JP2021024832A - ジフェニル尿素化合物誘導体 - Google Patents
ジフェニル尿素化合物誘導体 Download PDFInfo
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- JP2021024832A JP2021024832A JP2019145811A JP2019145811A JP2021024832A JP 2021024832 A JP2021024832 A JP 2021024832A JP 2019145811 A JP2019145811 A JP 2019145811A JP 2019145811 A JP2019145811 A JP 2019145811A JP 2021024832 A JP2021024832 A JP 2021024832A
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- Prior art keywords
- phenyl
- dibromo
- group
- urea
- tetrazol
- Prior art date
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- -1 Diphenylurea compound Chemical class 0.000 title claims abstract description 126
- 230000033228 biological regulation Effects 0.000 claims abstract description 22
- 108091006671 Ion Transporter Proteins 0.000 claims abstract description 21
- 102000037862 Ion Transporter Human genes 0.000 claims abstract description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 168
- 239000004202 carbamide Substances 0.000 claims description 140
- 230000015572 biosynthetic process Effects 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000005843 halogen 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 16
- 230000008859 change Effects 0.000 claims description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 235000013399 edible fruits Nutrition 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 235000013877 carbamide Nutrition 0.000 claims description 9
- 229940045136 urea Drugs 0.000 claims description 9
- 239000001569 carbon dioxide Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 7
- 235000015816 nutrient absorption Nutrition 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 235000015097 nutrients Nutrition 0.000 claims description 6
- FVZCYQZOCLQWQQ-UHFFFAOYSA-N 1-(3,5-dibromophenyl)-3-[2,4-dibromo-6-(2H-tetrazol-5-yl)phenyl]urea Chemical compound C1=C(C=C(C=C1Br)Br)NC(=O)NC2=C(C=C(C=C2Br)Br)C3=NNN=N3 FVZCYQZOCLQWQQ-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- LGUZYOMAMZJQSQ-UHFFFAOYSA-N O=C(NC1=CC(Br)=CC(C(F)(F)F)=C1)NC(C(C1=NNN=N1)=CC(Br)=C1)=C1Br Chemical compound O=C(NC1=CC(Br)=CC(C(F)(F)F)=C1)NC(C(C1=NNN=N1)=CC(Br)=C1)=C1Br LGUZYOMAMZJQSQ-UHFFFAOYSA-N 0.000 claims description 5
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- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
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- 125000004122 cyclic group Chemical group 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 102100021467 Histone acetyltransferase type B catalytic subunit Human genes 0.000 description 10
- 101000898976 Homo sapiens Histone acetyltransferase type B catalytic subunit Proteins 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical group [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
Abstract
Description
本発明者らは、新規なN,N’−ジフェニル尿素化合物誘導体化合物を多数合成した。そして、これらの新規なジフェニル尿素化合物誘導体が孔辺細胞や維管束系で機能するKAT1のチャネルを阻害し、その結果、気孔開口を優位に阻害することを見出した。
で示されるジフェニル尿素化合物誘導体。
[2] 一般式(1)で示されるジフェニル尿素化合物誘導体が、一般式(1A)
で示される化合物誘導体である前項1に記載のジフェニル尿素化合物誘導体。
[5] 前項1〜3のいずれかに記載のジフェニル尿素化合物誘導体を含む植物の成長調整剤。
[6] 乾燥耐性の付与、炭酸ガス取り込み阻害による植物体の矮小化、成長調節、養分吸収の活性化と抑制、植物内養分循環の調節、作物サイズの調節、収穫時期の変化、植物体のみずみずしさの増強、植物体や実の糖度の調節(変化)、根の成長促進性の変化、及び葉の肉厚の変化から選択される少なくとも1種の機能を付与する、前項1〜3のいずれかに記載のジフェニル尿素化合物誘導体を用いた植物の育成方法。
で示されるジフェニル尿素化合物誘導体。
R8としては、特にテトラゾリル−5−イル基が好ましい。
(1)N−[3,5−ジメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA25)
(2)N−[3−メチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA26)
(3)N−[4−メチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA27)
(4)N−フェニル−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA28)
(5)N−[3−メトキシフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA29)
(6)N−[4−メトキシフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA30)
(7)N−[4−トリフルオロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA32)
(8)N−[3−トリフルオロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA33)
(9)N−[4−クロロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA35)
(10)N−[3−クロロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA36)
(11)N−[3−ブロモ,5−トリフロロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA38)
(12)N−[3,5−ジブロモフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA39)
(13)N−[3,5−ジフルオロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA40)
