JP6164761B2 - オーキシン生合成阻害剤 - Google Patents
オーキシン生合成阻害剤 Download PDFInfo
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- JP6164761B2 JP6164761B2 JP2016092258A JP2016092258A JP6164761B2 JP 6164761 B2 JP6164761 B2 JP 6164761B2 JP 2016092258 A JP2016092258 A JP 2016092258A JP 2016092258 A JP2016092258 A JP 2016092258A JP 6164761 B2 JP6164761 B2 JP 6164761B2
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- 0 COC(CCC(*=C1)=CC2C1=CCC=C2)=[U] Chemical compound COC(CCC(*=C1)=CC2C1=CCC=C2)=[U] 0.000 description 4
- VSJKSBKNCMEPQV-UHFFFAOYSA-N CC(CC(C=C1)=CCC1Oc1ccccc1)C(OC)=O Chemical compound CC(CC(C=C1)=CCC1Oc1ccccc1)C(OC)=O VSJKSBKNCMEPQV-UHFFFAOYSA-N 0.000 description 1
- RGYLGWTULWUTIZ-SFHVURJKSA-N CCCCOC([C@H](Cc1ccccc1)ON(C(c1c2cccc1)=O)C2=O)=O Chemical compound CCCCOC([C@H](Cc1ccccc1)ON(C(c1c2cccc1)=O)C2=O)=O RGYLGWTULWUTIZ-SFHVURJKSA-N 0.000 description 1
- BVKWEDMDDPDNOH-UHFFFAOYSA-N COC(C(Cc(cc1)ccc1-c(cc1)ccc1Cl)O)=O Chemical compound COC(C(Cc(cc1)ccc1-c(cc1)ccc1Cl)O)=O BVKWEDMDDPDNOH-UHFFFAOYSA-N 0.000 description 1
- MHISCNIFNLWBHZ-UHFFFAOYSA-N COC(C(Cc1cccc(Cl)c1)ON(C(c1ccccc11)=O)C1=O)=O Chemical compound COC(C(Cc1cccc(Cl)c1)ON(C(c1ccccc11)=O)C1=O)=O MHISCNIFNLWBHZ-UHFFFAOYSA-N 0.000 description 1
- QCVAMUSFEMFEHV-UHFFFAOYSA-N COC(C1OC1c1ccc(cc(cc2)OC)c2c1)=O Chemical compound COC(C1OC1c1ccc(cc(cc2)OC)c2c1)=O QCVAMUSFEMFEHV-UHFFFAOYSA-N 0.000 description 1
- MBAFLLOIOMMQTQ-GGYWPGCISA-N COC([C@H](Cc1cc(cccc2)c2cc1)ON(C(C1C2=CC=CC1)=O)C2=O)=O Chemical compound COC([C@H](Cc1cc(cccc2)c2cc1)ON(C(C1C2=CC=CC1)=O)C2=O)=O MBAFLLOIOMMQTQ-GGYWPGCISA-N 0.000 description 1
- JKZSLMCYHHTCDV-UHFFFAOYSA-N Cc(cc(CC(C(O)=O)ON)cc1)c1Cl Chemical compound Cc(cc(CC(C(O)=O)ON)cc1)c1Cl JKZSLMCYHHTCDV-UHFFFAOYSA-N 0.000 description 1
- MVGQQBSQAVKAEE-UHFFFAOYSA-N Cc1c(CC(C(OC)=O)ON(C(c2ccccc22)=O)C2=O)ccc(Cl)c1 Chemical compound Cc1c(CC(C(OC)=O)ON(C(c2ccccc22)=O)C2=O)ccc(Cl)c1 MVGQQBSQAVKAEE-UHFFFAOYSA-N 0.000 description 1
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Description
[式中、
R1は置換若しくは非置換のアリール基(但し、非置換のフェニルは除く)、置換若しくは非置換のヘテロアリール基、置換若しくは非置換のヘテロシクロアルキル基、置換若しくは非置換のアリール縮合シクロアルキル基、又は置換若しくは非置換のアリール縮合へテロシクロアルキル基であり;
R2は水素、又は置換若しくは非置換のアルキル基であり;
R3及びR4は、同一又は異なり、水素、又は置換若しくは非置換のアシル基であるか、或いはR3及びR4が一緒になって置換若しくは非置換のアルキリデン基を形成するか、或いはR3及びR4が結合している窒素原子と共に置換若しくは非置換の環状イミド基を形成し;
