JPH03190881A - Benzyloxazopyrroloquinolines - Google Patents
BenzyloxazopyrroloquinolinesInfo
- Publication number
- JPH03190881A JPH03190881A JP32735089A JP32735089A JPH03190881A JP H03190881 A JPH03190881 A JP H03190881A JP 32735089 A JP32735089 A JP 32735089A JP 32735089 A JP32735089 A JP 32735089A JP H03190881 A JPH03190881 A JP H03190881A
- Authority
- JP
- Japan
- Prior art keywords
- agent
- benzyl
- salts
- promoting
- opq
- 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 abstract description 10
- 150000003839 salts Chemical class 0.000 claims description 7
- 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 29
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract description 14
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 230000001737 promoting effect Effects 0.000 abstract 4
- 208000002177 Cataract Diseases 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 208000019423 liver disease Diseases 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 23
- 229960005190 phenylalanine Drugs 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 150000003863 ammonium salts Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 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
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-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
- 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
- 159000000001 potassium salts Chemical class 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 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
- 238000001429 visible spectrum Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 150000008547 L-phenylalanines Chemical class 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
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000006378 damage Effects 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
- 239000008057 potassium phosphate buffer Substances 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
- 239000011734 sodium Substances 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
- 238000009423 ventilation Methods 0.000 description 1
- 239000003357 wound healing promoting agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ペンジルオキサシ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 penzyloxacypyrroloquinolines.
〔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−）リカルボキシーＩＨ−オキサゾ［５，４−ｈ］
−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.
10-) Recarboxy IH-oxazo[5,4-h]
Only -pyrrolo[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と記す）とフェニルアラニンとを反応
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
が得られることを見出し、本発明を完成した。[Means and effects for solving the problem] The present inventors,
In the course of intensive research into highly physiologically active oxazopyrroquinoline compounds, we discovered that a novel oxazopyrroquinoline compound can be obtained by reacting pyrroloquinoline quinone (hereinafter referred to as PQQ) with phenylalanine. The invention has been completed.
すなわち、本発明は、５−ベンジル−２，８゜１０−ト
リカルボキシ−ＩＨ−オキサゾ［５，４−ｈ］ −ピロ
ロ［２，３−ｆ］キノリンおよびその塩である。That is, the present invention is 5-benzyl-2,8°10-tricarboxy-IH-oxazo[5,4-h]-pyrrolo[2,3-f]quinoline and salts thereof.
しかるに、この化合物は、式
５−ベンジル−２，８，１０−トリカルボキシ−Ｌ Ｈ
−オキサゾ［５，４，−ｈ］−ピロロ［２３−ｆ］キノ
リン（以下 ベンジルＯＰＱ と記す）の塩、すなわ
ち、ベンジル○ＰＱ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（ベンジルＯＰＱおよびベンジルＯＰＱ
塩を総称して以下ベンジルＯＰＱ類と記すこともある）
。However, this compound has the formula 5-benzyl-2,8,10-tricarboxy-L H
-oxazo[5,4,-h]-pyrrolo[23-f]quinoline (hereinafter referred to as benzyl OPQ) salt, that is, benzyl○PQ salt, includes alkali metal salts, alkaline earth metal salts, ammonium salts and Substituted ammonium salts (benzyl OPQ and benzyl OPQ)
(Salts may be collectively referred to as benzyl 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.
本発明のベンジル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 benzyl OPQ salts of the present invention include sodium salts, potassium salts, magnesium salts, calcium salts, ammonium salts, trimethylammonium salts, triethylammonium salts, triethanolammonium salts, and the like.
本発明のベンジル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とフ
ェニルアラニンあるいはＰＱＱ塩とフェニルアラニンか
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 benzyl OPQs of the present invention include synthetic methods and fermentation methods using microorganisms, but the method of synthesizing from PQQ and phenylalanine or PQQ salt and phenylalanine is relatively simple and practical. .
ＰＱＱとフェニルアラニンあるいはＰＱＱ塩とフェニル
アラ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塩とを総称して以下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など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 phenylalanine or PQQ salt and phenylalanine, the PQQ or PQQ salt used (PQQ and PQQ salt are collectively referred to as PQQ)
) 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, trimethylammonium and triethylammonium salts, and triethanol. Examples include hydroxyalkyl-substituted ammonium salts such as ammonium salts.
また、フェニルアラニンは、Ｄ体、Ｌ体およびこれらの
混合物のいずれでもよい。Moreover, phenylalanine may be any of D-form, L-form and mixtures thereof.
