56495-82-0Relevant academic research and scientific papers
Identification of novel ROS inducers: Quinone derivatives tethered to long hydrocarbon chains
Hong, Yeonsun,Sengupta, Sandip,Hur, Wooyoung,Sim, Taebo
, p. 3739 - 3750 (2015/05/27)
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.
Ultrasound-assisted Wittig reaction: A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones
Wu, Li-Qiang,Yang, Chun-Guang,Yang, Li-Ming,Yang, Li-Juan
experimental part, p. 47 - 50 (2010/04/05)
A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones is described. Ultrasound-assisted Wittig reaction of alkyltriphenyl phosphonium bromides with o-vanillin in basic aqueous conditions followed by reduction with Na/n-BuOH gave 2-methoxy-6-alkylphenols. Oxidation of 2-methoxy-6-alkylphenols with Fremy's salt produced the title compounds.
A high-yielding synthesis of the naturally occurring antitumour agent irisquinone
Hadfield, John A.,McGown, Alan T.,Butler, John
, p. 82 - 88 (2007/10/03)
A short, high-yielding synthesis of the antitumour agent irisquinone (1) is described. The key steps are the palladium catalysed coupling reaction of dec-9-yn-1-ol with iodide (2) to form alkyne (3) and the Fremy's salt oxidation of phenol (7).
Synthesis of Natural Compounds with Alkyl-methoxy-1,4-benzoquinone Structure
Pfeifer, Jochen,Gerlach, Hans
, p. 131 - 138 (2007/10/02)
The 1,4-benzoquinones 1-7 occurring in various plants and having interesting biological properties have been synthesized from the tetrahydropyranyl ethers 17 and 21.Reaction with n-butyllithium gave selectively the ortho-lithiated compounds.These could be alkylated with the haloalkenes 13-16 and haloalkanes to give the substituted phenols 18-20 and 22-25 in high yield after methanolysis.Alkylations of the methoxyisopropylether 8 of 10-undecyn-1-ol with bromobutane and bromohexane gave 9 and 10.These alkynols could be selectively hydrogenated with Lindlar-Palladium catalyst to give the (Z)-alkenols 11 and 12 which could be converted into the bromoalkenes 13, 14 and the iodoalkenes 15, 16.Oxidation of the phenols 18-20 and 22-25 with molecular oxygen in the presence of salcomine as catalyst produced the substituted 1,4-benzoquinones 1-3 and 26-29 in high yield.Selective hydrolysis with perchloric acid converted 26-29 into the natural products 4-7. - Key Words: Tetrahydropyranyl-ethers / ortho-Lithiation / ortho-Alkylation / 1,4-Benzoquinones, alkyl-methoxy- / 1,4-Benzoquinones, alkyl-hydroxy-methoxy-
