compound d: N-(2-(6-methoxyl group benzo [d] thiazole-2-formamyl)-6-aminomethyl phenyl)-2,4 dichloro benzene methane amide
    Verbindung: N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-3-chlorobenzamide
    Compound f:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-3-chlorobenzamide
    Compound g:N-(2-(6-oxyethyl group benzo [d] thiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM
    Compound h:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-3,4-dimethoxy BM
    Compound i: N-(2-(6-oxyethyl group benzo [d] thiazole-2-formamyl)-phenyl)-2-methoxy benzamide
    Compound j:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-2-methoxy benzamide
    Compound k:N-(2-(6-methoxyl group benzo [d] thiazole-2-formamyl)-phenyl)-2-methoxy benzamide
    Compound l:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-fluorobenzamide
    Compound m:N-(2-(6-fluoro benzothiazole-2-formamyl)-phenyl)-4-fluorobenzamide
    Compound n:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-fluorobenzamide
    Compound o:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-4-fluorobenzamide
    Compound p:N-(2-(the 6-chlorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2,4 difluorobenzene methane amide
    Compound q:N-(2-(the 6-fluorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2,4 difluorobenzene methane amide
    Compound r:N-(2-(the 6-chlorobenzene is [d] thiazole-2-formamyl also)-phenyl)-2-methyl benzamide
    Compound s:N-(2-(benzo [d] thiazole-2-formamyl)-6-aminomethyl phenyl)-2-methyl benzamide
    Compound t:N-(2-(benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-2-methyl benzamide
    Compound u:N-(2-(4-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-chlorobenzamide
    Compound v:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-phenyl)-4-chlorobenzamide
    Compound w:N-(2-(the 6-fluorobenzene is [d] thiazole-2-formamyl also)-phenyl)-4-chlorobenzamide
    Compound x:N-(2-(6-methyl benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-4-chlorobenzamide
    Compound y:N-(2-(benzo [d] thiazole-2-formamyl)-4-aminomethyl phenyl)-4-chlorobenzamide.
  3. 3. the application of compound according to claim 1 and 2 in Antiphytoviral
  4. 4. the application of compound according to claim 1 and 2 in the preparation cancer therapy drug.
  5. 5. the preparation method who contains N-(2-(replacing benzothiazole-2-formamyl)-phenyl)-benzamide derivatives according to claim 1; The preparation method who it is characterized in that general formula (I) compound be with substituted benzoic acid, to replace anthranilic acid, replace benzothiazole ammonia, thionyl chloride and acetic anhydride be raw material; Through perchlorizing, acidylate, cyclisation and open loop four-step reaction; Synthesize and contain benzothiazole ring o-benzoyl aminobenzoyl aminated compounds, its synthetic route is:
    Figure FSA00000544564300031
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