RU2806038C1 - Application of 3'-(4-bromobenzoyl)-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]-3,5'(1 'h,4h)-dione as agent with antimicrobial activity against s. aureus culture - Google Patents
Application of 3'-(4-bromobenzoyl)-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]-3,5'(1 'h,4h)-dione as agent with antimicrobial activity against s. aureus culture Download PDFInfo
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- -1 3'-(4-bromobenzoyl)-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]-3,5'(1 'h,4h)-dione Chemical compound 0.000 title claims abstract description 11
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 125000003003 spiro group Chemical group 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 125000005605 benzo group Chemical group 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- YGIOZWYWHHODMZ-UHFFFAOYSA-N 8-(4-bromobenzoyl)-3,4-dihydropyrrolo[2,1-c][1,4]oxazine-1,6,7-trione Chemical compound BrC1=CC=C(C(=O)C=2C(C(N3C=2C(OCC3)=O)=O)=O)C=C1 YGIOZWYWHHODMZ-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000000813 microbial effect Effects 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
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000013207 serial dilution Methods 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 применению индивидуальных соединений класса спиро[бензо[b][1,4]тиазин-2,2'-пиррол]-3,5'-дионов в качестве средств, обладающих противомикробной активностью, 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 use of individual compounds of the class of spiro[benzo[b][1,4]thiazin-2,2'-pyrrole]-3,5'-diones as agents with antimicrobial activity, which can be used as starting products for the synthesis of new heterocyclic systems and in pharmacology.
Заявленные соединения 3'-ароил-4'-гидрокси-1'-(2-гидроксиэтил)спиро[бензо[b][1,4]тиазин-2,2'-пиррол]-3,5'(1'H,4H)-дионы и способ их синтеза известен из уровня техники. Заявляемые соединения являются продуктами взаимодействия 8-ароил-3,4-дигидро-1H-пирроло[2,1-с][1,4]оксазин-1,6,7-трионов с о-аминотиофенолом («Синтез спиро[бензотиазин-2,2'-пирролов] реакцией пирроло[2,1-с][1,4]оксазинтрионов с о-аминотиофенолом», Третьяков Н.А., Дмитриев М.В., Масливец А.Н., ЖОрХ, 2020, 56, №5, 802-806. [Synthesis of Spiro[1,4-benzothiazine-2,2'-pyrroles] by the Reaction of Pyrrolo[2,l-c][l,4]oxazinetriones with 2-Aminobenzenethiol. Tretyakov N.A., Dmitriev M.V., Maslivets A.N. Russ. JOC, 2020, 56(5), 935-938. doi: 10.1134/S1070428020050292]), образующихся по следующей схеме:The claimed compounds are 3'-aroyl-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]-3,5'(1'H, 4H)-diones and the method for their synthesis are known from the prior art. The claimed compounds are products of the interaction of 8-aroyl-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-triones with o-aminothiophenol (“Synthesis of spiro[benzothiazine- 2,2'-pyrroles] by the reaction of pyrrolo[2,1-с][1,4]oxazinetriones with o-aminothiophenol", Tretyakov N.A., Dmitriev M.V., Maslivets A.N., ZhORKh, 2020, 56, No. 5, 802-806. [Synthesis of Spiro[1,4-benzothiazine-2,2'-pyrroles] by the Reaction of Pyrrolo[2,l-c][l,4]oxazinetriones with 2-Aminobenzenethiol. Tretyakov N.A. , Dmitriev M.V., Maslivets A.N. Russ. JOC, 2020, 56(5), 935-938. doi: 10.1134/S1070428020050292]), formed according to the following scheme:
Противомикробная активность 3'-ароил-4'-гидрокси-1'-(2-гидроксиэтил)спиро[бензо[b][1,4]тиазин-2,2'-пиррол]-3,5'(1'H,4Н)-дионов ранее не была исследована.Antimicrobial activity of 3'-aroyl-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]-3,5'(1'H, 4H)-diones has not been studied previously.
Задачей изобретения является изыскание новых соединений, обладающих противомикробной активностью, и расширение арсенала средств воздействия на живой организм.The objective of the invention is to find new compounds with antimicrobial activity and expand the arsenal of means of influencing a living organism.
