CN102584810B - Benzothiazole ketone compound and application thereof - Google Patents
Benzothiazole ketone compound and application thereof Download PDFInfo
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- -1 Benzothiazole ketone compound Chemical class 0.000 title claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical class C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 241000219112 Cucumis Species 0.000 claims description 10
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 10
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 241000193738 Bacillus anthracis Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 241001465180 Botrytis Species 0.000 claims description 3
- 241000813090 Rhizoctonia solani Species 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 abstract 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 24
- XGSZDHKEBSXMHV-UHFFFAOYSA-N 2-(2-oxo-1,3-benzothiazol-3-yl)acetohydrazide Chemical compound C1=CC=C2SC(=O)N(CC(=O)NN)C2=C1 XGSZDHKEBSXMHV-UHFFFAOYSA-N 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 238000004809 thin layer chromatography Methods 0.000 description 19
- 239000007787 solid Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 5
- 235000010603 pastilles Nutrition 0.000 description 5
- 241000209094 Oryza Species 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- YVAIFZYQODGYQY-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)CNC2=C1 YVAIFZYQODGYQY-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000194103 Bacillus pumilus Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- JKXJNTQPXAFAEH-UHFFFAOYSA-N 1,3-benzothiazole;oxadiazole Chemical class C1=CON=N1.C1=CC=C2SC=NC2=C1 JKXJNTQPXAFAEH-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical class N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 description 1
- MXNBDFWNYRNIBH-UHFFFAOYSA-N 3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1 MXNBDFWNYRNIBH-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- FFMXLRXJGJMUDC-UHFFFAOYSA-N C(=O)O.ClC1=CC=CC(=C1)Cl Chemical compound C(=O)O.ClC1=CC=CC(=C1)Cl FFMXLRXJGJMUDC-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- CKMXAIVXVKGGFM-UHFFFAOYSA-N p-cumic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1 CKMXAIVXVKGGFM-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
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- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2(3H)-ketone compound, the structure is shown in the formula (I). Further application of the compound as a bacteriacide is disclosed.
Description
(1) technical field
The present invention relates to a kind of 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds and application thereof.
(2) background technology
As a member in fused heterocycle system, benzothiazole derivant has biological activity widely, as desinsection (Pharmazie, 2003,58,527), sterilization (Molecules, 1997,2,36), antiviral (organic chemistry, 2007,27,279) (U.S.Patent 5424443 in, weeding, 1995-06-13) and plant growth regulating (J.Agric.Food Chem., 1981,29,640) isoreactivity plays an important role in novel pesticide initiative.Simultaneously, 1,3,4-oxadiazole analog derivative also has the biological activity of wide spectrum, as desinsection (Pest Manage Sci., 2003,59,933) (U.S.Patent 4124373 in, weeding, 1978-11-07) and sterilization (Eur.J.Med.Chem., 1996,31,819) isoreactivity, and part 1, the successful commercialization of 3,4-oxadiazole compounds, as Sha Chong Ji Evil worm ketone (agricultural chemicals collected translation, 1989,55), Chu Cao Ji Evil humulone (world pesticide, 2006,28 (6): 15) etc. 11 (6):.In view of benzothiazole and 1,3,4-oxadiazole compounds all have excellent activity, utilize the synthetic novel benzothiazole compound that contains 1,3,4-oxadiazole rings that has both structures concurrently of active substructure joining method design, be expected to have good biological activity.As (E-J.Chem. such as B.Rajeeva, 2009,6 (3), 775) a series of benzothiazole oxadiazoles compounds have been synthesized, raw survey result show its under 100mg/L concentration to subtilis (Bacillus subtilis), bacillus pumilus (Bacillus pumilus), intestinal bacteria (Escherichia coli) and Pseudomonas aeruginosa (Pseudomonas aeruginosa) all have certain restraining effect.
The serial 3-that the present invention designs and synthesizes ((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds, its structure and bioactivity research have been showed no bibliographical information.
(3) summary of the invention
The object of the present invention is to provide a kind of 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds and uses thereof.
The technical solution used in the present invention is:
A kind of 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds, structure is suc as formula shown in (I):
In formula (I), it is monosubstituted, polysubstituted or be not substituted that H on phenyl ring is substituted base Rn, n is 0～5 integer, n represents the number of substituent R on phenyl ring, during n=0, represent that the H on phenyl ring is not substituted, during n=1, it is monosubstituted that H on expression phenyl ring is substituted base R, n=2～5 o'clock, it is polysubstituted that the H on expression phenyl ring is substituted base Rn, and the substituent R on different the position of substitution can be identical or different, described substituent R is the alkyl of C1～C8, the alkoxyl group of C1～C3, halogen or nitro, and described halogen is F, Cl, Br or I.
