- New iodo- and nitro-substituted pyrroles
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Treating 2,5-dimethyl-4-ethoxycarbonyl- and 2,5-dimethyl-4-carboxypyrroles with iodine furnished 3-iodo-2,5-dimethyl-4-ethoxycarbonyl- and 3,4-diiodo-2,5-dimethylpyrroles. It was established that 3-iodo-2,5-dimethyl-4- ethoxycarbonylpyrrole reacted at heating with silver nitrite to afford 2,5-dimethyl-3-nitro-4-ethoxycarbonylpyrrole, and the same reagent oxidized 3,4-diiodo-2,5-dimethylpyrrole to give 3,4-diiodo-2-methyl-5-formylpyrrole. 2005 Pleiades Publishing, Inc.
- Mironov,Kharitonova,Efimkin,Solomentseva
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- Design, synthesis and biological activities of pyrrole-3-carboxamide derivatives as EZH2 (enhancer of zeste homologue 2) inhibitors and anticancer agents
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Zeste enhancer homolog 2 (EZH2) is highly expressed in various malignant tumors, which could silence tumor suppressor genes via trimethylation of H3K27. Herein was first reported a novel series of pyrrole-3-carboxamide derivatives carrying a pyridone fragment as EZH2 inhibitors. By combining computational modeling, in vitro cellular assays and further rational structure-activity relationship exploration and optimization, compound DM-01 showed powerful inhibition towards EZH2. DM-01 was found to have significant ability to reduce the cellular H3K27me3 level in K562 cells in the Western blot test. Meanwhile, our data showed that knockdown EZH2 in A549 cells resulted in a decrease of cell sensitivity to DM-01 at 50 and 100 μM. DM-01 could also increase the transcription expression of DIRAS3 in a dose-dependent manner, a tumor suppressor in the downstream of EZH2, suggesting it was worth investigating further as a lead compound.
- Zhou, Qifan,Jia, Lina,Du, Fangyu,Dong, Xiaoyu,Sun, Wanyu,Wang, Lihui,Chen, Guoliang
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supporting information
p. 2247 - 2255
(2020/02/20)
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- Pyrrole-3-formamide compound as well as preparation method and application thereof
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The invention belongs to the technical field of medicines, and relates to a pyrrole-3-formamide compound as well as a preparation method and application thereof, in particular to a pyrrole-3-formamidecompound shown as a formula (I) or (II) and a pharmaceutically-acceptable salt thereof, wherein R to R and X are defined in the claims and description. The preparation of the compound mainly comprises performing Knorr pyrrole synthesis, Hantzsch pyrrole synthesis, decarboxylation, alkylation, hydrolysis, condensation, cyclization and reduction on ethyl acetoacetate or tert-butyl acetoacetate serving as the raw material. The pyrrole-3-formamide compound and the pharmaceutically-acceptable salt thereof have good treatment effects on tumors, and can be applied to the preparation of anti-tumor drugs. (The formulas (I) and (II) are shown in the description).
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Paragraph 0124; 0160; 0161
(2019/02/25)
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- The pyrrolecarboxylic acid production
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PROBLEM TO BE SOLVED: To provide a novel production method of pyrrole carboxylic acids, with which carbon dioxide can be utilized as a carbon source and a pyrrole carboxylic acid useful as a production raw material of medicines and agrochemicals is easily produced by making 1H-pyrrole react with carbon dioxide so that a carboxy group is directly introduced into a pyrrole skeleton in a low pressure of 1 MPa or less.SOLUTION: In introducing a carboxy group into a pyrrole skeleton by directly carboxylating 1H-pyrrole with carbon dioxide in a reaction solvent and in the presence of a catalyst, an excess of basic catalyst over 1H-pyrrole is used as the catalyst so that a pyrrole carboxylic acid is produced by introducing a carboxy group into a pyrrole skeleton in a low pressure of 1 MPa or less. The basic catalyst is lithium t-butoxide.
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Paragraph 0035; 0036; 0037
(2017/09/02)
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- Synthesis and structure-activity relationships of a series of pyrrole cannabinoid receptor agonists
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We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB1 and CB2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB1 partial agonist properties.
- Tarzia, Giorgio,Duranti, Andrea,Tontini, Andrea,Spadoni, Gilberto,Mor, Marco,Rivara, Silvia,Plazzi, Pier Vincenzo,Kathuria, Satish,Piomelli, Daniele
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p. 3965 - 3973
(2007/10/03)
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