59020-02-9Relevant academic research and scientific papers
A new synthesis of isoaurones: Cytotoxic activity of compounds related to the alleged structure of isoaurostatin
Rizzi, Eleonora,Dallavalle, Sabrina,Merlini, Lucio,Beretta, Giovanni Luca,Pratesi, Graziella,Zunino, Franco
, p. 4313 - 4316 (2005)
A new synthesis of isoaurones related to the alleged structure of isoaurostatin, via Heck intramolecular cyclization of cinnamic esters of 2-iodophenols, is reported. The cytotoxic activity of these isoaurones is lower than that of the structurally very similar 4-arylcoumarins.
Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
Sahani, Rajkumar Lalji,Patil, Manoj D.,Wagh, Sachin Bhausaheb,Liu, Rai-Shung
, p. 14878 - 14882 (2018/10/15)
The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.
Inhibitory activities against topoisomerase I and II by isoaurostatin derivatives and their structure-activity relationships
Suzuki, Keitarou,Okawara, Tadashi,Higashijima, Tatuya,Yokomizo, Kazumi,Mizushima, Tohru,Otsuka, Masami
, p. 2065 - 2068 (2007/10/03)
Isoaurostatin A (IAS-A) isolated from Thermomonospora alba showed weak inhibition against topoisomerase (topo) I (IC50 = 307 μM). To get more strong inhibition, derivatives of IAS-A were prepared and their structure-activity relationships against topo I and II were investigated. The addition of hydroxyl group on aromatic rings increased the activities, 3-(3,4,5-trihydroxybenzylidene)-5-hydroxy-3H-benzofuran-2-one (IAS-9) showed strong inhibition (IC50 = 3 μM) against topo I. And also, the increasing of hydroxyl group increased growth inhibition against a variety of cancer cells, and IAS-9 showed most potent inhibition. Unlike camptothecin and etoposide, IAS-9 neither stabilized DNA-topo cleavable complex nor intercalated into DNA, and it inhibited topo I and II noncompetitively. The inhibitory activities also increased by opening of lactone ring in the molecule of IAS-9.
Regio et Diastereochimie de la Cycloaddition du Tetrafluoroborate du 2-Benzoyl-1,2-dihydroisoquinoleine-1-carbonitrile avec Quelques (Z)- et (E)-3-Arylidene-3H-benzofuran-2-ones
Msaddek, Moncef,Rammah, Mohamed,Ciamala, Kabula,Vebrel, Joel,Laude, Bernard
, p. 825 - 832 (2007/10/03)
The reaction of 2-benzoyl-1,2-dihydroisoquinoline-1-carbonitrile tetrafluoroborate salt with 3-arylidene-2-(3H)-benzofuranones (Z) or (E) leads to a single spirocompound irrespective of the double bond geometry of the starting olefin.In an acidic medium, the spirocompound yields quantitatively a tetrasubstituted pyrrole.The regio- and stereochemistry of the reaction was established from NMR data.