When the H on described phenyl ring is not substituted, representing does not have substituting group on phenyl ring.
Described substituent R is preferably 1～2, i.e. n=1～2 in preferred Rn.
Further, described substituent R is preferably alkyl, methoxyl group, F, Cl, Br or the nitro of C1～C5, more preferably methyl, ethyl, n-propyl, sec.-propyl, the tertiary butyl, n-pentyl, F, Cl, nitro or methoxyl group.
More specifically described substituent R n most preferably be adjacent methyl, a methyl, to methyl, to ethyl, to n-propyl, p-isopropyl, to the tertiary butyl, to n-pentyl, m-chloro, 2,4-dichloro, a fluorine, to fluorine, O-methoxy, to methoxyl group or a nitro.
The present invention also provides described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) preparation method of benzo [d] thiazole-2 (3H)-one compounds, described method is: suc as formula the 2-shown in (II) (2-oxo benzo [d] thiazole-3-yl) acethydrazide with suc as formula the benzoic acid derivative shown in (III), in phosphorus oxychloride, under reflux state, carry out ring-closure reaction, after TLC monitoring to reaction finishes, reaction solution separation and purification makes suc as formula 3-((5-aryl-1 shown in (I), 3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds;
In formula (III), the H on phenyl ring is substituted base R and replaces or be not substituted, the combination of one or more in the alkyl that described substituent R is C1～C8, the alkoxyl group of C1～C3, halogen or nitro, and described halogen is F, Cl, Br or I;
Described is 1: 1.0～1.3: 10.0～50.0 suc as formula the 2-shown in (II) (2-oxo benzo [d] thiazole-3-yl) acethydrazide, suc as formula the ratio of the amount of substance that feeds intake of the benzoic acid derivative shown in (III), phosphorus oxychloride; Be preferably 1: 1.0～1.1: 20.0～35.0.
The present invention adopts thin-layer chromatography (TLC) method monitoring reaction performance, and the reaction times is generally 3～12 hours.The concrete reaction times is relevant with reactant.
The method of reaction solution separation and purification of the present invention is: after reaction finishes, the concentrated phosphorus oxychloride of removing of reaction solution, resistates makes suc as formula 3-((5-aryl-1 shown in (I) with recrystallization solvent recrystallization, 3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds.
Described recrystallization solvent is preferably one or more the mixed solution in ethanol, ethyl acetate, normal hexane, sherwood oil.
Of the present invention can reference (Il Farmaco suc as formula the 2-shown in (II) (2-oxo benzo [d] thiazole-3-yl) acethydrazide, 1999,54:842-845) method is synthesized: 2 (3H)-benzothiazolones, salt of wormwood and acetone are dropped into reaction flask, drip methyl chloroacetate, drip and finish, reflux 4 hours, the ratio of the amount of substance of 2 (3H)-benzothiazolones, salt of wormwood, methyl chloroacetate is 1: 1.15: 1.1.Reaction solution is cooling, pours frozen water into, stirs 1 hour, filters, and filter cake washing, obtains 2-(2-oxo benzo [d] thiazole-3-yl) methyl acetate.2-(2-oxo benzo [d] thiazole-3-yl) methyl acetate and 85% hydrazine hydrate are dissolved in ethanol, reflux 24 hours, reaction solution is cooling, filter, filter cake washing, be dried and obtain 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide, the ratio of the amount of substance of described-(2-oxo benzo [d] thiazole-3-yl) methyl acetate and 85% hydrazine hydrate is 1: 20.