(14)N−[3−クロロ,5−フルオロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA42)
(15)N−[3−クロロ,5−トリフルオロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA43)
(16)N−[3,5−ジクロロ,4−メチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA44)
(17)N−[3,5−ジトリフルオロメチルフェニル]−N’−[2,6−ジブロモ−4−(2H−テトラゾール−5−イル)フェニル]尿素(UA45)
これら新規ジフェニル尿素化合物誘導体を下記合成例1〜17により説明する。
2,4−ジブロモ−6−(2H−テトラゾール−5−イル)アニリン(0.345mmol,100mg)のテトラヒドロフラン溶液(4.0mL)に、3,5−ジメチルフェニルイソシアネート(0.627mmol,90mL)を加えて、加熱還流下20時間撹拌した。減圧下溶媒を留去し、残渣をシリカゲルカラムクロマトグラフィー(トルエン:アセトン=15:1)に付し、UA25(43.2mg,収率30%)を白色固体として得た。
。
[ジフェニル尿素化合物誘導体がそれぞれ単独に濃度30μMに添加された時の比電流(Relative current)の測定]
KAT1の発現した卵母細胞を入れた測定液(120mM KCl,1mM MgCl2,1mM CaCl2,10mM HEPES−NaOH pH7.3)に 6種類の新規ジフェニル尿素化合物誘導体(UA38、UA39、UA42、UA43、UA44及びUA45)及び公知のジフェニル尿素化合物誘導体N−[3,5−ビス(トリフロロメチル)フェニル]−N’−[2,4−ジクロロ−6−(2H−テトラゾール−5−イル)フェニル]尿素(No.44)をそれぞれ単独に終濃度30μMとなるように添加し,卵母細胞の生体膜に発現したKAT1のK+電流量を,二電極膜電位固定装置を用いて電気生理学的に測定した。結果を図1に示す。なお、図1中「Mock」とは、化合物を含まない(無添加)時の電気生理学的な電流値を標準として、その比電流を1とした。
[ジフェニル尿素化合物誘導体がそれぞれ単独に濃度10μMにおける気孔開口に対する阻害実験]
2種類の新規ジフェニル尿素化合物誘導体(UA38、UA44)及び公知のジフェニル尿素化合物誘導体N−[3,5−ビス(トリフロロメチル)フェニル]−N’−[2,4−ジクロロ−6−(2H−テトラゾール−5−イル)フェニル]尿素(No.44)がそれぞれ単独で濃度10μMに添加し、下記の手順で気孔開口に対する阻害実験を行った。なお、図2中「Mock」とは、化合物を含まない(無添加)時の気孔開口を標準として、その比気孔開度を1とした。
Claims (6)
- 一般式(1)
で示されるジフェニル尿素化合物誘導体。 - 前記一般式(1A)で示されるジフェニル尿素化合物誘導体が、N−[3,5−ジメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA25)、N−[3−メチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA26)、N−[4−メチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA27)、N−フェニル−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA28)、N−[3−メトキシフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA29)、N−[4−メトキシフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA30)、N−[4−トリフルオロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA32)、N−[3−トリフルオロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA33)、N−[4−クロロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA35)、N−[3−クロロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA36)、N−[3−ブロモ,5−トリフロロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA38)、N−[3,5−ジブロモフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA39)、N−[3,5−ジフルオロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA40)、N−[3−クロロ,5−フルオロフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA42)、N−[3−クロロ,5−トリフルオロメチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA43)、N−[3,5−ジクロロ,4−メチルフェニル]−N’−[2,4−ジブロモ−6−(2H−テトラゾール−5−イル)フェニル]尿素(UA44)、またはN−[3,5−ジトリフルオロメチルフェニル]−N’−[2,6−ジブロモ−4−(2H−テトラゾール−5−イル)フェニル]尿素(UA45)である請求項1または2に記載のジフェニル尿素化合物誘導体。
- 請求項1〜3のいずれかに記載のジフェニル尿素化合物誘導体を含む植物のイオン輸送体の機能制御剤。
- 請求項1〜3のいずれかに記載のジフェニル尿素化合物誘導体を含む植物の成長調整剤。
- 乾燥耐性の付与、炭酸ガス取り込み阻害による植物体の矮小化、成長調節、養分吸収の活性化と抑制、植物内養分循環の調節、作物サイズの調節、収穫時期の変化、植物体のみずみずしさの増強、花芽や実の形成の調節、植物体や実の糖度の調節(変化)、茎及び根の成長速度(促進・遅延)の調節、及び葉の肉厚の変化から選択される少なくとも1種の機能を付与する、請求項1〜3のいずれかに記載のジフェニル尿素化合物誘導体を用いる植物の育成方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002039987A2 (en) * | 2000-11-14 | 2002-05-23 | Neurosearch A/S | Use of malaria parasite anion channel blockers for treating malaria |
JP2005538152A (ja) * | 2002-09-05 | 2005-12-15 | ニューロサーチ、アクティーゼルスカブ | ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 |
WO2006089871A2 (en) * | 2005-02-23 | 2006-08-31 | Neurosearch A/S | Diphenylurea derivatives useful as erg channel openers for the treatment of cardiac arrhythmias |
JP2007504202A (ja) * | 2003-09-04 | 2007-03-01 | ポセイドン ファーマシュティカルズ アクティーゼルスカブ | 心臓不整脈を治療するためのergチャネル開口薬 |
JP7111359B2 (ja) * | 2018-02-08 | 2022-08-02 | 国立大学法人東北大学 | 植物のカリウムイオン輸送体の機能制御剤及び植物の育成方法 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002039987A2 (en) * | 2000-11-14 | 2002-05-23 | Neurosearch A/S | Use of malaria parasite anion channel blockers for treating malaria |
JP2005538152A (ja) * | 2002-09-05 | 2005-12-15 | ニューロサーチ、アクティーゼルスカブ | ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 |
JP2007504202A (ja) * | 2003-09-04 | 2007-03-01 | ポセイドン ファーマシュティカルズ アクティーゼルスカブ | 心臓不整脈を治療するためのergチャネル開口薬 |
WO2006089871A2 (en) * | 2005-02-23 | 2006-08-31 | Neurosearch A/S | Diphenylurea derivatives useful as erg channel openers for the treatment of cardiac arrhythmias |
JP7111359B2 (ja) * | 2018-02-08 | 2022-08-02 | 国立大学法人東北大学 | 植物のカリウムイオン輸送体の機能制御剤及び植物の育成方法 |
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