JP6583737B2 - アブシジン酸誘導体 - Google Patents
アブシジン酸誘導体 Download PDFInfo
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- JP6583737B2 JP6583737B2 JP2016550137A JP2016550137A JP6583737B2 JP 6583737 B2 JP6583737 B2 JP 6583737B2 JP 2016550137 A JP2016550137 A JP 2016550137A JP 2016550137 A JP2016550137 A JP 2016550137A JP 6583737 B2 JP6583737 B2 JP 6583737B2
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- Prior art keywords
- group
- compound
- phenyl
- salt
- naphthyl
- Prior art date
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- 150000003529 abscisic acid derivatives Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 99
- -1 pentafluorosulfanyl group Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 22
- 108091005721 ABA receptors Proteins 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 7
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 239000005648 plant growth regulator Substances 0.000 claims description 6
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000012360 testing method Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
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- 241000196324 Embryophyta Species 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
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- 230000000052 comparative effect Effects 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 241000219195 Arabidopsis thaliana Species 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 230000007226 seed germination Effects 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 7
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- 230000000694 effects Effects 0.000 description 6
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
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- 101000688229 Leishmania chagasi Protein phosphatase 2C Proteins 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- 230000003042 antagnostic effect Effects 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 108090000623 proteins and genes Proteins 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- CITCNHIMAONQEL-UHFFFAOYSA-N 2-but-2-ynyl-4-methylbenzenesulfonic acid Chemical compound CC#CCC1=CC(C)=CC=C1S(O)(=O)=O CITCNHIMAONQEL-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000208822 Lactuca Species 0.000 description 3
- 108700019535 Phosphoprotein Phosphatases Proteins 0.000 description 3
- 102000045595 Phosphoprotein Phosphatases Human genes 0.000 description 3
- 239000005987 S-Abscisic acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000012064 sodium phosphate buffer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- NITUNGCLDSFVDL-UHFFFAOYSA-N 3-phenylprop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC=C1 NITUNGCLDSFVDL-UHFFFAOYSA-N 0.000 description 2
- FTUHRUAOAHSJNW-UHFFFAOYSA-N 3-phenylprop-2-ynyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC#CC1=CC=CC=C1 FTUHRUAOAHSJNW-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
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- 239000000654 additive Substances 0.000 description 2