3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds described in the present invention also provides is as the application of sterilant.The fungicidal activity that contriver adopts pastille potato agar substratum (PDA) method to carry out melon anthrax bacteria (Cucurbit anthracnose), melon ash arrhizus bacteria (Cinerea Botrytis) and rice sheath blight disease (Rhizoctonia solani) to synthetic compound is in an embodiment measured, and general sieve concentration is 50mg/L.Life is surveyed result and is shown, compound (I) all shows certain inhibition activity to all for examination bacterial classifications; Compound I d (Rn=is to methyl), Im (Rn=is to fluorine), Io (Rn=is to methoxyl group) are to the inhibiting rate of melon anthrax bacteria all more than 50%, and wherein the inhibiting rate of Id is 70.63%; Compound I j (Rn=m-chloro), Im (Rn=is to fluorine), In (Rn=O-methoxy), Io (Rn=is to methoxyl group) are to the inhibiting rate of melon ash arrhizus bacteria all more than 70%, and wherein the inhibiting rate of Im, Io is all greater than 80%; (phenyl ring unsubstituted, n=0), Il (fluorine between Rn=), Im (Rn=is to fluorine) be to the inhibiting rate of rice sheath blight disease all more than 50%, wherein the inhibiting rate of Il is 87.37% to Compound I a.
Compared with prior art, beneficial effect of the present invention is embodied in:
The invention provides the novel 3-of a class ((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds, this compounds preparation is simple, shows good bacteriostatic activity.
(4) embodiment
Below in conjunction with embodiment, the invention will be further described, but protection scope of the present invention is not limited to this.
(phenyl ring is without replacement, n=0) synthetic for embodiment 1 derivative I a
2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide reference (Il Farmaco, 1999,54:842-845) method is synthetic: 2 (3H)-benzothiazolones (0.1mol), salt of wormwood (0.115mol) and acetone (180mL) are dropped into reaction flask, drip methyl chloroacetate (0.11mol), drip and finish, reflux 4 hours.Reaction solution is cooling, pours frozen water into, stirs 1 hour, filters, and filter cake washing, obtains 2-(2-oxo benzo [d] thiazole-3-yl) methyl acetate: white solid, 20.5g, yield 92.0%, m.p.91-92 ℃ of (literature value: 92-94 ℃).2-(2-oxo benzo [d] thiazole-3-yl) methyl acetate (0.01mol) and 85% hydrazine hydrate (0.2mol) are dissolved in to 100mL ethanol, reflux 24 hours, reaction solution is cooling, filter, filter cake washing, dry 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide that obtains: white solid, 1.86g, yield 83.5%, m.p.211-212 ℃ (literature value: 211 ℃).
2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), phenylformic acid (10mmol) are added in 50mL reaction flask, then add phosphorus oxychloride (200mmol), stir, be heated to reflux, react 5 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 10mL ethyl alcohol recrystallization, obtains faint yellow solid 2.02g, i.e. derivative I a.166～168 ℃ of fusing points, yield is 65.2%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：5.47(s，2H，CH
2)，7.21～8.03(m，9H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
16H
11N
3O
2S：C，62.12；H，3.58；N，13.58；found：C，62.31；H，3.55；N，13.62。
Embodiment 2 derivative I b's (the adjacent methyl of Rn=) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), o-toluic acid (10mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (200mmol), stirring, be heated to reflux, react 6 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 10mL ethyl alcohol recrystallization, obtains faint yellow solid 2.09g, i.e. derivative I b.187～189 ℃ of fusing points, yield is 64.7%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：2.65(s，3H，CH
3)，5.48(s，2H，CH
2)，7.21～7.90(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
17H
13N
3O
2S：C，63.14；H，4.05；N，12.99；found：C，63.33；H，4.03；N，13.04。
Embodiment 3 derivative I c's (methyl between Rn=) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), m-methyl benzoic acid (11mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (250mmol), stirring, be heated to reflux, react 9 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 15mL re-crystallizing in ethyl acetate, obtains faint yellow solid 2.35g, i.e. derivative I c.146～148 ℃ of fusing points, yield is 72.7%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：2.65(s，3H，CH
3)，5.48(s，2H，CH
2)，7.21～7.90(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
17H
13N
3O
2S：C，63.14；H，4.05；N，12.99；found：C，63.37；H，4.03；N，13.03。
