RU2840006C1 - 5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione as agent having antimicrobial activity with respect to staphylococcus aureus, escherichia coli cultures and antifungal activity with respect to candida albicans culture and method for synthesis thereof - Google Patents
5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione as agent having antimicrobial activity with respect to staphylococcus aureus, escherichia coli cultures and antifungal activity with respect to candida albicans culture and method for synthesis thereof Download PDFInfo
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- -1 5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione Chemical compound 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 8
- 241000222122 Candida albicans Species 0.000 title claims abstract description 6
- 241000588724 Escherichia coli Species 0.000 title claims abstract description 6
- 230000000843 anti-fungal effect Effects 0.000 title claims abstract description 5
- 241000191967 Staphylococcus aureus Species 0.000 title claims abstract description 4
- 229940095731 candida albicans Drugs 0.000 title claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004202 carbamide Substances 0.000 claims abstract description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims abstract description 4
- FXAUZCQGFOUJDB-UHFFFAOYSA-N 5-phenylfuran-2,3-dione Chemical compound O=C1C(=O)OC(C=2C=CC=CC=2)=C1 FXAUZCQGFOUJDB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229920001817 Agar Polymers 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
- 239000008272 agar Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical class OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
Изобретение относится к области органической химии, а именно к структуре, противомикробной и противогрибковой активности и способу получения новых индивидуальных соединений класса 1,3-диазолов содержащих оксогруппы, непосредственно присоединенные к гетероциклическому кольцу, которые могут быть использованы в качестве исходных продуктов для синтеза новых гетероциклических систем и в фармакологии.The invention relates to the field of organic chemistry, namely to the structure, antimicrobial and antifungal activity and a method for obtaining new individual compounds of the 1,3-diazoles class containing oxo groups directly attached to a heterocyclic ring, which can be used as starting products for the synthesis of new heterocyclic systems and in pharmacology.
Известен способ синтеза структурных аналогов заявленного соединения - 5-(2-арил-2-оксоэтилиден)имидазолидин-2,4-дионов, являющихся продуктами взаимодействия 5-арилфуран-2,3-дионов с мочевиной (Andreichikov Yu. S., Nekrasov D. D., Rudenko M. A., Nalimova Yu. A. Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with N-substituted ureas and their thio and seleno analogs. Chem. Heterocycl. Compd.1988, 10, 1411-1413), образующихся по следующей схеме:A method is known for synthesizing structural analogs of the claimed compound - 5-(2-aryl-2-oxoethylidene)imidazolidine-2,4-diones, which are products of the reaction of 5-arylfuran-2,3-diones with urea (Andreichikov Yu. S., Nekrasov D. D., Rudenko M. A., Nalimova Yu. A. Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with N-substituted ureas and their thio and seleno analogs. Chem. Heterocycl. Compd. 1988, 10, 1411-1413), formed according to the following scheme:
К недостаткам данного способа относится невозможность получить 5-гидрокси-5-(2-оксо-2-фенилэтил)имидазолидин-2,4-дион с высокой биологической активностью.The disadvantages of this method include the inability to obtain 5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione with high biological activity.
Задачей изобретения является разработка простого способа синтеза неописанных в литературе (5-гидрокси-5-(2-оксо-2-фенилэтил)имидазолидин-2,4-дионов и расширение арсенала средств воздействия на живой организм.The objective of the invention is to develop a simple method for synthesizing (5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-diones) not described in the literature and to expand the arsenal of means of influencing a living organism.
Поставленная задача осуществляется путем взаимодействия 5-фенилфуран-2,3-диона с мочевиной в среде растворителя с последующим выделением целевого продукта, по следующей схеме:The task is accomplished by reacting 5-phenylfuran-2,3-dione with urea in a solvent medium, followed by isolation of the target product, according to the following scheme:
Процесс ведут при температуре 83-84°С, а в качестве растворителей используют дихлорэтан и ДМСО.The process is carried out at a temperature of 83-84°C, and dichloroethane and DMSO are used as solvents.
