- Identification of novel ROS inducers: Quinone derivatives tethered to long hydrocarbon chains
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We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 μM) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 μM) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.
- Hong, Yeonsun,Sengupta, Sandip,Hur, Wooyoung,Sim, Taebo
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p. 3739 - 3750
(2015/05/27)
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- Practical synthesis of β-oxo benzo[d]thiazolyl sulfones: Scope and limitations
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In this paper, we discuss our new synthetic approach towards functionalized benzo[d]thiazolyl (BT) sulfones, based on the reunion of alkyl BT sulfones and various electrophiles (e.g. R-CO-X, RO-CO-X, RS-CO-X, Ts-X...). All important aspects of this coupling reaction, including relevant and undesirable side reactions, are evaluated by means of calculations and competitive experiments. The scope and limitations of this method are established. The Royal Society of Chemistry 2012.
- Pospiil, Jii,Robiette, Raphael,Sato, Hitoshi,Debrus, Kevin
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supporting information; experimental part
p. 1225 - 1234
(2012/03/07)
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- Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones
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A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.
- Pospisil, Jiri,Sato, Hitoshi
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supporting information; experimental part
p. 2269 - 2272
(2011/06/11)
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- Carbanions Derived from 2-Alkylthiobenzothiazoles. A Novel α-Lithiomethyl Mercaptan Synthon for Mercaptomethylation.
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2-Methylthiobenzothiazole readily gives a methyl group lithio derivative which reacts cleanly with electrophiles.The products are conveniently converted into the corresponding thiols by BuLi at -78 deg C, and this sequence thus provides a convenient two-step mercaptomethylation procedure for alkyl halides, aldehydes, and ketones.
- Katritzky, Alan R.,Aurrecoechea, Jose M.,Vazques de Miguel, Luis M.
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p. 769 - 774
(2007/10/02)
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