JP2007254352A - Imidazoquinoxalinone chemical luminescent substance, method for producing the same and emission spectrometry method - Google Patents
Imidazoquinoxalinone chemical luminescent substance, method for producing the same and emission spectrometry method Download PDFInfo
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Abstract
Description
本発明は、イミダゾ[1,2-a]キノキザリン化合物に関する。本発明のイミダゾ[1,2-a]キノキザリン化合物およびその塩は、化学発光することができる化合物であり、スーパーオキシドアニオンの発光分析用試薬として利用することができ、生体内外のスーパーオキシドアニオンを検出することによる疾病の診断あるいは疾患の研究に寄与するものとして使用できる。 The present invention relates to imidazo [1,2-a] quinoxaline compounds. The imidazo [1,2-a] quinoxaline compound and the salt thereof of the present invention are compounds capable of chemiluminescence, and can be used as reagents for luminescence analysis of superoxide anions. It can be used to contribute to diagnosis of diseases or research of diseases by detection.
近年、光による可視化技術が必須技術として要求されている。活性酸素の可視化分析もその一つである。活性酸素を光シグナルに変換する方法に化学発光法があり、イミダゾ[1,2-a]ピラジン-3-オン化合物がその発行物質として用いられている。さらに有用な発光物質の研究が盛んに行なわれている（例えば特許文献１）。 In recent years, light visualization technology has been required as an essential technology. Visualization analysis of active oxygen is one of them. There is a chemiluminescence method for converting active oxygen into a light signal, and an imidazo [1,2-a] pyrazin-3-one compound is used as an issuance material. In addition, research on useful luminescent materials has been actively conducted (for example, Patent Document 1).
活性酸素の一つであるスーパーオキシドアニオンとの反応により発光が誘起され、スーパーオキシドアニオンを光シグナルとして検出する発光物質であって、実用化が期待できる発光機能が優良な化学発光化合物を提供することが、本発明の課題である。 Provided is a luminescent substance that detects superoxide anion as a light signal, which emits light by reaction with superoxide anion, which is one of active oxygen, and has an excellent light emitting function that can be expected to be put to practical use. That is the subject of the present invention.
この出願の発明者は、前記のような背景において、スーパーオキシドアニオン検出用の発光化合物を創出するために鋭意検討した結果、本発明に至った。
すなわち、本発明は、次の化学式１、
That is, the present invention has the following chemical formula 1,
さらに本発明は、上述の発光試薬を検体溶液と接触させた後、発光強度を測定することを特徴とするスーパーオキシドアニオンの分析方法である。 Furthermore, the present invention is a method for analyzing a superoxide anion, wherein the luminescence intensity is measured after contacting the above-mentioned luminescent reagent with a sample solution.
本明細書中で「アルキル基」とは、置換基を有していてもよい炭素数1〜20個の直鎖状または分岐鎖状のアルキル基をいい、例えば、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、デシル、ウンデシル、ドデシル、テトラデシル、ペンタデシル、ヘキサデシル、ヘプタデシル、オクタデシル、ノナデシル、イコサニルなどの直鎖の基または、分岐状に結合した基をいう。 In the present specification, the “alkyl group” means a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, for example, methyl, ethyl, propyl, butyl , Pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosanyl, or a group bonded in a branched manner.
次に、本明細書で「アルコキシル基」とは、例えば、メトキシ、エトキシ、プロポキシ、ブトキシ、ペンチルオキシ、ヘキシルオキシ、メチキシエトキシ、メトキシプロポキシ、エトキシエトキシ、エトキシプロポキシ、メトキシエトキシエトキシ基などの炭素数1〜20個のアルコキシル基が直鎖上にまたは分岐状に結合したものなどをあげることができる。 Next, in the present specification, the “alkoxyl group” means, for example, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methoxyethoxy, methoxypropoxy, ethoxyethoxy, ethoxypropoxy, methoxyethoxyethoxy group, etc. Examples include those in which ˜20 alkoxyl groups are bonded on a straight chain or in a branched form.
本明細書で「アリール基」とは、フェニル、ナフチルなどの炭素数6〜20個の芳香族炭化水素をあげることができる。そして、本明細書で「複素環」とは、例えば、フラン、チオフェン、ピロール、オキサゾール、イソオキサゾール、トリアゾール、イソチアゾール、イミダゾール、ピラゾール、フラザン、ピラン、ピリジン、ピリダジン、ピリミジン、ピラジンなどをあげることができる。又、本明細書で「ハロゲン原子」とは、フッ素、塩素、臭素、ヨウ素などをあげることができる。 In the present specification, examples of the “aryl group” include aromatic hydrocarbons having 6 to 20 carbon atoms such as phenyl and naphthyl. In this specification, “heterocycle” includes, for example, furan, thiophene, pyrrole, oxazole, isoxazole, triazole, isothiazole, imidazole, pyrazole, furazane, pyran, pyridine, pyridazine, pyrimidine, pyrazine and the like. Can do. In the present specification, examples of the “halogen atom” include fluorine, chlorine, bromine, iodine and the like.
本発明による イミダゾ[1,2-a]
キノキザリン-（５H）-１-オン化合物は、スーパーオキシドアニオンを検出する試薬として実用的に有用である。
Imidazo [1,2-a] according to the invention
Quinoxalin- (5H) -1-one compounds are practically useful as reagents for detecting superoxide anions.
本発明の発光化合物は、上述の化学式１で表されるイミダゾ[1,2-a]キノキザリン化合物またはその塩であり、さらに本発明のスーパーオキシドアニオンの発光分析用試薬は上述のイミダゾ[1,2-a]キノキザリン化合物またはその塩の少なくとも一つを有効成分として含有することを特徴とするスーパーオキシドアニオンの発光検出試薬である The luminescent compound of the present invention is an imidazo [1,2-a] quinoxaline compound represented by the above chemical formula 1 or a salt thereof, and the superoxide anion luminescence analysis reagent of the present invention is the above-described imidazo [1,2 A luminescent detection reagent for a superoxide anion comprising at least one of a 2-a] quinoxaline compound or a salt thereof as an active ingredient
。
本発明の発光化合物は、具体的には、化学式１で表されるイミダゾ[1,2-a]キノキザリン化合物またはその塩であって、残基が各々、R7が酸素原子であるイミダゾ[1,2-a]キノキザリン-（５H）-１-オン化合物（化学式２）又はその塩の化合物、あるいはR２が水素原子あるいはアリール基あるいは複素環である化合物、あるいはR３が水素原子である化合物、あるいはR４が水素原子あるいはアルコキシル基又はアミノ基又はアリール基又は複素環である化合物、あるいはR５が水素原子あるいはアルコキシル基あるいはアリール基あるいは複素環である化合物、あるいはR６が水素原子である化合物である。
.
Specifically, the luminescent compound of the present invention is an imidazo [1,2-a] quinoxaline compound represented by the chemical formula 1 or a salt thereof, wherein each of the residues is R 7 is an oxygen atom. , 2-a] Quinoxalin- (5H) -1-one compound (chemical formula 2) or a salt thereof, a compound in which R 2 is a hydrogen atom, an aryl group or a heterocyclic ring, or a compound in which R 3 is a hydrogen atom Or a compound in which R 4 is a hydrogen atom, an alkoxyl group, an amino group, an aryl group or a heterocyclic ring, a compound in which R 5 is a hydrogen atom, an alkoxyl group, an aryl group or a heterocyclic ring, or R 6 is a hydrogen atom A compound.
より具体的には、化学式２で表されるイミダゾ[1,2-a]キノキザリン化合物またはその塩におけるR１がアルキル基である化合物、あるいはR２が水素原子あるいはアリール基あるいは複素環である化合物、あるいはR３が水素原子である化合物、あるいはR５が水素原子あるいはアルコキシル基あるいはアリール基あるいは複素環である化合物、あるいはR６が水素原子である化合物である。 More specifically, in the imidazo [1,2-a] quinoxaline compound represented by the chemical formula 2 or a salt thereof, a compound in which R 1 is an alkyl group, or a compound in which R 2 is a hydrogen atom, an aryl group or a heterocyclic ring Or a compound in which R 3 is a hydrogen atom, a compound in which R 5 is a hydrogen atom, an alkoxyl group, an aryl group or a heterocyclic ring, or a compound in which R 6 is a hydrogen atom.
本発明においてスーパーオキシドアニオンの分析用試薬の有効成分として使用されるこれらのイミダゾ[1,2-a] キノキザリン-（５H）-１-オン化合物は、以上のとおりのものであり、その合成法として例えば下記の例をあげることができるが、これに限定されるものではない。 In the present invention, these imidazo [1,2-a] quinoxalin- (5H) -1-one compounds used as active ingredients of the superoxide anion analysis reagent are as described above, and their synthesis methods For example, the following examples can be given, but the invention is not limited thereto.
次の化学式３で示される2−アミノキノキザリン化合物、
は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R３ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R４ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R５ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、無置換あるいは置換されていてもよいハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R６ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環を示す）を、次の化学式４又化学式５で示されるa-ケトアルデヒド化合物、又はあるいはa-ケトアルデヒド同等化合物、
Is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, a halogen atom, an unsubstituted or substituted alkoxyl group, an unsubstituted or substituted May be a carboxyl group, an unsubstituted or substituted formyl group, an unsubstituted or substituted alkyloxycarbonyl group, an unsubstituted or substituted aryloxycarbonyl group, an unsubstituted or substituted An alkylcarbonyl group which may be substituted, an arylcarbonyl group which may be unsubstituted or substituted, or a heterocyclic ring which may be unsubstituted or substituted, and R 3 may be a hydrogen atom, unsubstituted or substituted Alkyl group, unsubstituted or optionally substituted aryl group, halogen Atom, unsubstituted or substituted alkoxyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted formyl group, unsubstituted or substituted alkyloxycarbonyl Group, an aryloxycarbonyl group which may be unsubstituted or substituted, an alkylcarbonyl group which may be unsubstituted or substituted, an arylcarbonyl group which may be unsubstituted or substituted, or an unsubstituted or substituted group R 4 is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, a halogen atom, an unsubstituted or substituted alkoxyl group , Unsubstituted or optionally substituted carboxyl group, Alternatively, an optionally substituted formyl group, an unsubstituted or substituted alkyloxycarbonyl group, an unsubstituted or substituted aryloxycarbonyl group, an unsubstituted or substituted alkylcarbonyl group , An arylcarbonyl group which may be unsubstituted or substituted, or a heterocyclic ring which may be unsubstituted or substituted, and R 5 is a hydrogen atom, an alkyl group which may be unsubstituted or substituted, unsubstituted or substituted Aryl group which may be substituted, halogen atom which may be unsubstituted or substituted, alkoxyl group which may be unsubstituted or substituted, carboxyl group which may be unsubstituted or substituted, unsubstituted or substituted An optionally substituted formyl group, an unsubstituted or substituted a Alkyloxycarbonyl group, aryloxycarbonyl group which may be unsubstituted or substituted, alkylcarbonyl group which may be unsubstituted or substituted, arylcarbonyl group which may be unsubstituted or substituted, or unsubstituted or substituted R 6 may be a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or optionally substituted aryl group, a halogen atom, an unsubstituted or substituted alkyl group. Good alkoxyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted formyl group, unsubstituted or substituted alkyloxycarbonyl group, unsubstituted or substituted Good aryloxycarbonyl group, unsubstituted or substituted An alkylcarbonyl group which may be substituted, an arylcarbonyl group which may be unsubstituted or substituted or a heterocyclic ring which may be unsubstituted or substituted), a-ketoaldehyde represented by the following chemical formula 4 or 5 A compound or an a-ketoaldehyde equivalent compound,
この縮合反応の条件として、使用しうる反応溶媒は四塩化炭素，クロロホルム，塩化メチレン，ベンゼン，トルエン，キシレン，クロロベンゼン，ピリジン，THF，エーテル、DMF、メタノール、エタノール、プロパノール、ブタノールのごときハロゲン系溶媒，芳香族炭化水素，エーテル系溶媒，アセトアミド系溶媒、アルコールおよび水、あるいはこれらの混合溶媒から適宜選択されるが、これに限定されるものではない。 As the conditions for this condensation reaction, usable reaction solvents are halogenated solvents such as carbon tetrachloride, chloroform, methylene chloride, benzene, toluene, xylene, chlorobenzene, pyridine, THF, ether, DMF, methanol, ethanol, propanol, and butanol. , Aromatic hydrocarbon, ether solvent, acetamide solvent, alcohol and water, or a mixed solvent thereof, but is not limited thereto.
