RU2809149C1 - USE OF 5-(4-CHLOROPHENYL)-N-(3-CYANO-4,5,6,7-TETRAHYDROBENZO[b]THIOPHEN-2-YL)-1-ETHYL-1H-PYRAZOLE-3-CARBOXAMIDE AS AN ANTIMICROBIAL AGENT - Google Patents
USE OF 5-(4-CHLOROPHENYL)-N-(3-CYANO-4,5,6,7-TETRAHYDROBENZO[b]THIOPHEN-2-YL)-1-ETHYL-1H-PYRAZOLE-3-CARBOXAMIDE AS AN ANTIMICROBIAL AGENT Download PDFInfo
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- RU2809149C1 RU2809149C1 RU2023107969A RU2023107969A RU2809149C1 RU 2809149 C1 RU2809149 C1 RU 2809149C1 RU 2023107969 A RU2023107969 A RU 2023107969A RU 2023107969 A RU2023107969 A RU 2023107969A RU 2809149 C1 RU2809149 C1 RU 2809149C1
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- chlorophenyl
- tetrahydrobenzo
- pyrazole
- thiophen
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- -1 5-(4-CHLOROPHENYL)-N-(3-CYANO-4,5,6,7-TETRAHYDROBENZO[b]THIOPHEN-2-YL)-1-ETHYL-1H-PYRAZOLE-3-CARBOXAMIDE Chemical compound 0.000 title claims abstract description 9
- 239000004599 antimicrobial Substances 0.000 title claims abstract 3
- 229940125904 compound 1 Drugs 0.000 abstract description 8
- 230000000845 anti-microbial effect Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 2
- 229960000969 phenyl salicylate Drugs 0.000 description 2
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Abstract
Description
Изобретение относится к области органической химии, к новым биологически активным производным пиразолкарбоновых кислот, а именно к 5-(4-хлорфенил)-N-(3-циано-4,5,6,7-тетрагидробензо[b]тиофен-2-ил)-1-этил-1H-пиразол-3-карбоксамиду формулы 1:The invention relates to the field of organic chemistry, to new biologically active derivatives of pyrazolecarboxylic acids, namely 5-(4-chlorophenyl)-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl )-1-ethyl-1H-pyrazole-3-carboxamide of formula 1:
обладающего противомикробной активностью, что позволяет предположить его использование в медицине в качестве лекарственного средства с противомикробными свойствами.possessing antimicrobial activity, which suggests its use in medicine as a drug with antimicrobial properties.
Наиболее близким по структуре соединением можно считать 3-(4-хлорфенил)-N-фенил-1Н-пиразол-5-краоксамид, но для него было показано отсутствие противомикроной активности [Ghasempour L. et al. Preparation of New Spiropyrazole, Pyrazole and Hydantoin Derivatives and Investigation of Their Antioxidant and Antibacterial Activities // Chemistry & Biodiversity. - 2021. - T. 18. - №. 9. - C. e2100197].The closest compound in structure can be considered 3-(4-chlorophenyl)-N-phenyl-1H-pyrazole-5-craoxamide, but it has been shown to lack antimicron activity [Ghasempour L. et al. Preparation of New Spiropyrazole, Pyrazole and Hydantoin Derivatives and Investigation of Their Antioxidant and Antibacterial Activities // Chemistry & Biodiversity. - 2021. - T. 18. - No. 9. - C. e2100197].
Эталоном сравнения был выбран фенилсалицилат формулы 2:Phenyl salicylate of formula 2 was chosen as the standard of comparison:
который широко применяется в лечебной практике, и являются аналогами по действию [Машковский М.Д. Лекарственные средства. - 16-е изд., перераб., испр. и доп. - М.: ООО «Новая волна», 2010. - с. 472].which is widely used in medical practice, and are analogues in action [Mashkovsky M.D. Medicines. - 16th ed., revised, corrected. and additional - M.: New Wave LLC, 2010. - p. 472].
Задачей изобретения является поиск в ряду производных веществ с выраженным противомикробным и действием, и низкой токсичностью.The objective of the invention is to search in a series of derivatives for substances with a pronounced antimicrobial effect and low toxicity.
Поставленная задача достигается получением 5-(4-хлорфенил)-N-(3-циано-4,5,6,7-тетрагидробензо[b]тиофен-2-ил)-1-этил-1Н-пиразол-3-карбоксамида, который обладает противомикробной активностью.The goal is achieved by obtaining 5-(4-chlorophenyl)-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-1-ethyl-1H-pyrazole-3-carboxamide, which has antimicrobial activity.
