RU2809000C1 - Method of producing methyl 1-{[2-(2-chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cycloalkane-1-carboxylate - Google Patents
Method of producing methyl 1-{[2-(2-chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cycloalkane-1-carboxylate Download PDFInfo
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- methyl
- chlorophenyl
- hydrazinylidene
- chlorobenzoyl
- cycloalkane
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 title claims abstract description 7
- 125000000716 hydrazinylidene group Chemical group [*]=NN([H])[H] 0.000 title claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 33
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011701 zinc Substances 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 7
- HJRVKBPHIYZIJK-UHFFFAOYSA-N 2,5-bis(2-chlorophenyl)-1,3,4-oxadiazole Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)O1 HJRVKBPHIYZIJK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 150000004702 methyl esters Chemical class 0.000 claims abstract description 3
- 238000002955 isolation Methods 0.000 claims abstract 2
- 238000009835 boiling Methods 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 229940126601 medicinal product Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 13
- 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 9
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 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
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- -1 acyl hydrazones Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 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
- 239000003814 drug 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
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 238000003756 stirring Methods 0.000 description 2
- 229940099259 vaseline Drugs 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
- 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
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 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
- 230000004071 biological effect Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- BUTPBERGMJVRBM-UHFFFAOYSA-N methanol;methylsulfinylmethane Chemical compound OC.CS(C)=O BUTPBERGMJVRBM-UHFFFAOYSA-N 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
- 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
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Abstract
Description
Изобретение относится к области органической химии, а именно способу получения метил 1-{[2-(2-хлоробензоил)гидразинилиден](2-хлорофенил)метил}циклоалкан-1-карбоксилатов 1а, б формулы:The invention relates to the field of organic chemistry, namely to a method for producing methyl 1-{[2-(2-chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cycloalkane-1-carboxylates 1a, b of the formula:
Данные соединения могут быть применены в медицине, фармакологии, ветеринарии.These compounds can be used in medicine, pharmacology, and veterinary medicine.
Известны структурные аналоги заявляемых соединений, обладающие биологической активностью [J.P.M. R.F.M. Frade, F.M.F. Santos, J.A.S. Coelho, C.A.M. Afonso, P.M.P. Gois, A.F. Trindade /NHC catalysed direct addition of HMF to diazo compounds: synthesis of acyl hydrazones with antitumor activity // RSC Adv. - 2014. - Vol. 4. - №55. - P. 29352-29356. DOI: 10.1039/c4ra03710 с]. Синтез структурных аналогов осуществляется по следующей схеме:Structural analogs of the claimed compounds are known that have biological activity [JPM RFM Frade, FMF Santos, JAS Coelho, CAM Afonso, PMP Gois, AF Trindade /NHC catalysed direct addition of HMF to diazo compounds: synthesis of acyl hydrazones with antitumor activity // RSC Adv. - 2014. - Vol. 4. - No. 55. - P. 29352-29356. DOI: 10.1039/c4ra03710 p]. The synthesis of structural analogues is carried out according to the following scheme:
К недостаткам данного способа относится невозможность получения 1-{[2-(2-хлоробензоил)гидразинилиден](2-хлорофенил)метил}циклоалкан-1-карбоксилатов. Также способ синтеза структурных аналогов предполагает необходимость работы в инертной атмосфере аргона.The disadvantages of this method include the impossibility of obtaining 1-{[2-(2-chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cycloalkane-1-carboxylates. Also, the method for synthesizing structural analogues requires working in an inert atmosphere of argon.
Задачей изобретения является разработка простого способа синтеза неописанных в литературе 1-{[2-(2-хлоробензоил)гидразинилиден](2-хлорофенил)метил}циклоалкан-1-карбоксилатов 1а, б.The objective of the invention is to develop a simple method for the synthesis of 1-{[2-(2-chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cycloalkane-1-carboxylates 1a, b, which are not described in the literature.