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- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- HGZKJNHJABSJTC-UHFFFAOYSA-N but-2-ynyl 4-methylbenzenesulfonate Chemical compound CC#CCOS(=O)(=O)C1=CC=C(C)C=C1 HGZKJNHJABSJTC-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- FRYANWYSCROOCU-UHFFFAOYSA-N pentafluoro-(4-iodophenyl)-$l^{6}-sulfane Chemical compound FS(F)(F)(F)(F)C1=CC=C(I)C=C1 FRYANWYSCROOCU-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000014284 seed dormancy process Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/22—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by sulfur atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
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Description
通常、植物ではPP2CがプロテインキナーゼSnRK2を脱リン酸化して不活性状態を維持している。植物がストレスを受けると、アブシジン酸が合成され、標的となる器官に輸送された後にアブシジン酸受容体と結合する。アブシジン酸がアブシジン酸受容体に結合すると、アブシジン酸受容体とPP2Cが複合体を形成し、PP2Cによる脱リン酸化が抑制される。その結果、SnRK2が自己リン酸化を起こして活性化状態へと変化し、下流のイオンチャネル及び転写因子などを活性化し、アブシジン酸応答が誘導される。
化合物(IV)を施用された植物は、ストレスによりアブシジン酸が合成されたとしても、化合物(IV)が、アブシジン酸とアブシジン酸受容体の結合及びそれに引き続くPP2Cとの複合体形成を阻害するため、アブシジン酸応答が誘導されなくなる。このため、化合物(IV)は植物の成長を調節することが可能となる。
1H NMR (270 MHz, CD3OD):δ 0.81 (3H, s), 0.92 (3H, s), 1.51 (1H, dd, J = 13.2 and 9.9 Hz), 1.55 (3H, d, J = 1.65 Hz), 1.63 (1H, ddd, J = 13.2, 6.6 and 1.3 Hz), 1.92 (3H, d, J = 1.3 Hz), 4.09 (1H, m), 5.43 (1H, m), 5.60 (1H, q, J = 1.0 Hz), 6.12 (1H, dd, J = 16.2 and 0.7 Hz), 7.58 (1H, dd, J = 16.2 and 0.7 Hz)
1H NMR (270 MHz, CDCl3):δ 2.39 (3H, s), 4.95 (2H, s), 7.24-7.37 (7H, m), 7.85 (2H, m)
1H NMR (270 MHz, CDCl3): δ 1.91 (2H, m), 2.45 (3H, s), 2.60 (2H, t, J=7.6 Hz), 4.00 (2H, t, J=6.3 Hz), 7.04-7.23 (5H, m), 7.43 (2H, m), 7.78 (2H, m)
1H NMR (500 MHz, CDCl3):δ 0.92 (3H, s, H3-9'), 1.06 (3H, s, H3-8'), 1.67 (3H, m, H3-7'), 1.72 (1H, dd, J = 13.1 and 9.5 Hz, H-5'), 1.90 (1H, m, H-5'), 2.01 (3H, d, J = 0.6 Hz, H3-6), 4.27 (1H, m, H-4'), 4.42 (1H, d, J = 15.9 Hz, H-1"), 4.47 (1H, d, J = 15.9 Hz, H-1"), 5.68 (1H, brs, H-3'), 5.71 (1H, s, H-2), 6.21 (1H, d, J = 15.9 Hz, H-5), 7.31 (3H, m, H-6", 7" and 8"), 7.44 (2H, m, H-5" and 9"), 7.74 (1H, d, J = 15.9 Hz, H-4)
13C NMR (125 MHz, CDCl3):δ 17.7 (C7'), 21.5 (C6), 22.7 (C8'), 25.3 (C9'), 39.7 (C6'), 40.7 (C5'), 56.1 (C1"), 72.3 (C4'), 79.3 (C1'), 85.5 (C2"), 86.0 ( C3"), 117.0 (C2), 122.7 (C4"), 124.6 (C3'), 126.5 (C4), 128.3 (C6" and 8"), 128.4 (C7"), 131.7 (C5" and 9"), 139.1 (C2'), 140.3 (C5), 152.2 (C3), 170.6 (C1)
UVλmax (MeOH) nm(ε): 242.4 (27600), 250.4 (29000)
HRMS (m/z): [M+Na]+ calc'd. for C24H28O4Na, 403.1885; found, 403.1880.
1H NMR (500 MHz, CD3OD):δ 0.95 (3H, s, H3-9'), 1.07 (3H, s, H3-8'), 1.70 (3H, dd, J = 1.5 and 1.5 Hz, H3-7'), 1.76 (1H, dd, J = 13.1 and 9.8 Hz, H-5'), 1.92 (1H, ddd, J = 13.1, 6.4 and 1.5 Hz, H-5'), 2.01 (3H, d, J = 1.2 Hz, H3-6), 4.41 (1H, m, H-4'), 4.60 (2H, d, J = 1.5 Hz, OCH2-), 5.70 (1H, brs, H-2), 5.73 (1H, m, H-3'), 6.22 (1H, d, J = 16.2 Hz, H-5), 7.44 (1H, dd, J = 8.2 and 7.3 Hz, H-6''), 7.54 (2H, m, H-10'' and 11''), 7.65 (1H, dd, J = 7.3 and 1.2 Hz, H-5''), 7.73 (1H, d, J = 16.2 Hz, H-4), 7.88 (2H, m, H-7'' and 12''), 8.30 (1H, d, J = 8.2 Hz, H-9'')
13C NMR(125 MHz, CD3OD):δ 18.4 (C7'), 21.4 (C6), 23.3 (C8'), 25.7 (C9'), 40.9 (C6'), 41.7 (C5'), 56.8 (C1''), 74.1 (C4'), 80.2 (C1'), 84.8 (C2''), 91.9 (C3''), 118.8 (C2), 121.5 (C8''), 125.6 (C3'), 126.3 (C6''), 126.9 (C9''), 127.5 (C11''), 127.9 (C10''), 128.2 (C4), 129.4 (C12''), 130.0 (C7''), 131.5 (C5''), 134.6 (C4'‘ or 13''), 134.7 (C4'‘ or 13''), 141.1 (C5), 141.2 (C2'), 151.4 (C3), 169.8 (C1)
UVλmax (MeOH) nm(ε): 226.8 (59700), 262.2 (18000), 297.0 (13700), 310.4 (8410)
HRMS (m/z): [M+Na]+ calc'd. for C28H30O4Na, 453.2042; found 453.2045.
