RU2809147C1 - Use of 5-(4-methoxyphenyl)-4-spiro-2,4-dihydro-3h-pyrazol-3-ones as agents with antioxidant activities - Google Patents
Use of 5-(4-methoxyphenyl)-4-spiro-2,4-dihydro-3h-pyrazol-3-ones as agents with antioxidant activities Download PDFInfo
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- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- ASDRGEKUFQCMBN-UHFFFAOYSA-N 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1=NN=C(C=2C=CC(OC)=CC=2)O1 ASDRGEKUFQCMBN-UHFFFAOYSA-N 0.000 description 2
- -1 4-(4-Methoxyphenyl)-2,3-diazaspiro[4.4]non-3-en-1-one Chemical compound 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- RGSHEIWREAOYDZ-UHFFFAOYSA-N 4-ethyl-3-phenyl-1,4-dihydropyrazol-5-one Chemical compound CCC1C(=O)NN=C1C1=CC=CC=C1 RGSHEIWREAOYDZ-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-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
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 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
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000000126 in silico method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- BUTPBERGMJVRBM-UHFFFAOYSA-N methanol;methylsulfinylmethane Chemical compound OC.CS(C)=O BUTPBERGMJVRBM-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RNWRVPVPLQMTAP-UHFFFAOYSA-N methyl 1-bromocyclohexane-1-carboxylate Chemical compound COC(=O)C1(Br)CCCCC1 RNWRVPVPLQMTAP-UHFFFAOYSA-N 0.000 description 1
- YGWINKVROAENAL-UHFFFAOYSA-N methyl 1-bromocyclopentane-1-carboxylate Chemical compound COC(=O)C1(Br)CCCC1 YGWINKVROAENAL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
Abstract
Description
Изобретение относится к области органической химии, а именно к 5-(4-метоксифенил)-4-спиро-2,4-дигидро-3H-пиразол-3-онам формулы 1а, б:The invention relates to the field of organic chemistry, namely to 5-(4-methoxyphenyl)-4-spiro-2,4-dihydro-3H-pyrazol-3-ones of formula 1a, b:
обладающим антиоксидантной активностью, которые могут быть использованы в фармакологии.possessing antioxidant activity, which can be used in pharmacology.
Аналогом по структуре заявляемым соединениям является 3-фенил-4-этил-1H-пиразол-5(4H)-он, обладающий биологической активностью [R.V. Ragavan, К.М. Kumar, V. Vijayakumar, S. Sarveswari, S. Ramaiah, A. Anbarasu, S. Karthikeyan, P. Giridharan, N.S. Kumari / beta-Keto esters from ketones and ethyl chloroformate: a rapid, general, efficient synthesis of pyrazolones and their antimicrobial, in silico and in vitro cytotoxicity studies // Org Med Chem Lett. 2013. Vol.3. №1. P. 6. DOI: 10.1186/2191-2858-3-6], формулы: The structural analogue of the claimed compounds is 3-phenyl-4-ethyl-1H-pyrazol-5(4H)-one, which has biological activity [R.V. Ragavan, K.M. Kumar, V. Vijayakumar, S. Sarveswari, S. Ramaiah, A. Anbarasu, S. Karthikeyan, P. Giridharan, N.S. Kumari / beta-Keto esters from ketones and ethyl chloroformate: a rapid, general, efficient synthesis of pyrazolones and their antimicrobial, in silico and in vitro cytotoxicity studies // Org Med Chem Lett. 2013. Vol.3. No. 1. P. 6. DOI: 10.1186/2191-2858-3-6], formulas:
Задачей изобретения является изыскание в ряду 5-арил-4-замещенных-2,4-дигидро-3H-пиразол-3-онов новых соединений, обладающих биологической активностью и расширение арсенала средств воздействия на живой организм.The objective of the invention is to find new compounds among 5-aryl-4-substituted-2,4-dihydro-3H-pyrazol-3-ones that have biological activity and expand the arsenal of means of influencing a living organism.
Поставленная задача решается синтезом 5-метоксифенил-4-спиро-2,4-дигидро-3H-пиразол-3-онов 1а, б, которые обладают умеренной антиоксидантной активностью.This problem is solved by the synthesis of 5-methoxyphenyl-4-spiro-2,4-dihydro-3H-pyrazol-3-ones 1a, b, which have moderate antioxidant activity.
Синтезируют заявляемые соединения 1а, б путем взаимодействия 2,5-метоксифенил-1,3,4-оксадазола 2 с метил 1-бромциклоалканкарбоксилатами 3а, б и цинком в среде растворителя с последующим выделением целевых продуктов, по следующей схеме:The claimed compounds 1a, b are synthesized by reacting 2,5-methoxyphenyl-1,3,4-oxadazole 2 with methyl 1-bromocycloalkanecarboxylates 3a, b and zinc in a solvent, followed by isolation of the target products, according to the following scheme:
Процесс ведут при температуре 105-115°С, а в качестве растворителя используют толуол.The process is carried out at a temperature of 105-115°C, and toluene is used as a solvent.
Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.
