RU2810077C1 - Use of dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate as an agent having antioxidant activity - Google Patents
Use of dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate as an agent having antioxidant activity Download PDFInfo
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- -1 dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate Chemical compound 0.000 title claims abstract description 18
- 230000003078 antioxidant effect Effects 0.000 title abstract description 13
- 239000003795 chemical substances by application Substances 0.000 title abstract 2
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DTDGAYDYOODVHD-UHFFFAOYSA-N dimethyl 4,5-dioxo-1-phenylpyrrole-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(N(C=1C(=O)OC)C1=CC=CC=C1)=O)=O DTDGAYDYOODVHD-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RWYJLUIRTJBSDS-UHFFFAOYSA-N n-hydroxy-4-methoxybenzenecarboximidoyl chloride Chemical compound COC1=CC=C(C(Cl)=NO)C=C1 RWYJLUIRTJBSDS-UHFFFAOYSA-N 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WIFCKLPZYYALGY-UHFFFAOYSA-N 1h-pyrrole-2,3-dione Chemical class O=C1NC=CC1=O WIFCKLPZYYALGY-UHFFFAOYSA-N 0.000 description 1
- WAFJZFSZIXSXKH-UHFFFAOYSA-N 5H-pyrrolo[3,4-d][1,2]oxazole Chemical compound c1noc2c[nH]cc12 WAFJZFSZIXSXKH-UHFFFAOYSA-N 0.000 description 1
- JSUVCAQGWVUMPD-QXUQJYLISA-N Arjuna Natural products O([C@H]([C@@H](O)C=O)[C@H]1[C@H](O)COC(=O)c2c(c(O)c(O)c(O)c2)-c2c(O)c(O)c3OC(=O)c4c(c(O)c(O)c5OC(=O)c2c3-c45)-c2c(O)c(O)c(O)cc2C(=O)O1)C(=O)c1cc(O)c(O)c(O)c1 JSUVCAQGWVUMPD-QXUQJYLISA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010957 regioselective [3+2] cycloaddition Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Abstract
Description
Изобретение относится к области фармакологии и медицины, а именно к применению индивидуального соединения диметил 3-(4-метоксифенил)-6-оксо-7-фенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-8,9-дикарбоксилата (1) формулыThe invention relates to the field of pharmacology and medicine, namely to the use of the individual compound dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8 -diene-8,9-dicarboxylate (1) formula
обладающего антиоксидантной активностью.possessing antioxidant activity.
Заявленное соединение диметил 3-(4-метоксифенил)-6-оксо-7-фенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-8,9-дикарбоксилат (1) и способ его синтеза известны из уровня техники. Соединение (1) получается в результате взаимодействия 4,5-диметоксикарбонил-1-фенил-1H-пиррол-2,3-диона (2) с 4-метоксифенилнитрилоксидом (3) [Moroz A.A. Regioselective [3+2] cycloaddition of nitrile oxides to 1H-pyrrole-2,3-diones: synthesis of spiro[pyrroledioxazoles] / A.A. Moroz, M.V. Dmitriev, A.N. Maslivets // Chemistry of Heterocyclic Compounds. - 2021. - V. 57. - №. 12. - P. 1230-1234. DOI: 10.1007/s10593-021-03047-6], согласно схеме, представленной ниже:The claimed compound is dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate (1) and the method for its synthesis is known from the prior art. Compound (1) is obtained by reacting 4,5-dimethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione (2) with 4-methoxyphenylnitrile oxide (3) [Moroz A.A. Regioselective [3+2] cycloaddition of nitrile oxides to 1H-pyrrole-2,3-diones: synthesis of spiro[pyrroledioxazoles] / A.A. Moroz, M.V. Dmitriev, A.N. Maslivets // Chemistry of Heterocyclic Compounds. - 2021. - V. 57. - No. 12. - P. 1230-1234. DOI: 10.1007/s10593-021-03047-6], according to the diagram presented below:
Из уровня техники также известно, что структурные аналоги заявляемого соединения - этил 3-арил-6-оксо-7,8-дифенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-9-карбоксилаты (4) общей формулыIt is also known from the prior art that structural analogues of the claimed compound are ethyl 3-aryl-6-oxo-7,8-diphenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-9 -carboxylates (4) of the general formula
где R=ОМе, Br,where R=ОМе, Br,
проявляют противомикробную активность [Патент RU 2763734 С1. Этил 3-арил-6-оксо-7,8-дифенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-9-карбоксилаты, обладающие противомикробной активностью / М.В. Дмитриев, А.И. Масливец, С.Ю. Баландина, А.А. Мороз; заявл. 23.06.2021; опубл. 30.12.2021. Бюл. №1].exhibit antimicrobial activity [Patent RU 2763734 C1. Ethyl 3-aryl-6-oxo-7,8-diphenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-dien-9-carboxylates with antimicrobial activity / M.V. Dmitriev, A.I. Maslivets, S.Yu. Balandina, A.A. Freezing; application 06/23/2021; publ. 12/30/2021. Bull. No. 1].
