18159-22-3Relevant articles and documents
Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides
Nemoto, Koji,Onozawa, Satoru,Egusa, Naoki,Morohashi, Naoya,Hattori, Tetsutaro
, p. 4512 - 4514 (2009)
The Lewis acid-mediated carboxylation of arenes with CO2 has been successfully applied to 1-substituted indoles and pyrroles by using dialkylaluminum chlorides instead of aluminum trihalides. Thus, the carboxylation of 1-methylindoles, 1-benzyl-, and 1-phenylpyrroles proceeds regioselectively with the aid of an equimolar amount of Me2AlCl under CO2 pressure (3.0 MPa) at room temperature to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in 61-85% yields, while the same treatment of 1,2,5-trimethylpyrrole affords the 3-carboxylic acid in 52% yield.
Catalyst-Controlled Chemodivergent Reactions of 2-Pyrrolyl-α-diazo-β-ketoesters and Enol Ethers: Synthesis of 1,2-Dihydrofuran Acetals and Highly Substituted Indoles
France, Stefan,Guerra Faura, Gabriel,Nguyen, Tena
supporting information, p. 10088 - 10104 (2021/07/31)
A catalyst-controlled, chemodivergent reaction of pyrrolyl-α-diazo-β-ketoesters with enol ethers is reported. While Cu(II) catalysts selectively promoted a [3 + 2] cycloaddition to provide pyrrolyl-substituted 2,3-dihydrofuran (DHF) acetals, dimeric Rh(II) catalysts afforded 6-hydroxyindole-7-carboxylates via an unreported [4 + 2] benzannulation. The choice of enol ether proved to be crucial in determining both regioselectivity and yield of the respective products (up to 91% yield for Cu(II) and 82% for Rh(II) catalysis). Furthermore, the DHF acetals were shown to serve as precursors to 7-hydroxyindole-6-carboxylates (isomeric to the indoles formed from Rh) and highly substituted furans in the presence of Lewis acids. Thus, from a common pyrrolyl-α-diazo-β-ketoester, up to three unique heterocyclic scaffolds can be achieved based on catalyst selection.
Design and synthesis of non-peptide mimetics mapping the immunodominant myelin basic protein (MBP83-96) epitope to function as T-cell receptor antagonists
Yannakakis, Mary-Patricia,Simal, Carmen,Tzoupis, Haralambos,Rodi, Maria,Dargahi, Narges,Prakash, Monica,Mouzaki, Athanasia,Platts, James A.,Apostolopoulos, Vasso,Tselios, Theodore V.
, (2017/06/19)
Encephalitogenic T cells are heavily implicated in the pathogenesis of multiple sclerosis (MS), an autoimmune demyelinating disease of the central nervous system. Their stimulation is triggered by the formation of a trimolecular complex between the human
PYRROLO AND PYRAZOLOPYRIMIDINES AS UBIQUITIN-SPECIFIC PROTEASE 7 INHIBITORS
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Paragraph 2020; 2021, (2016/08/03)
The invention relates to inhibitors of USP7 inhibitors useful in the treatment of cancers, neurodegenerative diseases, immunological disorders, inflammatory disorders, cardiovascular diseases, ischemic diseases, viral infections and diseases, and bacterial infections and diseases, having the Formula: where m, n, X1, X2, R1-R5, R5′ and R6 are described herein.
A reductive-coupling plus nazarov cyclization sequence in the asymmetric synthesis of five-membered carbocycles
Kerr, Daniel J.,White, Jonathan M.,Flynn, Bernard L.
supporting information; experimental part, p. 7073 - 7084 (2010/12/25)
Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.