Из патентной и технической литературы не были выявлены способы получения 5-(2-арил-2-оксоэтилиден)имидазолидин-2,4-дионы, имеющие сходные признаки с заявляемым способом, а именно, не использовались исходные продукты, растворители, в которых проходит реакция, и интервал температур.From the patent and technical literature, no methods for obtaining 5-(2-aryl-2-oxoethylidene)imidazolidine-2,4-diones having similar features to the claimed method were identified, namely, the starting products, solvents in which the reaction takes place, and temperature range were not used.
Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.
Пример 1. 5-гидрокси-5-(2-оксо-2-фенилэтил)имидазолидин-2,4-дион (4).Example 1. 5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione (4).
К раствору 0.006 моль 5-фенилфуран-2,3-диона (3) в 10 мл дихлорэтана добавляли раствор 0.007 моль мочевины в 1 мл ДМСО, кипятили 5 минут, охлаждали, перекристаллизовывали из этилацетата. Выход 65%, т.пл. 191-193°С. Соединение (4) C11H10N2O4.A solution of 0.007 mol urea in 1 ml DMSO was added to a solution of 0.006 mol 5-phenylfuran-2,3-dione (3) in 10 ml dichloroethane, the mixture was boiled for 5 minutes, cooled, and recrystallized from ethyl acetate. Yield 65%, mp 191-193°C. Compound (4) C 11 H 10 N 2 O 4 .
Найдено, %: С 56.33; Н 4.43; N 11.98Found, %: C 56.33; H 4.43; N 11.98
Вычислено, %: С 56.41; Н 4.30; N 11.96.Calculated, %: C 56.41; H 4.30; N 11.96.
Соединение (4) - светло-желтое высокоплавкое кристаллическое вещество, растворимое в ДМСО, ДМФА, ацетоне, этилацетате, ацетонитриле, спиртах, труднорастворимое в хлороформе, толуоле и ароматических углеводородах, нерастворимое в алканах и воде. Устойчиво при хранении в обычных условиях.Compound (4) is a light yellow, high-melting crystalline substance, soluble in DMSO, DMF, acetone, ethyl acetate, acetonitrile, alcohols, sparingly soluble in chloroform, toluene and aromatic hydrocarbons, insoluble in alkanes and water. Stable when stored under normal conditions.
В ИК спектре соединения (4), записанном в виде пасты в вазелиновом масле, присутствуют полосы валентных колебаний двух NH групп в виде узких пиков при 3484 и 3335 см-1, валентные колебания группы ОН при 3147 см-1 и двух карбонитов имидазолидиндионового цикла при 1780 см-1 и при 1715 см-1, а так же ароильной карбонильной группы при 1621 см-1.In the IR spectrum of compound (4), recorded as a paste in vaseline oil, there are bands of stretching vibrations of two NH groups in the form of narrow peaks at 3484 and 3335 cm -1 , stretching vibrations of the OH group at 3147 cm -1 and two carbonites of the imidazolidinedione ring at 1780 cm -1 and at 1715 cm -1 , as well as an aroyl carbonyl group at 1621 cm -1 .
В спектре ЯМР !Н соединения (4), записанном в растворе в ДМСО-d6, кроме сигналов пяти протонов ароматического кольца, присутствуют два дублета протонов метиленовой группы при 3.49 м.д. и 3.69 м.д., синглет протона группы ОН при 6.65 м.д., синглеты протонов NH групп при 8.12 м.д. и 10.55 м.д.In the NMR spectrum of compound (4), recorded in a solution in DMSO-d 6 , in addition to the signals of five protons of the aromatic ring, there are two doublets of protons of the methylene group at 3.49 ppm and 3.69 ppm, a singlet of the proton of the OH group at 6.65 ppm, singlets of protons of NH groups at 8.12 ppm and 10.55 ppm.
Пример 2. Фармакологическое исследование соединения (4) на наличие противомикробной активности.Example 2. Pharmacological study of compound (4) for antimicrobial activity.
