JPH04211646A - Quinone derivative - Google Patents
Quinone derivativeInfo
- Publication number
- JPH04211646A JPH04211646A JP2812191A JP2812191A JPH04211646A JP H04211646 A JPH04211646 A JP H04211646A JP 2812191 A JP2812191 A JP 2812191A JP 2812191 A JP2812191 A JP 2812191A JP H04211646 A JPH04211646 A JP H04211646A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- lower alkyl
- agent
- group
- 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.)
- Pending
Links
- 150000004059 quinone derivatives Chemical class 0.000 title claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 32
- 239000002904 solvent Substances 0.000 abstract description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract description 3
- 239000003435 antirheumatic agent Substances 0.000 abstract description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract description 3
- 239000007800 oxidant agent Substances 0.000 abstract description 3
- MZCRAYAEHXORKH-UHFFFAOYSA-N 6-(4-methoxyphenyl)-2,3-dimethyl-4-sulfanylidenecyclohexa-2,5-dien-1-one Chemical compound C1=CC(OC)=CC=C1C1=CC(=S)C(C)=C(C)C1=O MZCRAYAEHXORKH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003810 Jones reagent Substances 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000003443 antiviral agent Substances 0.000 abstract description 2
- 150000003573 thiols Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- -1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QIXDHVDGPXBRRD-UHFFFAOYSA-N 2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 description 1
- AIACLXROWHONEE-UHFFFAOYSA-N 2,3-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C=CC1=O AIACLXROWHONEE-UHFFFAOYSA-N 0.000 description 1
- NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は新規なキノン誘導体に関
する。TECHNICAL FIELD This invention relates to novel quinone derivatives.
【０００２】0002
【従来技術とその課題】本発明のキノン誘導体は文献未
載の新規化合物であり、本発明は後記するように医薬品
として有用な上記化合物を提供することを目的とする。BACKGROUND OF THE INVENTION The quinone derivative of the present invention is a novel compound that has not been described in any literature, and the object of the present invention is to provide the above-mentioned compound useful as a pharmaceutical, as described later.
【０００３】0003
【課題を解決するための手段】本発明によれば下記一般
式（１）で表わされるキノン誘導体が提供される。According to the present invention, a quinone derivative represented by the following general formula (1) is provided.
【０００４】0004
【化２】
〔式中Ｒ１ 及びＲ２ はそれぞれ同一又は異なって水
素原子、低級アルキル基又は低級アルコキシ基を示すか
又は互いに結合して−（ＣＨ２ ）４ −基を示す。Ｒ
３ は水素原子又は低級アルキル基を示す。Ｒ４ 、Ｒ
５ 及びＲ６ はそれぞれ水素原子、低級アルキル基、
低級アルコキシ基、ヒドロキシル基、カルボキシル基又
はハロゲン原子を示す。Ｘは炭素原子又は窒素原子を示
す。〕上記一般式（１）で表わされる本発明のキノン誘
導体は、抗菌、抗ウイルス、抗炎症、抗リウマチ等の各
種薬理作用を示し、抗菌剤、抗ウイルス剤、抗炎症剤、
抗リウマチ剤等の医薬品として有用である。[In the formula, R1 and R2 are the same or different and represent a hydrogen atom, a lower alkyl group, or a lower alkoxy group, or combine with each other to represent a -(CH2)4- group. R
3 represents a hydrogen atom or a lower alkyl group. R4, R
5 and R6 are each a hydrogen atom, a lower alkyl group,
Indicates a lower alkoxy group, hydroxyl group, carboxyl group, or halogen atom. X represents a carbon atom or a nitrogen atom. ] The quinone derivative of the present invention represented by the above general formula (1) exhibits various pharmacological actions such as antibacterial, antiviral, antiinflammatory, and antirheumatic, and is used as an antibacterial agent, antiviral agent, antiinflammatory agent,
It is useful as a medicine such as an anti-rheumatic agent.
