CA2002021A1 - Inhibition de la ketol-acide reductoisomerase par des derives d'oxalylhydroxamate - Google Patents
Inhibition de la ketol-acide reductoisomerase par des derives d'oxalylhydroxamateInfo
- Publication number
- CA2002021A1 CA2002021A1 CA 2002021 CA2002021A CA2002021A1 CA 2002021 A1 CA2002021 A1 CA 2002021A1 CA 2002021 CA2002021 CA 2002021 CA 2002021 A CA2002021 A CA 2002021A CA 2002021 A1 CA2002021 A1 CA 2002021A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- atoms
- methyl
- optionally substituted
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108010000200 Ketol-acid reductoisomerase Proteins 0.000 title claims abstract description 42
- 230000005764 inhibitory process Effects 0.000 title abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 42
- 230000008569 process Effects 0.000 claims abstract description 35
- 230000012010 growth Effects 0.000 claims abstract description 31
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 21
- 230000000813 microbial effect Effects 0.000 claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 43
- -1 2-pentyl Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 24
- 238000003556 assay Methods 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 230000001580 bacterial effect Effects 0.000 claims description 15
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 5
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 4
- 238000011534 incubation Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 239000008366 buffered solution Substances 0.000 claims description 3
- QVIOSGUKMDGWNN-UHFFFAOYSA-N n-hydroxy-n-isopropyloxamic acid Chemical compound CC(C)N(O)C(=O)C(O)=O QVIOSGUKMDGWNN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000419 plant extract Substances 0.000 claims description 3
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000002285 radioactive effect Effects 0.000 claims description 3
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 101710148054 Ketol-acid reductoisomerase (NAD(+)) Proteins 0.000 abstract description 16
- 101710099070 Ketol-acid reductoisomerase (NAD(P)(+)) Proteins 0.000 abstract description 16
- 101710151482 Ketol-acid reductoisomerase (NADP(+)) Proteins 0.000 abstract description 16
- 102000004190 Enzymes Human genes 0.000 description 44
- 108090000790 Enzymes Proteins 0.000 description 44
- 229940088598 enzyme Drugs 0.000 description 44
- 150000004702 methyl esters Chemical class 0.000 description 40
- 239000003112 inhibitor Substances 0.000 description 38
- 241000196324 Embryophyta Species 0.000 description 32
- 239000000243 solution Substances 0.000 description 24
- 150000005693 branched-chain amino acids Chemical class 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000001419 dependent effect Effects 0.000 description 14
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 13
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 10
- 208000006278 hypochromic anemia Diseases 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- 230000036962 time dependent Effects 0.000 description 10
- 241000894006 Bacteria Species 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 7
- 239000007806 chemical reaction intermediate Substances 0.000 description 7
- 229960000310 isoleucine Drugs 0.000 description 7
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000004474 valine Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 108010000700 Acetolactate synthase Proteins 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- 108090001042 Hydro-Lyases Proteins 0.000 description 6
- 102000004867 Hydro-Lyases Human genes 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- WTLNOANVTIKPEE-UHFFFAOYSA-N 2-acetyloxypropanoic acid Chemical compound OC(=O)C(C)OC(C)=O WTLNOANVTIKPEE-UHFFFAOYSA-N 0.000 description 5
- 108010022181 Phosphopyruvate Hydratase Proteins 0.000 description 5
- 102000012288 Phosphopyruvate Hydratase Human genes 0.000 description 5
- 125000003431 oxalo group Chemical group 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 4