Антиоксидантные свойства диметил 3-(4-метоксифенил)-6-оксо-7-фенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-8,9-дикарбоксилата (1) или его близких аналогов не изучены. Из уровня техники можно выделить 5'-арил-2'-фенилспиро[3H-индол-3,3'(3'аН)-[2H]пирроло[3,4-d]изоксазол]-2,4',6'(1H,5'H,6'aH)-трионы (5) [Synthesis and evaluation of novel spiro[oxindole-isoxazolidine] derivatives as potent antioxidants / M. Kaur, B. Singh, B. Singh, A. Arjuna // Journal of Heterocyclic Chemistry. - 2017. - V. 54. -№. 2. - P. 1348-1354. DOI: 10.1002/jhet.2712], обладающие антиоксидантной активностью:Antioxidant properties of dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate (1) or its close analogues have not been studied. From the prior art, 5'-aryl-2'-phenylspiro[3H-indole-3,3'(3'aH)-[2H]pyrrolo[3,4-d]isoxazole]-2,4',6' can be isolated (1H,5'H,6'aH)-triones (5) [Synthesis and evaluation of novel spiro[oxindole-isoxazolidine] derivatives as potent antioxidants / M. Kaur, B. Singh, B. Singh, A. Arjuna // Journal of Heterocyclic Chemistry. - 2017. - V. 54. -No. 2. - P. 1348-1354. DOI: 10.1002/jhet.2712], which have antioxidant activity:
где R=Н, F, Cl, Br, I, Me, OMe, OH, C2H5.where R=H, F, Cl, Br, I, Me, OMe, OH, C 2 H 5 .
Целью изобретения является изыскание новых соединений, обладающих антиоксидантной активностью, что позволит расширить ассортимент потенциальных антиоксидантных препаратов.The purpose of the invention is to find new compounds with antioxidant activity, which will expand the range of potential antioxidant drugs.
Поставленная задача решается получением и исследованием антиоксидантной активности диметил 3-(4-метоксифенил)-6-оксо-7-фенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-8,9-дикарбоксилата (1).The problem is solved by obtaining and studying the antioxidant activity of dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9 -dicarboxylate (1).
Заявляемое соединение (1) синтезируют путем взаимодействия 4,5-диметоксикарбонил-1-фенил-1H-пиррол-2,3-диона (2) с 4-метоксифенилнитрилоксидом (3), образующимся in situ из 4-метокси-N-гидроксибензимидоил хлорида и триэтиламина, в соотношении 1:1 в среде безводного этилацетата с последующим выделением целевого продукта.The claimed compound (1) is synthesized by reacting 4,5-dimethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione (2) with 4-methoxyphenylnitrile oxide (3), formed in situ from 4-methoxy-N-hydroxybenzimidoyl chloride and triethylamine, in a 1:1 ratio in anhydrous ethyl acetate, followed by isolation of the target product.
Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.
Пример 1. Получение диметил 3-(4-метоксифенил)-6-оксо-7-фенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-8,9-дикарбоксилата (1).Example 1. Preparation of dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate (1 ).
