105512-18-3Relevant academic research and scientific papers
Synthesis of 4-substituted-3-Hydroxyquinolin-2(1H)-ones with anticancer activity
Paterna, Roberta,Padanha, Rita,Russo, Roberto,Frade, Raquel F.M.,Faustino, Hélio,Gois, Pedro M.P.
, (2020)
Herein we show that the 3-hydroxyquinolin-2(1H)-one (3HQ) core is a suitable platform to develop new compounds with anticancer activity against MCF-7 (IC50 up to 4.82 μM) and NCI–H460 (IC50 up to 1.8 μM) cancer cell lines. The ring-expansion reaction of isatins with diazo esters catalysed by di-rhodium (II) complexes proved to be a simple and effective strategy to synthesize 4-carboxylate-3HQs (yields up to 92%). 4-Carboxamide-3HQs were more efficiently prepared using NHS-diazoacetate in yields up to 88%. This innovative methodology enabled the construction of “peptidic-like” 3HQs, with several amino acid substituents. Among this series, the L-leucine derivative induced the cell death of MCF-7 (IC50 of 15.1 μM) and NCI–H460 (IC50 of 2.7 μM) cancer cell lines without causing any appreciable cytotoxicity against the non-cancer cell model (CHOK1).
Photocatalytic gem-Difluoroolefination Reactions by a Formal C?C Coupling/Defluorination Reaction with Diazoacetates
Li, Fang,Pei, Chao,Koenigs, Rene M.
supporting information, (2021/12/14)
The photolysis of diazoalkanes to conduct singlet carbene transfer reactions of colored diazoalkanes has recently attracted significant interest in organic synthesis. Herein, we describe a photocatalytic approach that allows the access of triplet carbene
Palladium-Catalyzed C(sp3)-C(sp2) Cross-Couplings of O -(α-Bromoacyl) Cyanohydrins with Boronic Acids: An Entry to Enantioenriched N -Acylated β-Amino Alcohols
Hertzberg, Robin,Dinér, Peter,Moberg, Christina
, p. 3175 - 3182 (2016/09/12)
Suzuki-type cross-coupling of enantiomerically enriched O-(α-bromoacyl) cyanohydrins with aromatic boronic acids substituted with electron-withdrawing or electron-donating groups gave the expected coupling products in high yields without racemization. These substrates exhibit higher reactivities than analogous substrates lacking the nitrile function, probably as a result of π-coordination of the nitrile to palladium. Reduction of the nitrile group of the products, with accompanying intramolecular acyl transfer, provides access to biologically interesting N-acylated β-amino alcohols.
Preparation of a novel silica gel-adsorbed Br?nsted acid catalyst for the solvent-free esterification of bromoacetic acid with benzyl alcohol
Funabiki, Kazumasa,Komeda, Takuya,Sakaida, Yuta,Kubota, Yasuhiro,Matsui, Masaki
, p. 116 - 120 (2013/02/23)
A new bifunctional Br?nsted acid catalyst that contains two sulfo groups was prepared. The adsorption of this new bifunctional Br?nsted acid catalyst on silica gel made it possible to be reused 10 times without a loss of catalytic activity in the solvent-free esterification of bromoacetic acid with an equiv. of benzyl alcohol without the formation of dibenzyl ether.
Phosphorofluoridic acid-catalyzed condensation reaction of carboxylic acids with 1-arylalkyl alcohols leading to esters under solvent-free conditions
Murai, Toshiaki,Tanaka, Nagisa,Higashijima, Shinji,Miura, Hidetoshi
supporting information; experimental part, p. 668 - 669 (2011/04/22)
Phosphorofluoridic acid with an L-menthyl group catalyzed condensation reaction between carboxylic acids and 1-arylalkyl alcohols under solvent-free conditions to give esters in moderate to high yields. Results using aliphatic acids are shown. Copyright
N,N′-ditosylhydrazine: A convenient reagent for facile synthesis of diazoacetates
Torna, Tatsuya,Shimokawa, Jun,Fukuyama, Tohru
, p. 3195 - 3197 (2008/02/10)
A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N′-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.