Пример 1. 4-(4-Метоксифенил)-2,3-диазаспиро[4.4]нон-3-ен-1-он (1а).Example 1. 4-(4-Methoxyphenyl)-2,3-diazaspiro[4.4]non-3-en-1-one (1a).
К смеси 2,0 г измельченного в мелкую стружку цинка, каталитического количества сулемы, 2.82 г (0.01 моль) 2,5-бис(4-метоксифенил)-1,3,4-оксадиазола 2, 20 мл безводного толуола и 2 мл ГМФТА добавляли по каплям при перемешивании смесь 4.55 г (0.022 моль) метилового эфира 1-бромциклопентанкарбоновой кислоты 3а в 10 мл безводного толуола. Затем реакционную смесь кипятили 4 ч, охлаждали, декантировали, гидролизовали 5%-ным раствором уксусной кислоты, органический слой отделяли, из водного слоя продукты реакции дважды экстрагировали толуолом. После сушки органической фазы безводным сульфатом натрия толуол отгоняли, продукт дважды перекристаллизовывали из этанола. Выход 45%, Т. пл. 190-192°С.To a mixture of 2.0 g of finely ground zinc, a catalytic amount of sublimate, 2.82 g (0.01 mol) 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole 2, 20 ml of anhydrous toluene and 2 ml of HMPTA a mixture of 4.55 g (0.022 mol) of 1-bromocyclopentanecarboxylic acid methyl ester 3a in 10 ml of anhydrous toluene was added dropwise with stirring. Then the reaction mixture was boiled for 4 hours, cooled, decanted, hydrolyzed with a 5% solution of acetic acid, the organic layer was separated, and the reaction products were extracted twice from the aqueous layer with toluene. After drying the organic phase with anhydrous sodium sulfate, the toluene was distilled off, and the product was recrystallized twice from ethanol. Yield 45%, mp. 190-192°C.
Спектр ИК, v, см-1: 3168 (NH), 1691 (СО). Спектр ЯМР 1Н, δ, м.д.: 1.95-2.05 м (2Н), 2.10-2.21 м (6Н) [(СН2)4], 3.85 с (3Н, МеО), 6.93 д (2Наром., J 8.8 Гц), 7.68 д (2Наром., J 8.8 Гц) (4-МеОС6Н4), 8.65 с (1Р, NH).IR spectrum, v, cm -1 : 3168 (NH), 1691 (CO). 1H NMR spectrum, δ, ppm: 1.95-2.05 m (2H), 2.10-2.21 m (6H) [( CH2 ) 4 ], 3.85 s (3H, MeO), 6.93 d (2H arom ., J 8.8 Hz), 7.68 d (2H arom ., J 8.8 Hz) (4-MeOC 6H 4 ), 8.65 s (1P, NH).
Соединение 1а представляет собой белое кристаллическое вещество, легкорастворимое в ДМСО, хлороформе, ацетоне, трудно растворимое в спирте и алканах, нерастворимое в воде. Устойчиво при хранении в обычных условиях.Compound 1a is a white crystalline substance, readily soluble in DMSO, chloroform, acetone, sparingly soluble in alcohol and alkanes, insoluble in water. Stable when stored under normal conditions.
Пример 2. 4-(4-Метоксифенил)-2,3-диазаспиро[4.5]дец-3-ен-1-он (1б).Example 2. 4-(4-Methoxyphenyl)-2,3-diazaspiro[4.5]dec-3-en-1-one (1b).
К смеси 2,0 г измельченного в мелкую стружку цинка, каталитического количества сулемы, 2.82 г (0.01 моль) 2,5-бис(4-метоксифенил)-1,3,4-оксадиазола 2, 20 мл безводного толуола и 2 мл ГМФТА добавляли по каплям при перемешивании смесь 4.86 г (0.022 моль) метилового эфира 1-бромциклогексанкарбоновой кислоты 36 в 10 мл безводного толуола. Затем реакционную смесь кипятили 4 ч, охлаждали, декантировали, гидролизовали 5%-ным раствором уксусной кислоты, органический слой отделяли, из водного слоя продукты реакции дважды экстрагировали толуолом. После сушки органической фазы безводным сульфатом натрия толуол отгоняли, продукт дважды перекристаллизовывали из этанола. Выход 49%, Т.пл. 190-191°С.To a mixture of 2.0 g of finely ground zinc, a catalytic amount of sublimate, 2.82 g (0.01 mol) 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole 2, 20 ml of anhydrous toluene and 2 ml of HMPTA a mixture of 4.86 g (0.022 mol) of 1-bromocyclohexanecarboxylic acid methyl ester 36 in 10 ml of anhydrous toluene was added dropwise with stirring. Then the reaction mixture was boiled for 4 hours, cooled, decanted, hydrolyzed with a 5% solution of acetic acid, the organic layer was separated, and the reaction products were extracted twice from the aqueous layer with toluene. After drying the organic phase with anhydrous sodium sulfate, the toluene was distilled off, and the product was recrystallized twice from ethanol. Yield 49%, m.p. 190-191°C.