К раствору 1.0 ммоль 4,5-диметоксикарбони-1-фенил-1H-пиррол-2,3-диона (2) в 4 мл безводного этилацетата последовательно добавляли 1.0 ммоль 4-метокси-N-гидроксибензимидоил хлорида (3) и 1.0 ммоль триэтиламина. Реакционную массу выдерживали при комнатной температуре в течение 24 ч, затем разбавляли 20 мл дихлорметана. Образовавшийся раствор переносили в делительную воронку и отмывали водой (3*10 мл). Органический слой сушили над Na2SO4. Растворители упаривали при пониженном давлении, остаток перекристаллизовывали из этилового спирта. Выход 41%, т.пл. 165-166°С (разл., EtOH).To a solution of 1.0 mmol of 4,5-dimethoxycarboni-1-phenyl-1H-pyrrole-2,3-dione (2) in 4 ml of anhydrous ethyl acetate, 1.0 mmol of 4-methoxy-N-hydroxybenzimidoyl chloride (3) and 1.0 mmol of triethylamine were successively added . The reaction mass was kept at room temperature for 24 hours, then diluted with 20 ml of dichloromethane. The resulting solution was transferred to a separatory funnel and washed with water (3*10 ml). The organic layer was dried over Na 2 SO 4 . The solvents were evaporated under reduced pressure, and the residue was recrystallized from ethyl alcohol. Yield 41%, mp. 165-166°C (dec., EtOH).
Соединение (1) C22H18N2O8.Compound (1) C 22 H 18 N 2 O 8 .
Найдено, %: С С 60.14; Н 4.09; N 6.36.Found, %: C C 60.14; H 4.09; N 6.36.
Вычислено, %: 60.28; Н 4.14; N 6.39.Calculated, %: 60.28; H 4.14; N 6.39.
Соединение (1) - бледно-желтое кристаллическое вещество, легкорастворимое в ДМСО, ДМФА, хлороформе, дихлорметане, трудно растворимое в ацетоне, спиртах, нерастворимое в воде и алканах. Устойчиво при хранении в обычных условиях.Compound (1) is a pale yellow crystalline substance, readily soluble in DMSO, DMF, chloroform, dichloromethane, sparingly soluble in acetone, alcohols, insoluble in water and alkanes. Stable when stored under normal conditions.
ИК спектр, ν, см-1: 1772, 1753, 1716, 1627, 1606. Спектр ЯМР 1H (400 МГц, CDCl3), δ, м.д.: 3.72 (3Н, с, ОМе), 3.79 (3Н, с, ОМе), 3.86 (3Н, с, ОМе), 6.94-6.98 (2Н, м, Н Ar), 7.28-7.32 (2Н, м, Н Ar), 7.41-7.49 (3Н, м, Н Ar), 7.74-7.80 (2Н, м, Н Ar). Спектр ЯМР 13С (101 МГц, CDCl3), 8, м.д.: 52.3, 53.7, 55.6, 104.9, 105.8, 114.2, 114.5 (2С), 126.4 (2С), 129.1 (2С), 129.6, 129.8 (2С), 132.6, 152.3, 159.0, 160.1, 160.7, 162.8, 168.9.IR spectrum, ν, cm -1 : 1772, 1753, 1716, 1627, 1606. NMR spectrum 1 H (400 MHz, CDCl 3 ), δ, ppm: 3.72 (3H, s, OMe), 3.79 (3H , s, OMe), 3.86 (3H, s, OMe), 6.94-6.98 (2H, m, H Ar), 7.28-7.32 (2H, m, H Ar), 7.41-7.49 (3H, m, H Ar) , 7.74-7.80 (2H, m, H Ar). 13 C NMR spectrum (101 MHz, CDCl 3 ), 8, ppm: 52.3, 53.7, 55.6, 104.9, 105.8, 114.2, 114.5 (2C), 126.4 (2C), 129.1 (2C), 129.6, 129.8 ( 2C), 132.6, 152.3, 159.0, 160.1, 160.7, 162.8, 168.9.
Пример 2. Исследование диметил 3-(4-метоксифенил)-6-оксо-7-фенил-1,4-диокса-2,7-диазаспиро[4.4]нон-2,8-диен-8,9-дикарбоксилата (1) на наличие антиоксидантной активности.Example 2: Study of dimethyl 3-(4-methoxyphenyl)-6-oxo-7-phenyl-1,4-dioxa-2,7-diazaspiro[4.4]non-2,8-diene-8,9-dicarboxylate (1 ) for the presence of antioxidant activity.
