FIELD: organic chemistry.
SUBSTANCE: invention relates to organic chemistry, to novel biologically active substances of the class of substituted thienopyrrolopyrimidines. Disclosed is 5-amino-3-(morpholine-4-carbonyl)-1-(2-oxo-2-(4-fluorophenyl)ethylidene)-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e]pyrrolo[1,2-a]pyrimidine-2(1H)-one of formula:
having anti-inflammatory activity. 5-amino-3-(morpholine-4-carbonyl)-1-(2-oxo-2-(4-fluorophenyl)ethylidene)-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e]pyrrolo[1,2-a]pyrimidin-2(1H)-one is obtained by interaction of nitrile of 2-((2-oxo-5-(4-fluorophenyl)furan-3(2H)-ylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid with 3-morpholino-3-oxopropane nitrile in presence of 1 equivalent of diisopropylethylamine (DIPEA). Reaction takes place in dioxane while stirring and temperature of 90 °C with subsequent extraction of target products using known methods.
EFFECT: obtaining a compound with high output, having pronounced anti-inflammatory activity, as well as low toxicity.
1 cl
| Title |
Year |
Author |
Number |
| 5-AMINO-1-(2-OXO-2-PHENYLETHYLIDENE)-3-(PYRROLIDINE-1-CARBONYL)-6,7,8,9-TETRAHYDROBENZO[4,5]THIENO[3,2-e]PYRROLO[1,2-a]PYRIMIDIN-2(1H)-ONE, WHICH HAS ANALGESIC ACTIVITY |
2023 |
- Parkhoma Kseniia Iurevna
- Lipin Dmitrii Vladimirovich
- Makhmudov Ramiz Ragibovich
- Shipilovskikh Sergei Aleksandrovich
|
RU2810252C1 |
| N'-(IMINO(2-((6-(2-METHOXYPHENYL)-2-(4-NITROBENZOYL)-3-OXO-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[B]THIOPHEN-3-YL)METHYL)-4-NITROBENZOHYDRAZIDE, HAVING ANTI-INFLAMMATORY ACTIVITY |
2024 |
- Shipilovskikh Sergej Aleksandrovich
- Makhmudov Ramiz Ragibovich
- Lipin Dmitrij Vladimirovich
|
RU2831250C1 |
| 1-AMINO-1,6-DIOXO-6-(4-CHLOROPHENYL)-2-CYANO-4-(3-CYANO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHEN-2-YL)AMINO)HEXA -2,4-DIEN-3-OLATE POTASSIUM WITH ANTI-INFLAMMATORY ACTIVITY |
2022 |
- Shipilovskikh Sergei Aleksandrovich
- Makhmudov Ramiz Ragibovich
- Lipin Dmitrii Vladimirovich
- Kozlov Danil Anatolevich
|
RU2798468C1 |
| ETHYL ETHER 2-AMINO-(3-CYANO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHEN-2-YL)-5-(2-(4-ETHYLPHENYL)-2-OXOETHYLIDENE)-4-OXO- 4,5-DIHYDRO-1H-PYRROL-3-CARBOXYLIC ACID WITH ANALGESIC ACTIVITY |
2023 |
- Shipilovskikh Sergei Aleksandrovich
- Makhmudov Ramiz Ragibovich
- Lipin Dmitrii Vladimirovich
- Parkhoma Kseniia Iurevna
|
RU2810070C1 |
| 4-(4-METHOXYPHENYL)-4-OXO-N-PHENYL-2-((3-CYANO-4,5,6,7-TETRAHYDROBENZO[b]THIOPHEN-2-YL)AMINO)BUT-2-ENAMIDE WITH ANALGESIC ACTIVITY |
2023 |
- Shipilovskikh Sergei Aleksandrovich
- Makhmudov Ramiz Ragibovich
- Gorbunova Irina Aleksandrovna
|
RU2810072C1 |
| AMIDE (E)-2-AMINO-4-OXO-5-(2-OXO-2-PHENYLETHYLIDENE)-1-(3-ETHOXYCARBONYL)-4,5,6-7-TETRAHYDROBENZO[B]THIOPHEN-2-YL)4,5-DIHYDRO-1H-PYRROLE-3-CARBOXYLIC ACID, HAVING ANTIMICROBIAL ACTIVITY |
2020 |
- Shipilovskikh Sergej Aleksandrovich
- Rubtsov Aleksandr Evgenevich
- Makhmudov Ramiz Ragibovich
- Tkachenko Aleksandr Georgievich
- Nesterova Larisa Yurevna
|
RU2738405C1 |
| (E)-5-AMINO-2-OXO-1-((E)-2-OXO-4-PHENYLBUT-3-EN-1-YLIDENE)-1,2,6,7,8,9-HEXAHYDROBENZO[4,5]THIENO[3,2-E]PYRROLO[1,2-A]PYRIMIDINE-3-CARBOXAMIDE, HAVING ANTICANCER ACTIVITY IN PULMONARY MELANOMA THERAPY |
2023 |
- Karpov Timofei Evgenevich
- Rogova Anna
- Timin Aleksandr Sergeevich
- Shipilovskikh Sergei Aleksandrovich
|
RU2815045C1 |
| 4-BROMO-N'-((2-((2-(4-BROMOBENZOYL)-3-OXO-6-PHENYL-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[B]THIOPHEN-3-YL)(IMINO)METHYL)BENZOHYDRAZIDE, HAVING ANALGESIC ACTIVITY |
2024 |
- Shipilovskikh Sergei Aleksandrovich
- Makhmudov Ramiz Ragibovich
- Lipin Dmitrii Vladimirovich
|
RU2829963C1 |
| APPLICATION OF 2-[(1,4-DIOXO-1-R-4-(4-METHOXYPHENYL)BUT-2-ENE-2-YL)AMINO]-4,5,6,7-TETRAHYDROBENZO[b]THIOPHENE-3-CARBOXYLIC ACID AMIDES AS AN ANALGESIC MEDICINAL PRODUCT |
2021 |
- Shipilovskikh Sergej Aleksandrovich
- Rubtsov Aleksandr Evgenevich
- Makhmudov Ramiz Ragibovich
- Shipilovskikh Darya Aleksandrovna
|
RU2779193C1 |
| N-ETHYL-2-((3-OXO-6-(4-FLUOROPHENYL)-2-ETHYL-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[b]THIOPHENE-3-CARBOXIMIDE HYDRAZIDE, HAVING ANTIMICROBIAL ACTIVITY |
2024 |
- Shipilovskikh Sergei Aleksandrovich
- Makhmudov Ramiz Ragibovich
- Lipin Dmitrii Vladimirovich
|
RU2831253C1 |
