34450-60-7Relevant articles and documents
Asymmetric total synthesis of naturally occurring spirocyclic tetranorsesquiterpenoid lanceolactone A
Acharyya, Ranjan Kumar,Nanda, Samik
, p. 5027 - 5035 (2018/07/25)
Asymmetric total synthesis of naturally occurring γ-butenolide containing [4.4]spiro-tetrahydrofuran lanceolactone A has been reported in the present work. Bimetallic ("Pd-Cu") cascade cyclization was the crucial reaction employed for the construction of the γ-butenolide framework of the natural product. Subsequently, iodocyclization and reductive deiodination through a transfer hydrogenation reaction were applied to access the target molecule in an efficient manner.
7-Step total synthesis of (+)-EBC-329: Photoisomerisation reveals new: Seco -casbane family member
Vanden Berg, Timothy J.,Pinkerton, David M.,Williams, Craig M.
supporting information, p. 7102 - 7105 (2017/09/07)
The first seco-casbane, EBC-329, isolated from the Australian rainforest, was synthesised from (+)-2-carene in seven steps. This endeavour not only established the absolute stereochemical assignment as (8R,9S)-EBC-329, but also identified, via photoisomer
Chemistry and biology of deoxynyboquinone, a potent inducer of cancer cell death
Bair, Joseph S.,Palchaudhuri, Rahul,Hergenrother, Paul J.
supporting information; experimental part, p. 5469 - 5478 (2010/07/03)
Deoxynyboquinone (DNQ) is a potent antineoplastic agent with an unknown mechanism of action. Here we describe a facile synthetic route to this anthraquinone, and we use this material to determine the mechanism by which DNQ induces death in cancer cells. DNQ was synthesized in seven linear steps through a route employing three palladium-mediated coupling reactions. Experiments performed on cancer cells grown in hypoxia and normoxia strongly suggest that DNQ undergoes bioreduction to its semiquinone, which then is re-oxidized by molecular oxygen, forming superoxide that induces cell death. Furthermore, global transcript profiling of cells treated with DNQ shows elevation of transcripts related to oxidative stress, a result confirmed at the protein level by Western blotting. In contrast to most other antineoplastic agents that generate reactive oxygen species (ROS), DNQ potently induces death of cancer cells in culture, with IC50 values between 16 and 210 nM. In addition, unlike the experimental therapeutic elesclomol, DNQ is still able to induce cancer cell death under hypoxic conditions. This mechanistic understanding of DNQ will allow for a more comprehensive evaluation of the potential of direct ROS generation as an anticancer strategy, and DNQ itself has potential as a novel anticancer agent.