好ましくは化学式３〜５で示される化合物が溶解し、反応生成物である化学式２の化合物が分解しない溶媒が選択される。反応温度は０℃から溶媒の還流温度の間で選択される。反応時間は使用する反応溶媒，反応温度などにより異なるが，1分から12時間の間で適宜選択される。 Preferably, a solvent in which the compound represented by the chemical formulas 3 to 5 is dissolved and the compound of the chemical formula 2 as a reaction product is not decomposed is selected. The reaction temperature is selected between 0 ° C. and the reflux temperature of the solvent. The reaction time varies depending on the reaction solvent used, reaction temperature, etc., but is appropriately selected between 1 minute and 12 hours.
さらに、本発明のスーパーオキシドアニオンの分析用試薬は、以上のとおりのイミダゾ[1,2-a] キノキザリン-（５H）-１-オン化合物を有効成分とするものであれば、その他の物質、例えば、溶剤、緩衝剤、安定剤、界面活性剤等を含有してもよい。 Furthermore, the reagent for analysis of superoxide anion of the present invention may be any other substance as long as it contains the imidazo [1,2-a] quinoxalin- (5H) -1-one compound as described above as an active ingredient. For example, you may contain a solvent, a buffering agent, a stabilizer, surfactant, etc.
そして本発明は、スーパーオキシドアニオンを検出する方法をも提供する。すなわち、上記発光化合物あるいは上記発光化合物を有効成分とする発光剤をスーパーオキシドアニオンあるいはスーパーオキシドアニオンを含む物質と接触させることにより発光を発生させるところのスーパーオキシドアニオンの化学発光による検出方法であり、イミダゾ[1,2-a] キノキザリン-（５H）-１-オン化合物によって発せられる光の強度を測定することによりスーパーオキシドアニオンを簡便に分析することが可能となるのである。発光剤は、上記発光化合物を有効成分として1種以上を含有していればよく、発光剤用の担体、緩衝剤、界面活性剤、発光増強剤、増量剤、およびあるいは他の発光成分等を含有していてもよい。 The present invention also provides a method for detecting a superoxide anion. That is, a detection method by chemiluminescence of the superoxide anion that generates light by contacting the light-emitting compound or a light-emitting agent containing the light-emitting compound as an active ingredient with a superoxide anion or a substance containing a superoxide anion, By measuring the intensity of light emitted by the imidazo [1,2-a] quinoxalin- (5H) -1-one compound, the superoxide anion can be easily analyzed. The luminescent agent only needs to contain one or more of the above luminescent compounds as an active ingredient, and includes a carrier for the luminescent agent, a buffer, a surfactant, a luminescence enhancer, an extender, and / or other luminescent components. You may contain.
この時、添加する分析試薬の量等の分析条件は特に限定されない。具体的には、分析試薬の濃度は、分析系に影響を与えない程度であればよい。また、分析は、被検体に影響を与えない温度範囲で行なえばよい。例えば、一般に生体を被検体とし、水溶液中で分析を行なう場合には、約10〜40℃の温度範囲が好ましく例示される。 At this time, analysis conditions such as the amount of analysis reagent to be added are not particularly limited. Specifically, the concentration of the analysis reagent may be a level that does not affect the analysis system. The analysis may be performed in a temperature range that does not affect the subject. For example, in general, when a living body is used as a subject and analysis is performed in an aqueous solution, a temperature range of about 10 to 40 ° C. is preferably exemplified.
以下、実施例を示し、この発明の実施の形態についてさらに詳しく説明する。もちろん、この発明は以下の例に限定されるものではなく、細部については様々な態様が可能であることは言うまでもない。 Hereinafter, the present invention will be described in more detail with reference to examples. Of course, the present invention is not limited to the following examples, and it goes without saying that various aspects are possible in detail.
「2-Methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式６）の合成」
(0.10 g, 0.69 mmol), 40% aqueous pyruvic aldehyde (0.37 g), 5 mol/L 塩酸(0.35 mL), エタノール(2.0
mL) の混合物を密閉容器中80℃で2時間加熱し、その後、室温に戻し塩化メチレン（10 mL）を加え、シリカゲルカラムクロマトグラフィーに供した。酢酸エチルおよびメタノール/酢酸エチル（v/v = 1/9）で溶出し、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneを含む溶出液を減圧濃縮した。この残渣をメタノール−塩化メチレン混合液に溶解し、再度シリカゲルカラムクロマトグラフィーに供し、酢酸エチルおよびメタノール/酢酸エチル（v/v = 1/9）で溶出し、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneを含む溶出液を減圧濃縮した。残渣をメタノールに溶解し、酢酸エチルおよびヘキサンを加え、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneを粉体化しろ過した。粉体を室温で減圧乾燥し、2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（黄色粉末、0.191 g, 収率70％）を得た。
2-Methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 25 oC) d 2.40 (3H, s, Me), 7.30 (2H, m), 7.35 (1H, dd, J =
1.2 Hz, 8.6 Hz), 7.55 (1H, s, C4-H), 8.96 (1H, dd, J = 1.2
Hz, 7.9 Hz). IR (KBr) n 1144, 1255,
1274, 1327, 1452, 1487, 1571, 1596 cm-1. UV-VIS (MeOH) 224 nm (ε = 24100), 259 nm (ε = 9050),
430 nm (ε = 15100). ESI-MS
m/z 199.50 [M+1]+, Calcd for C11H9N3O:
199.07 [M].
"Synthesis of 2-Methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 6)"
(0.10 g, 0.69 mmol), 40% aqueous pyruvic aldehyde (0.37 g), 5 mol / L hydrochloric acid (0.35 mL), ethanol (2.0
The mixture was heated at 80 ° C. for 2 hours in a sealed container, then returned to room temperature, methylene chloride (10 mL) was added, and the mixture was subjected to silica gel column chromatography. Elution was performed with ethyl acetate and methanol / ethyl acetate (v / v = 1/9), and the eluate containing 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one was concentrated under reduced pressure. This residue was dissolved in a methanol-methylene chloride mixture, subjected to silica gel column chromatography again, and eluted with ethyl acetate and methanol / ethyl acetate (v / v = 1/9) to give 2-methylimidazo [1,2-a The eluate containing quinoxalin-1 (5H) -one was concentrated under reduced pressure. The residue was dissolved in methanol, ethyl acetate and hexane were added, and 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one was pulverized and filtered. The powder was dried under reduced pressure at room temperature to obtain 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (yellow powder, 0.191 g, yield 70%).
2-Methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 25 o C) d 2.40 (3H, s, Me), 7.30 (2H, m), 7.35 (1H, dd, J =
1.2 Hz, 8.6 Hz), 7.55 (1H, s, C 4 -H), 8.96 (1H, dd, J = 1.2
Hz, 7.9 Hz) .IR (KBr) n 1144, 1255,
1274, 1327, 1452, 1487, 1571, 1596 cm -1 .UV-VIS (MeOH) 224 nm (ε = 24100), 259 nm (ε = 9050),
430 nm (ε = 15100). ESI-MS
m / z 199.50 [M + 1] + , Calcd for C 11 H 9 N 3 O:
199.07 [M].
「7-Hydroxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式７）の合成」
(0.030 g, 0.19 mmol)を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に
7-hydroxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.025 g、収率63%)を得た。
7-Hydroxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 25 oC) d 2.47 (3H, s, Me), 6.93-6.96 (2H, m, C6,7-H),
8.04 (1H, s, C4-H), 8.84 (1H, d, J = 9.2 Hz, C9-H).
IR (KBr) n 1326, 1448, 1497, 1569, 1598, 1620, 1677 cm-1.
UV-VIS (MeOH) 229 nm (ε = 15800), 295 nm
(ε = 4420), 345 nm (ε = 1760), 437 (ε
= 9200). ESI-MS m/z 215.56 [M+1]+, Calcd for C11H9N3O2:
215.07 [M].
“Synthesis of 7-Hydroxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 7)”
(0.030 g, 0.19 mmol)
Similar to the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7-hydroxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
(0.025 g, 63% yield) was obtained.
7-Hydroxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 25 o C) d 2.47 (3H, s, Me), 6.93-6.96 (2H, m, C 6,7 -H),
8.04 (1H, s, C 4 -H), 8.84 (1H, d, J = 9.2 Hz, C 9 -H).
IR (KBr) n 1326, 1448, 1497, 1569, 1598, 1620, 1677 cm -1 .
UV-VIS (MeOH) 229 nm (ε = 15800), 295 nm
(ε = 4420), 345 nm (ε = 1760), 437 (ε
= 9200). ESI-MS m / z 215.56 [M + 1] + , Calcd for C 11 H 9 N 3 O 2 :
215.07 [M].
「7-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式８）の合成」
(0.056 g, 0.32 mmol) を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に
7-methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.026 g、収率36%)を得た。
7-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 25 oC) d 2.38 (3H, s, Me), 3.84 (3H, s, OMe), 6.80 (1H, d, J
= 3.0 Hz, C6-H), 6.88 (1H, dd, J = 3.0, Hz, 9.2 Hz, C8-H),
7.51 (1H, s, C4-H), 8.84 (1H, d, J = 9.2 Hz, C9-H).
IR (KBr) n cm-1. UV-VIS (MeOH) 227 nm (ε = 18200), 295 nm (ε = 4180), 435 nm (ε = 8440). ESI-MS m/z 229.66 [M+1]+, Calcd
for C12H11N3O2: 229.09 [M].
“Synthesis of 7-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 8)”
(0.056 g, 0.32 mmol)
Similar to the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7-methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
(0.026 g, yield 36%) was obtained.
7-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 25 o C) d 2.38 (3H, s, Me), 3.84 (3H, s, OMe), 6.80 (1H, d, J
= 3.0 Hz, C 6 -H), 6.88 (1H, dd, J = 3.0, Hz, 9.2 Hz, C 8 -H),
7.51 (1H, s, C 4 -H), 8.84 (1H, d, J = 9.2 Hz, C 9 -H).
IR (KBr) n cm -1 . UV-VIS (MeOH) 227 nm (ε = 18200), 295 nm (ε = 4180), 435 nm (ε = 8440). ESI-MS m / z 229.66 [M + 1 ] + , Calcd
for C 12 H 11 N 3 O 2 : 229.09 [M].
「7-Amino-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式９）の合成」
(0.019 g, 0.068 mmol) を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に
7-amino-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.0051 g、収率35%)を得た。
7-Amino-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (0.1% TFA/D2O : CD3OD
= 1 : 1, 27 oC) d 2.44 (3H, s),
7.30 (1H, dd, J = 2.4 Hz, 8.6 Hz, C8-H), 7.36 (1H, d, J
= 2.4 Hz, C6-H), 7.68 (1H, s, C4-H), 9.00 (1H, d, J
= 8.6 Hz, C9-H). IR (KBr) n 1221, 1272, 1332, 1490, 1576, 1609 cm-1. UV-VIS
(MeOH) 245 nm (ε = 17900), 306 nm
(ε =
6120), 441 (e = 10000). ESI-MS m/z 214.68 [M+1]+,
Calcd for C11H10N4O: 214.09 [M].
“Synthesis of 7-Amino-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 9)”
(0.019 g, 0.068 mmol)
Similar to the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7-amino-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
(0.0051 g, 35% yield) was obtained.
7-Amino-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (0.1% TFA / D 2 O: CD 3 OD
= 1: 1, 27 o C) d 2.44 (3H, s),
7.30 (1H, dd, J = 2.4 Hz, 8.6 Hz, C 8 -H), 7.36 (1H, d, J
= 2.4 Hz, C 6 -H), 7.68 (1H, s, C 4 -H), 9.00 (1H, d, J
= 8.6 Hz, C 9 -H) .IR (KBr) n 1221, 1272, 1332, 1490, 1576, 1609 cm -1 .UV-VIS
(MeOH) 245 nm (ε = 17900), 306 nm
(ε =
6120), 441 (e = 10000). ESI-MS m / z 214.68 [M + 1] + ,
Calcd for C 11 H 10 N 4 O: 214.09 [M].
