JPH03190880A - 2-methylthioethyloxazopyrroloquinolines - Google Patents
2-methylthioethyloxazopyrroloquinolinesInfo
- Publication number
- JPH03190880A JPH03190880A JP32734989A JP32734989A JPH03190880A JP H03190880 A JPH03190880 A JP H03190880A JP 32734989 A JP32734989 A JP 32734989A JP 32734989 A JP32734989 A JP 32734989A JP H03190880 A JPH03190880 A JP H03190880A
- Authority
- JP
- Japan
- Prior art keywords
- agent
- methylthioethyl
- promoting
- methionine
- salts
- 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- MMXZSJMASHPLLR-UHFFFAOYSA-N pyrroloquinoline quinone Chemical compound C12=C(C(O)=O)C=C(C(O)=O)N=C2C(=O)C(=O)C2=C1NC(C(=O)O)=C2 MMXZSJMASHPLLR-UHFFFAOYSA-N 0.000 abstract description 27
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract description 10
- 229930182817 methionine Natural products 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 4
- 244000005700 microbiome Species 0.000 abstract description 3
- 208000030507 AIDS Diseases 0.000 abstract description 2
- 102100034343 Integrase Human genes 0.000 abstract description 2
- 241001465754 Metazoa Species 0.000 abstract description 2
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 230000007198 pollen germination Effects 0.000 abstract description 2
- 239000003357 wound healing promoting agent Substances 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract 4
- 208000002177 Cataract Diseases 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 208000019423 liver disease Diseases 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 2-methylthioethyl Chemical group 0.000 description 26
- 150000003863 ammonium salts Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 229940124428 anticataract agent Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Landscapes
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、２−メチルチオエチルオキサゾピロロキノリ
ン類に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to 2-methylthioethyloxazopyrroquinolines.
〔従来の技術、発明が解決しようとする問題点〕オキサ
ゾピロロキノリン化合物としては、今まで２． ８．
１０−トリカルボキシ−１Ｈ−オキサゾ［５，４−ｈコ
ーピロロ［２，３−ｆ］キノリンのみが知られているが
、その生理活性は、実用するにはまだ十分なものではな
い。そこで生理活性がよりすぐれているオキサゾピロロ
キノリン系化合物の開発が望まれていた。[Prior art and problems to be solved by the invention] Until now, oxazopyrroquinoline compounds have been classified into 2. 8.
Only 10-tricarboxy-1H-oxazo[5,4-h corpyrolo[2,3-f]quinoline is known, but its physiological activity is not yet sufficient for practical use. Therefore, it has been desired to develop oxazopyrroquinoline compounds that have better physiological activity.
〔問題点を解決するための手段、作用〕本発明者らは、
生理活性の高いオキサゾピロロキノリン系化合物につい
て鋭意研究を重ねた過程において、ピロロキノリンキノ
ン（以下 ＰＱＱ七記す）とメチオニンとを反応させる
ことにより新規なオキサゾピロロキノリン化合物が得う
れることを見出し、本発明を完成した。[Means and effects for solving the problem] The present inventors,
In the course of intensive research on highly physiologically active oxazopyrroquinoline compounds, we discovered that a new oxazopyrroquinoline compound could be obtained by reacting pyrroloquinoline quinone (hereinafter referred to as PQQ) with methionine. , completed the invention.
すなわち、本発明は５−（２−メチルチオエチル）−２
，８，１０−１−リカルボキシー１Ｈ−オキサゾ［５，
１−ｈコーピロロ［２，３−ｆ］キノリンおよびその塩
である。That is, the present invention provides 5-(2-methylthioethyl)-2
,8,10-1-licarboxy 1H-oxazo[5,
1-h Corpyrolo[2,3-f]quinoline and its salts.
