- Asymmetric Reductive Amination/Ring-Closing Cascade: Direct Synthesis of Enantioenriched Biaryl-Bridged NH Lactams
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We report here a Ru-catalyzed enantioselective synthesis of biaryl-bridged NH lactams through asymmetric reductive amination and a spontaneous ring-closing cascade from keto esters and NH4OAc with H2 as reductant. The reaction features broad substrate generality and high enantioselectivities (up to >99percent ee). To showcase the practical utility, a highly enantioselective synthesis of 5-ethylindolobenzazepinone C, a promising antimitotic agent, has been rapidly completed. Furthermore, the amide group in the products enables versatile elaborations through directed C-H functionalization.
- Zhang, Yao,Liu, Yun-Qi,Hu, Le'An,Zhang, Xumu,Yin, Qin
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supporting information
p. 6479 - 6483
(2020/09/02)
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- A Versatile C–H Halogenation Strategy for Indole Derivatives under Electrochemical Catalyst- and Oxidant-Free Conditions
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Halogenated indoles are essential structural motifs in bioactive natural products. Reported herein is an economical and scalable electrochemical protocol for regioselective 3C–H halogenation of indole derivatives. This strategy provides access to a host of 3-iodo-, 3-bromo-, 3-chloro-, and 3-thiocyanoindole derivatives under mild conditions using inexpensive (pseudo)halide salts as the sole reagent. The optimized conditions do not require any supplementary electrolyte salts.
- Sun, Linhao,Zhang, Xing,Li, Zilong,Ma, Jimei,Zeng, Zhen,Jiang, Hong
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supporting information
p. 4949 - 4952
(2018/05/15)
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- Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes
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The first ring-forming thioboration reaction of C?C π bonds is reported. This catalyst-free method proceeds in the presence of a commercially available external electrophilic boron source (B-chlorocatecholborane) in good to high yields. The method is scalable and tolerates a variety of functional groups that are intolerant of other major borylation methods. The resulting borylated benzothiophenes participate in a variety of in situ derivatization reactions, showcasing that these borylated intermediates do not need to be isolated prior to downstream functionalization. This methodology has been extended to the synthesis of borylated dihydrothiophenes. Mechanistic experiments suggest that the operative mechanistic pathway is through boron-induced activation of the alkyne followed by electrophilic cyclization, as opposed to S?B σ bond formation, providing a mechanistically distinct pathway to the thioboration of C?C π bonds.
- Faizi, Darius J.,Davis, Ashlee J.,Meany, Fiach B.,Blum, Suzanne A.
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supporting information
p. 14286 - 14290
(2016/11/11)
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- Flexible synthesis of isomeric pyranoindolones and evaluation of cytotoxicity towards HeLa cells
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A hybrid pharmacophore approach for the synthesis of isomeric pyranoindolones was achieved by employing gold(III) chloride-catalyzed cycloisomerization of alkyne-tethered indole carboxylic acids in good to excellent yield. All the synthesized compounds were evaluated for their tumor cell growth inhibitory activity against human cervix adenocarcinoma (HeLa) which revealed that three compounds exhibited activity comparable with the standard cis-platin (IC50 = 0.08 μM). Molecular docking of all the compounds in Vaccinia H1-Related (VHR) Phosphatase receptor also supported that compound 7d as the most active with a free energy of binding as ?8.27 kcal/mol. [Figure not available: see fulltext.]
- Jeyaveeran,Praveen, Chandrasekar,Arun,Prince,Perumal
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p. 787 - 802
(2016/05/19)
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- Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma
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A highly regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones via gold(III) chloride catalyzed cycloisomerization of 3-ethynyl-indole-2-carboxylic acid was achieved in good to excellent yields. These compounds were screened for their in vitro cytotoxicity against human cervical (HeLa) cell lines. Out of ten compounds, three compounds (7d, 7e and 7j) showed comparable proliferation inhibitory activity against the standard drug cisplatin. Compound 7d was found to be the most efficacious with IC50 value of 0.22 μM.
- Praveen, Chandrasekaran,Ayyanar, Asairajan,Perumal, Paramasivan Thirumalai
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supporting information; experimental part
p. 4170 - 4173
(2011/08/06)
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- Efficient synthesis of the first n-methyloxoarcyriaflavin including an original central seven-membered cycle
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A new route to the first N-methyloxoarcyriaflavin was designed. The compound was obtained by a palladium-catalyzed Stille cross-coupling reaction, followed by an electrophilic cyclization onto a C-2 indolic position as a key step. Georg Thieme Verlag Stuttgart · New York.
- Bourderioux, Aurelie,Ouach, Aziz,Beneteau, Valerie,Merour, Jean-Yves,Routier, Sylvain
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scheme or table
p. 783 - 790
(2010/09/18)
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- Synthesis-driven mapping of the dictyodendrin alkaloids
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The dictyodendrin alkaloids have been described as the first telomerase inhibitors of marine origin. As such they represent interesting lead compounds in the quest for small molecule inhibitors of this tumor-marker enzyme. Described herein is the preparat
- Buchgraber, Philipp,Domostoj, Mathias M.,Scheiper, Bodo,Wirtz, Conny,Mynott, Richard,Rust, J?rg,Fürstner, Alois
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experimental part
p. 6519 - 6534
(2011/02/26)
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- TREATMENT OF PROTEIN FOLDING DISORDERS
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In certain embodiments, the invention is directed to a method for treating a protein folding disorder such as Alzheimer's disease, dementia, Parkinson's disease, Huntington's disease and prion-based spongiform encephalopathy. The method comprises the administration to a subject of a compound of the formula (I) wherein A and B are independently a mono- or bicyclic aromatic group or heteroaromatic cyclic group. In preferred embodiments, the compounds are bis-indole compounds.
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Page/Page column 106
(2010/11/25)
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- New indole derivatives as factor Xa inhibitors
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The present invention relates to compounds of formula I, in which R0; R1; R2; R3; R4; R5; R6; R7; Q; V, G and M have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is indicated. The invention furthermore relates to processes for the preparation of compounds of formula I, their use, in particular as pharmaceuticals for treating the foregoing conditions, and pharmaceutical preparations comprising them.
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Page/Page column 67
(2008/06/13)
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