「7-(Dimethylamino)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式１０）の合成」
を用い、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に7-(Dimethylamino)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.010 g、収率39%)を得た。
7-(Dimethylamino)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 24 oC) d 2.44 (3H, s, Me), 3.18 (6H, s, NMe), 7.04 (1H, br.s, C6-H),
7.21 (1H, d, J = 9.2 Hz, C8-H), 7.85 (1H, br.s, C4-H),
8.92 (1H, d, J = 9.2 Hz, C9-H). IR (KBr) n 1132, 1506, 1589 cm-1. UV-VIS (MeOH) 253 nm (ε = 17600), 304 nm (ε = 7000),
449 (e = 7730). ESI-MS m/z 242.74 [M+1]+,
Calcd for C13H14N4O: 242.12 [M].
"Synthesis of 7- (Dimethylamino) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 10)"
As in the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one, 7- (Dimethylamino) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
(0.010 g, 39% yield) was obtained.
7- (Dimethylamino) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 24 o C) d 2.44 (3H, s, Me), 3.18 (6H, s, NMe), 7.04 (1H, br.s, C 6 -H),
7.21 (1H, d, J = 9.2 Hz, C 8 -H), 7.85 (1H, br.s, C 4 -H),
8.92 (1H, d, J = 9.2 Hz, C 9 -H) .IR (KBr) n 1132, 1506, 1589 cm -1 .UV-VIS (MeOH) 253 nm (ε = 17600), 304 nm (ε = 7000),
449 (e = 7730). ESI-MS m / z 242.74 [M + 1] + ,
Calcd for C 13 H 14 N 4 O: 242.12 [M].
「2-Methyl-7-nitroimidazo[1,2-a]quinoxalin-1(5H)-one（化学式１１）の合成」
(0.092 g, 0.48 mmol) を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に
2-Methyl-7-nitroimidazo[1,2-a]quinoxalin-1(5H)-one
(0.042 g、収率36%)を得た。
2-Methyl-7-nitroimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 28 oC) d 2.40 (3H, s, Me), 7.49 (1H, s, C4-H), 8.06 (1H,
br.s, C6-H), 8.08 (1H, d, J = 8.5 Hz, C8-H), 9.04
(1H, d, J = 8.5 Hz, C9-H). IR (KBr) n 1267, 1335, 1489, 1533, 1594, 1617 cm-1. UV-VIS
(MeOH) 251 nm (ε = 14500), 272 nm
(ε =
12000), 432 (e = 16400). ESI-MS m/z 244.70 [M+1]+,
Calcd for C11H8N4O3: 244.06 [M].
“Synthesis of 2-Methyl-7-nitroimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 11)”
(0.092 g, 0.48 mmol)
Similar to the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-7-nitroimidazo [1,2-a] quinoxalin-1 (5H) -one
(0.042 g, yield 36%) was obtained.
2-Methyl-7-nitroimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 28 o C) d 2.40 (3H, s, Me), 7.49 (1H, s, C 4 -H), 8.06 (1H,
br.s, C 6 -H), 8.08 (1H, d, J = 8.5 Hz, C 8 -H), 9.04
(1H, d, J = 8.5 Hz, C 9 -H). IR (KBr) n 1267, 1335, 1489, 1533, 1594, 1617 cm -1 .UV-VIS
(MeOH) 251 nm (ε = 14500), 272 nm
(ε =
12000), 432 (e = 16400). ESI-MS m / z 244.70 [M + 1] + ,
Calcd for C 11 H 8 N 4 O 3 : 244.06 [M].
「8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式１２）の合成」
(0.055 g, 0.31 mmol) を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に反応を行い、反応液を氷冷し、生成した結晶をろ取し、エタノールで洗浄し、減圧乾燥を行なった。
8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.056 g、収率67%)を得た。
8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 24 oC) d 2.25 (3H, s, Me), 3.78 (3H, s, OMe), 6.88 (1H, dd, J
= 3.1 Hz, 8.6 Hz, C7-H), 7.22 (1H, d, J = 8.6 Hz, C6-H),
7.62 (1H, s, C4-H), 8.50 (1H, d, J = 3.1 Hz, C9-H).
IR (KBr) n 1234, 1348, 1448, 1499, 1607 cm-1.
UV-VIS (MeOH) 276 nm (ε = 8960), 350 nm
(ε = 1680), 440 (e = 15400). ESI-MS m/z 229.72 [M+1]+, Calcd for C12H11N3O2:
229.09 [M].
「8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 12) "
(0.055 g, 0.31 mmol)
The reaction is carried out in the same manner as in the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one, the reaction solution is ice-cooled, the formed crystals are filtered, washed with ethanol, and dried under reduced pressure. I did it.
8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.056 g, 67% yield) was obtained.
8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 24 o C) d 2.25 (3H, s, Me), 3.78 (3H, s, OMe), 6.88 (1H, dd, J
= 3.1 Hz, 8.6 Hz, C 7 -H), 7.22 (1H, d, J = 8.6 Hz, C 6 -H),
7.62 (1H, s, C 4 -H), 8.50 (1H, d, J = 3.1 Hz, C 9 -H).
IR (KBr) n 1234, 1348, 1448, 1499, 1607 cm -1 .
UV-VIS (MeOH) 276 nm (ε = 8960), 350 nm
(ε = 1680), 440 (e = 15400). ESI-MS m / z 229.72 [M + 1] +, Calcd for C 12 H 11 N 3 O 2 :
229.09 [M].
「7,8-Dimethoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式１３）の合成」
(0.050 g, 0.24 mmol) を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に反応を行い、反応液を氷冷し、生成した結晶をろ取し、エタノールで洗浄し、減圧乾燥を行なった。
7,8-Dimethoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.073 g、収率100%)を得た。
7,8-Dimethoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 24 oC) d 2.26 (3H, s, Me), 3.78 (3H, s, OMe), 3.80 (3H, s, OMe),
6.92 (1H, s, C6-H), 7.69 (1H, br.s, C4-H), 8.59 (1H, s, C9-H).
IR (KBr) n 1060, 1232, 1260, 1282, 1325, 1446, 1512 cm-1.
UV-VIS (MeOH) 227 nm (e = 17800), 275 nm
(ε = 9590), 330 nm (ε = 2550), 448 nm (ε = 12600). ESI-MS m/z 259.74 [M+1]+,
Calcd for C13H13N3O3: 259.10 [M].
「7,8-Dimethoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 13) "
(0.050 g, 0.24 mmol)
The reaction is carried out in the same manner as in the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one, the reaction solution is ice-cooled, the formed crystals are filtered, washed with ethanol, and dried under reduced pressure. I did it.
7,8-Dimethoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.073 g, 100% yield) was obtained.
7,8-Dimethoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 24 o C) d 2.26 (3H, s, Me), 3.78 (3H, s, OMe), 3.80 (3H, s, OMe),
6.92 (1H, s, C 6 -H), 7.69 (1H, br.s, C 4 -H), 8.59 (1H, s, C 9 -H).
IR (KBr) n 1060, 1232, 1260, 1282, 1325, 1446, 1512 cm -1 .
UV-VIS (MeOH) 227 nm (e = 17800), 275 nm
(ε = 9590), 330 nm (ε = 2550), 448 nm (ε = 12600). ESI-MS m / z 259.74 [M + 1] + ,
Calcd for C 13 H 13 N 3 O 3 : 259.10 [M].
「7,8-Methylendioxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式１４）の合成」
(0.086g, 0.46mmol)を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に
7,8-Methylendioxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.060 g、収率54%)を得た。
7,8-Methylendioxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 24 oC) d 2.45 (3H, s, Me), 6.15 (2H, s, CH2), 7.06 (1H,
s, C6-H), 8.08 (1H, s, C4-H), 8.58 (1H, s, C9-H).
IR (KBr) n 1035, 1218, 1271, 1316, 1483, 1575 cm-1.
UV-VIS (MeOH) 278 nm (e = 7360), 346 nm
(ε = 2700), 448 nm (ε = 11000).
ESI-MS m/z 243.69 [M+1]+, Calcd for C12H9N3O3:
243.06 [M].
"Synthesis of 7,8-Methylendioxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 14)"
(0.086g, 0.46mmol)
Similar to the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7,8-Methylendioxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
(0.060 g, 54% yield) was obtained.
7,8-Methylendioxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 24 o C) d 2.45 (3H, s, Me), 6.15 (2H, s, CH 2 ), 7.06 (1H,
s, C 6 -H), 8.08 (1H, s, C 4 -H), 8.58 (1H, s, C 9 -H).
IR (KBr) n 1035, 1218, 1271, 1316, 1483, 1575 cm -1 .
UV-VIS (MeOH) 278 nm (e = 7360), 346 nm
(ε = 2700), 448 nm (ε = 11000).
ESI-MS m / z 243.69 [M + 1] + , Calcd for C 12 H 9 N 3 O 3 :
243.06 [M].
「2-Methylimidazo[1,2-a]benzo[g]quinoxalin-1(5H)-one（化学式１５）の合成」
(0.056 g, 0.29 mmol) を用い、
2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に
2-Methylimidazo[1,2-a]benzo[g]quinoxalin-1(5H)-one
(0.011 g、収率15%)を得た。
2-Methylimidazo[1,2-a]benzo[g]quinoxalin-1(5H)-one
1H NMR (CD3OD, 40 oC) d 2.40 (3H, s, Me), 7.39 (1H, s), 7.45 (2H, m), 7.59 (1H,
s), 7.77 (1H, d, J = 7.9 Hz), 7.87 (1H, d, J = 7.9 Hz), 9.31 (1H,
s). IR (KBr) n 1080, 1148, 1186, 1257, 1476, 1597 cm-1.
UV-VIS (MeOH) 225 nm (e = 31100), 249 nm
(e = 35600), 442 nm (ε = 19700), 457 nm (ε = 19800).
ESI-MS m/z 249.76 [M+1]+, Calcd for C15H11N3O:
249.09 [M].
“Synthesis of 2-Methylimidazo [1,2-a] benzo [g] quinoxalin-1 (5H) -one (Chemical Formula 15)”
(0.056 g, 0.29 mmol)
Similar to the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methylimidazo [1,2-a] benzo [g] quinoxalin-1 (5H) -one
(0.011 g, 15% yield) was obtained.
2-Methylimidazo [1,2-a] benzo [g] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 40 o C) d 2.40 (3H, s, Me), 7.39 (1H, s), 7.45 (2H, m), 7.59 (1H,
s), 7.77 (1H, d, J = 7.9 Hz), 7.87 (1H, d, J = 7.9 Hz), 9.31 (1H,
s) .IR (KBr) n 1080, 1148, 1186, 1257, 1476, 1597 cm -1 .
UV-VIS (MeOH) 225 nm (e = 31100), 249 nm
(e = 35600), 442 nm (ε = 19700), 457 nm (ε = 19800).
ESI-MS m / z 249.76 [M + 1] + , Calcd for C 15 H 11 N 3 O:
249.09 [M].
「2-Methyl-7-(phenanthren-9-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式１６）の合成」
mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に2-Methyl-7-(phenanthren-9-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.016 g、収率62%)を得た。
2-Methyl-7-(phenanthren-9-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 28 oC) δ 2.33 (3H, s, Me), 7.38 (2H, m), 7.62-7.78 (5H,
m), 7.84 (1H, s), 7.90 (1H, d, J = 8.5 Hz), 8.06 (1H, d, J = 8.5
Hz), 8.89 (1H, d, J = 8.5 Hz), 8.96 (2H, m), and 11.04 (1H, d, J = 7.0
Hz, N-H). IR (KBr) 1554, 1595, 2883, and 3394 cm-1. UV-VIS (MeOH)
254 nm (e = 67200), 297 nm (e = 19000) , and 432 nm (e = 19600). ESI-MS m/z 374.06 [M-1]-, Calcd
for C25H17N3O: 375.14 [M].
「2-Methyl-7- (phenanthren-9-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 16) "
mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-7- (phenanthren-9-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.016 g, 62% yield) was obtained.
2-Methyl-7- (phenanthren-9-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 28 o C) δ 2.33 (3H, s, Me), 7.38 (2H, m), 7.62-7.78 (5H,
m), 7.84 (1H, s), 7.90 (1H, d, J = 8.5 Hz), 8.06 (1H, d, J = 8.5
Hz), 8.89 (1H, d, J = 8.5 Hz), 8.96 (2H, m), and 11.04 (1H, d, J = 7.0
Hz, NH) .IR (KBr) 1554, 1595, 2883, and 3394 cm -1 .UV-VIS (MeOH)
254 nm (e = 67200), 297 nm (e = 19000), and 432 nm (e = 19600). ESI-MS m / z 374.06 [M-1] - , Calcd
for C 25 H 17 N 3 O: 375.14 [M].
