104213-86-7Relevant articles and documents
Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells
Archana, Sivakumar,Geesala, Ramasatyaveni,Rao, Narasimha B.,Satpati, Suresh,Puroshottam, Giridhar,Panasa, Akhila,Dixit, Anshuman,Das, Amitava,Srivastava, Ajay Kumar
, p. 680 - 684 (2015)
An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-α) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines - ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC50 values less than 6.5 μM which corroborate the results of molecular docking studies.
Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes
Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.
, p. 178 - 198 (2020/12/22)
Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.
Copper-catalyzed cascade radical cyclization of alkynoates: Construction of aryldifluoromethylated coumarins
Chen, Zhiwei,Huang, Xiaoxiao,Tang, Wei,Zeng, Piaopiao
supporting information, p. 10223 - 10227 (2021/12/10)
A mild and simple method is reported for the construction of 3-difluoroarylmethylated coumarins using α,α-difluoroarylacetic acids as an easily handled difluoromethyl source in reaction with ester 3-arylpropiolates under the promotion of copper. The reaction involves a proposed radical-triggered domino decarboxylative aryldifluoromethylation/5-exo cyclization/ester migration process that directly forms Csp2-CF2Ar and C-C bonds with good functional group tolerance. This journal is
Ynamide-Mediated Intermolecular Esterification
Wang, Xuewei,Yang, Yang,Zhao, Yongli,Wang, Sheng,Hu, Wenchang,Li, Jinmei,Wang, Zihao,Yang, Fengling,Zhao, Junfeng
, p. 6188 - 6194 (2020/05/26)
An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The α-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the α-chiral center of carboxylic acids can be avoided.
Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes
Zaitceva, Olesia,Bénéteau, Valérie,Ryabukhin, Dmitry S.,Eliseev, Ivan I.,Kinzhalov, Mikhal A.,Louis, Benoit,Vasilyev, Aleksander V.,Pale, Patrick
supporting information, (2020/03/05)
Cyclometalated (ppy)PtII complexes (ppy = 2-phenylpyridinato-C2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and effi
Visible light-mediated: Ipso -annulation of activated alkynes: Access to 3-alkylated spiro[4,5]-trienones, thiaspiro[4,5]-trienones and azaspiro[4,5]-trienones
Manna, Sabyasachi,Someswara Ashwathappa, Puneeth Kumar,Prabhu, Kandikere Ramaiah
supporting information, p. 13165 - 13168 (2020/11/09)
A novel method for chemoselective difunctionalization of activated alkynes for synthesizing 3-alkylated spiro[4,5]-trienones, thiaspiro[4,5]-trienones and spirolactams has been uncovered using photoredox catalysis under visible light conditions. The rarel
Atom Transfer Oxidative Radical Cascade of Aryl Alkynoates towards 1,1-Dichalcogenide Olefins
Sahoo, Harekrishna,Ramakrishna, Isai,Mandal, Anup,Baidya, Mahiuddin
, p. 4549 - 4552 (2019/07/31)
An oxidative trifunctionalization of aryl alkynoates has been devised via the chalcogenide radical triggered intramolecular 1,4-aryl migration/decarboxylation cascade to prepare 1,1-dichalcogenide tetrasubstituted alkenes in high yields (up to 98 %). This operationally simple reaction proceeds under metal-free conditions, can be executed on gram scale, and highlights formal 1,1-difunctionalization of alkynes. Synthetic potential of this protocol was demonstrated through a twofold cascade rearrangement to access highly conjugated tetra-selenylated alkenes along with a cross-dehydrogenative annulation to prepare fluorene derivative.
Selectivity Controlled Palladium-Catalyzed Carbonylative Synthesis of Propiolates and Chromenones from Phenols and Alkynes
Zhu, Fengxiang,Wu, Xiao-Feng
supporting information, p. 3422 - 3425 (2018/06/11)
An interesting selectivity-controlled palladium-catalyzed oxidative carbonylation procedure for the synthesis of propiolates and chromenones has been developed. Starting from phenols and alkynes, under slightly different conditions, various propiolates an
Visible-light-mediated radical cascade reaction: Synthesis of 3-bromocoumarins from alkynoates
Feng, Shangbiao,Li, Jinlai,Liu, Zaimin,Sun, Haiyu,Shi, Hongliang,Wang, Xiaolei,Xie, Xingang,She, Xuegong
supporting information, p. 8820 - 8826 (2017/11/03)
A visible-light-mediated radical addition of alkynoates to generate 3-bromocoumarins by using N-bromosuccinimide as the bromo source has been accomplished. This procedure provides a bromo radical addition/spirocyclization/ester migration cascade reaction
Visible-Light-Promoted Dual C-C Bond Formations of Alkynoates via a Domino Radical Addition/Cyclization Reaction: A Synthesis of Coumarins
Feng, Shangbiao,Xie, Xingang,Zhang, Weiwei,Liu, Lin,Zhong, Zhuliang,Xu, Dengyu,She, Xuegong
supporting information, p. 3846 - 3849 (2016/08/16)
A visible-light-promoted, mild, and direct difunctionalization of alkynoates has been accomplished. This procedure provides a new strategy toward synthesis of the coumarin core structure by photoredox-mediated oxidation to generate the α-oxo radical, whic