しかるに、この化合物は、式 で表される。However, this compound has the formula It is expressed as
５−（２−メチルチオエチル）−２，８，１０トリカル
ボキシ−１Ｈ−オキサゾ［５，４，−ｈ、］−ピロロ［
２，ａ−ｆ］キノリン（以下 ２−メチルチオエチルＯ
ＰＱ と記す）の塩、すなわち、２−メチルチオエチ
ルＯＰＱ塩としては、アルカリ金属塩、アルカリ土類金
属塩、アンモニウム塩および置換アンモニウム塩などが
ある（２−メチルチオエチル○ＰＱおよび２−メチルチ
オエチルＯＰＱ塩を総称して以下２−メチルチオエチル
ＯＰＱ類と記すこともある）。5-(2-methylthioethyl)-2,8,10tricarboxy-1H-oxazo[5,4,-h,]-pyrrolo[
2,a-f]quinoline (hereinafter referred to as 2-methylthioethyl O
2-methylthioethyl OPQ salts include alkali metal salts, alkaline earth metal salts, ammonium salts and substituted ammonium salts (2-methylthioethyl○PQ and 2-methylthioethyl OPQ). The salts may be collectively referred to as 2-methylthioethyl OPQs below).
置換アンモニウム塩には、たとえば、アルキル置換アン
モニウム塩およびヒドロキシアルキル置換アンモニウム
塩などがある。Substituted ammonium salts include, for example, alkyl-substituted ammonium salts and hydroxyalkyl-substituted ammonium salts.
本発明の２−メチルチオエチルＯＰＱ塩の代表例として
は、ナトリウム塩、カリウム塩、マグネシウム塩、カル
シウム塩、アンモニウム塩、トリメチルアンモニウム塩
、トリエチルアンモニウム塩、トリエタノールアンモニ
ウム塩などがある。Representative examples of the 2-methylthioethyl OPQ salt of the present invention include sodium salt, potassium salt, magnesium salt, calcium salt, ammonium salt, trimethylammonium salt, triethylammonium salt, triethanolammonium salt, and the like.
本発明の２−メチルチオエチルＯＰＱ類を得る方法とし
ては、合成法および微生物を用いる発酵法などがあるが
、ＰＱＱとメチオニンあるいはＰＱＱ塩とメチオニンか
ら合成する方法が比較的簡単であり、しかも、実用的で
ある。Methods for obtaining the 2-methylthioethyl OPQs of the present invention include synthetic methods and fermentation methods using microorganisms, but the method of synthesizing from PQQ and methionine or PQQ salt and methionine is relatively simple and practical. It is true.
ＰＱＱとメチオニンあるいはＰＱＱ塩とメチオニンから
合成する場合には、使用されるＰＱＱまたはＰＱＱ塩（
ＰＱＱとＰＱＱ塩七を総称して以下ＰＱＱ類と記すこと
もある）は、発酵生産品あるいは合成品のいずれでも良
い。ＰＱＱ塩には、たとえば、ナトリウム塩およびカリ
ウム塩などのアルカリ金属塩、マグネシウム塩およびカ
ルシウム塩ナトのアルカリ土類金属塩、アンモニウム塩
、トリメチルアンモニウム塩およびトリエチルアンモニ
ウム塩などのアルキル置換アンモニウム塩ならびにトリ
エタノールアンモニウム塩などのヒドロキシアルキル置
換アンモニウム塩などがある。When synthesizing from PQQ and methionine or PQQ salt and methionine, the PQQ or PQQ salt used (
PQQ and PQQ salts (hereinafter sometimes referred to as PQQs) may be either fermented products or synthetic products. PQQ salts include, for example, alkali metal salts such as sodium and potassium salts, alkaline earth metal salts such as magnesium and calcium salts, alkyl-substituted ammonium salts such as ammonium salts, trimethylammonium salts and triethylammonium salts, and triethanolic salts. Examples include hydroxyalkyl-substituted ammonium salts such as ammonium salts.
また、メチオニンは、０体、Ｌ体およびこれらの混合物
のいずれでもよい。Further, methionine may be 0-form, L-form, or a mixture thereof.
これらのＰＱＱ類およびメチオニンは、いずれも市販品
を使用することができる。Commercially available products can be used for both of these PQQs and methionine.
＝３
メチオニンの使用量は、化学量論量以上であればよいが
、実用上、通常はＰＱＱ類に対して１モル倍以上、好ま
しくは１〜１０００モル倍程度とされる。=3 The amount of methionine used may be at least the stoichiometric amount, but in practice it is usually at least 1 mole, preferably about 1 to 1000 times the mole of PQQ.