Поставленная задача достигается путем кипячения 2,5-ди(2-хлорфенил)-1,3,4-оксадиазола 2 с метиловыми эфирами 1-бромциклоалканкарбоновых кислот 3а, б и цинком в среде толуола с последующей обработкой реакционной массы и выделением целевых продуктов 1а, б.The goal is achieved by boiling 2,5-di(2-chlorophenyl)-1,3,4-oxadiazole 2 with methyl esters of 1-bromocycloalkanecarboxylic acids 3a, b and zinc in toluene, followed by processing the reaction mass and isolating the target products 1a, b.
Из патентной и технической литературы не были выявлены способы получения, имеющие сходные признаки с заявленным способом, а именно, не использовались исходные продукты, растворитель, в котором проходит реакция, на основании чего можно сделать вывод о соответствии заявленного технического решения критерию «новизна» и «изобретательский уровень».From the patent and technical literature, no production methods were identified that have similar characteristics to the claimed method, namely, the starting products and the solvent in which the reaction takes place were not used, on the basis of which it can be concluded that the claimed technical solution meets the criteria of “novelty” and “ inventive step."
Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.
Пример 1. 1-{[2-(2-Хлоробензоил)гидразинилиден](2-хлорофенил)метил}циклопентан-1-карбоксилат 1а.Example 1. 1-{[2-(2-Chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cyclopentane-1-carboxylate 1a.
К смеси 2,0 г измельченного в мелкую стружку цинка, каталитического количества сулемы, 2 г (0,0069) моль 2,5-бис(2-хлорфенил)-1,3,4-оксадиазола 2, 20 мл безводного толуола и 2 мл ГМФТА добавляли по каплям при кипячении и перемешивании смесь 3.13 г (0,0151 моль) метил 1-бромциклопентанкарбоксилата 3а в 10 мл безводного толуола. Затем реакционную смесь кипятили 4 ч, охлаждали, декантировали с избытка цинка, 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 2.33 г (81%), т.пл. 144-145°С.To a mixture of 2.0 g of finely ground zinc, a catalytic amount of sublimate, 2 g (0.0069) mol of 2,5-bis(2-chlorophenyl)-1,3,4-oxadiazole 2, 20 ml of anhydrous toluene and 2 ml of HMPTA was added dropwise while boiling and stirring to a mixture of 3.13 g (0.0151 mol) of methyl 1-bromocyclopentanecarboxylate 3a in 10 ml of anhydrous toluene. Then the reaction mixture was boiled for 4 hours, cooled, decanted from excess zinc, 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 2.33 g (81%), m.p. 144-145°C.
Выделенное соединение 1а представляет собой белое кристаллическое вещество, легкорастворимое в хлороформе, ДМСО, ДМФА, растворимое в ацетоне, труднорастворимое в спирте, алканах и ароматических углеводородах, нерастворимое в воде. Устойчиво при хранении в обычных условиях.The isolated compound 1a is a white crystalline substance, readily soluble in chloroform, DMSO, DMF, soluble in acetone, sparingly soluble in alcohol, alkanes and aromatic hydrocarbons, insoluble in water. Stable when stored under normal conditions.
ИК спектр соединения (1а) снят в виде пасты в вазелиновом масле (ν, см-1): 3152 (NH), 1734, 1725, 1676, 1663(СО), 1621 (C=N).The IR spectrum of compound (1a) was taken as a paste in vaseline oil (ν, cm -1 ): 3152 (NH), 1734, 1725, 1676, 1663 (CO), 1621 (C=N).
Спектр ЯМР 1Н соединения (1а) снят в растворе CDCl3 при частоте 400 МГц δ, м.д.: 1.46-1.58 м (2Н), 1.65-1.84-2.57 м (2Н), 1.90-2.15 м (3Н), 2.22-2.55 м (1H) [(СН2)4], 3.49 с (2.1Н, МеО), 3.71 с (0.9Н, МеО), 7.15-7.85 м [8Н, 2 (2-ClC6H4)], 8.18 с (0.7Н, NH), 8.89 с (0.3Н, NH). 1H NMR spectrum of compound (1a) was recorded in CDCl 3 solution at a frequency of 400 MHz δ, ppm: 1.46-1.58 m (2H), 1.65-1.84-2.57 m (2H), 1.90-2.15 m (3H), 2.22-2.55 m (1H) [( CH2 ) 4 ], 3.49 s (2.1H, MeO), 3.71 s (0.9H, MeO), 7.15-7.85 m [8H, 2 (2- ClC6H4 ) ] , 8.18 s (0.7H, NH), 8.89 s (0.3H, NH).