これらのＰＱＱ類およびフェニルアラニンは、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 phenylalanine.
フェニルアラニンの使用量は、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。The amount of phenylalanine 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 amount 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. Typical 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、ｏ、 ｉ〜５
０ｍＭ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.
Generally unspecified, but in practice, usually o, i~5
0mM is preferred.
本発明におけるベンジル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 benzyl OPQs in the present invention, and for that purpose, it is necessary to supply oxygen to the reaction solution.
ベンジルＯＰＱ塩は、また一般にベンジルＯＰＱを含む
溶液に、目的とするベンジル○ＰＱ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。Benzyl OPQ salt can also generally be obtained by adding an alkali corresponding to the desired benzyl ○PQ salt to a solution containing benzyl OPQ.
このようにして得られた反応液からベンジル○ＰＱ類を
分離精製する方法としては種々ある。たとえば、ベンジ
ルＯＰＱ類を吸着する樹脂担体を用い央方法、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、ベンジルＯ
ＰＱ類を分離、精製することができる。There are various methods for separating and purifying benzyl○PQ from the reaction solution thus obtained. For example, there are central methods using resin carriers that adsorb benzyl OPQs, organic solvent extraction methods, precipitation methods, washing methods, and ultrafiltration methods.
By using these methods alone or in combination, benzyl O
PQs can be separated and purified.
そ
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。Since the compound of the present invention has the same skeletal structure as PQQ, 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−フェニルアラニン８．０ｇを蒸留水４００−に溶解
し、６Ｎ塩酸にてｐＨ４，０に調整してＬ−フェニルア
ラニン溶液を得た。Example 8.0 g of L-phenylalanine was dissolved in 400 g of distilled water, and the pH was adjusted to 4.0 with 6N hydrochloric acid to obtain an L-phenylalanine solution.
このＬ−フェニルアラニン溶液にＰ Ｑ Ｑ ８００ｍ
ｇを添加し、空気を通気しながら強く機械損はんしつつ
、３０°Ｃにて２６時間反応させた。この反応生成液を
６Ｎ塩酸にてｐＨ１，４に調整し、 ５°Ｃに冷却して
ベンジルＯＰＱを沈澱させた。P Q Q 800m to this L-phenylalanine solution
g was added thereto, and the mixture was allowed to react at 30° C. for 26 hours with air ventilation and strong mechanical damage. This reaction product solution was adjusted to pH 1.4 with 6N hydrochloric acid and cooled to 5°C to precipitate benzyl OPQ.
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 ＮａＯＨ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 adjusted to pH 8 with 5N NaOH.
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＋＋ｔ１２を加え十分に攪はんし
、ベンジル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++t12, an anion exchange carrier, was added to the obtained solution and thoroughly stirred. Benzyl OPQ was adsorbed onto this carrier, and then allowed to stand. The supernatant was removed and the carrier was separated.・Recovered.
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艷を流して洗浄した後、０．
４Ｍ食塩水５０００−を流し、引き続いてさらに０．５
Ｍ食塩水５０００＋ｕ９．０，６Ｍ食塩水５０００−の
順に流した。After washing the column with 200 liters of distilled water, the column was washed with 0.
4M saline solution 5000- was poured, followed by an additional 0.5
M saline solution 5000+u9.0 and 6M saline solution 5000- were poured in this order.
この時、反応液に含まれていたベンジルＯＰＱは０．５
Ｍ食塩水の溶出画分を中心に存在した。At this time, the benzyl OPQ contained in the reaction solution was 0.5
It was present mainly in the eluted fraction of M saline.
０．５Ｍ食塩水および０．６Ｍ食塩水のベンジルＯＰＱ
ジルＯＰＱ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℃で
乾燥して、７２４ｍｇのベンジルＯＰＱを得り。Benzyl OPQ in 0.5M saline and 0.6M saline
Zil OPQ was precipitated. The resulting precipitate was collected by centrifugation. After washing with IN hydrochloric acid and drying at about 70° C. under vacuum, 724 mg of benzyl OPQ was obtained.
得られたベンジルＯＰＱの色は、オレンジ色であり、２
４４〜２５０℃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 color of the obtained benzyl OPQ is orange, and 2
It gradually decomposed from 44 to 250°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、このベンジルＯＰＱの水溶液の色は、ベンジル○
ＰＱの濃度および水溶液のｐ Ｈによって異なるが、約
１．０ｍｇ／２のベンジルＯＰＱ水溶液は、水溶液のｐ
Ｈ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。In addition, the color of this aqueous solution of benzyl OPQ is
Although it varies depending on the concentration of PQ and the pH of the aqueous solution, a benzyl OPQ aqueous solution of about 1.0 mg/2 has a pH of about 1.0 mg/2.
