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Dharmendra Kumar Tiwari - One of the best experts on this subject based on the ideXlab platform.
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transition metal free quinoline synthesis from Acetophenones and anthranils via sequential one carbon homologation conjugate addition annulation cascade
Organic Letters, 2017Co-Authors: Sandip Balasaheb Wakade, Dipak Kumar Tiwari, Pothapragada Prabhakar S K Ganesh, Mandalaparthi Phanindrudu, Pravin R Likhar, Dharmendra Kumar TiwariAbstract:A transition-metal-free method for the construction of functionalized quinolines from readily available Acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 3-substituted quinolines.
Alexios-leandros Skaltsounis - One of the best experts on this subject based on the ideXlab platform.
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cytotoxic prenylated acetophenone dimers from acronychia pedunculata
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:Three new acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurall...
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Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata.
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:: Three new acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC(50) values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively.
Francesca Borrelli - One of the best experts on this subject based on the ideXlab platform.
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a new acetophenone derivative from flowers of helichrysum italicum roth don ssp italicum
Fitoterapia, 2014Co-Authors: Daniela Rigano, Carmen Formisano, Ester Pagano, Felice Senatore, Sonia Piacente, Milena Masullo, Raffaele Capasso, Angelo A Izzo, Francesca BorrelliAbstract:A new acetophenone derivative named gnaphaliol 9-O-propanoate (1) was isolated from the chloroform fraction of EtOH extract of Helichrysum italicum ssp. italicum flowers along with the five known Acetophenones 12-acetoxytremetone (2), 13-(2-methylpropanoyloxy)toxol (3), [2,3-dihydro-2-[1-(hydroxymethyl)ethenyl]-5-benzofuranyl]-ethanone (4), 1-[2-[1-[(acetyloxy)methyl]ethenyl]-2,3-dihydro-3-hydroxy-5-benzofuranyl]-ethanone (5) and gnaphaliol (6). The structures of compounds 1-6 were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The isolated compounds were investigated for their cytotoxicity, anti-inflammatory and antioxidant properties. Biological assays on human colonic epithelial cells showed that compound 2 possessed antioxidant effects reducing reactive oxygen species (ROS) production.
Sandip Balasaheb Wakade - One of the best experts on this subject based on the ideXlab platform.
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transition metal free quinoline synthesis from Acetophenones and anthranils via sequential one carbon homologation conjugate addition annulation cascade
Organic Letters, 2017Co-Authors: Sandip Balasaheb Wakade, Dipak Kumar Tiwari, Pothapragada Prabhakar S K Ganesh, Mandalaparthi Phanindrudu, Pravin R Likhar, Dharmendra Kumar TiwariAbstract:A transition-metal-free method for the construction of functionalized quinolines from readily available Acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 3-substituted quinolines.
Eirini Kouloura - One of the best experts on this subject based on the ideXlab platform.
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cytotoxic prenylated acetophenone dimers from acronychia pedunculata
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:Three new acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurall...
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Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata.
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:: Three new acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC(50) values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively.
