Синтез і дослідження нових семичленних структур на основі аміноіндолу
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Дата
2024
Науковий керівник
Укладач
Редактор
Назва журналу
ISSN
2304-0947
E-ISSN
2414-5963
Назва тому
Видавець
Одеський національний університет імені І. І. Мечникова
Анотація
Одним з найважливіших завдань сучасної органічної хімії є пошук та розробка простих методів синтезу нових біологічно активних речовин. В цій роботі показана можливість нового підходу до синтезу семичленних структур на основі 7-аміноіндолу.
Розроблені доступні схеми синтезу та вивчені властивості отриманих сполук. Показана перспективність вивчення біологічної активності синтезованих сполук з метою подальшого їх застосування у медичній практиці.
One of the most important tasks of modern organic chemistry is the search and development of simple methods for the synthesis of new biologically active substances. 1,4-diazepine derivatives are widely used in medicine due to their high biological activity (anxiolytic, hypnotic, sedative, etc.) and very low toxicity. This contributes to the development of the chemistry of other related systems, in particular the chemistry of 1,5-diazepines. Interest in such systems is due to the fact that substances with an interesting spectrum of biological activity were found among a small number of synthesized compounds. There are tranquilizers, analgesics, substances that reduce pressure and relieve cough more effectively than codeine among the compounds of this class. Taking into account this, as well as the fact that 1,5-diazepine derivatives have been studied relatively little, we developed an accessible method for the synthesis of new pyrrolo-1,5-diazepine derivatives and studied the properties of the synthesized compounds. The information given in the literature about the synthesis of this kind of systems has significant drawbacks (multi-stage, limited possibilities of introduction of substitutes and use of a catalyst based on a precious metal). We have developed a method that eliminates these drawbacks. New derivatives of 4,5-dihydropyrrolo[1,2,3-e,f][1,5]-benzdiazepin-6(7H)-one were synthesized according to the developed methods, and the properties of the synthesized compounds were studied. The structure of intermediate and final products was confirmed by the data of IR and UV spectroscopy, mass spectrometry. It was established that the synthesized compounds have selective features (absence of myorelaxation phenomenon), which distinguishes them from tranquilizers of the 1,4-benzdiazepines class. All studied compounds have an anticonvulsant effect, which is expressed to varying degrees depending on the structure. Violation of orientation reflexes and movement coordination was not recorded for all substances, even when relatively large doses were administered. The obtained pharmacological data on representatives of the class of pyrrolo[1,2,3-e,f][1,5]-benzdiazepin-6(7H)-ones may indicate that they are new psychotropic drugs.
One of the most important tasks of modern organic chemistry is the search and development of simple methods for the synthesis of new biologically active substances. 1,4-diazepine derivatives are widely used in medicine due to their high biological activity (anxiolytic, hypnotic, sedative, etc.) and very low toxicity. This contributes to the development of the chemistry of other related systems, in particular the chemistry of 1,5-diazepines. Interest in such systems is due to the fact that substances with an interesting spectrum of biological activity were found among a small number of synthesized compounds. There are tranquilizers, analgesics, substances that reduce pressure and relieve cough more effectively than codeine among the compounds of this class. Taking into account this, as well as the fact that 1,5-diazepine derivatives have been studied relatively little, we developed an accessible method for the synthesis of new pyrrolo-1,5-diazepine derivatives and studied the properties of the synthesized compounds. The information given in the literature about the synthesis of this kind of systems has significant drawbacks (multi-stage, limited possibilities of introduction of substitutes and use of a catalyst based on a precious metal). We have developed a method that eliminates these drawbacks. New derivatives of 4,5-dihydropyrrolo[1,2,3-e,f][1,5]-benzdiazepin-6(7H)-one were synthesized according to the developed methods, and the properties of the synthesized compounds were studied. The structure of intermediate and final products was confirmed by the data of IR and UV spectroscopy, mass spectrometry. It was established that the synthesized compounds have selective features (absence of myorelaxation phenomenon), which distinguishes them from tranquilizers of the 1,4-benzdiazepines class. All studied compounds have an anticonvulsant effect, which is expressed to varying degrees depending on the structure. Violation of orientation reflexes and movement coordination was not recorded for all substances, even when relatively large doses were administered. The obtained pharmacological data on representatives of the class of pyrrolo[1,2,3-e,f][1,5]-benzdiazepin-6(7H)-ones may indicate that they are new psychotropic drugs.
Опис
Ключові слова
7-аміноіндол, фенілгідразон, 1,5-піролодіазепін, 4,5-дигідропіроло[1,2,3-e,f][1,5]-бенздіазепін-6(7Н)-он, реакції Джеппа-Клінгемана, реакції Шмідта, 7-aminoindole, phenylhydrazone, 1,5-pyrrolodiazepine, 4,5-dihydropyrrolo[1,2,3-e,f][1,5]-benzodiazepin-6(7H)-one, reactions of Japp-Klingemann, the Schmidt reactions
Бібліографічний опис
Синтез і дослідження нових семичленних структур на основі аміноіндолу / Р. Ю. Іванова, М. В. Шестакова, О. Б. Ляшенко, Є. В. Савчук, О. М. Рахлицька, К. А. Філіпцова // Вісник Одеського національного університету. Хімія. – 2024. – Т. 29, вип. 1(87). – С. 70–77.
УДК
547.742: 547-327