「7-(5-Methoxy-1H-indol-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式１７）の合成」
0.069 mmol)を用い、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に7-(5-Methoxy-1H-indol-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.005 g、収率21%)を得た。
7-(5-Methoxy-1H-indol-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 26 oC) δ 2.44 (3H, s, Me), 3.86 (3H, s, OMe), 6.87 (1H,
dd, J = 1.2 Hz, 9.2 Hz, indo-H), 7.35 (1H, d, J = 9.2 Hz, indo7-H),
7.39 (1H, d, J = 1.2 Hz, indo-H), 7.55 (1H, s), 7.65 (1H, dd, J =
1.2 Hz, 8.5 Hz, C8-H), 7.68 (1H, d, J = 1.2 Hz, C6-H),
7.70 (1H, s), and 9.00 (1H, d, J = 8.5 Hz, C9-H). IR (KBr)
1616, 2942, and 3383 cm-1. UV-VIS (MeOH) 226 nm (e = 22400), 281 nm (e = 14900), and 438 nm (e = 10800). ESI-MS m/z 343.12 [M-1]-, Calcd
for C20H16N4O2: 344.13 [M].
“Synthesis of 7- (5-Methoxy-1H-indol-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 17)”
0.069 mmol) and 7- (5-Methoxy-1H-indol-3-yl) -2-methylimidazo [1] as in the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one , 2-a] quinoxalin-1 (5H) -one
(0.005 g, 21% yield) was obtained.
7- (5-Methoxy-1H-indol-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 26 o C) δ 2.44 (3H, s, Me), 3.86 (3H, s, OMe), 6.87 (1H,
dd, J = 1.2 Hz, 9.2 Hz, indo-H), 7.35 (1H, d, J = 9.2 Hz, indo 7 -H),
7.39 (1H, d, J = 1.2 Hz, indo-H), 7.55 (1H, s), 7.65 (1H, dd, J =
1.2 Hz, 8.5 Hz, C 8 -H), 7.68 (1H, d, J = 1.2 Hz, C 6 -H),
7.70 (1H, s), and 9.00 (1H, d, J = 8.5 Hz, C 9 -H). IR (KBr)
1616, 2942, and 3383 cm -1 . UV-VIS (MeOH) 226 nm (e = 22400), 281 nm (e = 14900), and 438 nm (e = 10800). ESI-MS m / z 343.12 [M -1] - , Calcd
for C 20 H 16 N 4 O 2 : 344.13 [M].
「7-(4-Hydroxyphenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式１８）の合成」
hydrochlorideの製造と同様に7-(4-Hydroxyphenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.014 g、収率50%)を得た。
7-(4-Hydroxyphenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 28 oC) δ 2.29 (3H, s, Me), 6.88 (2H, d, J = 8.5
Hz, Ph-H), 7.39 (1H, d, J = 1.2 Hz, C6-H), 7.41 (1H, dd, J
= 1.2 Hz, 8.6Hz, C8-H), 7.47 (2H, d, J = 8.5 Hz, Ph-H),
7.60 (1H, d, J = 6.1 Hz, C4-H), 8.80 (1H, d, J = 8.6
Hz, C9-H), 9.60 (1H, s, O-H), and 10.96 (1H, d, J = 6.1 Hz,
N-H). IR (KBr) 1590, 3029, and 3143 cm-1. UV-VIS (MeOH) 273 nm (e = 22300) and 434 nm (e = 11300). ESI-MS m/z 290.00 [M-1]-, Calcd
for C17H13N3O2: 291.10 [M].
7- (4-Hydroxyphenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 18) "
7- (4-Hydroxyphenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.014 g, yield 50%) was obtained.
7- (4-Hydroxyphenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 28 o C) δ 2.29 (3H, s, Me), 6.88 (2H, d, J = 8.5
Hz, Ph-H), 7.39 (1H, d, J = 1.2 Hz, C 6 -H), 7.41 (1H, dd, J
= 1.2 Hz, 8.6Hz, C 8 -H), 7.47 (2H, d, J = 8.5 Hz, Ph-H),
7.60 (1H, d, J = 6.1 Hz, C 4 -H), 8.80 (1H, d, J = 8.6
Hz, C 9 -H), 9.60 (1H, s, OH), and 10.96 (1H, d, J = 6.1 Hz,
NH). IR (KBr) 1590, 3029, and 3143 cm -1 . UV-VIS (MeOH) 273 nm (e = 22300) and 434 nm (e = 11300). ESI-MS m / z 290.00 [M-1 ] - , Calcd
for C 17 H 13 N 3 O 2 : 291.10 [M].
「7-(Furan-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式１９）の合成」
hydrochlorideの製造と同様に7-(Furan-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.010 g、収率34%)を得た。
7-(Furan-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 27 oC) δ 2.27 (3H, s, Me), 6.88 (1H, s, fura-H), 7.36
(1H, d, J = 1.8 Hz, C6-H), 7.43 (1H, dd, J = 1.8 Hz,
8.6 Hz, C8-H), 7.57 (1H, d, J = 5.5 Hz, C4-H),
7.77 (1H,m, fura-H), 8.15 (1H, s, fura-H), 8.78 (1H, d, J = 8.6 Hz, C9-H),
and 10.94 (1H, d, J = 5.5 Hz, N-H). IR (KBr) 1556, 2768, and 2884 cm-1.
UV-VIS (MeOH) 247 nm (e = 28500), 304 nm (e = 7100), and 433 nm (e = 19100). ESI- MS m/z 263.86 [M-1]-,
Calcd for C15H11N3O2 265.09 [M].
7- (Furan-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 19) "
7- (Furan-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.010 g, 34% yield) was obtained.
7- (Furan-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 27 o C) δ 2.27 (3H, s, Me), 6.88 (1H, s, fura-H), 7.36
(1H, d, J = 1.8 Hz, C 6 -H), 7.43 (1H, dd, J = 1.8 Hz,
8.6 Hz, C 8 -H), 7.57 (1H, d, J = 5.5 Hz, C 4 -H),
7.77 (1H, m, fura-H), 8.15 (1H, s, fura-H), 8.78 (1H, d, J = 8.6 Hz, C 9 -H),
and 10.94 (1H, d, J = 5.5 Hz, NH) .IR (KBr) 1556, 2768, and 2884 cm -1 .
UV-VIS (MeOH) 247 nm (e = 28500), 304 nm (e = 7100), and 433 nm (e = 19100). ESI- MS m / z 263.86 [M-1] - ,
Calcd for C 15 H 11 N 3 O 2 265.09 [M].
「2-Methyl-7-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式２０）の合成」
hydrochlorideの製造と同様に2-Methyl-7-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.013 g、収率46%)を得た。
2-Methyl-7-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 28 oC) δ 2.28 (3H, s, Me), 7.15 (1H, dd, J = 3.7
Hz, 4.9 Hz, thio4-H), 7.45 (1H, d, J = 1.2 Hz, C6-H),
7.47 (1H, d, J = 3.7 Hz, thio-H), 7.51 (1H, dd, J = 1.2 Hz, 8.5
Hz, C8-H), 7.57 (1H, d, J = 4.9 Hz, thio-H), 7.60 (1H, s, C4-H),
and 8.80 (1H, d, J = 8.5 Hz, C9-H). IR (KBr) 1557, 1675,
2873, and 3071 cm-1. UV-VIS (MeOH) 251 nm (e = 19100), 291 nm (e = 25600), and 434 nm (e = 19800). ESI-MS m/z 279.90 [M-1]-, Calcd
for C15H11N3OS: 281.06 [M].
“2-Methyl-7- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 20) "
2-Methyl-7- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.013 g, 46% yield) was obtained.
2-Methyl-7- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 28 o C) δ 2.28 (3H, s, Me), 7.15 (1H, dd, J = 3.7
Hz, 4.9 Hz, thio 4 -H), 7.45 (1H, d, J = 1.2 Hz, C 6 -H),
7.47 (1H, d, J = 3.7 Hz, thio-H), 7.51 (1H, dd, J = 1.2 Hz, 8.5
Hz, C 8 -H), 7.57 (1H, d, J = 4.9 Hz, thio-H), 7.60 (1H, s, C 4 -H),
and 8.80 (1H, d, J = 8.5 Hz, C 9 -H). IR (KBr) 1557, 1675,
2873, and 3071 cm -1 .UV-VIS (MeOH) 251 nm (e = 19100), 291 nm (e = 25600), and 434 nm (e = 19800). ESI-MS m / z 279.90 [M-1 ] - , Calcd
for C 15 H 11 N 3 OS: 281.06 [M].
「7-(Benzo[b]thiophen-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式２１）の合成」
0.072 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-(Benzo[b]thiophen-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.016 g、収率59%)を得た。
7-(Benzo[b]thiophen-3-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 30 oC) δ 2.31 (3H, s, Me), δ 7.43-7.5 (4H, m), 7.64 (1H, s), 7.88 (1H, s), 7.95 (1H,
dd, J = 1.2 Hz, 6.7 Hz), 8.10 (1H, dd, J = 1.2 Hz, 7.3 Hz), 8.92 (1H, d,
J = 8.9 Hz, C9-H), and 11.20 (1H, s, N-H). IR (KBr) 1601 and
2879 cm-1. UV-VIS (MeOH) 232 nm (e = 30500), 265 nm (e = 14800), 302 nm (e = 9600), and 432 nm (e = 12000). ESI-MS m/z 330.07 [M-1]-, Calcd
for C19H13N3OS: 331.08 [M].
「7- (Benzo [b] thiophen-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 21) "
0.072 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7- (Benzo [b] thiophen-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.016 g, 59% yield) was obtained.
7- (Benzo [b] thiophen-3-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 30 o C) δ 2.31 (3H, s, Me), δ 7.43-7.5 (4H, m), 7.64 (1H, s), 7.88 (1H, s), 7.95 (1H ,
dd, J = 1.2 Hz, 6.7 Hz), 8.10 (1H, dd, J = 1.2 Hz, 7.3 Hz), 8.92 (1H, d,
J = 8.9 Hz, C 9 -H), and 11.20 (1H, s, NH) .IR (KBr) 1601 and
2879 cm -1 . UV-VIS (MeOH) 232 nm (e = 30500), 265 nm (e = 14800), 302 nm (e = 9600), and 432 nm (e = 12000). ESI-MS m / z 330.07 [M-1] - , Calcd
for C 19 H 13 N 3 OS: 331.08 [M].
「7-(Benzo[b]thiophen-2-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one（化学式２２）の合成」
mmol)を用いて、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に7-(Benzo[b]thiophen-2-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
(0.003 g、収率6%)を得た。
7-(Benzo[b]thiophen-2-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 26 oC) δ 2.42 (3H, s, Me), 7.56 (1H, br.s), 7.63 (1H,
br.s), 7.72 (1H, d, JJ = 8.5 Hz, C8-H), 7.75 (1H, s), 7.84
(1H, d, J = 8.5 Hz), 7.86 (1H, d, J = 8.5 Hz), and 9.00 (1H, d, J
= 8.5 Hz, C9-H). IR (KBr) 1558, 1604, 2911, and 3212 cm-1.
UV-VIS (MeOH) 234 nm (e = 17300), 307 nm (e = 18700), and 433 nm (e = 8920). ESI-MS m/z 329.99 [M-1]-, Calcd
for C19H13N3OS: 331.08 [M].
“Synthesis of 7- (Benzo [b] thiophen-2-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one (Chemical Formula 22)”
In the same manner as in the production of 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one, 7- (Benzo [b] thiophen-2-yl) -2-methylimidazo [1,2 -a] quinoxalin-1 (5H) -one
(0.003 g, 6% yield) was obtained.
7- (Benzo [b] thiophen-2-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 26 o C) δ 2.42 (3H, s, Me), 7.56 (1H, br.s), 7.63 (1H,
br.s), 7.72 (1H, d, JJ = 8.5 Hz, C 8 -H), 7.75 (1H, s), 7.84
(1H, d, J = 8.5 Hz), 7.86 (1H, d, J = 8.5 Hz), and 9.00 (1H, d, J
= 8.5 Hz, C 9 -H) .IR (KBr) 1558, 1604, 2911, and 3212 cm -1 .