【０００５】本発明化合物を示す上記一般式（１）及び
その他の本明細書において、低級アルキル基としては、
メチル、エチル、プロピル、イソプロピル、ブチル、イ
ソブチル、ｔｅｒｔ−ブチル、ペンチル、ヘキシル基等
の直鎖又は分岐鎖状低級アルキル基を例示でき、低級ア
ルコキシ基としては、メトキシ、エトキシ、プロポキシ
、イソプロポキシ、ブトキシ、ペンチルオキシ、ヘキシ
ルオキシ基等の直鎖又は分岐鎖状低級アルコキシ基を例
示でき、またハロゲン原子には、弗素原子、塩素原子、
臭素原子及び沃素原子が包含される。[0005] In the above general formula (1) showing the compound of the present invention and others in this specification, the lower alkyl group is:
Examples include linear or branched lower alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, and hexyl groups, and examples of lower alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, Examples include linear or branched lower alkoxy groups such as butoxy, pentyloxy, and hexyloxy groups, and halogen atoms include fluorine atoms, chlorine atoms,
Included are bromine and iodine atoms.
【０００６】本発明化合物は、各種方法により製造でき
る。その具体例を下記反応工程式に示す。
〈反応工程式−１〉The compound of the present invention can be produced by various methods. A specific example thereof is shown in the reaction scheme below. <Reaction scheme-1>
【０００７】[0007]
【化３】
〔式中Ｒ１ 、Ｒ２ 、Ｒ３ 、Ｒ４ 、Ｒ５ 、Ｒ６
及びＸは前記に同じ。〕上記反応工程式−１に示す化
合物（２）とチオール誘導体（３）との反応は、例えば
エタノール、テトラヒドロフラン、Ｎ，Ｎ−ジメチルホ
ルムアミド（ＤＭＦ）等の不活性溶媒中で実施できる。
本反応における化合物（２）に対する化合物（３）の使
用割合は、通常１．０〜１．２倍モル量程度とするのが
よく、反応は一般に０〜３０℃の温度範囲にて約１〜１
５時間程度で完結する。上記で得られる化合物（４）は
、単離精製するか又はすることなく粗生成物のままで、
次の酸化反応に供することができる。[Formula R1 , R2 , R3 , R4 , R5 , R6
and X are the same as above. ] The reaction between the compound (2) shown in the above reaction scheme-1 and the thiol derivative (3) can be carried out in an inert solvent such as ethanol, tetrahydrofuran, N,N-dimethylformamide (DMF), etc. The ratio of compound (3) to compound (2) in this reaction is usually about 1.0 to 1.2 times the molar amount, and the reaction is generally carried out at a temperature range of about 1 to 30°C. 1
It will be completed in about 5 hours. The compound (4) obtained above is isolated and purified or remains as a crude product without purification,
It can be subjected to the next oxidation reaction.
【０００８】この化合物（４）の酸化反応は、例えばＤ
ＭＦ、ジクロロメタン、エタノール、アセトン等の不活
性溶媒中で、塩化第二鉄、無水クロム酸、ジョーンズ試
薬、セリックアンモニウムニトラート［（ＮＨ４ ）２
Ｃｅ（ＮＯ３ ）６ ］等の酸化剤を用いて実施でき
る。上記酸化剤の使用量は、化合物（４）に対して通常
１〜５倍モル量程度とすればよく、反応は一般に０〜３
０℃程度の温度下に、約０．５〜３時間程度で完結する
。This oxidation reaction of compound (4) can be carried out, for example, by D
Ferric chloride, chromic anhydride, Jones reagent, selic ammonium nitrate [(NH4)2] in an inert solvent such as MF, dichloromethane, ethanol, or acetone.
This can be carried out using an oxidizing agent such as Ce(NO3)6]. The amount of the oxidizing agent used is usually about 1 to 5 times the molar amount of compound (4), and the reaction is generally 0 to 3 times the molar amount.
The process is completed in about 0.5 to 3 hours at a temperature of about 0°C.
【０００９】上記反応工程式に示す方法により目的とす
る本発明化合物を収得できる。該目的化合物は、通常の
分離手段により容易に単離精製できる。この手段として
は、慣用される各種方法、例えば溶媒抽出法、再結晶、
吸着クロマトグラフィー、イオン交換クロマトグラフィ
ー等を例示できる。The desired compound of the present invention can be obtained by the method shown in the above reaction scheme. The target compound can be easily isolated and purified by conventional separation means. This can be achieved by various commonly used methods such as solvent extraction, recrystallization,
Examples include adsorption chromatography and ion exchange chromatography.