1H NMR (270 MHz, CDCl3):δ 0.92 (3H, s, H3-8’ or 9'), 1.05 (3H, s, H3-8' or 9’), 1.63-1.71 (4H, m, H3-7' and H-5’), 1.86 (1H, ddd, J = 13.2, 6.6 and 1.3 Hz, H-5’), 2.02 (3H, d, J = 1.0 Hz, H3-6), 2.43 (1H, t, J = 2.3 Hz, H-3’’), 4.16-4.23 (3H, m, H-4’ and H2-1’’), 5.64 (1H, m, H-3’), 5.72 (1H, s, H-2), 6.19 (1H, d, J = 16.2 Hz, H-5), 7.35 (1H, d, J = 16.2 Hz, H-4)
1H NMR (270 MHz, CDCl3):δ 0.93 (3H, s), 1.07 (3H, s), 1.63-1.73 (4H, m), 1.82-1.93 (1H, m), 2.02 (3H, s), 4.14-4.29 (3H, m), 5.68 (1H, m), 5.71 (1H, s), 6.20 (1H, d, J = 16.1 Hz), 7.52-7.60 (4H, m), 7.74 (1H, d, J = 16.1 Hz)
1H NMR (270 MHz, CDCl3):δ 0.90 (3H, s), 1.04 (3H, s), 1.65 (3H, s), 1.70 (1H, dd, J = 12.5 and 9.6 Hz), 1.89 (1H, dd, J = 12.5 and 6.6 Hz), 1.99 (3H, s), 3.85 (3H, s), 4.24 (1H, m), 4.36-4.48 (2H, m), 5.66 (1H, s), 5.71 (1H, s), 6.16 (1H, s), 6.81-6.87 (2H, m), 7.35-7.41 (2H, m), 7.73 (1H, s)
1H NMR (270 MHz, CDCl3):δ 0.93 (3H, s), 1.07 (3H, s), 1.68 (3H, s), 1.72 (1H, dd, J = 13.5 and 9.6 Hz), 1.90 (1H, dd, J = 13.5 and 6.9 Hz), 2.02 (3H, s), 2.60 (3H, s), 4.25 (1H, m), 4.46 (2H, m), 5.69 (1H, s), 5.72 (1H, s), 6.21 (1H, d, J = 16.2 Hz), 7.50-7.53 (2H, m), 7.74 (1H, d, J = 16.2 Hz), 7.89-7.92 (2H, m)
1H NMR (500 MHz, CDCl3): δ 0.91 (3H, s), 1.05 (3H, s), 1.66 (3H, m), 1.71 (1H, dd, J = 13.1 and 9.8 Hz), 1.89 (1H, m), 2.00 (3H, s), 2.34 (3H, s), 4.26 (1H, m), 4.41(1H, d, J = 15.9 Hz), 4.45(1H, d, J = 15.9 Hz), 5.67 (1H, s), 5.71 (1H, s), 6.19 (1H, d, J = 15.9 Hz), 7.10-7.12 (3H, m), 7.32-7.34 (2H, m), 7.74 (1H, d, J = 15.9 Hz)
1H NMR (500 MHz, CD3OD): δ 0.94 (3H, s), 1.04 (3H, s), 1.68 (3H, m), 1.69 (1H, dd, J = 13.0 and 9.3 Hz), 1.84 (1H, ddd, J = 13.0, 6.4 and 1.5 Hz), 2.01 (3H, d, J = 0.9 Hz), 4.27 (1H, m), 4.45 (1H, d, J = 16.4 Hz), 4.49 (1H, d, J = 16.4 Hz), 5.66 (1H, m), 5.71 (1H, m), 6.17 (1H, d, J = 16.1 Hz), 7.58-7.60 (2H, m), 7.68 (1H, d, J = 16.1 Hz), 7.79-7.82 (2H, m)
1H NMR (500 MHz, CDCl3): δ 0.91 (3H, s), 1.00 (3H, s), 1.62 (1H, dd), 1.66 (3H, s), 1.75 (1H, ddd, J=13.2, 6.3 and 1.0 Hz), 1.85 (2H, m), 2.01 (3H, s), 2.68 (2H, t, J=7.3 Hz), 3.49 (2H, m), 3.96 (1H, m), 5.58 (1H, m), 5.73 (1H, brs), 6.17 (1H, d, J=15.2 Hz), 7.20 (5H, m), 7.68 (1H, d, J=15.2 Hz)
