- Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells
-
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.
- Archana, Sivakumar,Geesala, Ramasatyaveni,Rao, Narasimha B.,Satpati, Suresh,Puroshottam, Giridhar,Panasa, Akhila,Dixit, Anshuman,Das, Amitava,Srivastava, Ajay Kumar
-
-
Read Online
- Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes
-
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.
- Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.
-
p. 178 - 198
(2020/12/22)
-
- Copper-catalyzed cascade radical cyclization of alkynoates: Construction of aryldifluoromethylated coumarins
-
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
- Chen, Zhiwei,Huang, Xiaoxiao,Tang, Wei,Zeng, Piaopiao
-
supporting information
p. 10223 - 10227
(2021/12/10)
-
- Ynamide-Mediated Intermolecular Esterification
-
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.
- Wang, Xuewei,Yang, Yang,Zhao, Yongli,Wang, Sheng,Hu, Wenchang,Li, Jinmei,Wang, Zihao,Yang, Fengling,Zhao, Junfeng
-
p. 6188 - 6194
(2020/05/26)
-
- Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes
-
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
- 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)
-
- 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
-
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
- Manna, Sabyasachi,Someswara Ashwathappa, Puneeth Kumar,Prabhu, Kandikere Ramaiah
-
supporting information
p. 13165 - 13168
(2020/11/09)
-
- Atom Transfer Oxidative Radical Cascade of Aryl Alkynoates towards 1,1-Dichalcogenide Olefins
-
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.
- Sahoo, Harekrishna,Ramakrishna, Isai,Mandal, Anup,Baidya, Mahiuddin
-
p. 4549 - 4552
(2019/07/31)
-
- Selectivity Controlled Palladium-Catalyzed Carbonylative Synthesis of Propiolates and Chromenones from Phenols and Alkynes
-
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
- Zhu, Fengxiang,Wu, Xiao-Feng
-
supporting information
p. 3422 - 3425
(2018/06/11)
-
- Visible-light-mediated radical cascade reaction: Synthesis of 3-bromocoumarins from alkynoates
-
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
- Feng, Shangbiao,Li, Jinlai,Liu, Zaimin,Sun, Haiyu,Shi, Hongliang,Wang, Xiaolei,Xie, Xingang,She, Xuegong
-
supporting information
p. 8820 - 8826
(2017/11/03)
-
- Visible-Light-Promoted Dual C-C Bond Formations of Alkynoates via a Domino Radical Addition/Cyclization Reaction: A Synthesis of Coumarins
-
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
- Feng, Shangbiao,Xie, Xingang,Zhang, Weiwei,Liu, Lin,Zhong, Zhuliang,Xu, Dengyu,She, Xuegong
-
supporting information
p. 3846 - 3849
(2016/08/16)
-
- Synthesis of 3-Sulfenylated Coumarins: BF3·Et2O-Mediated Electrophilic Cyclization of Aryl Alkynoates Using N-Sulfanylsuccinimides
-
A simple and efficient metal-free sulfenylation/cyclization of aryl alkynoates has been developed, obtaining various 3-sulfenylated coumarins in moderate to excellent yields. In the presence of BF3·Et2O, the stable and readily access
- Gao, Wen-Chao,Liu, Tao,Zhang, Bing,Li, Xing,Wei, Wen-Long,Liu, Qiang,Tian, Jun,Chang, Hong-Hong
-
p. 11297 - 11304
(2016/11/29)
-
- Visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids to coumarin derivatives under metal-free conditions
-
A visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids has been developed. The arylsulfonylation of alkynes was performed at room temperature under metal-free conditions to generate coumarin derivatives with wide functio
- Yang, Wenchao,Yang, Shuai,Li, Pinhua,Wang, Lei
-
supporting information
p. 7520 - 7523
(2015/05/04)
-
- Design, synthesis and anticancer properties of novel oxa/azaspiro[4,5]trienones as potent apoptosis inducers through mitochondrial disruption
-
Abstract A series of twenty seven oxa/azaspiro[4,5]trienone derivatives were synthesized and their anticancer properties have been explored. GI50 values of all these compounds were evaluated against four types of human cancer cell lines, i.e. MCF-7 (breast), DU-145 (prostate), A549 (lung) and HepG2 (liver). Five compounds of the series exhibited good anticancer potential against MCF-7 with GI50 values less than 2 μM. Detailed biological studies of the two representative compounds 9b and 9e revealed that they arrest cell cycle in G0/G1 phase and induce mitochondria mediated apoptosis, that was further confirmed by measurement of mitochondrial membrane potential (ΔΨm), intracellular ROS generation, caspase 9 activity and Annexin V-FITC assay. Furthermore, western blot analysis suggested that these compounds up-regulate the levels of p53, p21, p27 and Bax, and down-regulate the level of Bcl-2 confirming the apoptosis inducing properties.
- Yugandhar,Nayak, V. Lakshma,Archana, Sivakumar,Shekar, Kunta Chandra,Srivastava, Ajay Kumar
-
p. 348 - 357
(2015/08/11)
-
- Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters
-
Aryl alkynoate esters undergo gold-catalyzed spirocyclization under mild conditions, affording spirolactones in high yields. This approach obviates the need for stoichiometric halogenating reagents typically employed for alkyne activation in related trans
- Aparece, Mark D.,Vadola, Paul A.
-
supporting information
p. 6008 - 6011
(2015/01/08)
-
- Synthesis of spiro[4.5]trienones by intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes
-
A wide variety of 3-halospiro[4.5]trienones are readily prepared in good to excellent yields by the intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes under mild reaction conditions. ICl, I2, and Br2 are all effective electrophiles for this process under carefully optimized reaction conditions. Copyright
- Zhang, Xiaoxia,Larock, Richard C.
-
p. 12230 - 12231
(2007/10/03)
-
- 6-Endo-Dig vs. 5-Exo-Dig Ring Closure in o-Hydroxyaryl Phenylethynyl Ketones. A New Approach to the Synthesis of Flavones and Aurones
-
The aryl phenylpropynoates 3a-c, prepared by esterification of phenylpropynoic acid with the corresponding phenols, by means of N,N'-dicyclohexylcarbodiimide, give upon irradiation the o-hydroxyaryl phenylethynyl ketones 4a-c.The cyclization of these compounds in basic media follows two alternative pathways: 6-endo-dig ring closure, to give the flavones 8a-c, and /or 5-exo-dig ring closure , to give the aurones 9a-c.The predominance of one or the other cyclization mode is strongly influenced by the reaction conditions.Thus, the use of potassium carbonate in acetoneas cyclizing reagent favors the 6-endo-dig process, while the 5-exo-dig process becomes clearly enhanced when using sodium ethoxide or potassium carbonate in ethanol.The mechanistic implications of these facts are discussed within the framework of Baldwin's rules.From the preparative point of view, the above results disclose the synthetic possibilities of the key ketones 4 as precursors of flavones and aurones.
- Garcia, Hermenegildo,Iborra, Sara,Primo, Jaime,Miranda, Miguel A.
-
p. 4432 - 4436
(2007/10/02)
-