RU2039746C1 - 2-hydroxy-5-bromobenzoyl -6′- fluorochromone -3′-al)-hydrazone showing coagulating activity - Google Patents
2-hydroxy-5-bromobenzoyl -6′- fluorochromone -3′-al)-hydrazone showing coagulating activity Download PDFInfo
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- RU2039746C1 RU2039746C1 RU92015764A RU92015764A RU2039746C1 RU 2039746 C1 RU2039746 C1 RU 2039746C1 RU 92015764 A RU92015764 A RU 92015764A RU 92015764 A RU92015764 A RU 92015764A RU 2039746 C1 RU2039746 C1 RU 2039746C1
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- fluorochromone
- bromobenzoyl
- hydrazone
- hydroxy
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- -1 2-hydroxy-5-bromobenzoyl Chemical group 0.000 title abstract 2
- 230000001112 coagulating effect Effects 0.000 title 1
- 230000000694 effects Effects 0.000 claims abstract description 6
- 230000015271 coagulation Effects 0.000 claims description 5
- 238000005345 coagulation Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- GIKWQFLVYMVLKV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC(Br)=CC=C1O GIKWQFLVYMVLKV-UHFFFAOYSA-N 0.000 abstract description 3
- VHRMOTNEBIKURN-UHFFFAOYSA-N 6-fluoro-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(F)=CC=C21 VHRMOTNEBIKURN-UHFFFAOYSA-N 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 230000023555 blood coagulation Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000007423 decrease Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- XDPFHGWVCTXHDX-UHFFFAOYSA-M menadione sodium sulfonate Chemical compound [Na+].C1=CC=C2C(=O)C(C)(S([O-])(=O)=O)CC(=O)C2=C1 XDPFHGWVCTXHDX-UHFFFAOYSA-M 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Изобретение относится к химико-фармацевтической промышленности, а именно к новым биологическим активным веществам, на основе которых могут быть созданы новые препараты, обладающие коагуляционной активностью. The invention relates to the pharmaceutical industry, in particular to new biological active substances, on the basis of which new drugs with coagulation activity can be created.
Заявляемое соединение относится к новым производным хромона, а именно к замещенным гидразонам хромон-3-альдегида формулы
Приводимое в заявке производное хромона, его свойства и биологическая активность в литературе не описана.The inventive compound relates to new derivatives of chromon, namely, substituted hydrazones of chromon-3-aldehyde of the formula
The derivative of chromon cited in the application, its properties and biological activity are not described in the literature.
Ближайшим аналогом по структуре и действию к заявляемому соединению является викасол [1]
Целью изобретения является получение нового производного хромона, обладающего более выраженной коагуляционной активностью.The closest analogue in structure and action to the claimed compound is vicasol [1]
The aim of the invention is to obtain a new derivative of chromon with more pronounced coagulation activity.
Поставленная цель достигнута синтезом соединения формулы
П р и м е р. 2-Гидрокси-5-бромбензоил-(6l-фторхромон-3l-аль) гидразон. К раствору 1,9 г 6-фторхромон-3-альдегида (0,01 моль) в 15 мл сухого толуола прибавляют 2,31 г гидразида 5-бромсалициловой кислоты. Реакционную смесь нагревают на водяной бане в течение 3 ч, после чего растворитель отгоняют под вакуумом. После перекристаллизации из изопропилового спирта получают 2,35 г желтого кристаллического порошка. Выход продукта 73% от теоретического. Т.пл. 257-258оС.PRI me R. 2-Hydroxy-5-bromobenzoyl- (6 l- fluorochromon-3 l- al) hydrazone. To a solution of 1.9 g of 6-fluorochromone-3-aldehyde (0.01 mol) in 15 ml of dry toluene, 2.31 g of 5-bromosalicylic acid hydrazide are added. The reaction mixture was heated in a water bath for 3 hours, after which the solvent was distilled off in vacuo. After recrystallization from isopropyl alcohol, 2.35 g of a yellow crystalline powder are obtained. Product yield 73% of theoretical. Mp 257-258 about S.
Вычислено, С 50,38; Н 2,47; N 6,92. Calculated, C 50.38; H 2.47; N, 6.92.
С17Н10BrFN2O4
Найдено, С 51,04; Н 2,69; N 6,78.C 17 H 10 BrFN 2 O 4
Found, C, 51.04; H 2.69; N, 6.78.
