- Preparation method of 1-bromofluorenone
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The invention discloses a preparation method of 1-bromo fluorenone, and belongs to the field of organic chemical synthesis. The method is realized by the following steps of: reacting 2-bromophenyl acetonitrile serving as an initial raw material with nitrobenzene to synthesize 3-(2-bromophenyl)-5-benzoisoxazole; reducing 3-(2-bromophenyl)-5-benzoisoxazole by iron powder to obtain 2-aminobenzene-2'-bromobenzophenone, and finally performing intramolecular cyclization to synthesize 1-bromofluorenone with the content of 99.5% (HPLC) or above and the total yield of 76% or above. The synthesis methodis low in production cost and suitable for industrial production, and 1-bromofluorenone can be used in the fields of organic photoelectric materials, biomedicines and dyes.
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- 10-(4-Phenylpiperazine-1-carbonyl)acridin-9(10H)-ones and related compounds: Synthesis, antiproliferative activity and inhibition of tubulin polymerization
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As part of our continuing search for potent inhibitors of tubulin polymerization, two novel series of 42 10-(4-phenylpiperazine-1-carbonyl)acridin-9(10H)-ones and N-benzoylated acridones were synthesized on the basis of a retrosynthetic approach. All newly synthesized compounds were tested for antiproliferative activity and interaction with tubulin. Several analogs potently inhibited tumor cell growth. Among the compounds tested, 10-(4-(3-methoxyphenyl)piperazine-1-carbonyl)acridin-9(10H)-one (17c) exhibited excellent growth inhibitory effects on 93 tumor cell lines, with an average GI50 value of 5.4 nM. We were able to show that the strong cytotoxic effects are caused by disruption of tubulin polymerization, as supported by the EBI (N,N'-Ethylenebis(iodoacetamide)) assay and the fact that the most potent inhibitors of cancer cell growth turned out to be the most efficacious tubulin polymerization inhibitors. Potencies were nearly comparable or superior to those of the antimitotic reference compounds. Closely related to this, the most active analogs inhibited cell cycling at the G2/M phase at concentrations down to 30 nM and induced apoptosis in K562 leukemia cells. We believe that our work not only proves the excellent suitability of the acridone scaffold for the design of potent tubulin polymerization inhibitors but also enables synthetic access to further potentially interesting N-acylated acridones.
- Waltemate, Jana,Ivanov, Igor,Ghasemi, Jahan B.,Aghaee, Elham,Daniliuc, Constantin Gabriel,Müller, Klaus,Prinz, Helge
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supporting information
(2020/11/27)
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- Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds
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We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH2, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.
- Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal
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