313273-62-0Relevant academic research and scientific papers
Acid-activated carbon materials: Cheaper alternative catalysts for the synthesis of substituted quinolines
Lopez-Sanz, Jesus,Perez-Mayoral, Elena,Soriano, Elena,Omenat-Moran, Delia,Duran, Carlos J.,Martin-Aranda, Rosa Maria,Matos, Ines,Fonseca, Isabel
, p. 3736 - 3742 (2013)
We describe the first examples of Friedlaender reactions efficiently catalyzed by carbon materials. We report herein a series of acidic activated carbon materials, which can be considered as an environmentally friendly, cheaper alternative to the traditional acidic mesoporous silicates or even zeolites for the synthesis of quinolines/quinolones. Textural parameters of the acidic activated carbon materials together with their acidic properties are important factors that affect the reaction selectivity. Some mechanistic details have been addressed by computational calculations. Freeloading on the Friedlaender: Acidic microporous activated carbon materials containing sulfonic acid groups can be considered environmentally friendly and cheaper catalytic alternatives for the Friedlaender reaction compared to traditional acidic solids such as zeolites or even mesoporous silicates. The textural characteristics of the most efficient materials determine the parameters for the conversion and selectivity of the reaction. Copyright
Synthesis, crystal structure investigation, spectroscopic characterizations and DFT computations on a novel 1-(2-chloro-4-phenylquinolin-3-yl)ethanone
Murugavel,Stephen, C.S. Jacob Prasanna,Subashini,Reddy, H. Raveendranatha,Ananthakrishnan, Dhanabalan
, p. 134 - 145 (2016)
The title compound 1-(2-chloro-4-phenylquinolin-3-yl)ethanone (CPQE) was synthesised effectively by chlorination of 3-acetyl-4-phenylquinolin-2(1H)-one (APQ) using POCl3 reagent. Structural and vibrational spectroscopic studies were performed b
Synthetic Lethality in Pancreatic Cancer: Discovery of a New RAD51-BRCA2 Small Molecule Disruptor That Inhibits Homologous Recombination and Synergizes with Olaparib
Bagnolini, Greta,Milano, Domenico,Manerba, Marcella,Schipani, Fabrizio,Ortega, Jose Antonio,Gioia, Dario,Falchi, Federico,Balboni, Andrea,Farabegoli, Fulvia,De Franco, Francesca,Robertson, Janet,Pellicciari, Roberto,Pallavicini, Isabella,Peri, Sebastiano,Minucci, Saverio,Girotto, Stefania,Di Stefano, Giuseppina,Roberti, Marinella,Cavalli, Andrea
, p. 2588 - 2619 (2020/03/05)
Synthetic lethality is an innovative framework for discovering novel anticancer drug candidates. One example is the use of PARP inhibitors (PARPi) in oncology patients with BRCA mutations. Here, we exploit a new paradigm based on the possibility of triggering synthetic lethality using only small organic molecules (dubbed "fully small-molecule-induced synthetic lethality"). We exploited this paradigm to target pancreatic cancer, one of the major unmet needs in oncology. We discovered a dihydroquinolone pyrazoline-based molecule (35d) that disrupts the RAD51-BRCA2 protein-protein interaction, thus mimicking the effect of BRCA2 mutation. 35d inhibits the homologous recombination in a human pancreatic adenocarcinoma cell line. In addition, it synergizes with olaparib (a PARPi) to trigger synthetic lethality. This strategy aims to widen the use of PARPi in BRCA-competent and olaparib-resistant cancers, making fully small-molecule-induced synthetic lethality an innovative approach toward unmet oncological needs.
Triflic Anhydride Promoted Intramolecular Cyclization of N -Aryl Cinnamides: Access to Polysubstituted Quinolin-2(1 H)-ones
Zhang, Qian,Yuan, Jingwen,Yu, Mangfei,Zhang, Rui,Liang, Yongjiu,Huang, Peng,Dong, Dewen
, p. 4996 - 5002 (2017/10/06)
A facile and efficient synthesis of polysubstituted quinolin-2(1 H)-ones is developed via intramolecular cyclization of readily available N -aryl cinnamides promoted by triflic anhydride in N, N -dimethyl trifluoroacetamide (DTA) under mild conditions.