ИК-спектр, вазелиновое масло, 1650, 1570, 1150 (см-1)
Исследования биологической активности проводились в лаборатории фармакологического скрининга при кафедре органической химии ПФИ. Влияние соединения на свертываемость крови проводилось на бодрствующих белых крысах-самцах массой 200-230 г. Кровь для исследования брали из вены языка и записывали коагулограмму с помощью стандартного коагулографа Н-338-1. По записям на бумажной ленте рассчитывали время свертывания крови. Одновременно проводились серии опытов (в каждой серии по 6 животных) с введением внутрибрюшинно 1 мл физиологического раствора (контроль) и эталона викасола в дозе 10 мг/кг. Новое соединение в дозе 10 мг/кг, а также физраствор и эталон вводили в два приема: за 24 и за 1 ч до начала опыта. Эталонный препарат (викасол) предложен как препарат сравнения при исследовании коагуляционной активности.IR spectrum, liquid paraffin, 1650, 1570, 1150 (cm -1 )
Studies of biological activity were carried out in the laboratory of pharmacological screening at the Department of Organic Chemistry, PFI. The effect of the compound on blood coagulability was carried out on awake white male rats weighing 200-230 g. Blood was taken for examination from the tongue vein and a coagulogram was recorded using a standard H-338-1 coagulograph. Using paper tape records, coagulation time was calculated. At the same time, a series of experiments was carried out (in each series of 6 animals) with the introduction of intraperitoneal 1 ml of physiological saline (control) and a standard of vicasol at a dose of 10 mg / kg. The new compound at a dose of 10 mg / kg, as well as saline and standard was administered in two doses: 24 and 1 hour before the start of the experiment. The reference drug (vikasol) is proposed as a comparison drug in the study of coagulation activity.
Результаты опытов статистически обработаны [3] и приведены в таблице. The experimental results are statistically processed [3] and are shown in the table.
Определение острой токсичности и расчеты LD50 осуществляли по методу Кербера [2] Белым мышам массой 18-20 г внутрибрюшинно вводили по 0,5 мл суспензии исследуемого вещества, приготовленной с добавлением 1-2 капель Твина-80. На каждую дозу в опыте брали по 6 мышей. Установлено, что LD50 исследуемого вещества составляет более 1800 мг/кг, следовательно, данное соединение относится к классу практически нетоксичных соединений.Determination of acute toxicity and LD 50 calculations were carried out according to the Kerber method [2]. White mice weighing 18-20 g were injected intraperitoneally with 0.5 ml of a suspension of the test substance prepared with 1-2 drops of Tween-80. For each dose in the experiment, 6 mice were taken. It was found that the LD 50 of the test substance is more than 1800 mg / kg, therefore, this compound belongs to the class of practically non-toxic compounds.
Результаты проведенных исследований показывают, что заявляемое соединение обладает выраженным гемостатическим действием, превышающим действие лекарственного препарата викасола, являясь при этом практически нетоксичным. Это свидетельствует о целесообразности дальнейших исследований данного вещества с целью создания эффективного лекарственного препарата. The results of the studies show that the claimed compound has a pronounced hemostatic effect that exceeds the action of the drug Vikasol, while being practically non-toxic. This indicates the feasibility of further studies of this substance in order to create an effective drug.
Claims (1)
обладающий коагуляционной активностью.2-Hydroxy-5-bromobenzoyl- (6 ′ -fluorochromon-3 ′ -al) -hydrazone of the formula
possessing coagulation activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU92015764A RU2039746C1 (en) | 1992-12-30 | 1992-12-30 | 2-hydroxy-5-bromobenzoyl -6′- fluorochromone -3′-al)-hydrazone showing coagulating activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU92015764A RU2039746C1 (en) | 1992-12-30 | 1992-12-30 | 2-hydroxy-5-bromobenzoyl -6′- fluorochromone -3′-al)-hydrazone showing coagulating activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2039746C1 true RU2039746C1 (en) | 1995-07-20 |
| RU92015764A RU92015764A (en) | 1996-12-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU92015764A RU2039746C1 (en) | 1992-12-30 | 1992-12-30 | 2-hydroxy-5-bromobenzoyl -6′- fluorochromone -3′-al)-hydrazone showing coagulating activity |
Country Status (1)
| Country | Link |
|---|---|
| RU (1) | RU2039746C1 (en) |
-
1992
- 1992-12-30 RU RU92015764A patent/RU2039746C1/en active
Non-Patent Citations (3)
| Title |
|---|
| 1. Машковский М.Д. Лекарственные средства. М., 1985, т.1. с.512. * |
| 2. Першин Г.Н. Методы экспериментальной химиотерапии. М., 1971, с.526-531. * |
| 3. Урбах В.Ю. Математическая статистика для биологов и медиков. М., 1963. * |
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