Антиоксидантная активность изучалась фотометрическим методом Ferric Reducing/Antioxidant Power (FRAP) с использованием о-фенантролина [K.I. Berker, K. Guclu, I. Tor, R. Apak // Talanta. - 2007. - V. 72. - P. 1157-1165; Т.Г. Цюпко, И.С. Петракова, Н.С. Бриленок, Н.А. Николаева, Д.А. Чупрынина, З.А. Темердашев, В.И. Вершинин // Аналитика и контроль. - 2011. - Т. 15. - №. 3.- С.287-298].Antioxidant activity was studied by the Ferric Reducing/Antioxidant Power (FRAP) photometric method using o-phenanthroline [K.I. Berker, K. Guclu, I. Tor, R. Apak // Talanta. - 2007. - V. 72. - P. 1157-1165; T.G. Tsyupko, I.S. Petrakova, N.S. Brilenok, N.A. Nikolaeva, D.A. Chuprynina, Z.A. Temerdashev, V.I. Vershinin // Analytics and control. - 2011. - T. 15. - No. 3.- P.287-298].
Фотометрический FRAP реагент был приготовлен смешиванием 15.0 мМ раствора офенантролина, 20.0 мМ раствора FeCl3 и 25.0 мМ ацетатного буферного раствора (рН 3.6) в объемном соотношении 1:1:10. Растворы (концентрация 15 мкмоль/мл) исследуемых соединений и эталонов (агидол-1, аскорбиновая кислота) в ДМСО в количестве 10 мкл добавлялись к FRAP реагенту (190 мкл) в лунки 96-луночного планшета. Реакционная смесь инкубировалась при 37°С в течение 1 ч. Оптическую плотность реакционных смесей измеряли при 510 нм. Калибровка проводилась по свежеприготовленному раствору соли Мора в ацетатном буфере (рН 3.6). Результаты исследований приведены в Таблице.The photometric FRAP reagent was prepared by mixing 15.0 mM ofenanthroline solution, 20.0 mM FeCl 3 solution and 25.0 mM acetate buffer solution (pH 3.6) in a volume ratio of 1:1:10. Solutions (concentration 15 µmol/ml) of the test compounds and standards (agidol-1, ascorbic acid) in DMSO in an amount of 10 µl were added to the FRAP reagent (190 µl) into the wells of a 96-well plate. The reaction mixture was incubated at 37°C for 1 hour. The optical density of the reaction mixtures was measured at 510 nm. Calibration was carried out using a freshly prepared solution of Mohr's salt in acetate buffer (pH 3.6). The research results are shown in the Table.
В результате исследования выявлено, что соединение (1) проявляет умеренный антиоксидантный эффект.The study revealed that compound (1) exhibits a moderate antioxidant effect.
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| RU2641904C2 (en) * | 2014-06-05 | 2018-01-23 | Чайна Петролеум Энд Кемикал Корпорейшн | Connection of spatially hindered phenol, its obtaining and its application as antioxidant |
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| EP0342483A1 (en) * | 1988-05-20 | 1989-11-23 | Ethyl Corporation | Antioxidant |
| RU2475052C2 (en) * | 2007-07-25 | 2013-02-20 | Трофо | Application of at least one derivative of cholest-4-en-3-one oxime as antioxidant |
| RU2398583C2 (en) * | 2008-10-23 | 2010-09-10 | Республиканское Унитарное производственное предприятие "Белмедпрепараты" | Antioxidant and antihypoxic agent of 6-methyl-2-ethyl-3-hydrohypyridine succinate |
| RU2428410C1 (en) * | 2009-12-28 | 2011-09-10 | Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУ ВПО ПГФА Росздрава) | Dimethyl 4-phenylethylamino-2-(4-methoxyphenyl)-6-hydroxy-6-methyl-3-cyclohexene-1,3-dicarboxylate exhibiting anti-inflammatory action |
| RU2641904C2 (en) * | 2014-06-05 | 2018-01-23 | Чайна Петролеум Энд Кемикал Корпорейшн | Connection of spatially hindered phenol, its obtaining and its application as antioxidant |
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