- 244000024671 Brassica kaber Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 244000300264 Spinacia oleracea Species 0.000 description 4
- 235000009337 Spinacia oleracea Nutrition 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 108010046334 Urease Proteins 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 4
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- KPULXFNPTWGJQH-UHFFFAOYSA-N 3-hydroxy-4-oxo-4-propan-2-yloxybutanoic acid Chemical compound CC(C)OC(=O)C(O)CC(O)=O KPULXFNPTWGJQH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 3
- 101001135788 Pinus taeda (+)-alpha-pinene synthase, chloroplastic Proteins 0.000 description 3
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 3
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 230000009920 chelation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000019162 flavin adenine dinucleotide Nutrition 0.000 description 3
- 239000011714 flavin adenine dinucleotide Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000005080 plant death Effects 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229960003495 thiamine Drugs 0.000 description 3
- 235000019157 thiamine Nutrition 0.000 description 3
- 239000011721 thiamine Substances 0.000 description 3
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
- 102000004400 Aminopeptidases Human genes 0.000 description 2
- 108090000915 Aminopeptidases Proteins 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 102000029816 Collagenase Human genes 0.000 description 2
- 108060005980 Collagenase Proteins 0.000 description 2
- 241001394453 Delissea subcordata Species 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 229910015400 FeC13 Inorganic materials 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 108091022930 Glutamate decarboxylase Proteins 0.000 description 2
- 102000008214 Glutamate decarboxylase Human genes 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 108010014095 Histidine decarboxylase Proteins 0.000 description 2
- 102100037095 Histidine decarboxylase Human genes 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 102000004195 Isomerases Human genes 0.000 description 2
- 108090000769 Isomerases Proteins 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- 108090000128 Lipoxygenases Proteins 0.000 description 2
- 102000003820 Lipoxygenases Human genes 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 102000016387 Pancreatic elastase Human genes 0.000 description 2
- 108010067372 Pancreatic elastase Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 108090001109 Thermolysin Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 229960002424 collagenase Drugs 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000003345 scintillation counting Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- LCTONWCANYUPML-YZRHJBSPSA-N (1-14c)pyruvate Chemical compound CC(=O)[14C](O)=O LCTONWCANYUPML-YZRHJBSPSA-N 0.000 description 1
- FZENGILVLUJGJX-IHWYPQMZSA-N (Z)-acetaldehyde oxime Chemical compound C\C=N/O FZENGILVLUJGJX-IHWYPQMZSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- CTMXBOCTJPQVDZ-UHFFFAOYSA-N 2,2-dihydroxy-3-methylbutanoic acid Chemical compound CC(C)C(O)(O)C(O)=O CTMXBOCTJPQVDZ-UHFFFAOYSA-N 0.000 description 1
- PDGXJDXVGMHUIR-UHFFFAOYSA-N 2,3-Dihydroxy-3-methylpentanoate Chemical compound CCC(C)(O)C(O)C(O)=O PDGXJDXVGMHUIR-UHFFFAOYSA-N 0.000 description 1
- XOHUEYCVLUUEJJ-UHFFFAOYSA-I 2,3-Diphosphoglycerate Chemical compound [O-]P(=O)([O-])OC(C(=O)[O-])COP([O-])([O-])=O XOHUEYCVLUUEJJ-UHFFFAOYSA-I 0.000 description 1
- JTEYKUFKXGDTEU-UHFFFAOYSA-N 2,3-dihydroxy-3-methylbutanoic acid Chemical compound CC(C)(O)C(O)C(O)=O JTEYKUFKXGDTEU-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical class NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- DNOPJXBPONYBLB-UHFFFAOYSA-N 3-hydroxy-3-methyl-2-oxobutanoic acid Chemical compound CC(C)(O)C(=O)C(O)=O DNOPJXBPONYBLB-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 108090000531 Amidohydrolases Proteins 0.000 description 1
