195874-03-4Relevant academic research and scientific papers
Ketone-Directed Cobalt(III)-Catalyzed Regioselective C2 Amidation of Indoles
Shi, Xinxia,Xu, Weiyan,Wang, Rongchao,Zeng, Xiaofei,Qiu, Huayu,Wang, Min
, p. 3911 - 3920 (2020/03/23)
An efficient cobalt(III)-catalyzed method for the direct C-H amidation of unprotected indoles for 2-amino indole scaffold construction has been developed. With dioxazolone as the amidating reagent, a variety of 2-amino indole derivatives were achieved in moderate to excellent yields using an organic acid as the additive and a ketone as the directing group.
Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles
Adouama, Chérif,Budén, María E.,Guerra, Walter D.,Puiatti, Marcelo,Joseph, Beno?t,Barolo, Silvia M.,Rossi, Roberto A.,Médebielle, Maurice
supporting information, p. 320 - 324 (2019/01/10)
A novel approach for the synthesis of tetracyclic indoles and 7-azaindoles is reported. The strategy involves four steps, with a fast rt intramolecular α-arylation of ketones as key step. The reaction was inspected synthetically to achieve the synthesis of 11 novel tetracyclic structures with moderate to very good yields (39-85%). Theoretical combined with experimental studies led us to propose a probable polar mechanism (concerted SNAr).
Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles
Adouama, Chérif,Budén, María E.,Guerra, Walter D.,Puiatti, Marcelo,Joseph, Beno?t,Barolo, Silvia M.,Rossi, Roberto A.,Médebielle, Maurice
supporting information, (2019/01/08)
A novel approach for the synthesis of tetracyclic indoles and 7-azaindoles is reported. The strategy involves four steps, with a fast rt intramolecular α-arylation of ketones as key step. The reaction was inspected synthetically to achieve the synthesis of 11 novel tetracyclic structures with moderate to very good yields (39-85%). Theoretical combined with experimental studies led us to propose a probable polar mechanism (concerted SNAr).
Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria
Huggins, William M.,Barker, William T.,Baker, James T.,Hahn, Nicholas A.,Melander, Roberta J.,Melander, Christian
, p. 702 - 707 (2018/06/04)
In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.
ISOXAZOLE DERIVATIVE AS MUTATED ISOCITRATE DEHYDROGENASE 1 INHIBITOR
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Paragraph 0302; 0303, (2018/02/06)
It has been found that a compound of the general formula (I) having an isoxazole skeleton has excellent inhibitory activity against mutant IDH1 protein and inhibits the production of 2-HG by this protein, while the compound is also capable of effectively inhibiting the growth of various tumors expressing the protein. In the formula, R1, R2, R3, Y, and Z are as defined in claim 1.
Synthesis, protein kinase inhibitory potencies, and in vitro antiproliferative activities of meridianin derivatives
Giraud, Francis,Alves, Georges,Debiton, Eric,Nauton, Lionel,Théry, Vincent,Durieu, Emilie,Ferandin, Yoan,Lozach, Olivier,Meijer, Laurent,Anizon, Fabrice,Pereira, Elisabeth,Moreau, Pascale
scheme or table, p. 4474 - 4489 (2011/09/14)
The synthesis of new meridianin derivatives is described. The indolic ring system was substituted at the C-4 to C-7 positions either by a bromine atom or by nitro or amino groups. Additionally, an iodine atom or various aryl groups were introduced at the C-5 position of the 2-aminopyrimidine ring. These compounds as well as some of their synthetic intermediates were tested for their kinase inhibitory potencies and for their in vitro antiproliferative activities. We found that this series of compounds is particularly interesting in the development of new inhibitors of DYRK1A and CLK1 kinases. The most effective compounds toward these two kinase families are the 6- and 7-bromo derivatives 30, 33, and 34 that showed more than 45-fold selectivity toward DYRK1A/CLK1 kinases over the other kinases tested. Meridianin derivatives could thus be developed toward potent and selective inhibitors of key RNA splicing regulators and potential therapeutic agents.
Towards the syntheses of N-H and N-alkylated derivatives of meridianins
Simon, Ga?lle,Couthon-Gourves, Hélène,Haelters, Jean-Pierre,Corbel, Bernard,Kervarec, Nelly,Michaud, Fran?ois,Meijer, Laurent
, p. 793 - 801 (2008/03/29)
(Chemical Equation Presented) Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved by 1H and 13C NMR spectroscopy, NOE experiments and X-ray analysis.
Rapid synthesis of the N-methylwelwitindolinone skeleton
MacKay, James A.,Bishop, Raynauld L.,Rawal, Viresh H.
, p. 3421 - 3424 (2007/10/03)
(Chemical Equation Presented) An efficient, convergent synthesis of the core bicyclo[4.3.1]decane ring system of welwitindolinones is described. Key steps in the synthesis include an intramolecular palladium-catalyzed enolate arylation reaction to create
Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole
Moody, Christopher J.,Doyle, Kevin J.,Elliott, Mark C.,Mowlem, Timothy J.
, p. 2413 - 2419 (2007/10/03)
Model studies towards the synthesis of the cytotoxic marine natural product diazonamide A are described. Three model 3-phenylbenzo[b]furan derivatives 5, 8 and 10 were prepared using rhodium(II) catalysed decomposition of the diazophenylacetate 3, Claisen rearrangement of the ether 7, and a classical intramolecular Friedel-Crafts reaction as key steps. Only the aromatic benzofuran system proved satisfactory in palladium coupling reactions; diazoacetyl(benzofuranyl)indole 18 was prepared by Suzuki coupling of (benzofuran-7-yl)boronic acid 11 with 4-bromoindole 14 to give 17, followed by diazo-transfer. Rhodium(II) catalysed decomposition of 18 in acetonitrile resulted in the formation of the 3,4-bridged indole 19 rather than the desired oxazole 20.