UV-VIS (MeOH) 234 nm (e = 17300), 307 nm (e = 18700), and 433 nm (e = 8920). ESI-MS m / z 329.99 [M-1] - , Calcd
for C 19 H 13 N 3 OS: 331.08 [M].
「(E)-7-(3-Methoxystyryl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式２３）の合成」
(0.020 g, 0.072 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に(E)-7-(3-Methoxystyryl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.013 g、収率48%)を得た。
(E)-7-(3-Methoxystyryl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 23 oC)
2.27 (3H, s, Me), 3.79 (3H, s, OMe), 6.85 (1H, dd, J = 1.2 Hz, 7.9 Hz),
7.15 (1H, d, J = 16.5 Hz), 7.18 (2H, m), 7.27 (1H, d, J = 16.5
Hz), 7.29 (1H, t, J = 7.9 Hz), 7.36 (1H, d, J = 1.2 Hz), 7.47
(1H, dd, J = 1.2 Hz, 7.9 Hz), 7.58 (1H, s), 8.77 (1H, d, J = 7.9
Hz) and 11.00 (1H, s, N-H). IR (KBr) 1560, 1596, 2835, 2886, and 3396 cm-1.
UV-VIS (MeOH) 230 nm (e = 24100), 307 nm (e = 33900), and 434 nm (e = 23100). ESI-MS m/z 330.06 [M-1]-, Calcd
for C20H17N3O2: 331.13 [M].
「(E) -7- (3-Methoxystyryl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 23) "
(0.020 g, 0.072 mmol) and 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
(E) -7- (3-Methoxystyryl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.013 g, 48% yield) was obtained.
(E) -7- (3-Methoxystyryl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 23 o C)
2.27 (3H, s, Me), 3.79 (3H, s, OMe), 6.85 (1H, dd, J = 1.2 Hz, 7.9 Hz),
7.15 (1H, d, J = 16.5 Hz), 7.18 (2H, m), 7.27 (1H, d, J = 16.5
Hz), 7.29 (1H, t, J = 7.9 Hz), 7.36 (1H, d, J = 1.2 Hz), 7.47
(1H, dd, J = 1.2 Hz, 7.9 Hz), 7.58 (1H, s), 8.77 (1H, d, J = 7.9
Hz) and 11.00 (1H, s, NH) .IR (KBr) 1560, 1596, 2835, 2886, and 3396 cm -1 .
UV-VIS (MeOH) 230 nm (e = 24100), 307 nm (e = 33900), and 434 nm (e = 23100). ESI-MS m / z 330.06 [M-1] - , Calcd
for C 20 H 17 N 3 O 2 : 331.13 [M].
「7-(4-Methoxyphenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式２４）の合成」
hydrochlorideの製造と同様に7-(4-Methoxyphenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.015 g、収率56%)を得た。
7-(4-Methoxyphenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 50 oC) δ 2.29 (3H, s, Me), 3.81 (3H, s, OMe), 7.05 (2H,
d, J = 8.6 Hz, Ph-H), 7.43 (1H, s), 7.46 (1H, dd, J = 1.2 Hz, 7.9
Hz, C8-H), 7.54 (1H, d, J = 5.5 Hz, C4-H), 7.58
(2H, d, J = 8.5 Hz, Ph-H), 8.82 (1H, d, J = 7.9Hz, C9-H),
and 10.84 (1H, d, J = 5.5 Hz, N-H). IR (KBr) 1542, 1603, 2739, 2837, and
3367 cm-1. UV-VIS (MeOH) 269 nm (e = 34300) and 434 nm (e = 20900). ESI-MS m/z 303.98 [M-1]-, Calcd
for C18H15N3O2: 305.12 [M].
"7- (4-Methoxyphenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 24) "
7- (4-Methoxyphenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.015 g, 56% yield) was obtained.
7- (4-Methoxyphenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 50 o C) δ 2.29 (3H, s, Me), 3.81 (3H, s, OMe), 7.05 (2H,
d, J = 8.6 Hz, Ph-H), 7.43 (1H, s), 7.46 (1H, dd, J = 1.2 Hz, 7.9
Hz, C 8 -H), 7.54 (1H, d, J = 5.5 Hz, C 4 -H), 7.58
(2H, d, J = 8.5 Hz, Ph-H), 8.82 (1H, d, J = 7.9 Hz, C 9 -H),
and 10.84 (1H, d, J = 5.5 Hz, NH) .IR (KBr) 1542, 1603, 2739, 2837, and
3367 cm -1 . UV-VIS (MeOH) 269 nm (e = 34300) and 434 nm (e = 20900). ESI-MS m / z 303.98 [M-1] - , Calcd
for C 18 H 15 N 3 O 2 : 305.12 [M].
「2-Methyl-7-(5-methylthiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式２５）の合成」
0.083 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に2-Methyl-7-(5-methylthiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.018 g、収率64%)を得た。
2-Methyl-7-(5-methylthiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 23 oC) d 2.28 (3H, s, Me), 2.47 (3H, s, Me), 6.85 (1H, d, J =
2.4 Hz, thio-H), 7.28 (1H, d, J = 3.7 Hz, thio-H), 7.38 (1H, d, J =
2.4 Hz, C6-H), 7.44 (1H, dd, J = 2.4 Hz, 7.9 Hz, C8-H),
7.61 (1H, s, C4-H), 8.77 (1H, d, J = 7.9 Hz, C9-H),
and 10.97 (1H, s, N-H). IR (KBr) 1556, 1674, and 2731 cm-1. UV-VIS
(MeOH) 251 nm (e
= 17300), 300 nm (e = 27700), and 434 nm (e = 18600). ESI- MS m/z 293.98 [M-1]-, Calcd
for C16H13N3OS: 295.08 [M].
「2-Methyl-7- (5-methylthiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 25) "
0.083 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-7- (5-methylthiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.018 g, yield 64%) was obtained.
2-Methyl-7- (5-methylthiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 23 o C) d 2.28 (3H, s, Me), 2.47 (3H, s, Me), 6.85 (1H, d, J =
2.4 Hz, thio-H), 7.28 (1H, d, J = 3.7 Hz, thio-H), 7.38 (1H, d, J =
2.4 Hz, C 6 -H), 7.44 (1H, dd, J = 2.4 Hz, 7.9 Hz, C 8 -H),
7.61 (1H, s, C 4 -H), 8.77 (1H, d, J = 7.9 Hz, C 9 -H),
and 10.97 (1H, s, NH). IR (KBr) 1556, 1674, and 2731 cm -1 .UV-VIS
(MeOH) 251 nm (e
= 17300), 300 nm (e = 27700), and 434 nm (e = 18600). ESI- MS m / z 293.98 [M-1] - , Calcd
for C 16 H 13 N 3 OS: 295.08 [M].
「2-Methyl-7-(thiazol-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式２６）の合成」
hydrochlorideの製造と同様に2-Methyl-7-(thiazol-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.011 g、収率39%)を得た。
2-Methyl-7-(thiazol-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 27 oC) δ 2.29 (3H, s, Me), 7.63 (1H, s, C4-H),
7.74 (1H, dd, J = 1.8 Hz, 8.5 Hz, C8-H), 7.80 (1H, d, J =
3.1 Hz, thia-H), 7.84 (1H, d, J = 1.8 Hz, C6-H), 7.93 (1H, d,
J = 3.1 Hz, thia-H), 8.84 (1H, d, J = 8.5 Hz, C9-H),
and 11.06 (1H, br.s, N-H). IR (KBr) 1568, 1608, 2942, and 3060 cm-1.
UV-VIS (MeOH) 244 nm (e = 15300), 295 nm (e = 22900), and 430 nm (e = 20200). ESI- MS m/z 280.93 [M-1]-, Calcd
for C14H10N4OS: 282.06 [M].
“2-Methyl-7- (thiazol-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 26) "
2-Methyl-7- (thiazol-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.011 g, 39% yield) was obtained.
2-Methyl-7- (thiazol-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 27 o C) δ 2.29 (3H, s, Me), 7.63 (1H, s, C 4 -H),
7.74 (1H, dd, J = 1.8 Hz, 8.5 Hz, C 8 -H), 7.80 (1H, d, J =
3.1 Hz, thia-H), 7.84 (1H, d, J = 1.8 Hz, C 6 -H), 7.93 (1H, d,
J = 3.1 Hz, thia-H), 8.84 (1H, d, J = 8.5 Hz, C 9 -H),
and 11.06 (1H, br.s, NH) .IR (KBr) 1568, 1608, 2942, and 3060 cm -1 .
UV-VIS (MeOH) 244 nm (e = 15300), 295 nm (e = 22900), and 430 nm (e = 20200). ESI- MS m / z 280.93 [M-1] - , Calcd
for C 14 H 10 N 4 OS: 282.06 [M].
「2-Methyl-7-(1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式２７）の合成」
mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に2-Methyl-7-(1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.017 g、収率59%)を得た。
2-Methyl-7-(1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 24 oC) δ 2.28 (3H, s, Me), 7.38 (1H, d, J = 2.4 Hz,
C6-H), 7.44 (1H, dd, J = 2.4 Hz, 8.6 Hz, C8-H),
7.58 (1H, s, C4-H), 8.03 (2H, s, pyra-H), 8.77 (1H, d, J =
8.6 Hz, C9-H) and 11.00 (1H, s, N-H). IR (KBr) 1601 and 3179 cm-1.
UV-VIS (MeOH) 251 nm (e = 25100), 305 nm (e = 56700), and 434 nm (e = 14300). ESI-MS m/z 263.93 [M-1]-, Calcd
for C14H11N5O: 265.10 [M].
"2-Methyl-7- (1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 27) "
mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-7- (1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.017 g, 59% yield) was obtained.
2-Methyl-7- (1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 24 o C) δ 2.28 (3H, s, Me), 7.38 (1H, d, J = 2.4 Hz,
C 6 -H), 7.44 (1H, dd, J = 2.4 Hz, 8.6 Hz, C 8 -H),
7.58 (1H, s, C 4 -H), 8.03 (2H, s, pyra-H), 8.77 (1H, d, J =
8.6 Hz, C 9 -H) and 11.00 (1H, s, NH). IR (KBr) 1601 and 3179 cm -1 .
UV-VIS (MeOH) 251 nm (e = 25100), 305 nm (e = 56700), and 434 nm (e = 14300). ESI-MS m / z 263.93 [M-1] - , Calcd
for C 14 H 11 N 5 O: 265.10 [M].
「7-(2,2'-Bithiophen-5-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydorochloride
（化学式２８）の合成」
mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-(2,2'-Bithiophen-5-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydorochloride (0.001 g、収率4%)を得た。
7-(2,2'-Bithiophen-5-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydorochloride
1H NMR (DMSO-d6, 27 oC) δ 2.28 (3H, s, Me), 7.12 (1H, t, J = 3.7,
4.9 Hz, thio-H), 7.33 (1H, d, J = 3.7 Hz, thio-H), 7.36 (2H, d,), 7.45
(1H, d, J = 3.7 Hz, thio-H), 7.52 (2H:), 7.60 (1H, s, C4-H),
and 8.80 (1H, d, J = 8.5 Hz, C9-H). IR (KBr) 1559, 1662, and
2879 cm-1. UV-VIS (MeOH) 249 nm (e = 7800), 343 nm (e = 10600), and 427 nm (e = 7200). ESI-MS m/z 362.01 [M-1]-, Calcd
for C19H13N3OS2: 363.05 [M].
「7- (2,2'-Bithiophen-5-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydorochloride
Synthesis of (Chemical Formula 28) "
mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7- (2,2'-Bithiophen-5-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Hydorochloride (0.001 g, yield 4%) was obtained.
7- (2,2'-Bithiophen-5-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydorochloride
1 H NMR (DMSO-d 6 , 27 o C) δ 2.28 (3H, s, Me), 7.12 (1H, t, J = 3.7,
4.9 Hz, thio-H), 7.33 (1H, d, J = 3.7 Hz, thio-H), 7.36 (2H, d,), 7.45
(1H, d, J = 3.7 Hz, thio-H), 7.52 (2H :), 7.60 (1H, s, C 4 -H),
and 8.80 (1H, d, J = 8.5 Hz, C 9 -H). IR (KBr) 1559, 1662, and
2879 cm -1 . UV-VIS (MeOH) 249 nm (e = 7800), 343 nm (e = 10600), and 427 nm (e = 7200). ESI-MS m / z 362.01 [M-1] - , Calcd
for C 19 H 13 N 3 OS 2 : 363.05 [M].