- 102000004092 Amidohydrolases Human genes 0.000 description 1
- 241000219194 Arabidopsis Species 0.000 description 1
- 241000490494 Arabis Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YAHZABJORDUQGO-NQXXGFSBSA-N D-ribulose 1,5-bisphosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)C(=O)COP(O)(O)=O YAHZABJORDUQGO-NQXXGFSBSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 108700016168 Dihydroxy-acid dehydratases Proteins 0.000 description 1
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 101000621371 Homo sapiens WD and tetratricopeptide repeats protein 1 Proteins 0.000 description 1
- 101000892274 Human adenovirus C serotype 2 Adenovirus death protein Proteins 0.000 description 1
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical group C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 102000013009 Pyruvate Kinase Human genes 0.000 description 1
- 108020005115 Pyruvate Kinase Proteins 0.000 description 1
- 101000820656 Rattus norvegicus Seminal vesicle secretory protein 4 Proteins 0.000 description 1
- 102000000505 Ribonucleotide Reductases Human genes 0.000 description 1
- 108010041388 Ribonucleotide Reductases Proteins 0.000 description 1
- 108010003581 Ribulose-bisphosphate carboxylase Proteins 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 description 1
- WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 description 1
- 241000383558 Thalia <angiosperm> Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000007997 Tricine buffer Substances 0.000 description 1
- 102000005924 Triose-Phosphate Isomerase Human genes 0.000 description 1
- 108700015934 Triose-phosphate isomerases Proteins 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000005549 deoxyribonucleoside Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002083 enediols Chemical class 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 description 1
- 229940093632 flavin-adenine dinucleotide Drugs 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- HDKLIZDXVUCLHQ-UHFFFAOYSA-N non-3-en-2-one Chemical compound CCCCCC=CC(C)=O HDKLIZDXVUCLHQ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- KCRZDTROFIOPBP-UHFFFAOYSA-N phosphono 2,3-dihydroxypropanoate Chemical compound OCC(O)C(=O)OP(O)(O)=O KCRZDTROFIOPBP-UHFFFAOYSA-N 0.000 description 1
- LDKRAXXVBWHMRH-UHFFFAOYSA-N phosphonoacetohydroxamic acid Chemical compound ONC(=O)CP(O)(O)=O LDKRAXXVBWHMRH-UHFFFAOYSA-N 0.000 description 1
- 238000012809 post-inoculation Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940076788 pyruvate Drugs 0.000 description 1
- 239000012857 radioactive material Substances 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000002336 ribonucleotide Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000027772 skotomorphogenesis Effects 0.000 description 1
- UMCYUPVKJYJUCD-UHFFFAOYSA-M sodium 2-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]acetic acid hydroxide Chemical compound [OH-].[Na+].OCC(CO)(CO)NCC(O)=O UMCYUPVKJYJUCD-UHFFFAOYSA-M 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960002363 thiamine pyrophosphate Drugs 0.000 description 1
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 1
- 239000011678 thiamine pyrophosphate Substances 0.000 description 1
- YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000002601 urease inhibitor Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26696888A | 1988-11-03 | 1988-11-03 | |
| US266,968 | 1988-11-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2002021A1 true CA2002021A1 (fr) | 1990-05-03 |
Family
ID=23016744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2002021 Abandoned CA2002021A1 (fr) | 1988-11-03 | 1989-11-01 | Inhibition de la ketol-acide reductoisomerase par des derives d'oxalylhydroxamate |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2002021A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5192358A (en) * | 1990-07-12 | 1993-03-09 | Basf Aktiengesellschaft | Oxalic acid derivatives, their preparation and plant growth regulators containing them |
