89671-85-2Relevant academic research and scientific papers
Synthesis and evaluation of cyclic nitrone derivatives as potential anti-cancer agents
Zhou, Wei,Ju, Dongyan,Ao, Yuhui,Liu, Yu,Zhao, Jinbo
, p. 1309 - 1316 (2021/05/27)
Nitrones have been found to exhibit attractive biological values as immuno spin trapping agents. However, successful clinical cases of nitrone therapeutics are still lacking. Herein we report the synthesis and antiproliferative activity of a series of structurally diverse nitrone derivatives against a panel of 5 cancer cell lines, based on which indole- and pyrrole-fused were further evaluated by analogue preparation and in-vitro screening. Analogues with moderate to good potency were identified. This study shows the promise for further pursuit of nitrone-type small molecules in chemotherapy. [Figure not available: see fulltext.]
THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
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, (2019/06/13)
Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.
Asymmetric Nazarov Cyclizations Catalyzed by Chiral-at-Metal Complexes
Mietke, Thomas,Cruchter, Thomas,Larionov, Vladimir A.,Faber, Tabea,Harms, Klaus,Meggers, Eric
, p. 2093 - 2100 (2018/04/19)
The application of Lewis acidic chiral-at-metal complexes of iridium(III) and rhodium(III) as catalysts for the asymmetric polarized Nazarov cyclization of dihydropyran- and indole-functionalized α-unsaturated β-ketoesters is reported (overall 24 examples). For both substrate classes, catalyst loadings of 2 mol% were found to be sufficient for achieving high yields and high stereoselectivities. The cyclized dihydropyran products were isolated in 85–98% yield, with 89%–>99% ee, and trans/cis ratios of 15:1–50:1 (9 examples). The cyclized indole products were typically isolated in more than 70% yield and in up to 93% yield, typically with more than 90% ee and in up to 97% ee, and trans/cis ratios of 12:1–28:1 (15 examples). (Figure presented.).
A new approach to 1-substituted β-carbolines and isoquinolines utilizing tributyl[(Z)-2-ethoxyvinyl]stannane as a C-3,C-4 building block
Kamlah, Alexandra,Lirk, Florian,Bracher, Franz
, p. 837 - 845 (2016/01/20)
Starting from readily available indole-2-carboxylic acids, 1-substituted β-carbolines (among them the alkaloids harmane and isoharmine) are readily obtained via the corresponding 2-acylindoles, bromination at C-3, followed by a one-pot Stille cross-coupling with tributyl[(Z)-2-ethoxyvinyl]stannane, and ring closure with ammonium acetate. 1-Substituted isoquinolines are available in an analogous manner starting from 2-bromobenzoic acid.
Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of 2-nitrovinylarenes
Okuro, Kazumi,Gurnham, Joanna,Alper, Howard
, p. 4715 - 4720 (2011/07/08)
Ionic diamine rhodium complex (1) catalyzes the reductive N-cyclization of 2-vinylnitroarenes using carbon monoxide as a reducing agent to afford functionalized indoles. The catalytic system allows direct access to indoles with ester and ketone groups at the 2- or 3-position, in good yields.
4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione inhibitors of the checkpoint kinase Wee1. structure-activity relationships for chromophore modification and phenyl ring substitution
Palmer, Brian D.,Thompson, Andrew M.,Booth, R. John,Dobrusin, Ellen M.,Kraker, Alan J.,Lee, Ho H.,Lunney, Elizabeth A.,Mitchell, Lorna H.,Ortwine, Daniel F.,Smaill, Jeff B.,Swan, Leesa M.,Denny, William A.
, p. 4896 - 4911 (2007/10/03)
High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]-carbazole-1,3(2H,6H)- dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.
Cyclic indole and heteroindole derivatives and methods for making and using as pharmaceuticals
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, (2008/06/13)
The invention relates to novel, substituted, fused indole and heteroindole derivatives of the general formula I their tautomers, stereoisomers, mixtures and pharmaceutically acceptable salts, their synthesis and their use as pharmaceuticals, especially as
Cyclic indole and heteroindole derivatives and methods for making and using as pharmaceuticals
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Page 6, (2010/11/30)
The invention relates to novel, substituted, fused indole and heteroindole derivatives of the general formula I their tautomers, stereoisomers, mixtures and pharmaceutically acceptable salts, their synthesis and their use as pharmaceuticals, especially as
SYNTHESIS OF 2-ACYLINDOLES FROM α-(N-ISATINYL) KETONES
Gorgos, V. I.,Zorin, L. M.,Zhungietu, G. I.,Rekhter, M. A.
, p. 1179 - 1181 (2007/10/02)
2-Acylindoles were synthesized by the recyclization of N-phenacyl- and N-acetonylisatins in alkaline medium and the decarboxylation of 2-acylindolyl-3-carboxylic acids or their salts in basic or neutral media.