Synthesis of 2-Quinolinones through Palladium(II) Acetate Catalyzed Cyclization of N -(2-Formylaryl)alkynamides
Zhang, Jianbo,Han, Xiuling,Lu, Xiyan
supporting information, p. 1744 - 1748 (2015/07/20)
A Pd(OAc)2-catalyzed cyclization of N-(2-formylaryl)alkynamides initiated by the oxypalladation of alkynes was developed. The method provides a new approach for the efficient and atom-economical synthesis of 2-quinolinone derivatives.
Friedl?nder annulation: Scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines
Tanwar, Babita,Kumar, Dinesh,Kumar, Asim,Ansari, Md. Imam,Qadri, Mohammad Mohsin,Vaja, Maulikkumar D.,Singh, Madhulika,Chakraborti, Asit K.
, p. 9824 - 9833 (2015/12/01)
The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedl?nder and non-Friedl?nder products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of
Controlling ZIF-8 nano- and microcrystal formation and reactivity through zinc salt variations
Schejn, Aleksandra,Balan, Lavinia,Falk, Veronique,Aranda, Lionel,Medjahdi, Ghouti,Schneider, Raphael
, p. 4493 - 4500 (2014/05/20)
We report here a simple method for controlling the crystal size and morphology of zeolitic imidazolate framework-8 (ZIF-8) nanocrystals in methanol solution. ZIF-8 crystals were prepared by mixing 2-methylimidazole (Hmim) with various zinc salts for 1 h a
Synthesis and SAR studies of dual AKT/NF-κB inhibitors against melanoma
Barile, Elisa,De, Surya K.,Feng, Yongmei,Chen, Vida,Yang, Li,Ronai, Ze'ev,Pellecchia, Maurizio
, p. 520 - 533 (2013/11/06)
The protein Kinase B alpha (AKT) and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) pathways are central regulators of cellular signaling events at the basis of tumor development and progression. Both pathways are often up-regulated in different tumor types including melanoma. We recently reported the identification of compound 1 (BI-69A11) as inhibitor of the AKT and the NF-κB pathways. Here, we describe SAR studies that led to novel fluorinated derivatives with increased cellular potency, reflected in efficient inhibition of AKT and IKKs. Selected compounds demonstrated effective toxicity on melanoma, breast, and prostate cell lines. Finally, a representative derivative showed promising efficacy in an in vivo melanoma xenograft model. We describe SAR studies that led to compound 42 as a potent cellular inhibitor of phosphorylation of AKT1-3 and the NF-κB pathway in melanoma, breast, and prostate cell lines and showed remarkable efficacy in an in vivo melanoma xenograft model with the drug administered orally.
New inorganic-organic hybrid materials based on SBA-15 molecular sieves involved in the quinolines synthesis
López-Sanz, Jesús,Pérez-Mayoral, Elena,Soriano, Elena,Sturm, Marina,Martín-Aranda, Rosa María,López-Peinado, Antonio J.,?ejka, Ji?í
experimental part, p. 97 - 103 (2012/07/28)
In this paper we report on the first mesoporous catalyst based on SBA-15 incorporating simultaneously basic and acid functions able to promote the Friedl?nder reaction between 2-aminoaryl ketones and ethyl acetoacetate leading to quinolines 1 with high yi
Solvent-free synthesis and antibacterial studies of some quinolinones
Subashini, Radhakrishnan,Khan, Fazlur-Rahman Nawaz
experimental part, p. 485 - 489 (2012/06/16)
Solvent-free, microwave-induced condensation of 2-aminoaryl alkyl ketones and ethyl 3-oxobutanoate in the presence of amberlite Na sr1L gave quinolinones in high yield when compared to other catalysts. Further, N-alkylation of the quinolinones was carried
