13623-10-4Relevant academic research and scientific papers
Acyclic cucurbit[n]uril-type molecular containers: Influence of aromatic walls on their function as solubilizing excipients for insoluble drugs
Zhang, Ben,Isaacs, Lyle
, p. 9554 - 9563 (2014)
We studied the influence of the aromatic sidewalls on the ability of acyclic CB[n]-type molecular containers (1a-1e) to act as solubilizing agents for 19 insoluble drugs including the developmental anticancer agent PBS-1086. All five containers exhibit go
Intramolecular Benzyne–Phenolate [4+2] Cycloadditions
Hirano, Keiichi,Nishii, Arata,Ohmori, Ken,Suzuki, Keisuke,Takiguchi, Hiromu,Takikawa, Hiroshi,Tanaka, Masato,Uchiyama, Masanobu,Yagishita, Hirotoshi
, p. 12440 - 12444 (2020)
An intramolecular benzyne–phenolate [4+2] cycloaddition is reported. Benzyne precursors, having vicinal halogen-sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph3MgLi or nBuLi for halogen–metal exchange to form various benzobarrelenes.
Ruthenium-catalyzed oxidative dearomatization of phenols to 4-(tert-butylperoxy)cyclohexadienones: Synthesis of 2-substituted quinones from p-substituted phenols
Murahashi, Shun-Ichi,Miyaguchi, Noriko,Noda, Shinji,Naota, Takeshi,Fujii, Akiko,Inubushi, Yasutaka,Komiya, Naruyoshi
scheme or table, p. 5355 - 5365 (2011/11/14)
The ruthenium-catalyzed oxidation of phenols with tert-butylhydroperoxide efficiently gives the corresponding 4-(tert-butylperoxy)cyclohexadienones. The oxidation proceeds selectively because of ruthenium's ability for rapid single-electron transfer. This biomimetic oxidation reaction is highly useful to obtain the metabolic compounds desired for confirming the safety of medicines and related compounds. Typically, the first metabolic compound of the female hormone estrone is readily obtained by this biomimetic oxidation reaction. The resulting 4-(tert-butylperoxy)cyclohexadienones are versatile synthetic intermediates, which can be transformed into 2-substituted 1,4-benzoquinones by treatment with acid catalysts. Acid-promoted rearrangement followed by a Diels-Alder reaction provides a new strategy for the synthesis of fused cyclic compounds, such as naphthoquinone and anthraquinone derivatives, from readily available phenols. The nonnatural 1,4-diacetoxy steroidal skeleton is obtained by the oxidation of estrone followed by zinc-mediated migration. Vitamin K 3 is synthesized selectively from p-cresol in an overall 79 % yield in 4 steps, and the synthesis includes the ruthenium-catalyzed oxidation.
Direct access to 1,4-dihydroxyanthraquinones: The Hauser annulation reexamined with p-quinones
Mal, Dipakranjan,Ray, Sutapa,Sharma, Indrajeet
, p. 4981 - 4984 (2008/02/05)
(Chemical Equation Presented) 3-Phenylsulfanylphthalides (e.g. 8a) readily react with p-benzoquinones in the presence of LiOtBu in THF to furnish 1,4-dihydroxyanthraquinones in good yields and one-pot operations.
Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists
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, (2008/06/13)
Compounds represented by the following (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, aryl-alkyl, heteroaryl-alkyl or cycloalkyl-alkyl, R2 is H, alkyl or haloalkyl, the polymethylene chain (II), is saturated or may contain a carbon-carbon double bond, while n is 2, 3, 4, W is O or S, Y is an unsubsituted or substituted phenylene, naphthylene or 1, 2, 3, 4 tetrahydronaphthylene, R3 is H, alkyl or haloalkyl. R4 is H, alkyl, haloalkyl or a substituted or unsubstituted benzyl, are useful for modulating a peroxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus.
Modulators of peroxisome proliferator activated receptors
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, (2008/06/13)
The present invention is directed to compounds represented by Structural Formula I and pharmaceutically acceptable salts, solvates and hydrates thereof, and methods of making, methods of using and pharmaceutical compositions having compounds represented b
SYNTHESIS AND CONFIGURATION OF SOME NEW BICYCLIC 3-ARYLIDENE- AND 3-HETEROARYLIDENE-2-OXINDOLES
Buzzetti, Franco,Pinciroli, Vittorio,Brasca, M. Gabriella,Crugnola, Angelo,Fustinoni, Silvia,Longo, Antonio
, p. 69 - 76 (2007/10/02)
The synthesis of a novel class of bicyclic 3-arylidene- and 3-heteroarylidene-2-oxindoles possessing tyrosine kinase inhibitory activity is described.Compounds 1-16 have been prepared by condensation of 2-oxindole with a (hetero)aromatic aldehyde belonging to the naphthalene, tetralin, quinoline or indole series.The compounds so obtained were single E or Z isomers or separable mixtures thereof.The single E or Z isomers could be partially transformed into their isomers by acid or basic catalysis.The E/Z configuration assignment was achieved by 1H NMR spectroscopy on the basis of chemical shifts and NOE data obtained from NOESY spectra.
cinnamamide analogs as inhibitors of protein tyrosine kinases
Buzzetti,Brasca,Crugnola,Fustinoni,Longo,Penco,Dalla Zonca,Comoglio
, p. 615 - 636 (2007/10/02)
Protein tyrosine kinases (PTK) arc important signal transducing enzymes involved in the modulation of normal cellular growth and differentiation and have been associated with the etiology of various human cancers. The development of properly designed inhibitors, which block their function by interfering with the substrate binding, may therefore offer an unique target for selective anticancer chemotherapy. Here we describe synthesis and biochemical testing of a novel series of non-peptide PTK inhibitors which have as characteristic active pharmacophore the cinnamamide moiety. For testing we used an exogenous substrate kinase assay based on the phosphorylation of (Val)-angiotensin II with radiolabelled ATP by the catalytic domain of the PTK encoded by the v-abl oncogene (p45 v-abl). The most potent compounds were found in the class of 3-arylidene-2-oxindoles (II) with IC50 values in the 1μM range. Among these the 2-tetralylmethylene-, 4-quinolylmethylene-, 5-quinolylmethylene- and 3-indolylmethylene-2-oxindole compounds of formulae 16, 20, 21 and 24 respectively were selected for further investigation.
Synthesis and Demethylation of New 5,6,7,8-Tetrahydro-4,9-dimethoxy-1H-benzindole
Malesani, Giorgio,Ferlin, Maria Grazia,Masiero, Sergio
, p. 633 - 637 (2007/10/02)
The title compound 17 was prepared in good yield starting from 5,6,7,8-tetrahydro-1-naphthol (9) by an advantageous synthesis route consisting of eight steps, as indicated in Scheme 2.Demethylation by reflux heating with anhydrous aluminium chloride in dry benzene furnished 4,9-dihydroxy- and 4,9-dioxo-5,6,7,8-tetrahydro-1H-benzindoles (compounds 18 an 19, respectively).All new products were identified on the basis of spectral and analytical data.
