118159-94-7Relevant academic research and scientific papers
Method for preparing phenyl-2-(2'-cyanophenyl) acetylene compound through palladium catalysis
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Paragraph 0038; 0072-0077, (2020/10/05)
The invention discloses a method for preparing a phenyl-2-(2'-cyanophenyl) acetylene compound shown as a formula (IV) through palladium catalysis. The preparation method comprises the following steps:taking palladium chloride as a catalyst, sodium carbonate as an alkali and dimethyl sulfoxide as a solvent, carrying out sufficient reactions in the presence of oxygen, and carrying out after-treatment on the reaction product to obtain the phenyl-2-(2'-cyanophenyl) acetylene compound, wherein the benzonitrile compound is shown as a formula (I), acetylene is shown as a formula (II), and the iodobenzene compound is shown as a formula (III). The method is efficient and meets the green and environment-friendly requirements; and the catalytic system has wide adaptability and is suitable for large-scale production of pharmaceutical and chemical intermediates.
Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases
Kumpan, Katerina,Nathubhai, Amit,Zhang, Chenlu,Wood, Pauline J.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Lehti?, Lari,Threadgill, Michael D.
, p. 3013 - 3032 (2015/08/03)
Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.
TANKYRASE INHIBITORS
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Page/Page column 84, (2014/06/24)
The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.
A Novel Ethynylation of Pyridines by Reissert-Henze Type Reaction
Nishiwaki, Nagatoshi,Minakata, Satoshi,Komatsu, Mitsuo,Ohshiro, Yoshiki
, p. 773 - 776 (2007/10/02)
Reaction of N-benzoyloxypyridinium chloride, Reissert-Henze salt, with silver acetylide gave the pyridine ethynylated selectively at 2-position.The reaction is applicable to various substituted pyridines and pyridine homologs.
Condensed Heteroaromatic Ring Systems. XV. Synthesis of Pyranopyridinones from Halopyridinecarbonitriles
Sakamoto, Takao,An-Naka, Masayuki,Kondo, Yoshinori,Araki, Tomio,Yamanaka, Hiroshi
, p. 1890 - 1894 (2007/10/02)
Four kinds of pyranopyridinones were synthesized from pyridinecarbonitriles containing a chlorine or bromine substituent at the adjacent position to the cyano group by the palladium-catalyzed cross-coupling reaction with terminal acetylenes followed by in