シロイヌナズナ(Arabidopsis thaliana,Col−0)種子を70%エタノール水溶液500μLに30分,続いて100%エタノール溶液500μLに1分浸漬し,蒸留水1mLで5回洗浄した後に,種子を蒸留水に浸漬させ,暗所下,4℃で3日間春化処理した。試料のメタノール溶液を1.5mL容マイクロチューブに入れ,減圧下にてメタノールを除去し,70℃の0.5%寒天水溶液(含1/2MS培地無機塩類)を加え,撹拌した後に96穴プレートに入れ,試料を含む培地とした。試料は,実施例1〜9及び比較例1の濃度はいずれも3μMになるように調製した。また,ABAを投与する場合,ABAの濃度が0.3μMになるように調製した。ここに春化処理済みのシロイヌナズナ種子を20−30粒ずつ播種し,22℃,連続光下で培養して,その発芽数を経時的に観察した。下記式(1)にしたがって発芽率を計算した。なお,メタノールを用いて同様に培地を調製したものをコントロールとして用いた。結果を表1に示す。実施例1〜9の化合物をABAと共投与すると、ABAにより低下した種子の発芽率が回復することが明らかとなった。
発芽率(%)=発芽数(個)/播種数(個)×100…(1)
実施例1の化合物の処理濃度を0.3μMから30μMまで変化させて、試験例1と同様の試験を行った。結果を図1に示す。この濃度範囲でも、実施例1の化合物をABAと共投与すると、ABAにより低下した種子の発芽率が回復することが確認された。
また,シロイヌナズナに代えて、レタス(Lactuca sativa)及びチンゲンサイ(Brassica rapa var. chinensis)を用いて、試験例2と同様の試験を行った。レタス及びチンゲンサイの種子に対しても、実施例1及び2の化合物はABA共投与により、ABAにより低下した種子の発芽率が回復した。
実施例1の化合物と比較例1の化合物の種子発芽率の回復効果を比較するため、化合物の処理濃度を0.3μMから3μMまで変化させて、試験例2と同様の試験を行った。結果を図2に示す。実施例1の化合物は、比較例1の化合物よりも種子発芽率の回復効果に優れることが明らかとなった。
シロイヌナズナのPYR/PYL/RCARタンパク質(PYL,アブシジン酸受容体)又はタンパク質脱リン酸化酵素HAB1がコードされたプラスミド(pGex−2T−GST−HAB1又はpET28−6xHis−PYL)を大腸菌(HAB1:BL21(DE3)pLysS,PYL:BL21−codonplus(DE3)−RIPL)に形質転換した。前培養(30℃,180rpm,15時間)と本培養(30℃,180rpm,4時間)を行った培養液に,イソプロピル−β−チオガラクトピラノシドを加え,タンパク質発現(16℃,150rpm,18時間)した粗酵素液を,FPLCを用いて精製し,組換PYL(PYR1,PYL1−6,PYL8−10)及びHAB1を調製した。96穴プレートにβ−メルカプトエタノール,塩化マンガン水溶液,HAB1,PYL,試料のジメチルスルホキシド溶液,超純水を順に加え,22℃で30分静置した後に,HAB1の人口基質であるp−ニトロフェニルホスフェートを加えて反応を開始し,マイクロプレートリーダー(TECAN,インフィニットTM N200 NanoQuant)に入れた。p−ニトロフェニルホスフェートの加水分解産物であるp−ニトロフェノールの405nmの吸光度を反応開始3分後に測定し,下記式(2)にしたがってHAB1の活性を計算した。なお,ジメチルスルホキシドのみを加えた画分をコントロールとして,その時の活性を100%とした。その結果を図3及び表2に示す。実施例1及び4〜9の化合物は、ABA受容体のアンタゴニストとして作用することが明らかとなった。
HAB1比活性(%)=サンプル添加時の吸光度/コントロールの吸光度×100…(2)
試験例5と同様の手順で,組換PYL5のリン酸ナトリウムバッファー溶液を調製し,これを等温滴定型カロリメーター(GE Healthcare,MicroCal iTC200)の反応セルに入れ,実施例1の化合物のリン酸ナトリウムバッファー溶液をシリンジ内に入れた。その後,上記のカロリメーターを20℃に設定し,測定を行った。実施例7〜9の化合物についても上記と同様の測定を行った。比較対象としてABAおよび比較例1の化合物のリン酸ナトリウムバッファー溶液を用いた結果を表3に示す。実施例1及び7〜9の化合物の解離定数KdはABA及び比較例1の化合物よりも低く、ABA受容体へ親和性が強いことが明らかとなった。