Поставленная задача решается тем, что соединение 3'-(4-бромбензоил)-4'-гидрокси-1'-(2-гидроксиэтил)спиро[бензо[b][1,4]тиазин-2,2'-пиррол]-3,5'(1'H,4H)-дион проявляет высокую противомикробную активность в концентрации в 1000 мкг/мл в отношении культур S. aureus.The problem is solved by the fact that the compound 3'-(4-bromobenzoyl)-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]- 3,5'(1'H,4H)-dione exhibits high antimicrobial activity at a concentration of 1000 μg/ml against S. aureus cultures.
Синтезируют заявляемое соединение путем взаимодействия 8-(4-бромбензоил)-3,4-дигидро-1H-пирроло[2,1-с][1,4]оксазин-1,6,7-триона с о-аминотиофенолом в среде растворителя с последующим выделением целевых продуктов, по следующей схеме:The claimed compound is synthesized by reacting 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with o-aminothiophenol in a solvent environment followed by isolation of target products according to the following scheme:
Процесс ведут при комнатной температуре, а в качестве растворителя используют безводный диоксан.The process is carried out at room temperature, and anhydrous dioxane is used as a solvent.
Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.
Пример 1. 3'-(4-Бромбензоил)-4'-гидрокси-1'-(2-гидроксиэтил)спиро[бензо[b][1,4]тиазин-2,2'-пиррол]-3,5'(1'Н,4H)-дион (4)Example 1. 3'-(4-Brombenzoyl)-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazine-2,2'-pyrrole]-3,5' (1'H,4H)-dione (4)
К раствору 1.5 ммоль 8-(4-бромбензоил)-3,4-дигидро-1H-пирроло[2,1-с][1,4]оксазин-1,6,7-триона (3) в 15 мл 1,4-диоксана приливали раствор 1.5 ммоль о-аминотиофенола в 5 мл 1,4-диоксана при комнатной температуре, растворитель упаривали. Выход 87%, т.пл. 195-197°С.To a solution of 1.5 mmol 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-с][1,4]oxazine-1,6,7-trione (3) in 15 ml 1, 4-dioxane was added to a solution of 1.5 mmol o-aminothiophenol in 5 ml of 1,4-dioxane at room temperature, the solvent was evaporated. Yield 87%, mp. 195-197°C.
Соединение (4) C20H15BrN2O5S.Compound (4) C 20 H 15 BrN 2 O 5 S.
Найдено, %: С 50.79; Н 3.02; N 5.47; S 6.87Found, %: C 50.79; H 3.02; N 5.47; S 6.87
Вычислено, %: С 50.54; Н 3.18; N 5.89; S 6.75.Calculated, %: C 50.54; H 3.18; N 5.89; S 6.75.
Соединение (4) - светло-желтое кристаллическое вещество, легкорастворимое в ДМСО и ДМФА, трудно растворимое в менее полярных органических растворителях, нерастворимое в воде и алканах. Устойчиво при хранении в обычных условиях.Compound (4) is a light yellow crystalline substance, readily soluble in DMSO and DMF, sparingly soluble in less polar organic solvents, insoluble in water and alkanes. Stable when stored under normal conditions.
В ИК спектре соединения (4), записанном в виде пасты в вазелиновом масле, присутствуют полосы валентных колебаний спиртовой группы ОН в виде узкого пика при 3450 см-1, енольной группы ОН в виде широкой полосы при 3147 см-1, двух лактамных карбонильных групп при 1712 и 1661 см-1, и ароильной карбонильной группы при 1633 см-1.The IR spectrum of compound (4), recorded as a paste in petroleum jelly, contains bands of stretching vibrations of the alcohol group OH in the form of a narrow peak at 3450 cm -1 , the enol group OH in the form of a broad band at 3147 cm -1 , and two lactam carbonyl groups at 1712 and 1661 cm -1 , and the aroyl carbonyl group at 1633 cm -1 .
В спектре ЯМР 1Н соединения (4), записанном в растворе в ДМСО-d6, кроме сигналов протонов ароматических колец, присутствует группа из 4 метиленовых протонов этоксильного заместителя при: 3.28-3.58 м.д. (м, 4Н, NCH 2CH 2OH), уширенный синглет протона этоксильной группы ОН при 4.98 м.д, и синглет протона группы NH тиазинового фрагмента при 11.11 м.д.In the 1H NMR spectrum of compound (4), recorded in solution in DMSO-d 6, in addition to the signals of the protons of the aromatic rings, there is a group of 4 methylene protons of the ethoxy substituent at: 3.28-3.58 ppm. (m, 4H, NC H 2 C H 2 OH), a broadened singlet of the proton of the OH ethoxy group at 4.98 ppm, and a singlet of the proton of the NH group of the thiazine fragment at 11.11 ppm.
Пример 2. Фармакологическое исследование соединения (4) на наличие противомикробной активностиExample 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 (ОСО) на 5 ME с использованием денситометра. После ряда разведений конечная концентрация клеток в опыте составляла 2,5×105 клеток/мл.For research, we used the generally accepted method of two-fold serial dilutions in a liquid nutrient medium using the micromethod [Guide to the experimental (preclinical) study of new pharmacological substances - M.: Institute of Medicine, 2005]. Initial dilutions of microorganisms were prepared in physiological solution from a daily agar culture according to the optical turbidity standard (OTS) at 5 IU using a densitometer. After a series of dilutions, the final cell concentration 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 (штамм 906), Escherichia coli (штамм 1257), Candida albicans (РКПГУ 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 (strain 906), Escherichia coli (strain 1257), Candida albicans (RKPGU 1353/1277), obtained at the Federal State Budgetary Institution "Scientific Center for Expertise of Medical Products" Ministry of Health and Social Development of Russia. The fact of inhibition (growth inhibition) of microbial cells in drug dilutions was noted after 20 hours of thermostatting at 37°C. The final results were recorded 7 days after seeding on RPA agar slants. The maximum concentration of compounds tested was 1000.0 μg/ml. Antimicrobial (inhibitory, bactericidal) activity was assessed based on the minimum effective concentration.
Анализ полученных данных показал:Analysis of the data obtained showed:
• соединение 4 обладает ингибирующим действием в отношении культур S. aureus в концентрации 1000,0 мкг/мл.• compound 4 has an inhibitory effect against S. aureus cultures at a concentration of 1000.0 μg/ml.
Предлагаемое вещество 3'-(4-бромбензоил)-4'-гидрокси-1'-(2-гидроксиэтил)спиро[бензо[b][1,4]тиазин-2,2'-пиррол]-3,5'(1'H,4Н)-дион (4) обладает фармакологической активностью, а именно противомикробной активностью в отношении культур S. aureus, и может найти применение в фармакологии в качестве потенциального лекарственного средства.The proposed substance is 3'-(4-bromobenzoyl)-4'-hydroxy-1'-(2-hydroxyethyl)spiro[benzo[b][1,4]thiazin-2,2'-pyrrole]-3,5'( 1'H,4H)-dione (4) has pharmacological activity, namely antimicrobial activity against S. aureus cultures, and can be used in pharmacology as a potential drug.
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| RU2806038C1 true RU2806038C1 (en) | 2023-10-25 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090270375A1 (en) * | 2006-08-30 | 2009-10-29 | Actelion Pharmaceuticals Ltd. | Spiro antibiotic derivatives |
| RU2790377C1 (en) * | 2022-07-05 | 2023-02-17 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Application of 9-benzoyl-8-hydroxy-6-(2-hydroxy-5-chlorophenyl)-2-phenyl-1-thia-3,6-diazaspiro[4.4]nona-2,8-diene-4,7-dione as an antifungal agent against cryptococcus neoformans |
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090270375A1 (en) * | 2006-08-30 | 2009-10-29 | Actelion Pharmaceuticals Ltd. | Spiro antibiotic derivatives |
| RU2790377C1 (en) * | 2022-07-05 | 2023-02-17 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Application of 9-benzoyl-8-hydroxy-6-(2-hydroxy-5-chlorophenyl)-2-phenyl-1-thia-3,6-diazaspiro[4.4]nona-2,8-diene-4,7-dione as an antifungal agent against cryptococcus neoformans |
Non-Patent Citations (1)
| Title |
|---|
| Tret’yakov, N. A. et al. Synthesis of Spiro[1,4-benzothiazine-2,2’-pyrroles] by the Reaction of Pyrrolo[2,1-c][1,4]oxazinetriones with 2-Aminobenzenethiol. Russian Journal of Organic Chemistry, 2020, 56(5), 935-938. D. A. Lega, et al. IN VITRO ANTIMICROBIAL ACTIVITY EVALUATION OF 2-AMINO-3-R-6-ETHYL-4,6 DIHYDROPYRANO[3,2-c][2,1] BENZOTHIAZINE 5,5-DIOXIDES WITH 4-ARYLSUBSTITUENT AND SPIROFUSED WITH 2-OXOINDOLINE CORE. УКРАIНСЬКИЙ БІОФАРМАЦЕВТИЧНИЙ ЖУРНАЛ, 2016, 3(44), 24-32. * |
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