R5は水素、又は置換若しくは非置換のアルキルであり;
XはO、NH、又はCH2である]
の化合物又はその塩若しくは溶媒和物。
(2)R1がクロロフェニル、ブロモフェニル、ビフェニル、フェノキシフェニル、4−クロロ−3−メチルフェニル、4−クロロ−2−メチルフェニル、ジクロロフェニル、6−メトキシ−2−ナフチル、ナフチル、又はキノリニルであり;
R2がC1−6アルキルであり;
R3が水素であり、且つR4がアセチル、又はベンゾイルであるか、或いはR3及びR4が一緒になってプロパン−2−イリデンを形成するか、或いはR3及びR4が結合している窒素原子と共にフタルイミド、又はスクシンイミドを形成し;
R5が水素であり;
XがOである;
(1)に記載の化合物又はその塩若しくは溶媒和物。
(3)一般式(I’):
[式中、
R1’は置換若しくは非置換のアリール基、置換若しくは非置換のヘテロアリール基、置換若しくは非置換のヘテロシクロアルキル基、置換若しくは非置換のアリール縮合シクロアルキル基、又は置換若しくは非置換のアリール縮合へテロシクロアルキル基であり;
R2’は水素、又は置換若しくは非置換のアルキル基であり;
R3’及びR4’は、同一又は異なり、水素、又は置換若しくは非置換のアシル基であるか、或いはR3’及びR4’が一緒になって置換若しくは非置換のアルキリデン基を形成するか、或いはR3’及びR4’が結合している窒素原子と共に置換若しくは非置換の環状イミド基を形成し;
R5’は水素、又は置換若しくは非置換のアルキルであり;
X’はO、NH、又はCH2である
(但し、R1’が非置換のフェニルの場合、R2’、R3’及びR4’は同時に水素ではない)]
の化合物又はその塩若しくは溶媒和物を含むオーキシン生合成阻害剤。
(4)R1’がクロロフェニル、ブロモフェニル、ビフェニル、フェノキシフェニル、4−クロロ−3−メチルフェニル、4−クロロ−2−メチルフェニル、ジクロロフェニル、6−メトキシ−2−ナフチル、ナフチル、又はキノリニルであり;
R2’がC1−6アルキルであり;
R3’が水素であり、且つR4’がアセチル、又はベンゾイルであるか、或いはR3’及びR4’が一緒になってプロパン−2−イリデンを形成するか、或いはR3’及びR4’が結合している窒素原子と共にフタルイミド、又はスクシンイミドを形成し;
R5’が水素であり;
X’がOである;
(3)に記載のオーキシン生合成阻害剤。
(5)一般式(I”):
[式中、
R1”は置換若しくは非置換のアリール基(但し、非置換のフェニルは除く)、置換若しくは非置換のヘテロアリール基、置換若しくは非置換のヘテロシクロアルキル基、置換若しくは非置換のアリール縮合シクロアルキル基、又は置換若しくは非置換のアリール縮合へテロシクロアルキル基であり;
R2”は水素であり;
R3”及びR4”は水素であり;
R5”は水素であり;
X”はO、NH、又はCH2である]
の化合物又はその塩、溶媒和物若しくはプロドラッグを含むトリプトファンアミノトランスフェラーゼ阻害剤。
(6)R1”がブロモフェニル、ビフェニル、フェノキシフェニル、4−クロロ−3−メチルフェニル、6−メトキシ−2−ナフチル、ナフチル、又はキノリニルであり;
R2”が水素であり;
R3”及びR4”が水素であり;
R5”が水素であり;
X”がO、NH、又はCH2である;
(5)に記載のトリプトファンアミノトランスフェラーゼ阻害剤。
(7)(3)又は(4)に記載のオーキシン生合成阻害剤を植物に適用することを含む、前記植物におけるオーキシンの生合成を阻害する方法。
(8)(5)又は(6)に記載のトリプトファンアミノトランスフェラーゼ阻害剤を植物に適用することを含む、前記植物におけるトリプトファンアミノトランスフェラーゼを阻害する方法。
(9)(5)又は(6)に記載のトリプトファンアミノトランスフェラーゼ阻害剤とトリプトファンアミノトランスフェラーゼとをインビトロで接触させることを含む、前記トリプトファンアミノトランスフェラーゼの阻害方法。
(10)(1)若しくは(2)に記載の化合物、(3)若しくは(4)に記載のオーキシン生合成阻害剤、又は(5)若しくは(6)に記載のトリプトファンアミノトランスフェラーゼ阻害剤を植物に適用することを含む、前記植物の成長を調節する方法。
(11)(1)若しくは(2)に記載の化合物、(3)若しくは(4)に記載のオーキシン生合成阻害剤、又は(5)若しくは(6)に記載のトリプトファンアミノトランスフェラーゼ阻害剤を植物に適用することを含む、前記植物の除草方法。
本発明は更に、一般式(I”):
[式中、R1”〜R5”及びX”は以下に示す通りである]
の化合物又はその塩、溶媒和物若しくはプロドラッグを含むトリプトファンアミノトランスフェラーゼ阻害剤に関する。
本発明の化合物はオーキシンの生合成を阻害するため、トリプトファンアミノトランスフェラーゼをインビボ(植物中)及びインビトロで阻害するため、及び植物の成長を調節するために使用することができる。インビトロでトリプトファンアミノトランスフェラーゼを阻害する場合には、プロドラッグ化していない阻害剤を使用することが好ましい。
図2−2に従って各種化合物を合成した。
(1)内生IAA定量試験(シロイヌナズナ)