Embodiment 4 derivative I d's (Rn=is to methyl) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), p-methylbenzoic acid (10.5mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (300mmol), stirring, be heated to reflux, react 12 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and 15mL normal hexane recrystallization for resistates, obtains faint yellow solid 2.37g, i.e. derivative I d.183～185 ℃ of fusing points, yield is 73.4%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：2.42(s，3H，CH
3)，5.45(s，2H，CH
2)，7.20～7.91(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
17H
13N
3O
2S：C，63.14；H，4.05；N，12.99；found：C，63.29；H，4.03；N，12.95。
Embodiment 5 derivative I e's (Rn=is to ethyl) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), ethyl benzoate (11mmol) is added in 50mL reaction flask, then add phosphorus oxychloride (350mmol), stir, be heated to reflux, react 12 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and 15mL sherwood oil recrystallization for resistates, obtains faint yellow solid 2.41g, i.e. derivative I e.174～176 ℃ of fusing points, yield is 71.3%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：1.31(t，J＝7.5，3H，CH
2 CH 3 )，2.42(s，3H，CH
3)，5.45(s，2H，CH
2)，7.20～7.91(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
18H
15N
3O
2S：C，64.08；H，4.48；N，12.45；found：C，64.20；H，4.44；N，12.52。
Embodiment 6 derivative I f's (Rn=is to n-propyl) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), align propylbenzoic acid (10.6mmol) and add in 50mL reaction flask, then add phosphorus oxychloride (250mmol), stir, be heated to reflux, react 7 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 15mL ethyl alcohol recrystallization, obtains faint yellow solid 2.45g, i.e. derivative I f.145～147 ℃ of fusing points, yield is 69.7%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：0.95(t，J＝7.5Hz，3H，CH
3)，1.65～1.69(m，2H，CH
2 CH 2 CH
3)，2.65(t，J＝7.5Hz，2H，
CH 2 CH
2CH
3)，5.45(s，2H，CH
2)，7.20～7.93(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
19H
17N
3O
2S：C，64.94；H，4.88；N，11.96；found：C，65.06；H，4.85；N，12.01。
Embodiment 7 derivative I g's (Rn=p-isopropyl) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), cuminic acid (10.8mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (240mmol), stirring, be heated to reflux, react 10 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and 20mL sherwood oil recrystallization for resistates, obtains faint yellow solid 2.36g, i.e. derivative I g.143～145 ℃ of fusing points, yield is 67.2%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：1.27(d，J＝7.0Hz，6H，CH
(CH 3 ) 2 )，2.94～2.99(m，1H，
CH(CH
3)
2)，5.46(s，2H，CH
2)，7.20～7.94(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
19H
17N
3O
2S：C，64.94；H，4.88；N，11.96；found：C，65.09；H，4.86；N，12.04。
Embodiment 8 derivative I h's (Rn=is to the tertiary butyl) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), p-tert-butyl benzoic acid (10mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (200mmol), stirring, be heated to reflux, react 12 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and the mixed solution recrystallization of 10mL ethyl acetate and 5mL ethanol for resistates, obtains faint yellow solid 2.25g, i.e. derivative I h.188～190 ℃ of fusing points, yield is 61.6%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：1.35(s，9H，C
(CH 3 ) 3 )，5.46(s，2H，CH
2)，7.21～7.95(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
20H
19N
3O
2S：C，65.73；H，5.24；N，11.50；found：C，65.81；H，5.22；N，11.54。
Embodiment 9 derivative I i's (Rn=is to n-pentyl) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), n-amylbenzene formic acid (11mmol) is added in 50mL reaction flask, then add phosphorus oxychloride (350mmol), stir, be heated to reflux, react 12 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and the mixed solution recrystallization of 10mL ethanol and 10mL normal hexane for resistates, obtains faint yellow solid 2.92g, i.e. derivative I i.196～198 ℃ of fusing points, yield is 77.0%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：0.90(t，J＝7.0Hz，3H，CH
3)，1.32～1.65(m，6H，CH
2 (CH 2 ) 3 CH
3)，2.66(t，J＝7.5Hz，2H，
CH 2 (CH
2)
3CH
3)，5.46(s，2H，CH
2)，7.21～7.93(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
21H
21N
3O
2S：C，66.47；H，5.58；N，11.07；found：C，66.54；H，5.55；N，11.11。
Embodiment 10 derivative I j's (Rn=m-chloro) is synthetic
2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), m-chlorobenzoic acid (10mmol) are added in 50mL reaction flask, then add phosphorus oxychloride (200mmol), stir, be heated to reflux, react 3 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and the mixed solution recrystallization of 10mL sherwood oil and 5mL normal hexane for resistates, obtains faint yellow solid 2.77g, i.e. derivative I j.171～173 ℃ of fusing points, yield is 80.5%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：5.47(s，2H，CH
