62099-65-4Relevant academic research and scientific papers
Synthesis of Indolo[2,3- c]quinolin-6(7 H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C-H Arylation
Szabó, Tímea,Papp, Marcell,Németh, Dóra Rita,Dancsó, András,Volk, Balázs,Milen, Mátyás
supporting information, p. 128 - 145 (2020/12/22)
The synthesis of variously substituted indolo[2,3-c]quinolin-6(7H)-ones was developed via Pd-catalyzed intramolecular C-H arylation. This method highlights a strategy for preparing indoloquinoline precursors bearing versatile functional groups and provide
Synthesis of new highly functionalized 1h-indole-2-carbonitriles via cross-coupling reactions
Hrizi, Asma,Cailler, Manon,Romdhani-Younes, Moufida,Carcenac, Yvan,Thibonnet, Jér?me
, (2021/09/06)
An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri-and tetra-substituted indole-2-carbonitriles.
Triarylmethane Fluorophores Resistant to Oxidative Photobluing
Butkevich, Alexey N.,Bossi, Mariano L.,Lukinavi?ius, Gra?vydas,Hell, Stefan W.
supporting information, p. 981 - 989 (2019/01/23)
Spectral stability of small-molecule fluorescent probes is required for correct interpretation and reproducibility of multicolor fluorescence imaging data, in particular under high (de)excitation light intensities of super-resolution imaging or in single-molecule applications. We propose a synthetic approach to a series of spectrally stable rhodamine fluorophores based on sequential Ru- and Cu-catalyzed transformations, evaluate their stability against photobleaching and photoconversion in the context of other fluorophores using chemometric analysis, and demonstrate chemical reactivity of fluorophore photoproducts. The substitution patterns providing the photoconversion-resistant triarylmethane fluorophores have been identified, and the applicability of nonbluing labels in live-cell STED nanoscopy is demonstrated.
Iron(III)-Catalyzed (4 + 2)-Cycloannulation of 2-Hydroxy Ketoxime Ethers with Indol-2-ylamides: Synthesis of Indole-Fused 2-Piperidinones
Schlegel, Marcel,Schneider, Christoph
, p. 5886 - 5892 (2019/04/25)
A highly regio- and diastereoselective (4 + 2)-cycloannulation process of indanone-derived 2-hydroxy ketoxime ethers with 1,4-bisnucleophilic indol-2-ylamides has been developed. In the presence of 5 mol % FeCl3, densely functionalized 2-piperidinones containing two new σ-bonds and two vicinal quaternary stereogenic centers were formed under mild reaction conditions in a one-pot operation. Moreover, most of the products directly precipitated out of the solution and were isolated by simple filtration without purification by column chromatography.
Novel inhibitors of Staphylococcus aureus RnpA that synergize with mupirocin
Lounsbury, Nicole,Eidem, Tess,Colquhoun, Jennifer,Mateo, George,Abou-Gharbia, Magid,Dunman, Paul M.,Childers, Wayne E.
supporting information, p. 1127 - 1131 (2018/02/21)
We recently discovered RnpA as a promising new drug discovery target for methicillin-resistant S. aureus (MRSA). RnpA is an essential protein that is thought to perform two required cellular processes. As part of the RNA degrasome Rnpa mediates RNA degradation. In combination with rnpB it forms RNase P haloenzymes which are required for tRNA maturation. A high throughput screen identified RNPA2000 as an inhibitor of both RnpA-associated activities that displayed antibacterial activity against clinically relevant strains of S. aureus, including MRSA. Structure-activity studies aimed at improving potency and replacing the potentially metabotoxic furan moiety led to the identification of a number of more potent analogs. Many of these new analogs possessed overt cellular toxicity that precluded their use as antibiotics but two derivatives, including compound 5o, displayed an impressive synergy with mupirocin, an antibiotic used for decolonizing MSRA whose effectiveness has recently been jeopardized by bacterial resistance. Based on our results, compounds like 5o may ultimately find use in resensitizing mupirocin-resistant bacteria to mupirocin.
Synthesis and evaluation of indole-containing 3,5-diarylisoxazoles as potential pro-apoptotic antitumour agents
Md Tohid, Siti Farah,Ziedan, Noha I.,Stefanelli, Fabio,Fogli, Stefano,Westwell, Andrew D.
