6636-32-4Relevant academic research and scientific papers
Fast and stable photochromic oxazines
Tomasulo, Massimiliano,Sortino, Salvatore,White, Andrew J. P.,Raymo, Francisco M.
, p. 8180 - 8189 (2005)
We have designed and synthesized two photochromic compounds incorporating fused indoline and benzooxazine fragments. Variable-temperature 1H NMR spectroscopy demonstrates that their central [1,3]oxazine ring opens thermally with free energy bar
Harnessing the Role of HDAC6 in Idiopathic Pulmonary Fibrosis: Design, Synthesis, Structural Analysis, and Biological Evaluation of Potent Inhibitors
Campiani, Giuseppe,Cavella, Caterina,Osko, Jeremy D.,Brindisi, Margherita,Relitti, Nicola,Brogi, Simone,Saraswati, A. Prasanth,Federico, Stefano,Chemi, Giulia,Maramai, Samuele,Carullo, Gabriele,Jaeger, Benedikt,Carleo, Alfonso,Benedetti, Rosaria,Sarno, Federica,Lamponi, Stefania,Rottoli, Paola,Bargagli, Elena,Bertucci, Carlo,Tedesco, Daniele,Herp, Daniel,Senger, Johanna,Ruberti, Giovina,Saccoccia, Fulvio,Saponara, Simona,Gorelli, Beatrice,Valoti, Massimo,Kennedy, Breándan,Sundaramurthi, Husvinee,Butini, Stefania,Jung, Manfred,Roach, Katy M.,Altucci, Lucia,Bradding, Peter,Christianson, David W.,Gemma, Sandra,Prasse, Antje
, p. 9960 - 9988 (2021/07/31)
Idiopathic pulmonary fibrosis (IPF) is an interstitial lung disease characterized by a progressive-fibrosing phenotype. IPF has been associated with aberrant HDAC activities confirmed by our immunohistochemistry studies on HDAC6 overexpression in IPF lung tissues. We herein developed a series of novelhHDAC6 inhibitors, having low inhibitory potency overhHDAC1 andhHDAC8, as potential pharmacological tools for IPF treatment. Their inhibitory potency was combined with lowin vitroandin vivotoxicity. Structural analysis of 6h and structure-activity relationship studies contributed to the optimization of the binding mode of the new molecules. The best-performing analogues were tested for their efficacy in inhibiting fibrotic sphere formation and cell viability, proving their capability in reverting the IPF phenotype. The efficacy of analogue 6h was also determined in a validated human lung model of TGF-β1-dependent fibrogenesis. The results highlighted in this manuscript may pave the way for the identification of first-in-class molecules for the treatment of IPF.
Preparation of Indolenines via Nucleophilic Aromatic Substitution
Huber, Florian,Roesslein, Joel,Gademann, Karl
, p. 2560 - 2564 (2019/03/19)
An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.
Efficient Synthesis of Chiral Indolines using an Imine Reductase from Paenibacillus lactis
Li, Hao,Luan, Zheng-Jiao,Zheng, Gao-Wei,Xu, Jian-He
supporting information, p. 1692 - 1696 (2015/06/02)
An enzymatic process for the efficient asymmetric reduction of 3H-indoles as well as 3H-indole iodides was developed for the first time. Using a new imine reductase identified from Paenibacillus lactis (PlSIR), various chiral indolines were facilely synthesized in good yields and excellent enantiopurities (up to >99% ee) under mild reaction conditions.
Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation
Lackner, Aaron D.,Samant, Andrew V.,Toste, F. Dean
, p. 14090 - 14093 (2013/10/21)
The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.
Fast and stable photochromic oxazines for fluorescence switching
Deniz, Erhan,Tomasulo, Massimiliano,Cusido, Janet,Sortino, Salvatore,Raymo, Francsco M.
scheme or table, p. 11773 - 11783 (2012/05/04)
The stringent limitations imposed by diffraction on the spatial resolution of fluorescence microscopes demand the identification of viable strategies to switch fluorescence under optical control. In this context, the photoinduced and reversible transforma
One-pot-one-step, microwave-assisted Fischer indole synthesis
Creencia, Evelyn Cuevas,Tsukamoto, Masayuki,Horaguchi, Takaaki
experimental part, p. 1095 - 1102 (2011/11/04)
The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4-tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p-toluenesulfonic acid (p-TSA), the reaction yielded 91% of 1,2,3,4-tetrahydrocarbazole. Thus, a series of indoles were prepared using microwaves in the presence of p-TSA catalyst.