この反応は溶媒を使用した液相で行われる。この溶媒の
代表例として水およびメタノールなどの低級脂肪族アル
コールなどがある。This reaction is carried out in the liquid phase using a solvent. Representative examples of this solvent include water and lower aliphatic alcohols such as methanol.
反応液中におけるＰＱＱ類の濃度範囲は、特に制限され
ず、溶媒の種類および反応条件などによって異なり、−
概に特定し得ないが、実用上、通常は、０．１〜５０ｍ
Ｍが好ましい。The concentration range of PQQs in the reaction solution is not particularly limited and varies depending on the type of solvent and reaction conditions.
Although it cannot be specified generally, in practice, it is usually 0.1 to 50 m.
M is preferred.
本発明における２−メチルチオエチルＯＰＱ類を得る反
応には酸素が必要であり、そのためには、反応液に酸素
を供給することが必要である。Oxygen is required for the reaction to obtain 2-methylthioethyl OPQs in the present invention, and for that purpose, it is necessary to supply oxygen to the reaction solution.
２−メチルチオエチルＯＰＱ塩は、また一般に２−メチ
ルチオエチルＯＰＱを含む溶液に、目的とする２−メチ
ルチオエチルＯＰＱ塩に対応するアルカリを添加するこ
とによっても得られる。2-Methylthioethyl OPQ salt can also generally be obtained by adding an alkali corresponding to the desired 2-methylthioethyl OPQ salt to a solution containing 2-methylthioethyl OPQ.
このようにして得られた反応液から２−メチルチオエチ
ルＯＰＱ類を分離精製する方法としては種々ある。たと
えば、２−メチルチオエチルＯＰる
Ｑ類を吸着する樹脂担体を用い売方法、有機溶媒抽出法
、沈澱法、洗浄法および限外ろ適法などがあり、これら
の方法を単独あるいは組み合わせて、２−メチルチオエ
チルＯＰＱ類を分離、精製することができる。There are various methods for separating and purifying 2-methylthioethyl OPQ from the reaction solution thus obtained. For example, there are methods using a resin carrier that adsorbs 2-methylthioethyl OP, organic solvent extraction method, precipitation method, washing method, and ultrafiltration method. Methylthioethyl OPQs can be separated and purified.
ン
本発明の化合物は、その骨格構造がＰＱＱと共通である
ことからＰＱＱと同様の生理活性を有し、ＰＱＱと同様
の用途、たとえば、微生物に対する生育促進剤、動物に
おける肝障害改善剤、組織修復促進作用による創傷癒合
剤、逆転写酵素阻害作用による抗エイズ剤および抗白内
障剤、植物における花粉発芽促進剤および花粉管伸長促
進剤などとして使用し得るものと推察される。The compound of the present invention has the same skeletal structure as PQQ, so it has the same physiological activity as PQQ, and can be used for the same purposes as PQQ, such as a growth promoter for microorganisms, an agent for improving liver damage in animals, and tissue. It is presumed that it can be used as a wound healing agent due to its repair-promoting effect, an anti-AIDS agent and anti-cataract agent due to its reverse transcriptase inhibitory effect, and a pollen germination promoter and pollen tube elongation promoter in plants.
以下、本発明を実施例によってさらに具体的に説明する
が、本発明はこれらの実施例に限定されるものではない
。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例
Ｌ−メチオニン７２ｇを蒸留水４００絨に溶解し、６Ｎ
塩酸にてｐＨ４，０に調整してＩ、−メチオニン溶液を
得た。Example L - Dissolve 72 g of methionine in 400 liters of distilled water and add 6N
The pH was adjusted to 4.0 with hydrochloric acid to obtain an I,-methionine solution.
このＩ、−メチオニン溶液にＰ Ｑ Ｑ ８００ｍｇを
添加し、空気を通気しながら強く機械損はんしつつ、３
０°Ｃにて２６時間反応させた。この反応生成液を６Ｎ
塩酸にてｐＨ１，５に調整し、 ５°Ｃに冷却して２−
メチルチオエチルＯＰＱを沈澱させた。800 mg of P Q Q was added to this I,-methionine solution, and the mixture was heated with strong mechanical damage while aerating the air for 3
The reaction was allowed to proceed at 0°C for 26 hours. This reaction product solution is 6N
Adjust the pH to 1.5 with hydrochloric acid, cool to 5°C, and
Methylthioethyl OPQ was precipitated.