シロイヌナズナ(col−0)を、1.0%スクロース及び0.8%寒天を含む1/2MS培地を用いた平置きプレートで連続白色光下、22℃で6日間培養した。その後、1.0%スクロースを含む1/2MS培地を用いて連続白色光下、22℃で24時間液体振とう培養した。続いて、本発明の化合物(30μM)を前記培地に添加し、連続白色光下、22℃で3時間液体振とう培養し、IAA内生量を定量した。IAA内生量は、LC−MS/MSを用いて、添野ら(Plant Cell Physiology 51: 524-536 (2010))に記載の方法により測定した。結果を図3に示す。
シロイヌナズナを、1.5%スクロース、0.8%寒天、及び30μMの本発明の化合物を含む1/2MS培地を用いた縦置きプレートで連続白色光下、22℃で8日間培養した。シロイヌナズナの形態を観察して、本発明の化合物の効果を検討した。
シロイヌナズナを、1.5%スクロース、0.8%寒天、及び100μMの本発明の化合物を含む1/2MS培地を用いた縦置きプレートで連続白色光下、22℃で8日間培養した。シロイヌナズナの形態を観察して、本発明の化合物の効果を検討した。
シロイヌナズナを、1.5%スクロース、0.8%寒天(KOK1169の場合は0.6%Gelriteを使用)、本発明の化合物、及びIAAを含む1/2MS培地を用いた縦置きプレートで連続白色光下、22℃で8日間培養した。シロイヌナズナの形態を観察して、本発明の化合物によって抑制される植物の成長が回復するかを検討した。
タバコを、1.5%スクロース、及び0.8%寒天を含む1/2MS培地を用いた縦置きプレートで連続白色光下、25℃で7日間培養した。その後、1.5%スクロース、0.8%寒天、及び100μMの本発明の化合物を含む1/2MS培地を用いた縦置きプレートに植え替え、連続白色光下、25℃で7日間培養した。タバコの形態を観察して、本発明の化合物の植物成長抑制効果を検討した。
レタスを、1.5%スクロース、0.8%寒天、及び30μMのKOK1101を含む1/2MS培地を用いた縦置きプレートで連続白色光下、25℃で6日間培養した。レタスの形態を観察して、本発明の化合物の植物成長抑制効果を検討した。
ArabidopsisのIAA生合成酵素トリプトファンアミノトランスフェラーゼ(TAA1)、及びフェニルアラニンアンモニアリアーゼ(PAL)に対する本発明の化合物の阻害活性について検討した。
本試験は、Cell (2008); 133: pp. 164-176に記載の方法に従って実施した。具体的には、終濃度が0.5MのBorate Buffer(pH 8.5)、0.3mMのL−Trp、1mMのSodium pyruvate、10μMのPLP、1μgのTAA1、及び1μMの本発明の化合物を35℃で30分間反応させた。その後、6NのHClを20μL添加して反応を停止し、A330を測定した。
本試験は、Phytochem. (2004); 65: pp. 1557-1564、及びJ. Plant Physiol. (2008); 165: pp. 1491-1499に記載の方法に従って実施した。具体的には、終濃度が0.1MのBorate Buffer(pH 8.5)、0.06mM(または60μM)のL−Phe、0.5μgのPAL2、及び15nMの本発明の化合物(容量500μL(1%DMSO))を35℃で15分間反応させた。その後、1NのHClを20μL添加して反応を停止し、A290を測定した。
KOK1168(50μM)含有培地に移植後6日目のイネ(日本晴)を図10(右図)に示す(左図はDMSO対照を示す)。KOK1168を用いた処理により、芽生えの生育が著しく阻害された。
KOK1168(100μM)入りプレートに移植後6日目のトマト(桃太郎)を図11(右図)に示す(左図はDMSO対照を示す)。KOK1168を用いた処理により、芽生えの生育が著しく阻害された。
KOK1168(100μM)入りプレートに移植後7日目のヒメツリガネゴケを図12(右図)に示す(左図はDMSO対照を示す)。KOK1168を用いた処理により、原糸体の成長が著しく抑制され、茎葉体への分化も阻害された。
Claims (7)
- R1が2−ナフチルであり、R2が水素であり、且つR3及びR4がそれぞれ水素である;或いは
R1が4−フェノキシフェニルであり、R2が水素であり、且つR3及びR4がそれぞれ水素である;
請求項1に記載の化合物又はその塩若しくは溶媒和物。 - R1’が2−ナフチルであり、R2’が水素であり、且つR3’及びR4’がそれぞれ水素である;或いは
R1’が4−フェノキシフェニルであり、R2’が水素であり、且つR3’及びR4’がそれぞれ水素である;
請求項3に記載のオーキシン生合成阻害剤。 - 請求項3又は4に記載のオーキシン生合成阻害剤を植物に適用することを含む、前記植物におけるオーキシンの生合成を阻害する方法。
- 請求項1若しくは2に記載の化合物、又は請求項3若しくは4に記載のオーキシン生合成阻害剤を植物に適用することを含む、前記植物の成長を調節する方法。
- 請求項1若しくは2に記載の化合物、又は請求項3若しくは4に記載のオーキシン生合成阻害剤を植物に適用することを含む、前記植物の除草方法。
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