Synthesis of 2-(N-benzylpyrrolyl)-benzimidazoles using polyphosphoric acid prompted cyclocondensation
Mochona, Bereket,Le, Laine,Gangapuram, Madhavi,Mateeva, Nelly,Ardley, Tiffany,Redda, Kinfe K.
experimental part, p. 1367 - 1371 (2010/12/29)
Synthesis of a series of 2-substituted benzimidazoles was carried out for screening anti-inflammatory activities. 2-(N-benzylpyrrolyl)-benzimidazoles 9a-k were synthesized from N-benzyl-2-pyrrole carboxylic acids 8a-d and 4-substituted-1,2-phenylenediamin
Structure-activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors
Teng, Xin,Keys, Heather,Yuan, Junying,Degterev, Alexei,Cuny, Gregory D.
body text, p. 3219 - 3223 (2009/04/06)
Necroptosis is a regulated caspase-independent cell death pathway resulting in morphology reminiscent of passive non-regulated necrosis. Several diverse structure classes of necroptosis inhibitors have been reported to date, including a series of [1,2,3]thiadiazole benzylamide derivatives. However, initial evaluation of mouse liver microsome stability indicated that this series of compounds was rapidly degraded. A structure-activity relationship (SAR) study of the [1,2,3]thiadiazole benzylamide series revealed that increased mouse liver microsome stability and increased necroptosis inhibitory activity could be accomplished by replacement of the 4-cyclopropyl-[1,2,3]thiadiazole with a 5-cyano-1-methylpyrrole. In addition, the SAR and the cellular activity profiles, utilizing different cell types and necroptosis-inducing stimuli, of representative [1,2,3]thiadiazole and pyrrole derivatives were very similar suggesting that the two compound series inhibit necroptosis in the same manner.
Synthesis and biological evaluation of enantiomerically pure pyrrolyloxazolidinones as a new class of potent and selective monoamine oxidase type A inhibitors
Mai,Artico, Marino,Esposito,Ragno,Sbardella,Massa
, p. 231 - 241 (2007/10/03)
Due to the key role played by monoamine oxidases (MAOs) in the metabolism of neurotransmitters, MAO inhibitors (MAOIs) represent an useful tool for the treatment of several neurological diseases. Among selective MAOIs, MAO-A inhibitors (e.g. clorgyline) are used as antidepressant and antianxiety drugs and are claimed to protect neuronal cells against apoptosis, and selective MAO-B inhibitors (e.g. L-deprenyl) can be used in the treatment of Parkinson's disease either alone or in combination with L-DOPA. However, they engender covalent bonds with the active site of the enzyme and induce irreversible inhibition; moreover, they tend to lose their initial selectivity at high dosages or with repeated administrations. Phenyloxazolidinones belong to third-generation-MAOIs, characterized by a selective and reversible inhibition of the enzyme. Among these molecules, the most representative are toloxatone and befloxatone, two selective and reversible MAO-A inhibitors used in therapy as antidepressant drugs. Going on our searches on CNS potentially active compounds containing a pyrrole moiety we prepared 3-(1H-pyrrol-1-yl)-2-oxazolidinones (1) and isomeric 3-(1H-pyrrol-2-and -3-yl)-2-oxazolidinones (2 and 3) as anti-MAO agents. Such derivatives resulted selective and reversible MAO-A inhibitors. The most potent compound is (R)-5-methoxymethyl-3-(1H-pyrrol-1-yl)-2-oxazolidinone (1b), endowed with very high potency (KiMAO-A=4.9 nM) and A-selectivity (A-selectivity=10,200, about 116-fold greater than that of befloxatone).
Method of using aryl-or heteroaryl-1-alkyl-pyrrole-2-carboxylic acid compounds in the treatment of interleukin-1 mediated conditions
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, (2008/06/13)
This invention relates to the method of using aryl- or heteroaryl-1-alkyl-pyrrole-2-carboxylic acid compounds to treat interleukin-1 mediated conditions.
Novel aryl-or heteroaryl-1-alkyl-pyrrole-2-carboxylic acid compounds useful in treating interleukin-1 mediated conditions
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, (2008/06/13)
This invention relates to novel aryl- or heteroaryl-1-alkyl-pyrrole-2-carboxylic acid compounds useful in treating interleukin-1 mediated conditions.