ИК спектр, v, см-1: 3198 (NH), 1685 (С=O). Спектр ЯМР 1Н, δ, м.д.: 1.24-2.34 м [10Н, (СН2)5], 3.84 с (3Н, ОСН3), 6.93 д (2Наром., J 8.7 Гц), 7.75 д (2Наром., J 8.7 Гц) (4-МеОС6Н4), 9.23 с (1Н, NH).IR spectrum, v, cm -1 : 3198 (NH), 1685 (C=O). 1H NMR spectrum, δ, ppm: 1.24-2.34 m [10H, ( CH2 ) 5 ], 3.84 s (3H, OCH3 ), 6.93 d (2H arom ., J 8.7 Hz), 7.75 d ( 2H arom ., J 8.7 Hz) (4-MeOC 6 H 4 ), 9.23 s (1H, NH).
Соединение 1б представляет собой белое кристаллическое вещество, легкорастворимое в ДМСО, хлороформе, ацетоне, трудно растворимое в спирте и алканах, нерастворимое в воде. Устойчиво при хранении в обычных условиях.Compound 1b is a white crystalline substance, readily soluble in DMSO, chloroform, acetone, sparingly soluble in alcohol and alkanes, insoluble in water. Stable when stored under normal conditions.
Пример 3. Исследование соединений (1а, б) на наличие антиоксидантной активности.Example 3. Study of compounds (1a, b) for the presence of antioxidant activity.
Антиоксидантная активность изучалась спектрофотометрическим методом по способности растворов исследуемых веществ улавливать ярко окрашенные радикалы 2,2-дифенил-1-пикрилгидразила (DPPH) [Moore J.С, Liangli L.Yu. P. 118-172. DOI: 10.1002/9780470228333.CH9 в [Wheat Antioxidants (ed. Liangli Yu). Wiley. 2007. DOI: 10.1002/9780470228333]].Antioxidant activity was studied by the spectrophotometric method by the ability of solutions of the studied substances to capture brightly colored 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals [Moore J.C, Liangli L.Yu. P. 118-172. DOI: 10.1002/9780470228333.CH9 in [Wheat Antioxidants (ed. Liangli Yu). Wiley. 2007. DOI: 10.1002/9780470228333]].
Фотометрический DPPH реагент содержал 0.2 мМ раствор DPPH в метаноле. Растворы (концентрация 15 мкмоль/мл) исследуемых соединений и эталонов (агидол-1, аскорбиновая кислота) в ДМСО в количестве 100 мкл добавлялись к DPPH реагенту (100 мкл) в лунки 96-луночного планшета. Реакционная смесь выдерживалась при 20°С в течение 20 мин. в темноте. Оптическую плотность реакционных смесей измеряли при 517 нм. Калибровка проводилась по свежеприготовленному раствору DPPH в смеси ДМСО-метанол, 1 к 1. Убыль радикала рассчитывали по формуле:The photometric DPPH reagent contained a 0.2 mM solution of DPPH in methanol. Solutions (concentration 15 µmol/ml) of the studied compounds and standards (agidol-1, ascorbic acid) in DMSO in an amount of 100 µl were added to the DPPH reagent (100 µl) into the wells of a 96-well plate. The reaction mixture was kept at 20°C for 20 minutes. In the dark. The optical density of the reaction mixtures was measured at 517 nm. Calibration was carried out using a freshly prepared DPPH solution in a DMSO-methanol mixture, 1 to 1. The loss of the radical was calculated using the formula:
Убыль радикала (%)=[(А0 - A1)/A0]⋅100, где А0 поглощение раствора DPPH без исследуемого образца, A1 поглощение раствора DPPH в присутствии исследуемого образца.Radical loss (%)=[(A 0 - A 1 )/A 0 ]⋅100, where A 0 is the absorption of the DPPH solution without the test sample, A 1 is the absorption of the DPPH solution in the presence of the test sample.
Результаты представлены в таблице.The results are presented in the table.
Как видно из таблицы, заявляемые соединения 1а, 6 проявляют умеренную антиоксидантную активность. Следовательно, заявляемые соединения могут найти применение в фармакологии.As can be seen from the table, the claimed compounds 1a, 6 exhibit moderate antioxidant activity. Consequently, the claimed compounds can find application in pharmacology.
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| WO2010055083A1 (en) * | 2008-11-14 | 2010-05-20 | Nycomed Gmbh | Novel pyrazolone-derivatives and their use as pd4 inhibitors |
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| WO2010055083A1 (en) * | 2008-11-14 | 2010-05-20 | Nycomed Gmbh | Novel pyrazolone-derivatives and their use as pd4 inhibitors |
Non-Patent Citations (1)
| Title |
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| Шушакова Е.Ю. и др., Взаимодействие метил 1-бромциклоалканкарбоксилатов с цинком и 2,5-диарил-1,3,4-оксадиазолами. Современные аспекты химии. Материалы IV молодежной школы-конференции, Пермь, 2017, с.57. Nikiforova Е.А. et al., Reaction of Reformatsky reagents with 2,5-diphenyl-1,3,4-oxadiazole. Mendeleev Communications, 2021, 31 (2), p.248-250. * |
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