When H was neutral to alkaline, the color was pale yellow, and when H was acidic, it was reddish and pale yellow.
次に、このベンジル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 values, IR spectrum, 'H-NMR spectrum, and visible/ultraviolet spectrum of this benzyl OPQ are shown.
１）元素分析値： Ｃ２２Ｈ１３Ｎ３０Ｔ・Ｈ２Ｏ（Ｍ
Ｗ ４４９．３７）
理論値（％）・Ｃ５８，８０Ｈ３，３６Ｎ ９．３５実
測値（％）：Ｃ５８，５２Ｈ３゜６１ Ｎ ９．１４２
）ＩＲスペクトル（ν□、値、 ｃｍ−’ ） ： （
ＫＢｒ）２７１０” ＝ ’、 ２４９０” ＝’、
１５７５ｂｒ＝’、 １４９０ｓｈ−’１１７０”、
９８０’、 ７１０’、 ６９０″、 ６６０”＝ ’
３ ） ’Ｈ−１１ＭＲスペクトル（δ値、 ｐｐｍ）
：（ＤＭＳＯ−ｄｅ、内部標準ＴＭＳ）
４．６７（ｓ、２Ｈ，Ｃｋ−ＣｅＨｓ）。1) Elemental analysis value: C22H13N30T・H2O(M
W 449.37) Theoretical value (%) C58,80H3,36N 9.35 Actual value (%): C58,52H3゜61 N 9.142
) IR spectrum (ν□, value, cm-'): (
KBr) 2710" = ', 2490"=',
1575br=',1490sh-'1170'',
980',710',690'',660''='
3) 'H-11MR spectrum (δ value, ppm)
: (DMSO-de, internal standard TMS) 4.67 (s, 2H, Ck-CeHs).
７、０２〜７．９０（ｍ、 ６Ｈ，ピロール環Ｃ−１４
，ＣＨ２−Ｃｅｋ）。7, 02-7.90 (m, 6H, pyrrole ring C-14
, CH2-Cek).
７、９６ （ｓ、 ＩＨ，ピリジン環Ｃ−１（）１２．
９５ （ｂｒｓ、ＩＨ，ピロール環Ｎ−Ｈ，）４）可視
・紫外部スペクトル（λｌｌ５ｘ値、 ｎｍ） ＋（１
０ｍＭリン酸カリウム緩衝液ｐＨ７，０）２５６．２７
３１１ｈ４１９
〔発明の効果〕
本発明の新規化合物は、新規なオキサゾピロロや７，７
化合物−ｃｂヨ、新、い、□ッ。□ヶとして、医薬ある
いは農薬としての用途が期待される。7,96 (s, IH, pyridine ring C-1()12.
95 (brs, IH, pyrrole ring N-H,)4) Visible/ultraviolet spectrum (λll5x value, nm) + (1
0mM potassium phosphate buffer pH 7,0) 256.27
311h419 [Effects of the Invention] The novel compounds of the present invention are novel oxazopyrrolo and 7,7
Compound-cb, new, □. □It is expected to be used as a medicine or agrochemical.
Claims (1)
オキサゾ［５，４−ｈ］−ピロロ［２，３−ｆ］キノリ
ンおよびその塩。5-benzyl-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 |
|---|---|---|---|
| JP32735089A JPH03190881A (en) | 1989-12-19 | 1989-12-19 | Benzyloxazopyrroloquinolines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32735089A JPH03190881A (en) | 1989-12-19 | 1989-12-19 | Benzyloxazopyrroloquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03190881A true JPH03190881A (en) | 1991-08-20 |
Family
ID=18198161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32735089A Pending JPH03190881A (en) | 1989-12-19 | 1989-12-19 | Benzyloxazopyrroloquinolines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03190881A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0670321A1 (en) * | 1994-03-03 | 1995-09-06 | Mitsubishi Gas Chemical Company, Inc. | Oxazopyrroloquinoline deivatives and use thereof |
-
1989
- 1989-12-19 JP JP32735089A patent/JPH03190881A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0670321A1 (en) * | 1994-03-03 | 1995-09-06 | Mitsubishi Gas Chemical Company, Inc. | Oxazopyrroloquinoline deivatives and use thereof |
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