63469-11-4Relevant academic research and scientific papers
Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid
Mélin, Léa,Abdullayev, Shuay,Fnaiche, Ahmed,Vu, Victoria,González Suárez, Narjara,Zeng, Hong,Szewczyk, Magdalena M.,Li, Fengling,Senisterra, Guillermo,Allali-Hassani, Abdellah,Chau, Irene,Dong, Aiping,Woo, Simon,Annabi, Borhane,Halabelian, Levon,LaPlante, Steven R.,Vedadi, Masoud,Barsyte-Lovejoy, Dalia,Santhakumar, Vijayaratnam,Gagnon, Alexandre
, p. 2982 - 3002 (2021/08/03)
The YAP-TEAD transcriptional complex is responsible for the expression of genes that regulate cancer cell growth and proliferation. Dysregulation of the Hippo pathway due to overexpression of TEAD has been reported in a wide range of cancers. Inhibition of TEAD represses the expression of associated genes, demonstrating the value of this transcription factor for the development of novel anti-cancer therapies. We report herein the design, synthesis and biological evaluation of LM98, a flufenamic acid analogue. LM98 shows strong affinity to TEAD, inhibits its autopalmitoylation and reduces the YAP-TEAD transcriptional activity. Binding of LM98 to TEAD was supported by 19F-NMR studies while co-crystallization experiments confirmed that LM98 is anchored within the palmitic acid pocket of TEAD. LM98 reduces the expression of CTGF and Cyr61, inhibits MDA-MB-231 breast cancer cell migration and arrests cell cycling in the S phase during cell division.
Decoquinate derivatives: A new class of potent antischistosomal agents against Schistosoma japonicum
Wang, Wen-Long,Song, Li-Jun,Hu, Bo-Chun,Miao, Li,Chen, Xiao-Yu,Fan, Wen-Hua,Yin, Xu-Ren,Shen, Shuang,Ding, Zhao-Feng,Yu, Chuan-Xin
, p. 1547 - 1552 (2017/07/17)
Decoquinate (1), an old and inexpensive coccidiostat, exhibited potent antimalarial activity, however, its antischistosomal activity against Schistosoma japonicum has not yet been evaluated. Based on decoquinate, a series of decoquinate derivatives was designed, synthesized, evaluated as a new class of antischistosomal agents against S. japonicum adult worms in vitro. Among them, compound 15 killed 100% of adult S. japonicum in 72?h at the concentration of 10?μmol/L in vitro, exhibited stronger worm-killing activity than PZQ in vitro and could serve as a promising lead compound to develop new antischistosomal agents.
Room temperature, metal-free arylation of aliphatic alcohols
Ghosh, Raju,Lindstedt, Erik,Jalalian, Nazli,Olofsson, Berit
, p. 54 - 57 (2014/05/06)
Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal-free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron
Liquid crystalline properties of dimers having o-, m- and p- positional molecular structures
Park, Joo-Hoon,Choi, Ok-Byung,Lee, Hwan Myung,Lee, Jin-Young,Kim, Sung-Jo,Cha, Eun-Hee,Kim, Dong-Hyun,Ramaraj,So, Bong-Keun,Kim, Kyung-Hwan,Lee, Soo-Min,Yoon, Kuk Ro
experimental part, p. 1647 - 1652 (2012/07/27)
With the objective to design and synthesis of Schiff's base symmetrical liquid crystal dimmers and to study the effect of molecular structure variation (o-ortho, m-meta, p-para) and change in alkoxy terminal chain length on mesomorphic properties of liquid crystals, We have synthesized Schiff base dimers from dialdehyde derivative containing 2-hydroxy-1,3-dioxypropylene as short spacer with aniline derivatives having different lengths of terminal alkoxy chains (n = 5, 7, 9). The chemical structure of the final products was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy and fourier transform infrared (FT-IR) spectroscopy. The mesomorphic properties and optical textures of the resultant dimers were characterized by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). The existence of smectic A phase transition was confirmed by the observation of batonnets and fan shaped textures in optical microscopy when compound were heated from crystalline phase. All of the dimers of this series, with the exception of 2S5 -ortho, -meta, -para, were thermotropic liquid crystal. The compound 2S9 -meta was monotropic, while the rest were enantiotropic. It was found that the change in terminal alkoxy chain length has pronounced effect on the mesomorphic properties. The temperature range of smectic A phase window widens with increasing alkoxy chain length.
