478043-88-8Relevant academic research and scientific papers
Novel β?hydroxy ketones: Synthesis, spectroscopic characterization, molecular docking, and anticancer activity studies
Guzel, Mustafa,Kanturk, Gokhan,Kucuk, Hatice Baspinar,Senturk, Ahmet Mesut,Yerlikaya, Serife,Yildiz, Tulay
, (2021/11/01)
In this study, a series of novel β?hydroxy ketone derivatives 3a-o were designed, synthesized, and evaluated for their anticancer activity. The structure of these compounds were characterized by IR, 1H and 13C NMR, mass spectrometry and elemental analysis methods. All the synthesized compounds were screened for anticancer activity against MCF-7 and U87 cells. Among them, compound 3l was appeared to be the most potent compound on both cancer cells; and IC50 dose was determined as 145 μM for MCF-7 cells and 6,6 μM for U87 cells. DNA ladder and Annexin V apoptotic marker tests were used and as a result, 3l caused the initiation of apoptosis on U87 cells. VDAC protein expression increased dramatically after U87 glioblastoma brain cancer cells were treated with compound 3l Additionally, the molecular modeling of these compounds was studied in FLT3 receptor, Estrogen receptor, and PARP2 receptor for the treatment of Acute Myeloid Leukemia (AML), breast cancer, and Glioblastoma (GBM) respectively. Their binding motifs and drug-like properties were investigated, and the results are highlighted in the discussion. Based on the results, compound 3l may have a potential drug candidate profile that can reverse the drug resistance profile.
NHC-Organocatalyzed CAr?O Bond Cleavage: Mild Access to 2-Hydroxybenzophenones
Janssen-Müller, Daniel,Singha, Santanu,Lied, Fabian,Gottschalk, Karin,Glorius, Frank
supporting information, p. 6276 - 6279 (2017/05/19)
A Truce–Smiles rearrangement of acyl-anion equivalents generated by N-heterocyclic carbene (NHC) catalysis has been achieved. The developed method includes CAr?O, CAr?S, or CAr?N bond cleavage for the formation of a CAr?C bond and enables access to 2-hydroxybenzophenones, an important structural motif that is present in several bioactive natural products. By utilizing this procedure, the alkaloid taxilamine was synthesized in three steps. DFT calculations and control experiments support a classical SNAr mechanism with a catalyst-bound Meisenheimer-type intermediate. The method features mild reaction conditions, excellent functional-group tolerance, and a broad substrate scope, including various classes of (hetero)arenes.
An organocatalytic method for the synthesis of some novel xanthene derivatives by the intramolecular Friedel-Crafts reaction
Yildiz, Tülay,Kü?ük, Hatice Ba?pinar
, p. 16644 - 16649 (2017/03/24)
An efficient organocatalytic method for the synthesis of new substituted 9-arylxanthenes (2a-2u) starting from diarylcarbinol compounds with an arenoxy group (1a-1u) has been developed using the intramolecular Friedel-Crafts reaction. The substrates were
Metal-free oxidative coupling: Xanthone formation via direct annulation of 2-aryloxybenzaldehyde using tetrabutylammonium bromide as a promoter in aqueous medium
Rao, Honghua,Ma, Xinyi,Liu, Qianzi,Li, Zhongfeng,Cao, Shengli,Li, Chao-Jun
supporting information, p. 2191 - 2196 (2013/10/01)
A metal-free intramolecular annulation of 2-aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde C-H bond and aromatic C-H bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron-donating and electron-withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.
Rearrangement of 2-aryloxybenzaldehydes to 2-hydroxybenzophenones by rhodium-catalyzed cleavage of aryloxy C-O bonds
Rao, Honghua,Li, Chao-Jun
supporting information; experimental part, p. 8936 - 8939 (2011/11/07)
Lost in the shuffle: An unprecedented rearrangement of the title compounds proceeds by the simultaneous rhodium-catalyzed cleavage of aryloxy C-O and aldehyde C-H bonds (see scheme). The reaction tolerates the presence of various catalytically reactive substituents such as aryl halides, nitrile, and esters.