2)，7.21～8.02(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
16H
10ClN
3O
2S：C，55.90；H，2.93；N，12.22；found：C，56.07；H，2.91；N，12.27。
Embodiment 11 derivative I k's (Rn=2,4-dichloro) is synthetic
2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), 2,4 dichloro benzene formic acid (10.5mmol) are added in 50mL reaction flask, add again phosphorus oxychloride (300mmol), stir, be heated to reflux, react 12 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 20mL ethyl alcohol recrystallization, obtains faint yellow solid 3.20g, i.e. derivative I k.162～163 ℃ of fusing points, yield is 84.6%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：5.49(s，2H，CH
2)，7.21～7.93(m，7H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
16H
9Cl
2N
3O
2S：C，50.81；H，2.40；N，11.11；found：C，50.97；H，2.38；N，11.15。
Embodiment 12 derivative I l's (fluorine between Rn=) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), m-fluorobenzoic acid (10.5mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (300mmol), stirring, be heated to reflux, react 8 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 15mL ethyl alcohol recrystallization, obtains faint yellow solid 2.75g, i.e. derivative I l.174～176 ℃ of fusing points, yield is 84.0%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：5.47(s，2H，CH
2)，7.21～7.83(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
16H
10FN
3O
2S：C，58.71；H，3.08；N，12.84；found：C，58.85；H，3.06；N，12.80。
Embodiment 13 derivative I m's (Rn=is to fluorine) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), parafluorobenzoic acid (10.2mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (280mmol), stirring, be heated to reflux, react 11 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 20mL re-crystallizing in ethyl acetate, obtains faint yellow solid 2.68g, i.e. derivative I m.192～194 ℃ of fusing points, yield is 82.0%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：5.46(s，2H，CH
2)，7.17～8.05(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
16H
10FN
3O
2S：C，58.71；H，3.08；N，12.84；found：C，58.82；H，3.07；N，12.88。
Embodiment 14 derivative I n's (Rn=O-methoxy) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), o-methoxybenzoic acid (11mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (250mmol), stirring, be heated to reflux, react 3 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 10mL ethyl alcohol recrystallization, obtains faint yellow solid 2.0g, i.e. derivative I n.173～174 ℃ of fusing points, yield is 59.0%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：3.92(s，3H，OCH
3)，5.47(s，2H，CH
2)，7.02～7.89(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
17H
13N
3O
3S：C，60.17；H，3.86；N，12.38；found：C，60.33；H，3.88；N，12.46。
Embodiment 15 derivative I o's (Rn=is to methoxyl group) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), anisic acid (11mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (200mmol), stirring, be heated to reflux, react 12 hours.TLC detects to reaction end, and reaction solution is concentrated sloughs phosphorus oxychloride, and resistates 10mL ethyl alcohol recrystallization, obtains faint yellow solid 3.22g, i.e. derivative I o.142～143 ℃ of fusing points, yield is 95.0%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(CDCl
3)δ：3.88(s，3H，OCH
3)，5.44(s，2H，CH
2)，6.98～7.97(m，8H，Ar-H)；Elemental?anal.(％)，calcd.for?C
17H
13N
3O
3S：C，60.17；H，3.86；N，12.38；found：C，60.38；H，3.82；N，12.44。
Embodiment 16 derivative I p's (nitro between Rn=) is synthetic
By 2-(2-oxo benzo [d] thiazole-3-yl) acethydrazide (2.25g, 10mmol), M-NITROBENZOIC ACID (10mmol) adds in 50mL reaction flask, then adds phosphorus oxychloride (350mmol), stirring, be heated to reflux, react 8 hours.TLC detects to reaction end, the concentrated phosphorus oxychloride of sloughing of reaction solution, and 20mL sherwood oil recrystallization for resistates, obtains faint yellow solid 3.20g, i.e. derivative I p.158～160 ℃ of fusing points, yield is 90.3%.
This compound
1h NMR and ultimate analysis data are as described below,
1H?NMR(DMSO-d
6)δ：5.51(s，2H，CH
2)，7.22～8.38(m，8H，Ar-H)；
Elemental?anal.(％)，calcd.for?C
16H
10N
4O
4S：C，54.23；H，2.84；N，15.81；found：C，54.40；H，2.82；N，15.87。
Embodiment 17 fungicidal activity tests
For trying target: melon anthrax bacteria (Cucurbit anthracnose), melon ash arrhizus bacteria (Cinerea Botrytis) and rice sheath blight disease (Rhizoctonia solani), above-mentioned bacterial classification is stored in 4～8 ℃ of refrigerators, testing front 2～3d is inoculated in culture dish from test tube slant, under optimal temperature, cultivate, standby.
