109556-74-3Relevant academic research and scientific papers
Synthesis and antiproliferative activity of 6-naphthylpterocarpans
Antus, Sándor,Bíró, Tamás,Gulácsi, Katalin,Kurtán, Tibor,Lisztes, Erika,Mándi, Attila,Szappanos, ádám,Tóth, Balázs István
supporting information, p. 2148 - 2162 (2020/03/27)
The Heck-oxyarylation of racemic 2-(1-naphthyl)-and 2-(2-naphthyl)-2H-chromene derivatives were carried out resulting diastereoselectively in (6S?,6aR?,11aR?)-6-(1-naphthyl)-and 6-(2-naphthyl)-pterocarpans as major products and bridged (6R?,12R?)-6,12-methanodibenzo[d,g][1,3]dioxocine derivatives as minor products. Antiproliferative activity of two 6-naphthylpterocarpans was identified by MTT assay against A2780 and WM35 human cancer cell lines with low micromolar IC50 values. The measured 0.80 and 3.51 μM IC50 values of the (6S?,6aR?,11aR?)-6-(1-naphthyl)pterocarpan derivative with 8,9-methylenedioxy substitution represent the best activities in the pterocarpan family. Enantiomers of the pterocarpan and dioxocine derivatives and their chiral 2-naphthylchroman-4-one and 2-naphthyl-2H-chromene precursors were separated by HPLC using chiral stationary phase. HPLC-ECD spectra were recorded and absolute configuration and low-energy solution conformations were determined by TDDFT-ECD calculations. Characteristic ECD transitions of the separated enantiomers were correlated with their absolute configuration.
Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
Hari Babu, Madala,Ranjith Kumar, Gadi,Kant, Ruchir,Sridhar Reddy, Maddi
, p. 3894 - 3897 (2017/04/04)
Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.
Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles
Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 946 - 950 (2014/04/03)
A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.
A simple and efficient method for the allylation of heteroarenes catalyzed by PdCl2
Yuan, Feng-Quan,Sun, Feng-Yi,Han, Fu-She
, p. 6837 - 6842 (2012/08/28)
The PdCl2-catalyzed allylation of heteroarenes is presented. Various heteroarenes including O-, N-, and S-based ones were allylated efficiently with a rich range of allylic acetates in the presence of only 2 mol % of PdCl2, without the need of bases/acids, additives, and external supporting ligands. In addition, the reactions were carried out under mild and simple conditions just by stirring the two reactants and catalyst in CH 2Cl2 at 60 °C. Moreover, the by-product produced was non-toxic acetic acid. Thus, the method presented in this work provides a general, clean, and operationally simple approach for the functionalization of heteroarenes. Finally, a preliminary mechanistic study suggested that the Pd(II) may be reduced in situ by the heteroarenes to Pd(0), which serves as the active metal center to catalyze the following allylations of heteroarenes via a Tsuji-Trost pathway.