【００１０】0010
【実施例】以下、本発明を更に詳しく説明するため本発
明化合物製造のための原料化合物の製造例を参考例とし
て、本発明化合物の製造例を実施例として夫々挙げる。EXAMPLES In order to explain the present invention in more detail, examples of the production of raw material compounds for producing the compounds of the present invention will be given as reference examples, and examples of production of the compounds of the present invention will be given as examples.
【００１１】[0011]
【参考例１】２，３−ジメチル−５−（４−メトキシフ
ェニル）チオ−１，４−ヒドロキノンの製造２，３−ジ
メチルベンゾキノン１．３６ｇとｐ−メトキシチオフェ
ノール１．４０ｇをエタノール１３５ｍｌに溶解し、室
温にて３時間攪拌した。反応終了後、混合液を減圧濃縮
し、残渣をシリカゲルカラムクロマトグラフィー（展開
溶媒；ジエチルエーテル：ｎ−ヘキサン＝１：２）にて
精製して、目的化合物１．９５ｇを得た。得られた化合
物の構造及び物性を第１表に示す。[Reference Example 1] Production of 2,3-dimethyl-5-(4-methoxyphenyl)thio-1,4-hydroquinone Add 1.36 g of 2,3-dimethylbenzoquinone and 1.40 g of p-methoxythiophenol to 135 ml of ethanol. The mixture was dissolved and stirred at room temperature for 3 hours. After the reaction was completed, the mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: diethyl ether: n-hexane = 1:2) to obtain 1.95 g of the target compound. The structure and physical properties of the obtained compound are shown in Table 1.
【００１２】0012
【参考例２〜８】参考例１と同様にして第１表に示す各
化合物を製造した。得られた各化合物の構造及び物性を
第１表に併記する。[Reference Examples 2 to 8] Compounds shown in Table 1 were produced in the same manner as in Reference Example 1. The structure and physical properties of each compound obtained are also listed in Table 1.
【００１３】[0013]
【表１】[Table 1]
【００１４】[0014]
【表２】[Table 2]
【００１５】[0015]
【表３】[Table 3]
【００１６】[0016]
【実施例１】２，３−ジメチル−５−（４−メトキシフ
ェニル）チオ−１，４−ベンゾキノンの製造参考例１で
得た化合物１．８ｇをＤＭＦ４５ｍｌに溶解し、これに
１０％塩化第二鉄水溶液４５ｍｌを加えて室温で４５分
間攪拌した。反応混合物を水中に注ぎ込み、酢酸エチル
にて抽出した。有機層を水洗後、無水硫酸マグネシウム
で乾燥した。濃縮後、シリカゲルカラムクロマトグラフ
ィー（展開溶媒；ジエチルエーテル：ｎ−ヘキサン＝１
：５）にて精製して、目的化合物１．５ｇを得た。得ら
れた化合物の構造及び物性を第２表に示す。[Example 1] Production of 2,3-dimethyl-5-(4-methoxyphenyl)thio-1,4-benzoquinone 1.8 g of the compound obtained in Reference Example 1 was dissolved in 45 ml of DMF, and 10% dichloromethane was added to the solution. 45 ml of diiron aqueous solution was added and stirred at room temperature for 45 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. After concentration, silica gel column chromatography (developing solvent; diethyl ether: n-hexane = 1
:5) to obtain 1.5 g of the target compound. The structure and physical properties of the obtained compound are shown in Table 2.
【００１７】[0017]
【実施例２〜８】参考例２〜８で得た各化合物を用い、
実施例１と同様にして、第２表に示す各化合物を製造し
た。得られた各化合物の構造及び物性を第２表に併記す
る。[Examples 2 to 8] Using each compound obtained in Reference Examples 2 to 8,
In the same manner as in Example 1, each compound shown in Table 2 was produced. The structure and physical properties of each compound obtained are also listed in Table 2.