「7-(4-Dimethylaminophenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式２９）の合成」
0.076 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-(4-Dimethylaminophenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.012 g、収率44%)を得た。
7-(4-Dimethylaminophenyl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 28 oC) δ 2.92 (3H, s), 2.98 (6H, s, Me), 6.86 (2H, d, J
= 8.6 Hz, Ph-H), 7.73 (2H, d, J = 8.6 Hz, Ph-H), 7.87 (1H, d, J =
8.6 Hz, C9-H), 8.10 (1H, dd, J = 1.2 Hz, 8.6 Hz, C8-H),
8.17 (1H, d, J = 1.2 Hz,C6-H), 9.59 (1H, s, C4-H),
and 11.01 (1H, s, N-H). IR (KBr) 1541, 1607, 2801, and 2872 cm-1.
UV-VIS (MeOH) 229 nm (e = 15800), 311 nm (e = 17300), and 437 nm (e = 10300). ESI-MS m/z 317.08 [M-1]-, Calcd
for C19H18N4O: 318.15 [M].
「7- (4-Dimethylaminophenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 29) "
0.076 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7- (4-Dimethylaminophenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.012 g, 44% yield) was obtained.
7- (4-Dimethylaminophenyl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 28 o C) δ 2.92 (3H, s), 2.98 (6H, s, Me), 6.86 (2H, d, J
= 8.6 Hz, Ph-H), 7.73 (2H, d, J = 8.6 Hz, Ph-H), 7.87 (1H, d, J =
8.6 Hz, C 9 -H), 8.10 (1H, dd, J = 1.2 Hz, 8.6 Hz, C 8 -H),
8.17 (1H, d, J = 1.2 Hz, C 6 -H), 9.59 (1H, s, C 4 -H),
and 11.01 (1H, s, NH) .IR (KBr) 1541, 1607, 2801, and 2872 cm -1 .
UV-VIS (MeOH) 229 nm (e = 15800), 311 nm (e = 17300), and 437 nm (e = 10300). ESI-MS m / z 317.08 [M-1] - , Calcd
for C 19 H 18 N 4 O: 318.15 [M].
「7-(Benzofuran-2-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式３０）の合成」
mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-(Benzofuran-2-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.007 g、収率26%)を得た。
7-(Benzofuran-2-yl)-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one hydrochloride
1H NMR (DMSO-d6, 28 oC) δ 2.30 (3H, s, Me), 7.28 (1H, t, J = 7.3
Hz, benzo-H), 7.35 (1H, t, J = 7.3 Hz,benzo-H), 7.42 (1H, s), 7.63 (1H,
s), 7.64 (1H, d, J = 7.9 Hz), 7.68 (1H, d, J = 7.3 Hz), 7.73 (1H,
d, J = 1.2 Hz, C6-H), 7.76 (1H, dd, J = 1.2 Hz, 8.6
Hz, C8-H), 8.88 (1H, d, J = 8.6 Hz, C9-H), and
11.04 (1H, s, N-H). IR (KBr) 1557, 1603, and 2764 cm-1. UV-VIS
(MeOH) 242 nm (e
= 19600), 309 nm (e = 42900), and 432 nm (e = 22300). ESI-MS m/z 314.01 [M-1]-, Calcd
for C19H13N3O2: 315.10 [M].
「7- (Benzofuran-2-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 30) "
mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7- (Benzofuran-2-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.007 g, 26% yield) was obtained.
7- (Benzofuran-2-yl) -2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one hydrochloride
1 H NMR (DMSO-d 6 , 28 o C) δ 2.30 (3H, s, Me), 7.28 (1H, t, J = 7.3
Hz, benzo-H), 7.35 (1H, t, J = 7.3 Hz, benzo-H), 7.42 (1H, s), 7.63 (1H,
s), 7.64 (1H, d, J = 7.9 Hz), 7.68 (1H, d, J = 7.3 Hz), 7.73 (1H,
d, J = 1.2 Hz, C 6 -H), 7.76 (1H, dd, J = 1.2 Hz, 8.6
Hz, C 8 -H), 8.88 (1H, d, J = 8.6 Hz, C 9 -H), and
11.04 (1H, s, NH). IR (KBr) 1557, 1603, and 2764 cm -1 . UV-VIS
(MeOH) 242 nm (e
= 19600), 309 nm (e = 42900), and 432 nm (e = 22300). ESI-MS m / z 314.01 [M-1] - , Calcd
for C 19 H 13 N 3 O 2 : 315.10 [M].
「7-(5-Chlorothiophen-2-yl)-2-methylimidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride
（化学式３１）の合成」
0.076 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-(5-Chlorothiophen-2-yl)-2-methylimidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride (0.014 g、収率52%)を得た。
7-(5-Chlorothiophen-2-yl)-2-methylimidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride
1H NMR (DMSO-d6, 27 oC) δ 2.27 (3H, s, Me), 7.17 (1H, d, J =
4.3Hz, thio-H), 7.35 (1H, d, J = 4.2 Hz, thio-H), 7.36 (1H, d, J
= 1.8 Hz), 7.46 (1H, dd, J = 1.8 Hz, 8.5 Hz, C8-H), 7.59 (1H,
s, C4-H), and 8.78 (1H, d, J = 8.5 Hz, C9-H). IR
(KBr) 1552, 1600, and 2737 cm-1. UV-VIS (MeOH) 250 nm (e = 13300), 299 nm (e = 22100), and 429 nm (e = 10700). ESI-MS m/z 313.95 [M-1]-, Calcd
for C15H10N3ClOS: 315.02 [M].
「7- (5-Chlorothiophen-2-yl) -2-methylimidazo
[1,2-a] quinoxalin-1 (5H) -one hydrochloride
Synthesis of (Chemical Formula 31) "
0.076 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7- (5-Chlorothiophen-2-yl) -2-methylimidazo as in the preparation of hydrochloride
[1,2-a] quinoxalin-1 (5H) -one hydrochloride (0.014 g, yield 52%) was obtained.
7- (5-Chlorothiophen-2-yl) -2-methylimidazo
[1,2-a] quinoxalin-1 (5H) -one hydrochloride
1 H NMR (DMSO-d 6 , 27 o C) δ 2.27 (3H, s, Me), 7.17 (1H, d, J =
4.3Hz, thio-H), 7.35 (1H, d, J = 4.2 Hz, thio-H), 7.36 (1H, d, J
= 1.8 Hz), 7.46 (1H, dd, J = 1.8 Hz, 8.5 Hz, C 8 -H), 7.59 (1H,
s, C 4 -H), and 8.78 (1H, d, J = 8.5 Hz, C 9 -H). IR
(KBr) 1552, 1600, and 2737 cm -1 .UV-VIS (MeOH) 250 nm (e = 13300), 299 nm (e = 22100), and 429 nm (e = 10700). ESI-MS m / z 313.95 [M-1] - , Calcd
for C 15 H 10 N 3 ClOS: 315.02 [M].
「2-Methyl-7-(thiophen-3-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式３２）の合成」
hydrochlorideの製造と同様に2-Methyl-7-(thiophen-3-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.015 g、収率54%)を得た。
2-Methyl-7-(thiophen-3-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 26 oC) δ 2.28 (3H, s, Me), 7.49 (2H, m), 7.54 (1H, dd, J
= 1.8 Hz, 8.5 Hz, C8-H), 7.59 (1H, s, C4-H), 7.67
(1H, dd, J = 3.1 Hz, 5.4 Hz, thio-H), 7.83 (1H, dd, J = 1.2 Hz, 3.1
Hz, thio-H), and 8.80 (1H, d, J = 8.5 Hz, C9-H). IR (KBr)
1556, 1676, 2742, and 2835 cm-1. UV-VIS 8MeOH) 265 nm (e = 25700) and 433 nm (e = 14700). ESI-MS m/z 279.94 [M-1]-, Calcd
for C15H11N3OS: 281.06 [M].
“2-Methyl-7- (thiophen-3-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 32) "
2-Methyl-7- (thiophen-3-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.015 g, 54% yield) was obtained.
2-Methyl-7- (thiophen-3-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 26 o C) δ 2.28 (3H, s, Me), 7.49 (2H, m), 7.54 (1H, dd, J
= 1.8 Hz, 8.5 Hz, C 8 -H), 7.59 (1H, s, C 4 -H), 7.67
(1H, dd, J = 3.1 Hz, 5.4 Hz, thio-H), 7.83 (1H, dd, J = 1.2 Hz, 3.1
Hz, thio-H), and 8.80 (1H, d, J = 8.5 Hz, C 9 -H). IR (KBr)
1556, 1676, 2742, and 2835 cm -1 . UV-VIS 8MeOH) 265 nm (e = 25700) and 433 nm (e = 14700). ESI-MS m / z 279.94 [M-1] - , Calcd
for C 15 H 11 N 3 OS: 281.06 [M].
「2-Methyl-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式３３）の合成」
0.089 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に2-Methyl-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.014 g、収率50%)を得た。
2-Methyl-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 26 oC) δ 2.27 (3H, s, Me), 3.86 (3H, s, Me), 7.32 (1H,
d, J = 1.8 Hz, C6-H), 7.38 (1H, dd, J = 1.8, 8.6 Hz, C8-H),
7.56 (1H, s, C4-H), 7.79 (1H, s, pyra-H), 8.09 (1H, s, pyra-H), 8.75
(1H, d, J = 8.6 Hz, C9-H), and 10.97 (1H, br.s, N-H). IR
(KBr) 1622 and 3414 cm-1. UV-VIS (MeOH) 253 nm (e = 29100), 306 nm (e = 6500), 434 nm (e = 17500). ESI-MS m/z 277.99 [M-1]-, Calcd
for C15H13N5O: 279.11 [M].
"2-Methyl-7- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 33) "
0.089 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-7- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.014 g, yield 50%) was obtained.
2-Methyl-7- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 26 o C) δ 2.27 (3H, s, Me), 3.86 (3H, s, Me), 7.32 (1H,
d, J = 1.8 Hz, C 6 -H), 7.38 (1H, dd, J = 1.8, 8.6 Hz, C 8 -H),
7.56 (1H, s, C 4 -H), 7.79 (1H, s, pyra-H), 8.09 (1H, s, pyra-H), 8.75
(1H, d, J = 8.6 Hz, C 9 -H), and 10.97 (1H, br.s, NH). IR
(KBr) 1622 and 3414 cm -1 .UV-VIS (MeOH) 253 nm (e = 29100), 306 nm (e = 6500), 434 nm (e = 17500). ESI-MS m / z 277.99 [M- 1] - , Calcd
for C 15 H 13 N 5 O: 279.11 [M].
「2-Methyl-7,8-bis(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
（化学式３４）の合成」
g, 0.66 mmol)を用い、2-methylimidazo[1,2-a]quinoxalin-1(5H)-oneの製造と同様に2-Methyl-7,8-bis(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
(0.014 g、収率58%)を得た。
2-Methyl-7,8-bis(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
1H NMR (CD3OD, 23 oC) δ 2.51 (3H, s, Me), 3.97 (3H, s, NMe), 3.99 (3H,
s, NMe), 7.55 (1H, s), 7.56 (1H, s), 7.61 (1H, s), 7.76 (1H, s), 7.82 (1H, s),
8.19 (1H, s), and 9.00 (1H, s). IR (KBr) 1501, 1612, 3073, and 3409 cm-1.
UV-VIS (MeOH) 252 nm (e = 38500) and 443 nm (e = 20500). ESI-MS m/z 358.10 [M-1]-, Calcd
for C19H17N7O: 359.15 [M].
“2-Methyl-7,8-bis (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of (Chemical Formula 34) "
g, 0.66 mmol), and 2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one as well as 2-Methyl-7,8-bis (1-methyl-1H-pyrazol-4 -yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
(0.014 g, 58% yield) was obtained.
