43073-12-7Relevant academic research and scientific papers
NOVEL BICYCLIC-COMPOUNDS FOR USE AS A MEDICAMENT, IN PARTICULAR FOR TREATMENT OF PARKINSON'S DISEASE
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, (2017/07/06)
The invention relates to novel small molecule compounds having a basic structure as depicted by formula (A), where in particular exemplary embodiments R1 is -OH, R2 is -NO2 and R3 is H, R4 and R5
Traceless and Chemoselective Amine Bioconjugation via Phthalimidine Formation in Native Protein Modification
Tung, Chun Ling,Wong, Clarence T. T.,Fung, Eva Yi Man,Li, Xuechen
supporting information, p. 2600 - 2603 (2016/06/15)
ortho-Phthalaldehyde (OPA) and its derivatives are found to react chemoselectively with amino groups on peptides and proteins rapidly and tracelessly under the physiological condition via formation of phthalimidines, which provides a novel and promising approach when performing bioconjugation on native proteins. The notable advantages of this method over the existing native protein lysine-labeling approaches include a traceless process, a self-reacting, specific and fast reaction, ease of operation, and the ability to use nonhydrolyzable reagents. Its applications have been effectively demonstrated including conjugation of peptides and proteins, and generation of an active PEGlyated l-asparaginase.
Identification of Potential Off-target Toxicity Liabilities of Catechol-O-methyltransferase Inhibitors by Differential Competition Capture Compound Mass Spectrometry
Von Kleist, Lisa,Michaelis, Simon,Bartho, Kathrin,Graebner, Olivia,Schlief, Marén,Dreger, Mathias,Schrey, Anna K.,Sefkow, Michael,Kroll, Friedrich,Koester, Hubert,Luo, Yan
, p. 4664 - 4675 (2016/06/13)
Structurally related inhibitors of a shared therapeutic target may differ regarding potential toxicity issues that are caused by different off-target bindings. We devised a differential competition capture compound mass spectrometry (dCCMS) strategy to ef
Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action
Parrino, Barbara,Carbone, Anna,Ciancimino, Cristina,Spanò, Virginia,Montalbano, Alessandra,Barraja, Paola,Cirrincione, Girolamo,Diana, Patrizia,Sissi, Claudia,Palumbo, Manlio,Pinato, Odra,Pennati, Marzia,Beretta, Giovanni,Folini, Marco,Matyus, Peter,Balogh, Balázs,Zaffaroni, Nadia
, p. 149 - 162 (2015/03/18)
Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progression and inducing apoptosis in cancer cells. These effects were associated to IIQ-mediated impairment of tubulin polymerization at pharmacologically significant concentrations of tested compounds. In addition, impaired DNA topoisomerase I functions and perturbation in telomere architecture were observed in cells exposed to micromolar concentrations of IIQ derivatives. The above results suggest that IIQ derivatives exhibit multi-target cytotoxic activities.
Efficient synthesis of selected phthalazine derivatives
Bunce, Richard A.,Harrison, Todd,Nammalwar, Baskar
, p. 123 - 126 (2013/01/16)
Four phthalazine derivatives have been prepared from substituted 2-bromobenzaldehyde acetals by a sequence involving: (1) lithiation and formylation; (2) deprotection; and (3) condensative cyclization with hydrazine. Two additional phthalazines were prepa
Application of the intramolecular isomerisation - Aldolisation from allylic alcohols and allylic silyl ethers to the synthesis of indanones and indenones
Petrignet, Julien,Roisnel, Thierry,Gree, Rene
, p. 7374 - 7384 (2008/03/14)
A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.
Reactivity of 3-ethoxycarbonyl isoquinolinium salts towards various nucleophilic reagents: Applications to the synthesis of new 1,2- dihydroisoquinoline-3-carboxylates
Meziane, Mohamed Ameziane Ait Amer,Bazureau, Jean Pierre
, p. 252 - 263 (2007/10/03)
Different types of novel 1,2-disubstituted 1,2-dihydro isoquinolines were synthesized by addition reactions of organolithium, alcoholates and borohydride reagents with various isoquinolinium salts. The leaving group character of the isoquinoline moiety was also evidenced.
A practical 'one-pot' synthesis of ethyl isoquinoline-3-carboxylate by domino reactions: A potential entry to constrained nonproteogenic amino acid derivatives
Ameur Meziane, Mohamed A?t,Royer, Sylvain,Bazureau, Jean Pierre
, p. 1017 - 1020 (2007/10/03)
Two simple and efficient 'one-pot' preparations of isoquinoline-3-carboxylates by domino reactions using phthalaldehydes and imidate (route A) or diethyl aminomalonate (route B) are described. The third route involves the use of ethyl glycinate, aminoacet
Benzocyclobutenes. Part 5. Synthesis of 4-Hydroxy-, 4,5-Dihydroxy-, and 3,6-Dihydroxy-benzocyclobutene-1,2-dione (Benzologues of Semisquaric and Squaric Acid)
Abou-Teim, Omar,Jansen, Robert B.,McOmie, John F. W.,Perry, David H.
, p. 1841 - 1846 (2007/10/02)
4-Methoxy- and 4,5-dimethoxy-benzocyclobutene-1,2-dione have been made by flash vacuum pyrolysis of the anthracene adducts of the corresponding phthalazine-1,4-diones which were prepared from the appropriate methoxyphthalic anhydrides. 3,6-Dimethoxybenzocyclobutene-1,2-dione has been prepared from 2-amino-3,6-dimethoxybenzoic acid via the addition of 3,6-dimethoxybenzyne to vinylidene chloride followed by hydrolysis of the resulting 1,1-dichloro-3,6-dimethoxybenzocyclobutene, bromination, and further hydrolysis.The three methoxy-diones and 4,5-dimethoxyphthalaldehyde have been demethylated by heating them with hydrobromic acid and the pKa values of the four hydroxy-compounds have been measured.Preliminary experiments on the synthesis of 4,5-dimethoxybenzocyclobutene are recorded.