A fast and stable photochromic switch based on the opening and closing of an oxazine ring
Tomasulo, Massimiliano,Sortino, Salvatore,Raymo, Francisco M.
, p. 1109 - 1112 (2007/10/03)
(Chemical Equation Presented) We have designed a molecular switch based on the photoinduced opening and thermal closing of an oxazine ring. Ultraviolet excitation of this molecule induces the cleavage of a [C-O] bond to form a p-nitrophenolate chromophore
Synthesis of a new series of indolinic aminoxyls. Reaction of indoles, 2-phenylbenzothiazole, 2-phenylbenzoxazole and 2-phenyl1,2-dihydro-4H-3,1-benzoxazin-4-one with organolithium reagents
Tommasi, Giampaolo,Bruni, Paolo,Greci, Lucedio,Sgarabotto, Paolo,Righi, Lara,Petrucci, Rita
, p. 2123 - 2128 (2007/10/03)
2-Alkyl-2-phenyl-3,3-dimethylindolines. obtained by 1,2 organolithium addition to 2-phenyl-3,3-dimethyl-3H-indole, are converted into a new series of aminoxyls by oxidation with m-chloroperoxybenzoic acid. Attempts to synthesise, in a similar way suitable precursors such as 1,2-dihydro-2-phenyl-2-alkylbenzothiazole, 1,2-dihydro-2-phenyl-2-alkylbenzoxazole and 1,2-dihydro-2-phenyl-2-alkyl-4H-3,1-benzoxazin-4-one for other new aminoxyls failed. In fact, 2-phenylbenzothiazole, 2-phenylbenzoxazole and 2-phenyl-4H-3,1-benzoxazin-4-one react with organolithium reagents affording products deriving from ring opening. Crystal structures of 2,3-dimethyl-3-phenyl-3H-indole and bis(2-triphenylmetriylaminophenyl) disulfide are also described.
Electronic and molecular structure of 2-phenyl-3,3-dimethyl-3H-indole molecular fluorescence probe and the molecular structure of its dimer
Belletete, M.,Brisse, F.,Durocher, G.,Gravel, D.,Heroux, A.,Popowycz, A.
, p. 63 - 80 (2007/10/02)
Crystallographic measurements as well as AMPAC and INDO/S calculations were performed on 2-phenyl-3,3-dimethyl-3H-indole (1).This fluorescent molecular probe was shown to dimerize in the solid and the X-ray structure shows that the dimer consists of two monomers linked by covalent bonds between the nitrogen atom (N1) of one molecule to the carbon atom C2 of the other molecule, and vice versa, thus forming a four-membered ring.It was observed that the dimer of 1 is labile in the presence of traces of acid and reverts back to the monomer.It is shown that AMPAC, while predicting good bond distances and angles, failed to predict the correct dihedral angle between the Phc ring and the indolic moiety.The semiempirical INDO/S method coupled to absorption and fluorescence spectral data in more than 18 non-polar, polar aprotic and/or protic solvents showed that the Phc ring should librate within a range of about 20 deg around the equilibrium dihedral angle of approximately 45 deg at room temperature in the ground electronic state of the molecule.This libration is responsible for the fact that the fluorescence quantum yields (ΦF) and lifetimes (ΤF) of 1 vary from 2.4 x 1E-4 to 0.12 and from 1 to 520 ps, respectively, in the various solvents investigated as a result of viscosity dependent fast internal conversion.Rates of internal conversion are shown to be dependent upon the bulk viscosity of the solvent as opposed to the microviscosity (free volume effect of the solvent), so that the Foerster-Hoffmann mechanism (ΦF = CΕ2/3) with an identical value of C applies in all solvents.This molecule may then be regarded as an excellent viscosity probe for heterogeneous systems and polymers in a very large range of viscosities.