Recovery room culture condition: the culture temperature for target after examination target and application of sample is 25 ± 5 ℃, and relative humidity is 65 ± 5%.
Adopt pastille potato agar substratum (PDA) method the synthetic compound of embodiment 1～16 and contrast medicament tricyclazole to be carried out to the fungicidal activity mensuration of above-mentioned target fungus, general sieve concentration is 50mg/L.
Concrete, testing method is evaluated SOP > > with reference to < < pesticide bioactivity.
Melon anthrax bacteria, melon ash arrhizus bacteria and rice sheath blight disease: with reference to the raw standard method NY/T1156.2-2006 that surveys, adopt pastille medium therapy: get each 500mg/L compound liquid 2mL, add in the PDA of the 18mL that is cooled to 45 ℃, making final concentration is the pastille culture medium flat plate of 50mg/L.Then from cultured test germ colony edge, get 6.5mm diameter mycelia piece, move on pastille substratum, every processing repeats for 4 times.Be disposed, the constant temperature biochemical cultivation case that is placed in 28 ℃ is cultivated, and after 4 days, measures colony diameter, calculates growth inhibition ratio.
Growth inhibition ratio (%)=[(blank colony diameter-processing colony diameter)/blank colony diameter] * 100%
Test result is in Table 1.
The fungicidal activity of table 13-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds
Claims (9)
1. a 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds, structure as shown in the formula (I):
In formula (I), it is monosubstituted, polysubstituted or be not substituted that H on phenyl ring is substituted base R, n is 0～5 integer, n represents the number of substituent R on phenyl ring, during n=0, represent that the H on phenyl ring is not substituted, during n=1, it is monosubstituted that H on expression phenyl ring is substituted base R, n=2～5 o'clock, it is polysubstituted that the H on expression phenyl ring is substituted base R, and the substituent R on different the position of substitution can be identical or different, described substituent R is the alkyl of C1～C8, the alkoxyl group of C1～C3, halogen or nitro, and described halogen is F, Cl, Br or I.
2. compound as claimed in claim 1, is characterized in that n=1～2 in described substituent R n.
3. compound as claimed in claim 1, is characterized in that described substituent R is alkyl, methoxyl group, F, Cl, Br or the nitro of C1～C5.
4. compound as claimed in claim 1, is characterized in that described substituent R is methyl, ethyl, n-propyl, sec.-propyl, the tertiary butyl, n-pentyl, F, Cl, nitro or methoxyl group.
5. compound as claimed in claim 1, it is characterized in that described substituent R n be adjacent methyl, a methyl, to methyl, to ethyl, to n-propyl, p-isopropyl, to the tertiary butyl, to n-pentyl, m-chloro, 2,4-dichloro, a fluorine, to fluorine, O-methoxy, to methoxyl group or a nitro.
6. 3-as claimed in claim 1 ((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds is as the application of sterilant, it is characterized in that described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds is as the application of the sterilant of melon anthrax bacteria (Cucurbit anthracnose), ash arrhizus bacteria (Cinerea Botrytis) or rice sheath blight disease (Rhizoctonia solani).
7. application as claimed in claim 6, it is characterized in that described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds is as the application of the sterilant of melon anthrax bacteria, described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) as shown in the formula (I), substituent R is to methyl, to fluorine or to methoxyl group to benzo [d] thiazole-2 (3H)-one compounds.
8. application as claimed in claim 6, it is characterized in that described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds is as the application of the sterilant of ash arrhizus bacteria, described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) as shown in the formula (I), substituent R is m-chloro to benzo [d] thiazole-2 (3H)-one compounds, to fluorine, to methoxyl group or O-methoxy.
9. application as claimed in claim 6, it is characterized in that described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl) benzo [d] thiazole-2 (3H)-one compounds is as the application of the sterilant of rice sheath blight disease, benzo [d] thiazole-2 (3H)-one compounds as shown in the formula (I) for described 3-((5-aryl-1,3,4-oxadiazole-2-yl) methyl), substituent R is to fluorine, a fluorine, or n=0.
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| US20090305285A1 (en) * | 2008-06-10 | 2009-12-10 | Shenzhen Mindray Bio-Medical Electronics Co., Ltd. | Asymmetric cyanine compounds, their preparation methods and their uses |
| CN101550135A (en) * | 2008-09-02 | 2009-10-07 | 四川大学 | Method for preparing AS-605240 and application thereof on preparing medicines for treating inflammatory diseases |
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