5539-66-2Relevant academic research and scientific papers
Design and synthesis of a novel triptycene-based ligand for modeling carboxylate-bridged diiron enzyme active sites
Li, Yang,Cao, Rui,Lippard, Stephen J.
, p. 5052 - 5055 (2011)
A novel triptycene-based ligand with a preorganized framework was designed to model carboxylate-bridged diiron active sites in bacterial multicomponent monooxygenase (BMM) hydroxylase enzymes. The synthesis of the bis(benzoxazole)-appended ligand L1 depicted was accomplished in 11 steps. Reaction of L1 with iron(II) triflate and a carboxylate source afforded the desired diiron(II) complex [Fe2L1(μ-OH)-(μ-O 2CArTol)(OTf)2].
Methylation of 1,8-dihydroxy-9,10-anthraquinone with and without use of solvent-free technique
Sereda, Grigoriy A.,Akhvlediani, David G.
, p. 9125 - 9126 (2003)
A convenient and environmentally friendly solvent-free procedure has been developed for dimethylation of 1,8-dihydroxy-9,10-anthraquinone with excellent yield. A highly selective monomethylation of 1,8-dihydroxy-9,10-anthraquinone in refluxing tetraglyme makes monomethylated peri-dihydroxy-9,10-anthraquinones easily available. Alternatively, irradiation in a domestic microwave oven has been employed for the solvent-free monomethylation of 1,8-dihydroxy-9,10-anthraquinone.
An efficient synthesis of 9-anthrone lactone derivatives via the Knoevenagel condensation and intramolecular cyclization
Gao, Liming,Guan, Jing,Lyu, Lili,Ma, Mingliang,Shan, Bin,Tan, Weiqiang,Xia, Yan,Yang, Qipeng,Zhan, Xiuzhi,Zheng, Jifang
supporting information, (2020/02/15)
One-step synthesis of 9-anthrone lactone derivatives from 1-acetyloxyanthraquinone with a variety of dicarbonyl substrates in the presence of K2CO3 by Knovenagel condensation and intramolecular cyclization is developed. Possible reaction mechanisms have been investigated using the density functional theory (DFT), which has been widely used in the study of reaction mechanism. The strategy could be useful for the synthesis of the core structure of marine natural product aspergiolide.
Efficient reductive Claisen rearrangement of prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones with iron powder in ionic liquids
Nadali, Samaneh,Khoshroo, Ali,Aghapour, Ghasem
, p. 883 - 895 (2018/06/07)
A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones to 1-hydroxy-2-(prop-2’-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF4 (1-methylimidazolium tetrafluoroborate), in short reaction times (5–35 min). Our study showed that 1-(prop-2’-enyloxy)anthraquinone is more active than 1-(2’-chloroprop-2’-enyloxy)anthraquinone to perform this rearrangement.
A facile and general approach to 3-((trifluoromethyl)thio)-4 H -chromen-4-one
Xiang, Haoyue,Yang, Chunhao
supporting information, p. 5686 - 5689 (2015/02/19)
A facile and efficient synthetic strategy to 3-((trifluoromethyl)thio)-4H-chromen-4-one was developed. AgSCF3 and trichloroisocyanuric acid were employed here to generate active electrophilic trifluoromethylthio species in situ. This reaction could proceed under mild conditions in a short reaction time and be insensitive to air and moisture.