2-Methyl-7,8-bis (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
1 H NMR (CD 3 OD, 23 o C) δ 2.51 (3H, s, Me), 3.97 (3H, s, NMe), 3.99 (3H,
s, NMe), 7.55 (1H, s), 7.56 (1H, s), 7.61 (1H, s), 7.76 (1H, s), 7.82 (1H, s),
8.19 (1H, s), and 9.00 (1H, s). IR (KBr) 1501, 1612, 3073, and 3409 cm -1 .
UV-VIS (MeOH) 252 nm (e = 38500) and 443 nm (e = 20500). ESI-MS m / z 358.10 [M-1] - , Calcd
for C 19 H 17 N 7 O: 359.15 [M].
「2-Methyl-8-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式３５）の合成」
0.089 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に2-Methyl-8-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.017 g、収率61%)を得た。
2-Methyl-8-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 23 oC) δ 2.27 (3H, s, Me), 3.88 (3H, s, NMe), 7.22 (1H,
d, J = 8.5 Hz, C6-H), 7.44 (1H, dd, J = 1.8, 8.5 Hz, C7-H),
7.58 (1H, s, C4-H), 7.75 (1H, s, pyra-H), 8.07 (1H, s, pyra-H), 8.97
(1H, d, J = 1.8 Hz, C9-H), and 11.05 (1H, br.s, NH). IR (KBr) 1570,
1607, 2773, 2940, 3074, and 3397 cm-1. UV-VIS (MeOH) 216 nm (e = 30300), 254 nm (e = 22900), 287 nm (e = 23600), and 446 nm (e = 21000). ESI-MS m/z 277.99 [M-1]-,
Calcd for C15H13N5O: 279.11 [M].
"2-Methyl-8- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 35) "
0.089 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-8- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.017 g, 61% yield) was obtained.
2-Methyl-8- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 23 o C) δ 2.27 (3H, s, Me), 3.88 (3H, s, NMe), 7.22 (1H,
d, J = 8.5 Hz, C 6 -H), 7.44 (1H, dd, J = 1.8, 8.5 Hz, C 7 -H),
7.58 (1H, s, C 4 -H), 7.75 (1H, s, pyra-H), 8.07 (1H, s, pyra-H), 8.97
(1H, d, J = 1.8 Hz, C 9 -H), and 11.05 (1H, br.s, NH) .IR (KBr) 1570,
1607, 2773, 2940, 3074, and 3397 cm -1 .UV-VIS (MeOH) 216 nm (e = 30300), 254 nm (e = 22900), 287 nm (e = 23600), and 446 nm (e = 21000). ESI-MS m / z 277.99 [M-1] - ,
Calcd for C 15 H 13 N 5 O: 279.11 [M].
「2-Methyl-7,8-di(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式３６）の合成」
mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に2-Methyl-7,8-di(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.016 g、収率62%)を得た。
2-Methyl-7,8-di(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 23 oC) δ 2.28 (3H, s, Me), 6.91 (1H, dd, J = 1.2
Hz, 3.7 Hz, thio-H), 6.95 (1H, dd, J = 1.2 Hz, 3.7 Hz, thio-H), 7.01
(1H, d, J = 3.7 Hz, thio-H), 7.03 (1H, d, J = 3.7 Hz), 7.31 (1H,
s,), 7.54 (2H, m, thio-H), 7.64 (1H, s), and 8.90 (1H, s). IR (KBr) 1560, 1602,
and 3422 cm-1. UV-VIS (MeOH) 226 nm (e = 29100), 267 nm (e = 29200), and 445 nm (e = 19100). ESI-MS m/z 362.01 [M-1]-, Calcd
for C19H13N3OS2 363.05 [M].
「2-Methyl-7,8-di (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 36) "
mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
2-Methyl-7,8-di (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.016 g, 62% yield) was obtained.
2-Methyl-7,8-di (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 23 o C) δ 2.28 (3H, s, Me), 6.91 (1H, dd, J = 1.2
Hz, 3.7 Hz, thio-H), 6.95 (1H, dd, J = 1.2 Hz, 3.7 Hz, thio-H), 7.01
(1H, d, J = 3.7 Hz, thio-H), 7.03 (1H, d, J = 3.7 Hz), 7.31 (1H,
s,), 7.54 (2H, m, thio-H), 7.64 (1H, s), and 8.90 (1H, s) .IR (KBr) 1560, 1602,
and 3422 cm -1 . UV-VIS (MeOH) 226 nm (e = 29100), 267 nm (e = 29200), and 445 nm (e = 19100). ESI-MS m / z 362.01 [M-1] - , Calcd
for C 19 H 13 N 3 OS 2 363.05 [M].
「2-Methyl-8-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
（化学式３７）の合成」
hydrochlorideの製造と同様に2-Methyl-8-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.016 g、収率57%)を得た。
2-Methyl-8-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO- d6, 24 oC) δ 2.28 (3H, s, Me), 7.14 (1H, t, J = 4.9
Hz, thio-H), 7.25 (1H, d, J = 8.5 Hz, C6-H), 7.44 (1H, d, J
= 3.1 Hz, thio-H), 7.54 (1H, d, J = 4.9 Hz, thio-H), 7.58 (2H, m),
9.10 (1H, s), and 11.10 (1H, s, N-H). IR (KBr) 1558, 1675, 2768, 2842, 2915,
3067, and 3145 cm-1. UV-VIS (MeOH) 302 nm (e = 31500) and 451 nm (e = 23900). ESI-MS m/z 279.95 [M-1]-, Calcd
for C15H11N3OS: 281.06 [M].
"2-Methyl-8- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
Synthesis of (Chemical Formula 37) "
2-Methyl-8- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.016 g, 57% yield) was obtained.
2-Methyl-8- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO- d 6 , 24 o C) δ 2.28 (3H, s, Me), 7.14 (1H, t, J = 4.9
Hz, thio-H), 7.25 (1H, d, J = 8.5 Hz, C 6 -H), 7.44 (1H, d, J
= 3.1 Hz, thio-H), 7.54 (1H, d, J = 4.9 Hz, thio-H), 7.58 (2H, m),
9.10 (1H, s), and 11.10 (1H, s, NH). IR (KBr) 1558, 1675, 2768, 2842, 2915,
3067, and 3145 cm -1 . UV-VIS (MeOH) 302 nm (e = 31500) and 451 nm (e = 23900). ESI-MS m / z 279.95 [M-1] - , Calcd
for C 15 H 11 N 3 OS: 281.06 [M].
「8-Methoxy-2-methyl-7-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式３８）の合成」
0.078 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に8-Methoxy-2-methyl-7-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.019 g、収率70%)を得た。
8-Methoxy-2-methyl-7-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 22 oC) δ 2.28 (3H, s, Me), 3.94 (3H, s,OMe), 7.15 (1H,
dd, J = 3.1, 4.9 Hz, thio4-H), 7.52 (1H, d, J = 3.1
Hz, thio-H), 7.58 (1H, s), 7.59 (1H, d, J = 4.9 Hz, thio-H), 7.66 (1H,
s), and 8.70 (1H, s). IR (KBr) 1567, 1591, 3018, and 3397 cm-1. UV-VIS
(MeOH) 207 nm (e
= 27300), 252 nm (e = 23900), 291 nm (e = 26200), and 445 nm (e = 21800). ESI-MS m/z 310.01 [M-1]-, Calcd
for C16H13N3O2S: 311.07 [M].
「8-Methoxy-2-methyl-7- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 38) "
0.078 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
8-Methoxy-2-methyl-7- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.019 g, 70% yield) was obtained.
8-Methoxy-2-methyl-7- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 22 o C) δ 2.28 (3H, s, Me), 3.94 (3H, s, OMe), 7.15 (1H,
dd, J = 3.1, 4.9 Hz, thio 4 -H), 7.52 (1H, d, J = 3.1
Hz, thio-H), 7.58 (1H, s), 7.59 (1H, d, J = 4.9 Hz, thio-H), 7.66 (1H,
s), and 8.70 (1H, s). IR (KBr) 1567, 1591, 3018, and 3397 cm -1. UV-VIS
(MeOH) 207 nm (e
= 27300), 252 nm (e = 23900), 291 nm (e = 26200), and 445 nm (e = 21800). ESI-MS m / z 310.01 [M-1] - , Calcd
for C 16 H 13 N 3 O 2 S: 311.07 [M].
「8-Methoxy-2-methyl-7-(thiophen-3-yl)imidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride（化学式３９）の合成」
0.078 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に8-Methoxy-2-methyl-7-(thiophen-3-yl)imidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride (0.019 g、収率70%)を得た。
8-Methoxy-2-methyl-7-(thiophen-3-yl)imidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride
1H NMR (DMSO-d6, 22 oC) δ 2.28 (3H, s, Me), 3.88 (3H, s, OMe), 7.42 (1H,
d, J = 4.9 Hz, thio-H), 7.43 (1H, s), 7.61 (1H, dd, J = 3.1, 4.9
Hz, thio-H), 7.66 (1H, s), 7.80 (1H, d, J = 3.1 Hz, thio-H), 8.70 (1H,
s), and 11.05 (1H, br.s). IR (KBr) 1499, 1590, and 3419 cm-1. UV-VIS
(MeOH) 211 nm (e
= 28800), 248 nm (e = 28800), 268 nm (e = 25700), and 444 nm (e = 20000). ESI-MS m/z 310.02 [M-1]-, Calcd
for C16H13N3O2S: 311.07 [M].
「8-Methoxy-2-methyl-7- (thiophen-3-yl) imidazo
Synthesis of [1,2-a] quinoxalin-1 (5H) -one hydrochloride (Chemical Formula 39) "
0.078 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
8-Methoxy-2-methyl-7- (thiophen-3-yl) imidazo as in the preparation of hydrochloride
[1,2-a] quinoxalin-1 (5H) -one hydrochloride (0.019 g, yield 70%) was obtained.
8-Methoxy-2-methyl-7- (thiophen-3-yl) imidazo
[1,2-a] quinoxalin-1 (5H) -one hydrochloride
1 H NMR (DMSO-d 6 , 22 o C) δ 2.28 (3H, s, Me), 3.88 (3H, s, OMe), 7.42 (1H,
d, J = 4.9 Hz, thio-H), 7.43 (1H, s), 7.61 (1H, dd, J = 3.1, 4.9
Hz, thio-H), 7.66 (1H, s), 7.80 (1H, d, J = 3.1 Hz, thio-H), 8.70 (1H,
s), and 11.05 (1H, br.s) .IR (KBr) 1499, 1590, and 3419 cm -1 .UV-VIS
(MeOH) 211 nm (e
= 28800), 248 nm (e = 28800), 268 nm (e = 25700), and 444 nm (e = 20000). ESI-MS m / z 310.02 [M-1] - , Calcd
for C 16 H 13 N 3 O 2 S: 311.07 [M].
「8-Methoxy-2-methyl-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式４０）の合成」
(0.020 g, 0.078 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に8-Methoxy-2-methyl-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.021 g、収率78%)を得た。
8-Methoxy-2-methyl-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 22 oC) δ 2.27(3H, s, Me), 3.89 (3H, s, OMe), 3.91 (3H,
s, OMe), 7.44 (1H, s), 7.63 (1H, s), 7.79 (1H, s), 8.11 (1H, s), 8.67 (1H, s),
and 11.00 (1H, br.s, NH). IR (KBr) 1567 and 3393 cm-1 .
UV-VIS (MeOH) 247 nm (e = 32500), 268 nm (e = 27900), and 445 nm (e = 20500). ESI-MS m/z 308.06 [M-1]-, Calcd
for C16H15N5O2 309.12 [M].
「8-Methoxy-2-methyl-7- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 40) "
(0.020 g, 0.078 mmol) and 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
8-Methoxy-2-methyl-7- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.021 g, 78% yield) was obtained.
8-Methoxy-2-methyl-7- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 22 o C) δ 2.27 (3H, s, Me), 3.89 (3H, s, OMe), 3.91 (3H,
s, OMe), 7.44 (1H, s), 7.63 (1H, s), 7.79 (1H, s), 8.11 (1H, s), 8.67 (1H, s),
and 11.00 (1H, br.s, NH) .IR (KBr) 1567 and 3393 cm -1 .
UV-VIS (MeOH) 247 nm (e = 32500), 268 nm (e = 27900), and 445 nm (e = 20500). ESI-MS m / z 308.06 [M-1] - , Calcd
for C 16 H 15 N 5 O 2 309.12 [M].