Спектр ЯМР 13С соединения (1а) снят в растворе CDCl3 при частоте 100 МГц δ, м.д.: 24.1, 24.2, 24.6, 34.0, 34.4, 35.2, 36.0, 52.2, 52.5, 62.4, 126.4, 127.4, 127.9, 129.0, 129.4, 129.7, 130.6, 130.7, 131.5, 132.0, 133.0, 135.2, 151.3, 155.3, 169.4, 174.3, 174.3. 13 C NMR spectrum of compound (1a) was recorded in CDCl 3 solution at a frequency of 100 MHz δ, ppm: 24.1, 24.2, 24.6, 34.0, 34.4, 35.2, 36.0, 52.2, 52.5, 62.4, 126.4, 127.4, 127. 9, 129.0, 129.4, 129.7, 130.6, 130.7, 131.5, 132.0, 133.0, 135.2, 151.3, 155.3, 169.4, 174.3, 174.3.
Соединение (1a) C21H20Cl2N2O3. Найдено, %: С 60.26; Н 4.64; N 6.49. Вычислено, %: С 60.15; Н 4.81; N 6.68.Compound (1a) C 21 H 20 Cl 2 N 2 O 3 . Found, %: C 60.26; H 4.64; N 6.49. Calculated, %: C 60.15; H 4.81; N 6.68.
Пример 2. 1-{[2-(2-Хлоробензоил)гидразинилиден](2-хлорофенил)метил}циклогексан-1-карбоксилат 1б.Example 2. 1-{[2-(2-Chlorobenzoyl)hydrazinylidene](2-chlorophenyl)methyl}cyclohexane-1-carboxylate 1b.
К смеси 2,0 г измельченного в мелкую стружку цинка, каталитического количества сулемы, 2 г (0,0069) моль 2,5-бис(2-хлорфенил)-1,3,4-оксадиазола 2, 20 мл безводного толуола и 2 мл ГМФТА добавляли по каплям при кипячении и перемешивании смесь 3.34 г (0,0151 моль) метил 1-бромциклогексанкарбоксилата 3б в 10 мл безводного толуола. Затем реакционную смесь кипятили 4 ч, охлаждали, декантировали с избытка цинка, 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 93 (%),т.пл. 120-122°С.To a mixture of 2.0 g of finely ground zinc, a catalytic amount of sublimate, 2 g (0.0069) mol of 2,5-bis(2-chlorophenyl)-1,3,4-oxadiazole 2, 20 ml of anhydrous toluene and 2 ml of HMPTA was added dropwise while boiling and stirring to a mixture of 3.34 g (0.0151 mol) of methyl 1-bromocyclohexanecarboxylate 3b in 10 ml of anhydrous toluene. Then the reaction mixture was boiled for 4 hours, cooled, decanted from excess zinc, 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 93 (%), m.p. 120-122°C.
Выделенное соединение 1б белое кристаллическое вещество, легкорастворимое в хлороформе, ДМСО, ДМФА, растворимое в ацетоне, труднорастворимое в спирте, алканах и ароматических углеводородах, нерастворимое в воде. Устойчиво при хранении в обычных условиях.The isolated compound 1b is a white crystalline substance, readily soluble in chloroform, DMSO, DMF, soluble in acetone, sparingly soluble in alcohol, alkanes and aromatic hydrocarbons, insoluble in water. Stable when stored under normal conditions.
ПК спектр соединения (1б) снят в виде пасты в вазелиновом масле (см-1): 3164 (NH), 1738, 1673, 1665 (СО), 1615 (C=N).The PC spectrum of compound (1b) was taken as a paste in vaseline oil (cm -1 ): 3164 (NH), 1738, 1673, 1665 (CO), 1615 (C=N).
Спектр ЯМР 1Н соединения (3б) снят в растворе CDCl3 при частоте 400 МГц δ, м.д.: 0.94-1.82 м (8Н), 2.01-2.57-2.40 м (2Н) [(СН2)5], 3.36 с (2.1Н, МеО), 3.63 с (0.9Н, МеО), 7.02 дд (1H, J 7.4 Гц, 1.9 Гц) 7.22-7.78 м [7Н, 2 (2-ClC6H4)], 8.06 с (0.7Н, NH), 8.80 с (0.3Н, NH). 1H NMR spectrum of compound (3b) was recorded in CDCl 3 solution at a frequency of 400 MHz δ, ppm: 0.94-1.82 m (8H), 2.01-2.57-2.40 m (2H) [(CH 2 ) 5 ], 3.36 s (2.1H, MeO), 3.63 s (0.9H, MeO), 7.02 dd (1H, J 7.4 Hz, 1.9 Hz) 7.22-7.78 m [7H, 2 (2-ClC 6 H 4 )], 8.06 s ( 0.7H, NH), 8.80 s (0.3H, NH).
Спектр ЯМР 13С соединения (1б) снят в растворе CDCl3 при частоте 100 МГц δ, м.д.: 23.0, 23.1, 25.1, 32.1, 32.3, 33.2, 51.7, 55.5, 126.3, 127.5, 128.8, 129.2, 129.9, 130.4, 130.6, 131.3, 131.4, 131.9, 132.8, 135.0, 152.7, 169.3, 172.8. 13 C NMR spectrum of compound (1b) was recorded in CDCl 3 solution at a frequency of 100 MHz δ, ppm: 23.0, 23.1, 25.1, 32.1, 32.3, 33.2, 51.7, 55.5, 126.3, 127.5, 128.8, 129.2, 12 9.9, 130.4, 130.6, 131.3, 131.4, 131.9, 132.8, 135.0, 152.7, 169.3, 172.8.
Соединение (1б) C22H22Cl2N2O3. Найдено, %: С 61.16; Н 5.24; N 6.39. Вычислено, %: С 60.98; Н 5.12; N 6.46.Compound (1b) C 22 H 22 Cl 2 N 2 O 3 . Found, %: C 61.16; H 5.24; N 6.39. Calculated, %: C 60.98; H 5.12; N 6.46.
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) [Methods for Antioxidant Capacity Estimation of Wheat and Wheat-Based Food Products / J. Moore, L. Yu // Wheat Antioxidants - Wiley, 2007. - 118-172. DOI: 10.1002/9780470228333.CH9; Wheat Antioxidants (ed. Liangli Yu). Wiley. 2007. DOI: 10.1002/9780470228333].Antioxidant activity was studied spectrophotometrically by the ability of solutions of the studied substances to capture brightly colored 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals [Methods for Antioxidant Capacity Estimation of Wheat and Wheat-Based Food Products / J. Moore, L. Yu // Wheat Antioxidants - Wiley, 2007. - 118-172. DOI: 10.1002/9780470228333.CH9; 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 исследований приведены в Таблице 1.The research results are shown in Table 1.
В результате исследования выявлено, что соединения (1а, б) проявляют умеренную антиоксидантную активность в отношении свободного радикала DPPH.The study revealed that compounds (1a, b) exhibit moderate antioxidant activity against the free radical DPPH.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1237661A1 (en) * | 1984-10-23 | 1986-06-15 | Институт химии им.В.И.Никитина | Method of producing acyl hydrazones of chloracetate aldehyde |
| CN111423339A (en) * | 2020-05-21 | 2020-07-17 | 宁夏师范学院 | Schiff base zinc ion fluorescent probe compound and synthesis and application thereof |
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1237661A1 (en) * | 1984-10-23 | 1986-06-15 | Институт химии им.В.И.Никитина | Method of producing acyl hydrazones of chloracetate aldehyde |
| CN111423339A (en) * | 2020-05-21 | 2020-07-17 | 宁夏师范学院 | Schiff base zinc ion fluorescent probe compound and synthesis and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| J.P.M. Antônio et al. / NHC catalysed direct addition of HMF to diazo compounds: synthesis of acyl hydrazones with antitumor activity / RSC Adv. - 2014. - Vol. 4. - No 55. - P. 29352-29356. * |
| Sevim Rollas, Sevgi Karakuş /The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones / Marmara Pharmaceutical Journal 16: 2012, р. 120-133. * |
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