Заявляемое соединение 1 синтезируют в две стадии из 2-{[3-Оксо-5-(4-хлорфенил)-2(3Н)-фуранилиден]амино}-4,5,6,7-тетрагидробензо[b]тиофен-3-карбонитрила и этилгидразина по схеме.The claimed compound 1 is synthesized in two stages from 2-{[3-Oxo-5-(4-chlorophenyl)-2(3H)-furanylidene]amino}-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carbonitrile and ethylhydrazine according to the scheme.
Пример 1. Смесь 0.368 г (1 ммоль) 2-{[3-Оксо-5-(4-хлорфенил)-2(3Н)-фуранилиден]амино}-4,5,6,7-тетрагидробензо[b]тиофен-3-карбонитрила и 0,06 г (1 ммоль) этилгидразина в 10 мл абсолютного толуола перемешивают на магнитной мешалке при температуре 110°С в течение 3 часов. После чего реакционную смесь охлаждают, выпавший осадок отфильтровывают и перекристаллизовывают из уксусной кислоты получая 0,36 г (87%) 5-(4-хлорфенил)-N-(3-циано-4,5,6,7-тетрагидробензо[b]тиофен-2-ил)-1-этил-1Н-пиразол-3-карбоксамида в виде белых кристаллов. Т.пл. 284-285°С (Уксусная кислота). Спектр ЯМР 1Н (400 МГц, DMSO-d6), d, м.д.: 1.38 т (3Н, СН3, J 7.2 Гц), 1.79 м (4Н, СН2), 2.52 м (2Н, СН2), 2.65 м (2Н, СН2), 4.27 к (2Н, СН2, J 7.2 Гц), 7.00 с (1Н, СН) 7.30-7.74 гр с. (4Наром), 10.92 с (1Н, NH). Спектр ЯМР 13С (101 МГц, DMSO-d6), d, м.д.:. 15.1, 21.6, 22.5, 23.4, 23.5, 45.1, 96.3,107.7,114.1, 127.9, 128.7, 128.9, 130.5, 131.2, 134.0, 143.3, 143.5, 145.7, 158.8.Example 1. A mixture of 0.368 g (1 mmol) 2-{[3-Oxo-5-(4-chlorophenyl)-2(3H)-furanylidene]amino}-4,5,6,7-tetrahydrobenzo[b]thiophene- 3-carbonitrile and 0.06 g (1 mmol) of ethylhydrazine in 10 ml of absolute toluene are stirred on a magnetic stirrer at a temperature of 110°C for 3 hours. After which the reaction mixture is cooled, the precipitate that forms is filtered off and recrystallized from acetic acid to obtain 0.36 g (87%) 5-(4-chlorophenyl)-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophen-2-yl)-1-ethyl-1H-pyrazole-3-carboxamide in the form of white crystals. T.pl. 284-285°C (Acetic acid). 1H NMR spectrum (400 MHz, DMSO-d 6 ), d, ppm: 1.38 t (3H, CH 3 , J 7.2 Hz), 1.79 m (4H, CH 2 ), 2.52 m (2H, CH 2 ), 2.65 m (2H, CH 2 ), 4.27 k (2H, CH 2 , J 7.2 Hz), 7.00 s (1H, CH) 7.30-7.74 g s. (4H arom ), 10.92 s (1H, NH). 13 C NMR spectrum (101 MHz, DMSO-d 6 ), d, ppm:. 15.1, 21.6, 22.5, 23.4, 23.5, 45.1, 96.3,107.7,114.1, 127.9, 128.7, 128.9, 130.5, 131.2, 134.0, 143.3, 143.5, 145.7, 158. 8.
Пример 2. Определение антимикробной активности проводили методом двукратных серийных разведений [Першин Г.Н. «Методы экспериментальной химиотерапии, 1971, с. 109] на музейных тест - культурах: Staphylococcus aurous, штамм 906; Escherichia coli, штамм 1257 (ФГБУ «Научный центр экспертизы средств медицинского применения», г. Москва). В опытах использовали 18 часовые агаровые тест - культуры (5*105 микробных тел в 1 мл среды). Для исследования брали растворы соединения 1 в диметилформамиде (ДМФА). Максимальная из испытанных концентраций была 1000 мкг/мл. Пробирки инкубировали при 37°C с последующим высевом через 20 часов и 7 суток в пробирки со скошенным мясопептонным агаром. Учет результатов проводили по наличию и характерному росту культур микроорганизмов на питательной среде.Example 2. Determination of antimicrobial activity was carried out by the method of two-fold serial dilutions [Pershin G.N. “Methods of experimental chemotherapy, 1971, p. 109] on museum test cultures: Staphylococcus aurous, strain 906; Escherichia coli, strain 1257 (FGBU "Scientific Center for Expertise of Medicinal Products", Moscow). In the experiments, 18-hour agar test cultures were used (5*10 5 microbial bodies in 1 ml of medium). Solutions of compound 1 in dimethylformamide (DMF) were taken for the study. The highest concentration tested was 1000 μg/ml. The tubes were incubated at 37°C, followed by seeding after 20 hours and 7 days into tubes with slanted meat peptone agar. The results were recorded based on the presence and characteristic growth of microorganism cultures on a nutrient medium.
