14963-91-8Relevant academic research and scientific papers
Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin
Wang, Yan-Hua,Qiu, Guanyinsheng,Zhou, Hongwei,Xie, Wenlin,Liu, Jin-Biao
supporting information, p. 3850 - 3855 (2019/06/17)
In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the structures of the corresponding precursors. It is believed that TBAB serves as a phase transfer catalyst and radical initiator in the reaction. Compared to previous methodologies, the synthetic procedure reported herein provides a more environmentally benign route for the synthesis of isocoumarins.
Synthesis and biological evaluation of 2,3-diaryl isoquinolinone derivatives as anti-breast cancer agents targeting ERα and VEGFR-2
Tang, Zhichao,Niu, Shaoxiong,Liu, Fei,Lao, Kejing,Miao, Jingshan,Ji, Jinzi,Wang, Xiang,Yan, Ming,Zhang, Luyong,You, Qidong,Xiao, Hong,Xiang, Hua
supporting information, p. 2129 - 2133 (2014/05/06)
The estrogen receptor α is recognized as important pharmaceutical target for breast cancer therapy, and vascular endothelial growth factor receptors (VEGFRs) play important roles in tumor angiogenesis including breast cancer. A series of 2,3-diaryl isoqui
Assembly of 3-substituted isocoumarins via a CuI-catalyzed domino coupling/addition/deacylation process
Cai, Shangjun,Wang, Fei,Xi, Chanjuan
experimental part, p. 2331 - 2336 (2012/05/05)
An efficient strategy for the synthesis of a variety of 3-substituted isocoumarins has been developed. The reaction proceeded from o-halobenzoic acids and 1,3-diketones via a copper(I)-catalyzed domino reaction in DMF under the action of K3PO4 at 90-120 °C without a ligand to afford the corresponding 3-substituted isocoumarin derivatives in good to excellent yields. o-Halobenzoic acids could be o-iodobenzoic acid, o-bromobenzoic acid, and o-chlorobenzoic acid derivatives. 1,3-Diketones could be alkyl- and aryl-substituted 1,3-diketones.
NHC-catalyzed oxidative cyclization reactions of 2-alkynylbenzaldehydes under aerobic conditions: Synthesis of O-Heterocycles
Park, Jong Hyub,Bhilare, Sachin V.,Youn, So Won
, p. 2228 - 2231 (2011/07/09)
Chemical equations presented. An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.
Synthesis of isocoumarin via PTSA-catalyzed annulation of diarylalkynes
Le Bras, Gaelle,Hamze, Abdallah,Messaoudi, Samir,Provot, Olivier,Le Calvez, Pierre-Benoit,Brion, Jean-Daniel,Alami, Mouad
experimental part, p. 1607 - 1611 (2009/04/03)
p-Toluenesulfonic acid (PTSA) in ethanol was used as a mild acid catalyst for the annulation of various functionalized diarylalkynes under microwave irradiation. This metal-free process allowed the synthesis of a range of 3-aryl-substituted isocoumarins in good yields. Georg Thieme Verlag Stuttgart.
Isocoumarins as estrogen receptor beta selective ligands: Isomers of isoflavone phytoestrogens and their metabolites
De Angelis, Meri,Stossi, Fabio,Waibel, Michael,Katzenellenbogen, Benita S.,Katzenellenbogen, John A.
, p. 6529 - 6542 (2007/10/03)
In a search for new ligands selective for the estrogen receptor beta (ERβ), we prepared a series of non-steroidal compounds having an isocoumarin core structure. An interesting feature of these derivatives is that they bear the same functionalities as the well-known ERβ -selective, isoflavone phytoestrogens daidzein and genistein, but in an isomeric arrangement. These compounds could be prepared efficiently by electrophilic cyclization of acetylenic ester precursors, followed by simple manipulations to introduce additional substituents. Through a reduction of some of the isocoumarins, we also obtained isomeric analogs of the isoflavone metabolites equol and dehydroequol. The compounds we prepared were evaluated in ER binding assays, and selected compounds were studied further in cell-based gene transcription assays. Several of the isocoumarins and their analogs are high-affinity ligands that show considerable selectivity for ERβ in terms of binding affinity, and strikingly high ERβ selectivity in terms of potency in gene transcription assays. Two of the best compounds, which combine high transcriptional potency with an ERβ selectivity greater than 1000, should prove to be excellent probes of ERβ function in vivo.