| US5672598A (en) * | 1995-03-21 | 1997-09-30 | The Procter & Gamble Company | Lactam-containing hydroxamic acids |
| FR2829363A1 (fr) * | 2001-09-10 | 2003-03-14 | Aventis Cropscience Sa | Utilisations d'inhibiteurs de l'acetohydroxyacide isomeroreductase pour le traitement des maladies fongiques des cultures |
-
1989
- 1989-11-01 CA CA 2002021 patent/CA2002021A1/fr not_active Abandoned
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5192358A (en) * | 1990-07-12 | 1993-03-09 | Basf Aktiengesellschaft | Oxalic acid derivatives, their preparation and plant growth regulators containing them |
| US5672598A (en) * | 1995-03-21 | 1997-09-30 | The Procter & Gamble Company | Lactam-containing hydroxamic acids |
| FR2829363A1 (fr) * | 2001-09-10 | 2003-03-14 | Aventis Cropscience Sa | Utilisations d'inhibiteurs de l'acetohydroxyacide isomeroreductase pour le traitement des maladies fongiques des cultures |
| WO2003022056A1 (fr) * | 2001-09-10 | 2003-03-20 | Bayer Cropscience Sa | Utilisations d'inhibiteurs de l'acetohydroxyacide isomeroreductase pour le traitement des maladies fongiques des cultures |
| JP2005501912A (ja) * | 2001-09-10 | 2005-01-20 | バイエル・クロツプサイエンス・エス・アー | 真菌病罹病性作物を処置するためのケトール酸レダクトイソメラーゼ阻害剤の使用 |
| US7166706B2 (en) | 2001-09-10 | 2007-01-23 | Bayer Cropscience S.A. | Use of ketol-acid reductoisomerase inhibitors to prevent or treat fungal infection of plants |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Harris | Cysteine and growth inhibition of Escherichia coli: threonine deaminase as the target enzyme | |
| Davis et al. | Analysis of the biochemical mechanism of drug resistance in certain bacterial mutants | |
| PL130553B1 (en) | Process for preparing novel diester of methanediol with derivatives of penicillanic acid | |
| Nakazawa et al. | Phthalate metabolism in Pseudomonas testosteroni: accumulation of 4, 5-dihydroxyphthalate by a mutant strain | |
| AU732841B2 (en) | Media for the culturing and specific identification of various candida species, and analytical processes | |
| Neuhaus | D-cycloserine and O-carbamyl-D-serine | |
| Wallace et al. | Developing ciprofloxacin analogues against plant DNA gyrase: a novel herbicide mode of action | |
| Schloss | Recent advances in understanding the mechanism and inhibition of acetolactate synthase | |
| US4623659A (en) | Polyhydroxybenzoic acid derivatives | |
| CA2116421A1 (fr) | Inhibiteurs de l'hydroxyphenylpyruvate dioxygenase et methode d'identification d'inhibiteurs | |
| US11247976B2 (en) | Synthetic ligands that modulate the activity of the RhlR quorum sensing receptor | |
| Epelbaum et al. | Metabolic effects of inhibitors of two enzymes of the branched-chain amino acid pathway in Salmonella typhimurium | |
| JP2007535475A (ja) | Sir2制御 | |
| Kaplancikli et al. | Synthesis and antituberculosis activity of new hydrazide derivatives | |
| Sykes et al. | Conjugative mapping of pyruvate, 2-ketoglutarate, and branched-chain keto acid dehydrogenase genes in Pseudomonas putida mutants | |
| Silverman et al. | 1-Benzylcyclopropylamine and 1-(aminomethyl)-1-phenylcyclopropane: an inactivator and a substrate of monoamine oxidase | |
| Mike et al. | Discovery of nicoyamycin A, an inhibitor of uropathogenic Escherichia coli growth in low iron environments | |
| AU2013302177A1 (en) | Antibacterial inhibitors | |
| ES2389216T3 (es) | Uso de colismicina A como inhibidor del estrés oxidativo | |
| Storer et al. | Comparison of the kinetics of the papain-catalyzed hydrolysis of glycine-and alanine-based esters and thiono esters | |
| Norris et al. | The use of amino acid analogues in biological studies | |
| RU2629369C1 (ru) | Четвертичные аммонийные производные 2-аминотиофен-3-карбоксилатов, обладающие противотуберкулезной активностью | |
| SU1520093A1 (ru) | Способ выделени бактерий рода SаLмоNеLLа | |
| Sakuda et al. | Biosynthesis of virginiae butanolide A | |
| JP2006521803A (ja) | 微生物の検出用及び/又は識別用の培地 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |