RU2081114C1 - 2,5-diaryl-1,3,4-thiadiazolines-2 showing antiviral activity - Google Patents
2,5-diaryl-1,3,4-thiadiazolines-2 showing antiviral activity Download PDFInfo
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- RU2081114C1 RU2081114C1 RU95112418A RU95112418A RU2081114C1 RU 2081114 C1 RU2081114 C1 RU 2081114C1 RU 95112418 A RU95112418 A RU 95112418A RU 95112418 A RU95112418 A RU 95112418A RU 2081114 C1 RU2081114 C1 RU 2081114C1
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Изобретение относится к поиску новых лекарственных средств, а именно к синтезу соединений, обладающих противовирусной активностью. С целью получения противовирусных средств с более высоким уровнем фармакологической активности синтезированы взаимодействием арилтиобензоилгидразонов с ароматическими альдегидами 2,5-диарил-1,3,4-тиадиазолины-2 (I, II), которые были подвергнуты испытаниям на противовирусную активность в отношении вируса пикорна. The invention relates to the search for new drugs, namely to the synthesis of compounds with antiviral activity. In order to obtain antiviral agents with a higher level of pharmacological activity, 2,5-diaryl-1,3,4-thiadiazolines-2 (I, II) were synthesized by the interaction of arylthiobenzoylhydrazones with aromatic aldehydes, which were tested for antiviral activity against picorn virus.
В результате испытаний исследуемые вещества показали себя эффективными ингибиторами размножения вируса ЭКХО-6 и имеют преимущества в сравнении с наиболее эффективным из известных в настоящее время антипикорнавирусных препаратов. As a result of tests, the studied substances proved to be effective inhibitors of the reproduction of the ECHO-6 virus and have advantages in comparison with the most effective antipicornavirus drugs currently known.
Токсические свойства исследовали на культурах, выращенных в пенициллиновых флаконах. Вещества растворяли в среде ИГЛА. МПК исследуемых веществ составляют соответственно для I 400 мкг/кг, для II 100 мкг/кг. Таким образом испытуемые вещества показали малую токсичность. Toxic properties were studied on cultures grown in penicillin vials. The substances were dissolved in the environment of the needle. The IPC of the studied substances are respectively 400 μg / kg for I, 100 μg / kg for II. Thus, the test substances showed low toxicity.
Способ получения. The method of obtaining.
Пример. Смешивают 0,015 г (0,01M) тиобензоилгидразона, 0,15 г (0,01M) 4-этоксибензальдегида, 10 мл этанола. Реакционную смесь нагревают 1 ч, фильтруют, промывают, сушат. Получают 2,42 г (85,21%) целевого продукта 1 в виде кристаллического порошка белого цвета с температурой плавления 82oC (из этанола).Example. 0.015 g (0.01 M) of thiobenzoylhydrazone, 0.15 g (0.01 M) of 4-ethoxybenzaldehyde, 10 ml of ethanol are mixed. The reaction mixture is heated for 1 h, filtered, washed, dried. 2.42 g (85.21%) of expected product 1 are obtained in the form of a white crystalline powder with a melting point of 82 ° C. (from ethanol).
Продукт растворим в органических растворителях, нерастворим в воде. The product is soluble in organic solvents, insoluble in water.
Характеристика соединений I и II приведена в табл.I. The characteristics of compounds I and II are given in table I.
Лабораторные испытания соединений I и II на противовирусную активность выполнены в Белорусском НИИ эпидемиологии и микробиологии. Исследования выполняли в сравнении с известным ингибитором пикорнавирусов 2-фенилхинолин-4 карбоновой кислотой. В связи с этим использовали также вариант вируса ЭКХО-6, устойчивый к действию препарата сравнения (табл.2). Laboratory tests of compounds I and II for antiviral activity were performed at the Belarusian Research Institute of Epidemiology and Microbiology. Studies were performed in comparison with the known inhibitor of picornaviruses 2-phenylquinoline-4 carboxylic acid. In this regard, the ECHO-6 virus variant resistant to the action of the reference drug was also used (Table 2).
В результате проведенных исследований видно, что в присутствии исследуемых веществ I и II наблюдается снижение титра вируса ЭКХО-6 как чувствительного, так и резистентного его вариантов, достигающее подавления размножения для исследуемых веществ: 1 на 3,0 lg ТЦД 50/мл, II на 4,5 lg ТЦД 50/мл в концентрациях 100 мкг/мл. В то же время 2-фенилхинолин-4 карбоновая кислота в концентрациях 150 мкг/мл и меньше совершенно неэффективна в отношении репродукции резистентного вируса ЭКХО-6. (Акт испытаний соединений I и II на противовирусную активность имеется).As a result of the studies, it is seen that in the presence of the studied substances I and II, a decrease in the titer of the ECHO-6 virus of both sensitive and resistant variants is observed, reaching suppression of reproduction for the studied substances: 1 per 3.0 lg TCD 50 / ml , II by 4.5 lg TCD 50 / ml at concentrations of 100 μg / ml. At the same time, 2-phenylquinoline-4 carboxylic acid in concentrations of 150 μg / ml or less is completely ineffective with respect to the reproduction of ECHO-6 resistant virus. (The test report of compounds I and II for antiviral activity is available).
Claims (1)
где I: R1 H; R2= 4-этокси;
II: R1 OH; R2 4-бром, обладающие противовирусной активностью.2,5-diaryl-1,3,4-theadiazolines-2 formulas
where I: R 1 H; R 2 = 4-ethoxy;
II: R 1 OH; R 2 4-bromine with antiviral activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU95112418A RU2081114C1 (en) | 1995-07-29 | 1995-07-29 | 2,5-diaryl-1,3,4-thiadiazolines-2 showing antiviral activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU95112418A RU2081114C1 (en) | 1995-07-29 | 1995-07-29 | 2,5-diaryl-1,3,4-thiadiazolines-2 showing antiviral activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2081114C1 true RU2081114C1 (en) | 1997-06-10 |
| RU95112418A RU95112418A (en) | 1997-06-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU95112418A RU2081114C1 (en) | 1995-07-29 | 1995-07-29 | 2,5-diaryl-1,3,4-thiadiazolines-2 showing antiviral activity |
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| Country | Link |
|---|---|
| RU (1) | RU2081114C1 (en) |
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1995
- 1995-07-29 RU RU95112418A patent/RU2081114C1/en active
Non-Patent Citations (1)
| Title |
|---|
| F.Rurtzer, Adv Hetcrocyclic chem., 1965, 5, 119. * |
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| Publication number | Publication date |
|---|---|
| RU95112418A (en) | 1997-06-27 |
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