【００１８】[0018]
【実施例９】２，３，６−トリメチル−５−（３，５−
ジ−ｔ−ブチル−４−ヒドロキシフェニル）チオ−１，
４−ベンゾキノンの製造
２，３，６−トリメチルベンゾキノン１．５ｇと２，６
−ジ−ｔ−ブチル−４−メルカプトフェノール２．６ｇ
とをエタノール１５０ｍｌに溶解し、室温にて３時間攪
拌した。反応終了後、混合液を減圧濃縮し、得られる残
渣をＤＭＦ２５ｍｌに溶解し、これに１０％塩化第二鉄
水溶液２５ｍｌを加え、室温で３０分間攪拌した。反応
混合物を水中に注ぎ込み、酢酸エチルにて抽出した。有
機層を水洗後、無水硫酸マグネシウムで乾燥し、濃縮後
、シリカゲルカラムクロマトグラフィー（展開溶媒；ジ
エチルエーテル：ｎ−ヘキサン＝１：１０）にて精製し
て、目的化合物１００ｍｇを得た。得られた化合物の構
造及び物性を第２表に示す。[Example 9] 2,3,6-trimethyl-5-(3,5-
di-t-butyl-4-hydroxyphenyl)thio-1,
Production of 4-benzoquinone 1.5 g of 2,3,6-trimethylbenzoquinone and 2,6
-di-t-butyl-4-mercaptophenol 2.6g
was dissolved in 150 ml of ethanol and stirred at room temperature for 3 hours. After the reaction was completed, the mixture was concentrated under reduced pressure, and the resulting residue was dissolved in 25 ml of DMF, to which 25 ml of a 10% ferric chloride aqueous solution was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography (developing solvent: diethyl ether: n-hexane = 1:10) to obtain 100 mg of the target compound. The structure and physical properties of the obtained compound are shown in Table 2.
【００１９】[0019]
【実施例１０〜１６】実施例９と同様にして、第２表に
示す各化合物を製造した。得られた各化合物の構造及び
物性を第２表に併記する。Examples 10 to 16 The compounds shown in Table 2 were produced in the same manner as in Example 9. The structure and physical properties of each compound obtained are also listed in Table 2.
【００２０】[0020]
【表４】[Table 4]
【００２１】[0021]
【表５】[Table 5]
【００２２】[0022]
【表６】[Table 6]
【００２３】[0023]
【表７】[Table 7]
【００２４】[0024]
【表８】[Table 8]
【００２５】[0025]
【表９】[Table 9]
Claims (1)
素原子、低級アルキル基又は低級アルコキシ基を示すか
又は互いに結合して−（ＣＨ２ ）４ −基を示す。Ｒ
３ は水素原子又は低級アルキル基を示す。Ｒ４ 、Ｒ
５ 及びＲ６ はそれぞれ水素原子、低級アルキル基、
低級アルコキシ基、ヒドロキシル基、カルボキシル基又
はハロゲン原子を示す。Ｘは炭素原子又は窒素原子を示
す。〕で表わされるキノン誘導体。Claim 1: General formula [Formula 1] [In the formula, R1 and R2 are each the same or different and represent a hydrogen atom, a lower alkyl group, or a lower alkoxy group, or combine with each other to represent a -(CH2)4- group . R
3 represents a hydrogen atom or a lower alkyl group. R4, R
5 and R6 are each a hydrogen atom, a lower alkyl group,
Indicates a lower alkoxy group, hydroxyl group, carboxyl group, or halogen atom. X represents a carbon atom or a nitrogen atom. ] A quinone derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2812191A JPH04211646A (en) | 1990-03-22 | 1991-02-22 | Quinone derivative |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2-73867 | 1990-03-22 | ||
| JP7386790 | 1990-03-22 | ||
| JP19331190 | 1990-07-20 | ||
| JP2-193311 | 1990-07-20 | ||
| JP2812191A JPH04211646A (en) | 1990-03-22 | 1991-02-22 | Quinone derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04211646A true JPH04211646A (en) | 1992-08-03 |
Family
ID=27286086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2812191A Pending JPH04211646A (en) | 1990-03-22 | 1991-02-22 | Quinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04211646A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006100495A1 (en) * | 2005-03-23 | 2006-09-28 | Syntopix Limited | Formulations |
-
1991
- 1991-02-22 JP JP2812191A patent/JPH04211646A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| BIOORG.CHEM=1978 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006100495A1 (en) * | 2005-03-23 | 2006-09-28 | Syntopix Limited | Formulations |
| WO2006100496A1 (en) * | 2005-03-23 | 2006-09-28 | Syntopix Limited | Antimicrobial agents |
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