「7-Methoxy-2-methyl-8-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式４１）の合成」
0.078 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-Methoxy-2-methyl-8-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.016 g、収率59%)を得た。
7-Methoxy-2-methyl-8-(thiophen-2-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 22 oC) δ 2.29 (3H, s, Me), 3.92 (3H, s, OMe), 6.96 (1H,
s), 7.15 (1H, dd, J = 3.7, 4.9 Hz, thio-H), 7.48 (1H, d, J = 3.7
Hz, thio-H), 7.56 (1H, d, J = 4.9 Hz, thio-H), 7.61 (1H,
br.s), 9.16 (1H, s), and 11.06 (1H, s, N-H). IR (KBr,) 1491, 1607, and 3434 cm-1.
UV-VIS (MeOH) 225 nm (e = 25300), 304 nm (e = 24700), 461 nm (e = 17200). ESI-MS m/z 310. 01 [M-1]-, Calcd
for C16H13N3O2S: 311.07 [M].
「7-Methoxy-2-methyl-8- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 41) "
0.078 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7-Methoxy-2-methyl-8- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.016 g, 59% yield) was obtained.
7-Methoxy-2-methyl-8- (thiophen-2-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 22 o C) δ 2.29 (3H, s, Me), 3.92 (3H, s, OMe), 6.96 (1H,
s), 7.15 (1H, dd, J = 3.7, 4.9 Hz, thio-H), 7.48 (1H, d, J = 3.7
Hz, thio - H), 7.56 (1H, d, J = 4.9 Hz, thio-H), 7.61 (1H,
br.s), 9.16 (1H, s), and 11.06 (1H, s, NH) .IR (KBr,) 1491, 1607, and 3434 cm -1 .
UV-VIS (MeOH) 225 nm (e = 25300), 304 nm (e = 24700), 461 nm (e = 17200). ESI-MS m / z 310. 01 [M-1] - , Calcd
for C 16 H 13 N 3 O 2 S: 311.07 [M].
「7-Methoxy-2-methyl-8-(thiophen-3-yl)imidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride（化学式４２）の合成」
0.078 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-Methoxy-2-methyl-8-(thiophen-3-yl)imidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride (0.014 g、収率52%)を得た。
7-Methoxy-2-methyl-8-(thiophen-3-yl)imidazo
[1,2-a]quinoxalin-1(5H)-one hydrochloride
1H NMR (DMSO-d6, 22 oC) δ 2.28 (3H, s, Me), 3.86 (3H, s, OMe), 6.95 (1H,
s), 7.39 (1H, dd, J = 1.2 Hz, 5.5 Hz, thio-H), 7.62 (2H, m), 7.75 (1H,
d, J = 1.2Hz, thio-H), 9.00 (1H, s), and 11.05 (1H, s, N-H). IR (KBr)
1495, 1608, 2938, 3066, and 3376 cm-1. UV-VIS (MeOH) 222 nm (e = 31900), 292 nm (e = 20300), and 453 nm (e = 16700). ESI-MS m/z 310.01 [M-1]-, Calcd
for C16H13N3O2S: 311.07 [M].
「7-Methoxy-2-methyl-8- (thiophen-3-yl) imidazo
Synthesis of [1,2-a] quinoxalin-1 (5H) -one hydrochloride (Chemical Formula 42) "
0.078 mmol), 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7-Methoxy-2-methyl-8- (thiophen-3-yl) imidazo as in the manufacture of hydrochloride
[1,2-a] quinoxalin-1 (5H) -one hydrochloride (0.014 g, yield 52%) was obtained.
7-Methoxy-2-methyl-8- (thiophen-3-yl) imidazo
[1,2-a] quinoxalin-1 (5H) -one hydrochloride
1 H NMR (DMSO-d 6 , 22 o C) δ 2.28 (3H, s, Me), 3.86 (3H, s, OMe), 6.95 (1H,
s), 7.39 (1H, dd, J = 1.2 Hz, 5.5 Hz, thio-H), 7.62 (2H, m), 7.75 (1H,
d, J = 1.2Hz, thio-H), 9.00 (1H, s), and 11.05 (1H, s, NH). IR (KBr)
1495, 1608, 2938, 3066, and 3376 cm -1. UV-VIS (MeOH) 222 nm (e = 31900), 292 nm (e = 20300), and 453 nm (e = 16700). ESI-MS m / z 310.01 [M-1] - , Calcd
for C 16 H 13 N 3 O 2 S: 311.07 [M].
「7-Methoxy-2-methyl-8-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride（化学式４３）の合成」
(0.020 g, 0.078 mmol)を用いて、8-Methoxy-2-methylimidazo[1,2-a]quinoxalin-1(5H)-one
hydrochlorideの製造と同様に7-Methoxy-2-methyl-8-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride (0.016 g、収率59%)を得た。
7-Methoxy-2-methyl-8-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]quinoxalin-1(5H)-one
hydrochloride
1H NMR (DMSO-d6, 22 oC) δ 2.28 (3H, s, Me), 3.89 (6H, s, OMe and NMe),
6.92 (1H, s), 7.60 (1H, s), 7.74 (1H, s), 8.07 (1H, s), and 9.00 (1H, s). IR
(KBr) 1563, 1613, 1674, 2940, 3085, and 3409 cm-1. UV-VIS (MeOH) 226
nm (e = 28500), 291 nm (e = 21000), and 455 nm (e = 15800). ESI-MS m/z 308.05 [M-1]-, Calcd
for C16H15N5O2 309.12 [M].
「7-Methoxy-2-methyl-8- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
Synthesis of hydrochloride (Chemical Formula 43) "
(0.020 g, 0.078 mmol) and 8-Methoxy-2-methylimidazo [1,2-a] quinoxalin-1 (5H) -one
7-Methoxy-2-methyl-8- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride (0.016 g, 59% yield) was obtained.
7-Methoxy-2-methyl-8- (1-methyl-1H-pyrazol-4-yl) imidazo [1,2-a] quinoxalin-1 (5H) -one
hydrochloride
1 H NMR (DMSO-d 6 , 22 o C) δ 2.28 (3H, s, Me), 3.89 (6H, s, OMe and NMe),
6.92 (1H, s), 7.60 (1H, s), 7.74 (1H, s), 8.07 (1H, s), and 9.00 (1H, s). IR
(KBr) 1563, 1613, 1674, 2940, 3085, and 3409 cm -1 .UV-VIS (MeOH) 226
nm (e = 28500), 291 nm (e = 21000), and 455 nm (e = 15800). ESI-MS m / z 308.05 [M-1] - , Calcd
for C 16 H 15 N 5 O 2 309.12 [M].
スーパーオキシドアニオンは、ヒポキサンチンにキサンチンオキシダーゼを作用させ，キサンチンを尿酸に変化させる過程で生じる。この系に上記の実施例で得たイミダゾ[1,2-a] キノキザリン-（５H）-１-オン化合物を共存させ，スーパーオキシドアニオン検出の性能を明らかにする。
KCl(0.2M)、EDTA(0.1mM)、3-モルホリノプロパンスルホン酸(MOPS)(20mM)を含む緩衝水溶液 (pH 7.2、0.5ml)に25℃で、ヒポキサンチン水溶液(0.3mM，0.5ml)、イミダゾ[1,2-a]
キノキザリン-（５H）-１-オン化合物水溶液(2.5x10-5M，40μl)およびキサンチンオキシダーゼ水溶液(0.37unit/ml，40μl)を加え、アロカ社ルミネッセンスリーダーＢＬ２０１を用いて発光強度を測定した（発光波長による発光量の補正はせず）。発光はキサンチンオキシダーゼ水溶液の添加後、強度を測定した。0分から1分の発光強度の測定結果を表１に示す。
The superoxide anion is generated in the process of causing xanthine oxidase to act on hypoxanthine and changing xanthine to uric acid. In this system, the imidazo [1,2-a] quinoxalin- (5H) -1-one compound obtained in the above example is coexisted to clarify the performance of superoxide anion detection.
Hypoxanthine aqueous solution (0.3 mM, 0.5 ml) at 25 ° C in a buffer aqueous solution (pH 7.2, 0.5 ml) containing KCl (0.2 M), EDTA (0.1 mM), 3-morpholinopropanesulfonic acid (MOPS) (20 mM) , Imidazo [1,2-a]
A quinoxaline- (5H) -1-one compound aqueous solution (2.5 × 10 −5 M, 40 μl) and a xanthine oxidase aqueous solution (0.37 unit / ml, 40 μl) were added, and the luminescence intensity was measured using a luminescence reader BL201 manufactured by Aloka (luminescence). The light emission amount is not corrected by wavelength). Luminescence was measured after the addition of an aqueous xanthine oxidase solution. Table 1 shows the measurement results of the emission intensity from 0 minute to 1 minute.
Claims (4)
は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R３ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R４ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R５ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、無置換あるいは置換されていてもよいハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環であり、R６ は水素原子、無置換あるいは置換されていてもよいアルキル基、無置換あるいは置換されていてもよいアリール基、ハロゲン原子、無置換あるいは置換されていてもよいアルコキシル基、無置換あるいは置換されていてもよいカルボキシル基、無置換あるいは置換されていてもよいホルミル基、無置換あるいは置換されていてもよいアルキルオキシカルボニル基、無置換あるいは置換されていてもよいアリールオキシカルボニル基、無置換あるいは置換されていてもよいアルキルカルボニル基、無置換あるいは置換されていてもよいアリールカルボニル基または無置換あるいは置換されていてもよい複素環を示す）
The imidazo [1] according to claim 2, wherein the 2-aminoquinoxaline compound represented by the following chemical formula 3 is subjected to a condensation reaction with an a-ketoaldehyde compound or an a-ketoaldehyde equivalent compound represented by the chemical formulas 4 to 5. , 2-a] A method for chemically synthesizing quinoxaline- (5H) -1-one luminescent compounds.
Is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, a halogen atom, an unsubstituted or substituted alkoxyl group, an unsubstituted or substituted May be a carboxyl group, an unsubstituted or substituted formyl group, an unsubstituted or substituted alkyloxycarbonyl group, an unsubstituted or substituted aryloxycarbonyl group, an unsubstituted or substituted An alkylcarbonyl group which may be substituted, an arylcarbonyl group which may be unsubstituted or substituted, or a heterocyclic ring which may be unsubstituted or substituted, and R 3 may be a hydrogen atom, unsubstituted or substituted Alkyl group, unsubstituted or optionally substituted aryl group, halogen Atom, unsubstituted or substituted alkoxyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted formyl group, unsubstituted or substituted alkyloxycarbonyl Group, an aryloxycarbonyl group which may be unsubstituted or substituted, an alkylcarbonyl group which may be unsubstituted or substituted, an arylcarbonyl group which may be unsubstituted or substituted, or an unsubstituted or substituted group R 4 is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, a halogen atom, an unsubstituted or substituted alkoxyl group , Unsubstituted or optionally substituted carboxyl group, Alternatively, an optionally substituted formyl group, an unsubstituted or substituted alkyloxycarbonyl group, an unsubstituted or substituted aryloxycarbonyl group, an unsubstituted or substituted alkylcarbonyl group , An arylcarbonyl group which may be unsubstituted or substituted, or a heterocyclic ring which may be unsubstituted or substituted, and R 5 is a hydrogen atom, an alkyl group which may be unsubstituted or substituted, unsubstituted or substituted Aryl group which may be substituted, halogen atom which may be unsubstituted or substituted, alkoxyl group which may be unsubstituted or substituted, carboxyl group which may be unsubstituted or substituted, unsubstituted or substituted An optionally substituted formyl group, an unsubstituted or substituted a Alkyloxycarbonyl group, aryloxycarbonyl group which may be unsubstituted or substituted, alkylcarbonyl group which may be unsubstituted or substituted, arylcarbonyl group which may be unsubstituted or substituted, or unsubstituted or substituted R 6 may be a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or optionally substituted aryl group, a halogen atom, an unsubstituted or substituted alkyl group. Good alkoxyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted formyl group, unsubstituted or substituted alkyloxycarbonyl group, unsubstituted or substituted Good aryloxycarbonyl group, unsubstituted or substituted There may be an alkylcarbonyl group, an even heterocyclic optionally be unsubstituted or substituted optionally aryl group or unsubstituted or substituted be)
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