, p. 263 - 270 (2013/01/15)
A series of novel indole-containing diarylisoxazoles has been synthesised, based on our previous work on the synthesis and pro-apoptotic antitumour activity of indole-based diaryl 1,2,4-oxadiazoles. Concise synthetic routes to both 3-(indol-2-yl)-5-phenylisoxazoles and 5-(indol-2-yl)-3-phenylisoxazoles have been developed with full regiochemical control, bearing substituents on the indole ring, indole nitrogen, and/or phenyl group. Additionally a series of the related 5-(1H-indol-5-yl)-3-phenylisoxazoles has been prepared. In vitro evaluation in human cancer cell lines Colo320 (colon) and Calu-3 (lung) revealed preferential antiproliferative activity within the 5-(indol-5-yl)-3- phenylisoxazole series (low micromolar IC50). Further analysis revealed the ability of the indol-5-yl series to induce expression of effector caspases-3 and -7, and retention of viability of the human bronchial smooth muscle cell (BSMC) control cell population (particularly for compounds 18c and 18e).
Antihyperlipidemic properties of novel N-(benzoylphenyl)-5-substituted-1H- indole-2-carboxamides in Triton WR-1339-induced hyperlipidemic rats
Al-Hiari, Yusuf,Shattat, Ghassan,Al-Qirim, Tariq,El-Huneidi, Waseem,Sheikha, Ghassan Abu,Hikmat, Suhair
experimental part, p. 8292 - 8304 (2011/12/14)
In the search for new potential antihyperlipidemic agents, the present study focuses on the synthesis of novel N-(benzoylphenyl)-5-substituted-1H- indole-2-carboxamides (compounds 8-12, 15, 16, 18) and investigating their antihyperlipidemic activity using
Synthesis and cytotoxicity of 1-phenylethanolamine carboxamide derivatives: Effects on the cell cycle
Babu, Balaji,Forrest, Lori,Weisbruch, Paul,Chavda, Sameer,Pati, Hari,Lee, Moses
experimental part, p. 1141 - 1152 (2011/10/03)
Seven novel analogues of 1-phenylethanolamine carboxamide derivatives, 3a-3g, related to carboxamides isolated from Isodon excisus were synthesized and evaluated for their cytotoxic and apoptosis-induction properties against murine B16 and leukemia L1210 cell lines. Compounds containing no substitution at the 4′-position (3a-3d) or containing a 4′-amino (3e-3g) group were investigated. Generally, the amino-containing compounds were slightly more active than their unsubstituted congeners. Also, the indole-containing compounds 3c and 3f gave the strongest cytotoxic activity (IC50 = 25-87 μM) against the growth of L1210 and B16 cancer cells. Compound 3f was subjected to flow cytometry studies and it was found to induce L1210 cells grown in culture to undergo apoptosis.
Indole-2-carboxamidines as novel NR2B selective NMDA receptor antagonists
Borza, Istvan,Kolok, Sandor,Ignacz-Szendrei, Gyoergyi,Greiner, Istvan,Tarkanyi, Gabor,Galgoczy, Kornel,Horvath, Csilla,Farkas, Sandor,Domany, Gyoergy
, p. 5439 - 5441 (2007/10/03)
A novel series of indole-2-carboxamidine derivatives was prepared and identified as NR2B selective NMDA receptor antagonists. The influence of the substituents on the indole skeleton as well as the substitution of the benzyl moiety on the biological activ
N2-Benzyl-N1-(1-(1-naphthyl)ethyl)-3-phenylpropane-1, 2-diamines and conformationally restrained indole analogues: Development of calindol as a new calcimimetic acting at the calcium sensing receptor
Kessler, Albane,Faure, Hélène,Petrel, Christophe,Ruat, Martial,Dauban, Philippe,Dodd, Robert H.
, p. 3345 - 3349 (2007/10/03)
The synthesis and calcimimetic activities of two new families of compounds are described. The most active derivatives of the first family, N 2-(2-chloro-(or 4-fluoro-)benzyl)-N1-(1-(1-naphthyl)ethyl) -3-phenylpropane-1,2-diamine (4b