Пример 3. Острую токсичность (ЛД50, мг/мл) соединения 1 определяли по методу Г.Н. Першина [Першин Г.Н. Методы экспериментальной химиотерапии // М., С. 100, 109-117 (1971)]. Соединение 1 вводили внутрибрюшинно белым мышам массой 16-18 г в виде взвеси в 2% крахмальной слизи и наблюдали за поведением и гибелью животных в течение 10 суток. Для исследуемого соединения 1 ЛД50 составляет > 1500 мг/кг.Example 3. Acute toxicity (LD 50 , mg/ml) of compound 1 was determined according to the method of G.N. Pershina [Pershin G.N. Methods of experimental chemotherapy // M., S. 100, 109-117 (1971)]. Compound 1 was administered intraperitoneally to white mice weighing 16-18 g in the form of a suspension in 2% starch mucus, and the behavior and death of the animals were observed for 10 days. For test compound 1, the LD 50 is > 1500 mg/kg.
Согласно классификации токсичности препаратов, соединение 1 относятся к V классу практически нетоксичных препаратов [Измеров Н.Ф., Саноцкий И.В., Сидоров К.К. Параметры токсикометрии промышленных ядов при однократном воздействии: Справочник. М., 1977. - с. 196].According to the classification of drug toxicity, compound 1 belongs to class V of practically non-toxic drugs [Izmerov N.F., Sanotsky I.V., Sidorov K.K. Parameters of toxicometry of industrial poisons with a single exposure: Handbook. M., 1977. - p. 196].
Как видно из таблицы, заявляемое соединение 1 превышает по противомикробной активности препарат сравнения (Фенилсалицилат). Таким образом, 5-(4-хлорфенил)-N-(3-циано-4,5,6,7-тетрагидробензо[b]тиофен-2-ил)-1-этил-1H-пиразол-3-карбоксамид проявляет более высокую активность, что делает возможным использовать его для создания новых лекарственных средств, целенаправленного действия. Кроме того, заявляемое соединение не проявляет острую токсичность.As can be seen from the table, the claimed compound 1 exceeds the comparison drug (Phenyl salicylate) in antimicrobial activity. Thus, 5-(4-chlorophenyl)-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-1-ethyl-1H-pyrazole-3-carboxamide exhibits more high activity, which makes it possible to use it to create new drugs with targeted action. In addition, the claimed compound does not exhibit acute toxicity.
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| RU2809149C1 true RU2809149C1 (en) | 2023-12-07 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2671573C1 (en) * | 2018-09-03 | 2018-11-02 | Алина Викторовна Шумадалова | 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide of maleic acid having antimicrobial activity |
| RU2776067C1 (en) * | 2021-07-19 | 2022-07-13 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | (e)-4-((5-(4- bromophenyl)-1-((2,4-dinitrophenyl)amino)-2-oxo-1,2-dihydro-3h-pyrrol-3-ylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazole-3-one, with antimicrobial activity |
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2671573C1 (en) * | 2018-09-03 | 2018-11-02 | Алина Викторовна Шумадалова | 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide of maleic acid having antimicrobial activity |
| RU2776067C1 (en) * | 2021-07-19 | 2022-07-13 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | (e)-4-((5-(4- bromophenyl)-1-((2,4-dinitrophenyl)amino)-2-oxo-1,2-dihydro-3h-pyrrol-3-ylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazole-3-one, with antimicrobial activity |
Non-Patent Citations (2)
| Title |
|---|
| GHASEMPOUR L. et al., Preparation of New Spiropyrazole, Pyrazole and Hydantoin Derivatives and Investigation of Their Antioxidant and Antibacterial Activities, Chem. Biodiversity, 2021, vol.18, no.9, p.e2100197. SHAMS H.Z. et al., Novel Synthesis and Antitumor Evaluation of Polyfunctionally Substituted Heterocyclic Compounds Derived from 2-Cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, Molecules, 2011, vol.16, no.1, p.52-73. * |
| МАШКОВСКИЙ М.Д., Лекарственные средства, 16-е изд., перераб., испр. и доп. - М.: Новая волна, 2012, 1216 с., стр.950. * |
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