この沈澱を遠心分離によって回収し、この沈澱に蒸留水
２５０−を加え、この液を５Ｎ Ｎａ１ｌ（にてｐＨ８
，１とし、沈澱を溶解した。This precipitate was collected by centrifugation, 250 ml of distilled water was added to this precipitate, and the solution was diluted with 1 liter of 5N Na (pH 8).
, 1 to dissolve the precipitate.
得られた溶液に陰イオン交換担体であるＤＥＡＥセファ
デックスＡ−２５５０−を加え十分に攪はんし、２−メ
チルチオエチルＯＰＱをこの担体に吸着させた後静置し
、上清を除いて、この担体を分離・回収した。DEAE Sephadex A-2550-, an anion exchange carrier, was added to the resulting solution and thoroughly stirred. After adsorbing 2-methylthioethyl OPQ to this carrier, it was allowed to stand, and the supernatant was removed. This carrier was separated and collected.
５０ｍｍφカラムに新しいＤＥＡＥ−セファデックスＡ
−２５７５−を充填し、その上に、回収した担体を充填
した。New DEAE-Sephadex A for 50mmφ column
-2575- was filled, and the recovered carrier was filled thereon.
このカラムに蒸留水２００−を流して洗浄した後、０．
４Ｍ食塩水４８００＋ｎ９を流し、引き続いてさらに０
．５Ｍ食塩水３０００ｍ９．０．６Ｍ食塩水２０００ｍ
！Ｑの順に流した。After washing the column with 200 ml of distilled water, 0.
Pour 4M saline solution 4800 + n9, then further 0
．． 5M saline solution 3000m9.0.6M saline solution 2000m
! I played them in Q order.
した。did.
５℃にて２−メチルチオエチル○ＰＱを沈澱させた。得
られた沈澱を遠心分離により回収し０．ＩＮ塩酸で洗浄
した後、真空下約７０°Ｃで乾燥して、 ４７０ｍｇの
２−メチルチオエチルＯＰＱを得た。2-Methylthioethyl○PQ was precipitated at 5°C. The resulting precipitate was collected by centrifugation. After washing with IN hydrochloric acid and drying at about 70°C under vacuum, 470 mg of 2-methylthioethyl OPQ was obtained.
得られた２−メチルチオエチル０ＰＱＯ色は、オレンジ
色であり、２５０〜２５８°Ｃから徐々に分解し、明確
な融点を示さなかった。また水に溶けやすく、中性下お
よびアルカリ性下では極めて溶けやすかった。また低級
アルコールにも溶けたがアセトンおよびジエチルエーテ
ルには溶けなかった。The obtained 2-methylthioethyl 0PQO color was orange, gradually decomposed from 250 to 258°C, and showed no clear melting point. It was also easily soluble in water, and extremely soluble under neutral and alkaline conditions. It was also soluble in lower alcohols, but not in acetone and diethyl ether.
また、この２−メチルチオエチルＯＰＱの水溶液の色は
、２−メチルチオエチルＯＰＱの濃度および水溶液のｐ
Ｈによって異なるが、約１０ｍｇ／ Ｑの２−メチルチ
オエチル○ＰＱ水溶液は、水溶液＝７−
のｐＨが中性からアルカリ性では淡黄色であり、酸性で
は赤みがかった淡黄色であった。The color of this aqueous solution of 2-methylthioethyl OPQ is determined by the concentration of 2-methylthioethyl OPQ and the p of the aqueous solution.
Although it varies depending on the pH, an aqueous solution of 2-methylthioethyl○PQ of about 10 mg/Q was pale yellow when the pH of the aqueous solution = 7- was neutral to alkaline, and was pale yellow with a reddish tinge when the pH was acidic.