シロイヌナズナ(Arabidopsis thaliana,Col−0)種子を5%ブリーチ+1%SDS水溶液500mL,70%エタノール水溶液500μL,70%エタノール水溶液500μLにそれぞれ1分間ずつ順に浸漬し,滅菌水1mLで5回洗浄した後に,0.1%寒天水溶液に懸濁した。オートクレーブで滅菌した発芽培地(含1/2MS培地無機塩類)を滅菌プラスチックシャーレに25mLずつ加え,ここに0.1%寒天水溶液に懸濁した種子を60−80粒ずつ播種し,暗所下,4℃で3日間春化処理した。これを22℃,連続光下で10日間培養した。滅菌した土(有機培養土:バーミキュライト=1:1)をプラスチックポット(50mm×50mm×50mm,35mm底面×35mm高さ)に40gずつ加えた。このプラスチックポット6個を3000mL容トレーにいれ,1000倍希釈HYPONeX(商品名(登録商標),株式会社ハイポネックスジャパン製)水溶液300mLを加え(深さ10mm),シロイヌナズナ実生を5株ずつプラスチックシャーレから移植した。これを22℃,16時間明期−8時間暗期下で培養し,0.1%DMSO(実施例7の化合物を含む)+0.1%アプローチBI(商品名(登録商標),花王株式会社製)水溶液1mL(実施例7の化合物の最終濃度が50μMになるように調製)を1日1回噴霧した。また,1週間ごとに2000倍希釈HYPONEX水溶液300mLを加えた。上記と同様の処理を比較例1の化合物を用いて行った。なお,上記化合物を含まない0.1%DMSO+0.1%アプローチBI水溶液1mLを1日1回噴霧したものをコントロールとして用いた。さらに,上記と同様の条件で,0.1%DMSO(実施例7の化合物を含む,比較例1の化合物を含む,又はこれらの化合物を含まない)+0.1%アプローチBI水溶液1mL(化合物を含む場合には、その最終濃度が50μMになるように調製)に,ABAを添加しABAの最終濃度が5μMになるように調製し,これを1日1回噴霧する試験を行った。3週間培養後のシロイヌナズナの生育状態を比較したところ,ABAのみを投与した場合,シロイヌナズナの生育が顕著に抑制された。これに対し,比較例1の化合物とABAを共投与した場合,ABAの生育抑制効果はほとんど改善されなかった。他方で,実施例7の化合物とABAを共投与した場合,ABAによる生育抑制効果が著しく改善され,コントロールと同程度までシロイヌナズナの生育が回復した。
Claims (7)
- 式(IV)で表される化合物又はその塩。
[Xが、エチレン基又はエテニレン基であるときは、R1は、フェニル基又はナフチル基であり、フェニル基及びナフチル基は、ハロゲン原子、水酸基、C1−6アルキル基、ハロゲン原子で置換されたC1−6アルキル基、C1−6アルコキシ基、アセチル基、アミノ基、アセチルアミノ基、フェニル基及びペンタフルオロスルファニル基からなる群から選択される置換基を有していてもよく、
Xが、エチニレン基であるときは、R1は、水素原子、フェニル基又はナフチル基であり、フェニル基及びナフチル基は、ハロゲン原子、水酸基、C1−6アルキル基、ハロゲン原子で置換されたC1−6アルキル基、C1−6アルコキシ基、アセチル基、アミノ基、アセチルアミノ基、フェニル基及びペンタフルオロスルファニル基からなる群から選択される置換基を有していてもよい。] - R2がフェニル基又は1−ナフチル基である、請求項2記載の化合物又はその塩。
- Xが、エチニレン基であり、R1が、水素原子、フェニル基又はナフチル基であり、フェニル基及びナフチル基は、ハロゲン原子、水酸基、C1−6アルキル基、ハロゲン原子で置換されたC1−6アルキル基、C1−6アルコキシ基、アセチル基、アミノ基、アセチルアミノ基、フェニル基及びペンタフルオロスルファニル基からなる群から選択される置換基を有していてもよい、請求項1記載の化合物又はその塩。
- Xが、エチレン基であり、R1が、フェニル基又はナフチル基であり、フェニル基及びナフチル基は、ハロゲン原子、水酸基、C1−6アルキル基、ハロゲン原子で置換されたC1−6アルキル基、C1−6アルコキシ基、アセチル基、アミノ基、アセチルアミノ基、フェニル基及びペンタフルオロスルファニル基からなる群から選択される置換基を有していてもよい、請求項1記載の化合物又はその塩。
- 請求項1〜5のいずれか一項記載の化合物又はその塩を含む、アブシジン酸受容体の阻害剤。
- 請求項1〜5のいずれか一項記載の化合物又はその塩を含む、植物成長調節剤。
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