Liquid-crystalline polymorphism of 4-heptyloxybenzylidene-4′- alkyloxyanilines and their phase equilibrium with 4-octyloxyphenyl 4-nitrobenzoate
Godzwon, Joanna,Sienkowska, Monika J.,Galewski, Zbigniew
scheme or table, p. 75 - 82 (2012/04/04)
This paper describes the synthesis and liquid-crystalline properties of the homologous series of 4-heptyloxybenzylidene-4′-alkyloxyanilines (7-n). Six of them are presented for the first time. Based on the polarization microscopy (POM and TOA methods) and the calorimetric (DSC) measurements following polymorphism has been detected: nematic, smectic C and smectic I mesophases. The presence of these mesophases was confirmed by the miscibility method, using 4-octyloxyphenyl 4-nitrobenzoate and terephtal-bis (4-butyloaniline) as a mesophase references. Extraordinary results have been found in the mixtures of the investigated compounds with 4-octyloxyphenyl 4-nitrobenzoate; Induced smectic A has been observed, which is connected with very strong intermolecular interactions. Additionally destabilization of nematic and smectic C phases was visible.
Smectic polymorphism of 4-nonyloxybenzylidene-4′-alkyloxyanilines
Godzwon, Joanna,Sienkowska, Monika J.,Galewski, Zbigniew
, p. 259 - 267 (2008/03/13)
This paper describes liquid-crystalline polymorphism of the homologous series of 4-nonyloxybenzylidene-4′-alkyloxyanilines. Based on the polarization microscopy (POM, TOA) and the calorimetric (DSC) measurements the following mesophases were detected: nematic, smectic A, smectic C, smectic B, smectic I and smectic G. The presence of these mesophases was confirmed by the miscibility method, using: 4-heptyloxybenzilidene-4′-pentylaniline, 4-hexyl-4′-decyloxyazobenzene and 4-nonyloxybenzilidene-4′-butylaniline as mesophase references. Influence of the alkyl chain length on the type of mesophases and entropic effects of phase transition are discussed.
The newborn surface of dull metals in organic synthesis. Bismuth-mediated solvent-free one-step conversion of nitroarenes to azoxy- and azoarenes
Wada, Shinobu,Urano, Mika,Suzuki, Hitomi
, p. 8254 - 8257 (2007/10/03)
When milled together with bismuth shots, nitroarenes are readily converted to azoxy- and/or azoarenes depending on substrates and conditions employed. Simple extraction with organic solvent followed by evaporation of the resulting dark pasty solid gave the product in good yield.
Kinetics of Phase-transfer Etherification Reactions of p-Chloronitrobenzene by Alkoxides
Lerner, Jaime de la Zerda,Cohen, Sasson,Sasson, Yoel
, p. 1 - 6 (2007/10/02)
The substitution reaction of chloride by alkoxide anions in p-chloronitrobenzene in a phase-transfer catalytic system has been studied and succesfully performed in high yield and without the occurrence of side reactions.The effect of several parameters has been experimentally investigated.In particular, the poisoning effect of the chloride anion produced throughout the reaction is studied and a practical answer to succesfully overcome this problem and increase yields is presented.A kinetic model based on the collected data is proposed.
EFFECT OF CHAIN BRANCHING ON MESOMORPHISM IN BROAD MOLECULES.
Dave,Kurian,Patel,Prajapati
, p. 311 - 317 (2007/10/02)
Two new homologous series of Schiff's bases were synthesized. The method of preparation and the liquid crystalline properties of these compounds are described. Both series are nematogenic; the smectic phase is absent even in higher members of the series. In series I, the C//2 and C//3 homologue exhibit two solid modifications. The influence of branching in the end alkoxy groups of these compounds on the mesomorphism is discussed. The mesomorphic properties of these compounds are compared with those of related compounds.