Для исследований использовали общепринятый метод двукратных серийных разведений в жидкой питательной среде микрометодом [Руководство по экспериментальному (доклиническому) изучению новых фармакологических веществ - М.: И-во Медицина, 2005]. Готовили исходные разведения микроорганизмов в физиологическом растворе из суточной агаровой культуры по оптическому стандарту мутности (ОСМ) на 5 ME с использованием денситометра. После ряда разведений конечная концентрация клеток в опыте составляла 2,5×105 клеток/мл.The generally accepted method of double serial dilutions in a liquid nutrient medium by the micromethod was used for the studies [Guide to the experimental (preclinical) study of new pharmacological substances - M.: I-vo Meditsina, 2005]. Initial dilutions of microorganisms were prepared in a physiological solution from a daily agar culture according to the optical standard of turbidity (OST) at 5 ME using a densitometer. After a series of dilutions, the final concentration of cells in the experiment was 2.5×10 5 cells/ml.
Противомикробные свойства химического вещества изучали на 3-х коллекционных условно-патогенных штаммах микроорганизмов: Staphylococcus aureus (АТСС 25923), Escherichia coli (АТСС 25922), Candida albicans (РКПГY 1353/1277), полученных в ФГБУ «Научный центр экспертизы средств медицинского применения» Минздравсоцразвития России. Факт ингибирования (торможения роста) микробных клеток в разведениях препаратов отмечали после 20-ти часового термостатирования при 37°С. Окончательные результаты фиксировали через 7 суток после высева на скошенный агар РПА. Максимально испытанная концентрация соединений соответствовала 1000,0 мкг/мл. Противомикробную (ингибирующую, бактерицидную) активность оценивали по минимально действующей концентрации.The antimicrobial properties of the chemical substance were studied on 3 collection opportunistic strains of microorganisms: Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), Candida albicans (РКПГУ 1353/1277), obtained in the Federal State Budgetary Institution "Scientific Center for Expertise of Medical Products" of the Ministry of Health and Social Development of the Russian Federation. The fact of inhibition (growth inhibition) of microbial cells in the dilutions of the drugs was noted after 20-hour thermostatting at 37 ° C. The final results were recorded 7 days after seeding on slanted RPA agar. The maximum tested concentration of the compounds corresponded to 1000.0 μg / ml. Antimicrobial (inhibitory, bactericidal) activity was assessed by the minimum effective concentration.
Анализ полученных данных показал: Analysis of the obtained data showed:
соединение 4 обладает ингибирующим действием в отношении культур S. aureus, Е. coli и С.albicans в концентрации 1000 мкг/мл для каждого из перечисленных; Compound 4 has an inhibitory effect on cultures of S. aureus , E. coli and C. albicans at a concentration of 1000 μg/ml for each of the listed;
Предлагаемое вещество 5-гидрокси-5-(2-оксо-2-фенилэтил)имидазолидин-2,4-дион (4) обладает фармакологической активностью, а именно противомикробной активностью в отношении культур S. aureus, Е. coli и противогрибковой активностью в отношении культуры С.albicans, и может найти применение в фармакологии в качестве потенциального лекарственного средства.The proposed substance 5-hydroxy-5-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione (4) has pharmacological activity, namely antimicrobial activity against S. aureus , E. coli cultures and antifungal activity against C. albicans culture, and can find application in pharmacology as a potential medicinal product.
Claims (6)
Publications (1)
| Publication Number | Publication Date |
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| RU2840006C1 true RU2840006C1 (en) | 2025-05-15 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002074752A1 (en) * | 2001-03-15 | 2002-09-26 | Astrazeneca Ab | Metalloproteinase inhibitors |
| RU2287525C2 (en) * | 2002-03-13 | 2006-11-20 | Смитклайн Бичам Корпорейшн | Derivatives of imidazolidine as inhibitors of peptide deformylase |
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002074752A1 (en) * | 2001-03-15 | 2002-09-26 | Astrazeneca Ab | Metalloproteinase inhibitors |
| RU2287525C2 (en) * | 2002-03-13 | 2006-11-20 | Смитклайн Бичам Корпорейшн | Derivatives of imidazolidine as inhibitors of peptide deformylase |
Non-Patent Citations (1)
| Title |
|---|
| ANDREICHIKOV YU. S., NEKRASOV D. D., RUDENKO M. A., et al "Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with N-substituted ureas and their thio and seleno analogs", CHEM. HETEROCYCL. COMPD., October 1988, v/24, pp. 1172-1174. * |
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