Synthesis and enhanced DNA cleavage activities of bis-tacnorthoamide derivatives
Wei, Li,Hu, Hong-Wen,Lu, Guo-Yuan,Shao, Ying,Zhou, Mi
, p. 8484 - 8492,9 (2012/12/13)
A new metal-free DNA cleaving reagent, bis-tacnorthoamide derivative 1 with two tacnorthoamide (tacnoa) units linked by a spacer containing anthraquinone, has been synthesized from triazatricyclo[5.2.1.04,10]decane and characterized by NMR and mass spectrometry. For comparison, the corresponding compounds mono-tacnorthoamide derivative 2 with one tacnorthoamide unit and 6 with two tacnorthoamide units linked by an alkyl (1,6-hexamethylene) spacer without anthraquinone have also been synthesized. The DNA-binding property investigated via fluorescence and CD spectroscopy suggests that compounds 1 and 2 have an intercalating DNA binding mode, and the apparent binding constants of 1, 2 and 6 are 1.3 × 107 M-1, 0.8 × 10 7 M-1 and 8 × 105 M-1, respectively. Agarose gel electrophoresis was used to assess plasmid pUC19 DNA cleavage activity promoted by 1, 2, 6 and parent tacnoa under physiological conditions, which gives rate constants kobs of 0.2126 ± 0.0055 h-1, 0.0620 ± 0.0024 h-1, 0.040 ± 0.0007 h-1 and 0.0043 ± 0.0002 h-1, respectively. The 50-fold and 15-fold rate acceleration over parent tacnoa is because of the anthraquinone moiety of compound 1 or 2 intercalating into DNA base pairs via a stacking interaction. Moreover, DNA cleavage reactions promoted by compound 1 give 5.3-fold rate acceleration over compound 6, which further demonstrates that the introduction of anthraquinone results in a large enhancement of DNA cleavage activity. In particular, DNA cleavage activity promoted by 1 bearing two tacnoa units is 3.3 times more effective than 2 bearing one tacnoa unit and the DNA cleavage by compound 1 was achieved effectively at a relatively low concentration (0.03 mM). This dramatic rate acceleration suggests the cooperative catalysis of the two positively charged tacnoa units in compound 1. The radical scavenger inhibition study and ESI-MS analysis of bis(2,4-dinitrophenyl) phosphate (BDNPP) and adenylyl(3′-5′) phosphoadenine (APA) cleavage in the presence of compound 1 suggest the cleavage mechanism would be via a hydrolysis pathway by cleaving the phosphodiester bond of DNA.
Photochemistry of 1, n -Dibenzyloxy-9,10-anthraquinones
Sarma, Saurav J.,Jones, Paul B.
supporting information; experimental part, p. 3806 - 3813 (2010/08/20)
Figure presented The photochemistry of a series of 9,10-anthraquinones with multiple benzyloxy substituents was investigated. In polar solvent, the expected Blankespoor oxidative cleavage reaction is the major reaction pathway, but in most cases, several minor products were observed. In nonpolar solvents, the abundance of these minor products increases dramatically. Four types of product were observed with the favored reaction pathway shifting with minor changes in substitution on the anthraquinone. Several types of product require cleavage of the C-O bond on the benzyloxy group and, apparently, follow a photo-Claisen-type mechanism. Others involve the expected 1,5-diradical but do not exhibit the single-electron transfer usually observed in the Blankespoor-type reaction. The results indicate the importance of considering the medium and photoredox behavior in anthraquinone photochemistry.
Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors
Dallavalle, Sabrina,Gattinoni, Sonia,Mazzini, Stefania,Scaglioni, Leonardo,Merlini, Lucio,Tinelli, Stella,Beretta, Giovanni L.,Zunino, Franco
, p. 1484 - 1489 (2008/09/20)
A series of structurally simple analogues of natural topopyrone C were synthesized and tested for cytotoxic and topoisomerase I inhibitory activities. The removal of the hydroxyl groups at the 5 and 9 positions resulted in an increased cytotoxic potency a
BeCl2 as a new highly selective reagent for dealkylation of aryl-methyl ethers
Sharghi, Hashem,Tamaddon, Fatemeh
, p. 13623 - 13640 (2007/10/03)
An efficient and simple method is introduced for the selective removal of methyl group from poly aryl-methyl ethers, in some important derivatives of benzophenones, xanthones, anthraquinones, aryl esters, benzamides and nitroanisoles with BeCl2.
2-Anthracenonyl acetic acids as 5-lipoxygenase inhibitors
Prinz, Helge,Mueller, Klaus
, p. 262 - 266 (2007/10/03)
The synthesis of 2-substituted anthracenonyl acetic acid (2-AA) derivatives is described. The key step is the Marschalk reaction of 1-hydroxy-8-methoxy-anthracenedione with glycolic acid. After protection of the resulting 2-anthracenonyl acetic acid derivative, the 2-monoalkylated derivatives are selectively obtained by direct alkylation. The methodology proves quite general and allows for the introduction of various substituents onto the 2-position of the carboxylic side chain. Reduction of the anthracenediones proceeds with concomitant protecting group removal and proves final 2-AA products in good yields. The results of initial biological studies demonstrate enhanced 5-lipoxygenase inhibition compared to anthralin.