次に、この２−メチルチオエチルＯＰＱの元素分析値、
ＩＲスペクトル、’Ｈ−ＮＭＲスペクトルおよび可視・
紫外部スペクトルを示す。Next, the elemental analysis value of this 2-methylthioethyl OPQ,
IR spectrum, 'H-NMR spectrum and visible/
The ultraviolet spectrum is shown.
１）元素分析値： Ｃ１Ｃ１３ＨＩ３Ｎ３０７Ｓ−Ｈ２
０（４３３Ｊ９）
理論値（％）：Ｃ４９，８８Ｈ３，４９Ｎ ９．７０実
測値（％）：Ｃ４９，６３Ｈ３，７７Ｎ ９．４９２）
ＩＲスペクトル（１／ＩＩＩＩＸ値、 Ｃｍ−’ ）：
（ＫＢｒ）２７７５”＝ｌ１２５００”＝’、１５７
５９．１５１０”＝’１１７５”、 ９７０“、８５０
’、 ７５０’、 ７２０”３） ’Ｈ−ＮＭＲスペク
トル （δ値、 ｐｐｍ） ：（ＤＭＳＯ−ｄ６、内部
標準＋ＴＭＳ）２、１３ （ｓ、 ３Ｈ，ＣＨ２−ＣＨ
２−３−Ｃｈ）。1) Elemental analysis value: C1C13HI3N307S-H2
0 (433J9) Theoretical value (%): C49,88H3,49N 9.70 Actual value (%): C49,63H3,77N 9.492)
IR spectrum (1/IIIX value, Cm-'):
(KBr)2775"=l12500"=', 157
59.1510"='1175", 970", 850
', 750', 720"3) 'H-NMR spectrum (δ value, ppm): (DMSO-d6, internal standard + TMS) 2, 13 (s, 3H, CH2-CH
2-3-Ch).
２．９８（ｔ、２８． ＣＨ２−Ｃｈ−３−ＣＨ３，Ｊ
＝７．７Ｈｚ）３、４５ （ｔ、 ２Ｈ，Ｃｊｌ−ＣＨ
２−３−ＣＨ３，Ｊ＝７．９Ｈｚ）７、２３ （ｄ、
１Ｈ，ピロール環Ｃ−用、 Ｊ＝２．０Ｈｚ）７、９９
（ｓ、 ＩＢ、ピリジン環Ｃ−旦）。2.98 (t, 28. CH2-Ch-3-CH3,J
=7.7Hz) 3, 45 (t, 2H, Cjl-CH
2-3-CH3, J = 7.9Hz) 7, 23 (d,
1H, for pyrrole ring C-, J=2.0Hz) 7, 99
(s, IB, pyridine ring C-dan).
１３、１４（ｂｒｓ、 １Ｈ，ピロール環Ｎ−旦、）一
４）可視・紫外部スペクトル（λｎａｘ値、 ｎｍ）
＋（１０ｍＭリン酸カリウム緩衝液ｐＨ７，０）２５６
、２７３”、 ４１８
〔発明の効果〕
として、医薬あるいは農薬としての用途が期待される。13, 14 (brs, 1H, pyrrole ring N-dan,)-4) Visible/ultraviolet spectrum (λnax value, nm)
+ (10mM potassium phosphate buffer pH 7,0) 256
, 273'', 418 [Effects of the Invention] Applications as medicines or agricultural chemicals are expected.
Claims (1)
ルボキシ−１Ｈ−オキサゾ［５，４−ｈ］−ピロロ［２
，３−ｆ］キノリンおよびその塩。5-(2-methylthioethyl)-2,8,10-tricarboxy-1H-oxazo[5,4-h]-pyrrolo[2
, 3-f] quinoline and its salts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32734989A JPH03190880A (en) | 1989-12-19 | 1989-12-19 | 2-methylthioethyloxazopyrroloquinolines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32734989A JPH03190880A (en) | 1989-12-19 | 1989-12-19 | 2-methylthioethyloxazopyrroloquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03190880A true JPH03190880A (en) | 1991-08-20 |
Family
ID=18198149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32734989A Pending JPH03190880A (en) | 1989-12-19 | 1989-12-19 | 2-methylthioethyloxazopyrroloquinolines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03190880A (en) |
-
1989
- 1989-12-19 JP JP32734989A patent/JPH03190880A/en active Pending
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