14581-83-0Relevant articles and documents
Synthesis of Glycosylated Chrysin Derivatives Via Ester Linkers
Fei, Gaishun,Fan, Xiaofei,Ma, Huiping,Fan, Pengchang,Jia, Zhengping,Jing, Linlin
, p. 602 - 610 (2016/08/31)
A series of glycosylated chrysin derivatives have been synthesized in good yields with simple procedures and mild reaction conditions. Six different kinds of sugar moieties were introduced through each ester linker.
Synthesis of photoreactive diazirinyl salicin derivative to elucidate functional analysis of the bitter taste receptor
Sakurai, Munenori,Yoshida, Takuma,Wang, Lei,Murai, Yuta,Masuda, Katsuyoshi,Sakihama, Yasuko,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto
, p. 698 - 705 (2015/03/04)
Salicin (salicyl alcohol glucoside) is a substance well known for its bitter taste. A photoreactive diazirinyl derivative of salicin will be utilized for the functional analysis of interactions between the bitter taste receptor and salicin. Glucosides of
Synthesis and biological evaluation of glycosylated psoralen derivatives
Chen, Chao-Yue,Sun, Jian-Guo,Liu, Fei-Yan,Fung, Kwok-Pui,Wu, Ping,Huang, Zhi-Zhen
experimental part, p. 2598 - 2606 (2012/05/20)
A novel route for the efficient synthesis of a target psoralen moiety, 4,4′-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives w
First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae
Belyanin, Maxim L.,Stepanova, Elena V.,Ogorodnikov, Vladimir D.
, p. 66 - 72 (2013/01/15)
The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products' synthesis is a selective removal of acetyl groups in the presence of other acyl groups.
Glycosylated tetrahydrosalens as multifunctional molecules for Alzheimer's therapy
Storr, Tim,Scott, Lauren E.,Bowen, Meryn L.,Green, David E.,Thompson, Katherine H.,Schugar, Harvey J.,Orvig, Chris
experimental part, p. 3034 - 3043 (2009/08/08)
The tetrahydrosalens N,N′-bis(2-hydroxybenzyl)-ethane-1,2-diamine (H2L1), N,N′-bis(2-hydroxybenzyl)-(-)-1,2- cyclohexane-(1R,2R)-diamine (H2L2), N,N′-bis(2- hydroxybenzyl)-N,N′-dimethyl-ethane-1,2-diamine (H2L 3), N,N′-bis(2-hydroxybenzyl)-N,N′-dibenzyl-ethane-1,2- diamine (H2L4), and N,N′-bis(2-(4-tert-butyl) hydroxybenzyl)-ethane-1,2-diamine (H2L5), as well as their prodrug glycosylated forms, GL1-5, have been prepared and evaluated in vitro for their potential use as Alzheimer's disease (AD) therapeutics. Dysfunctional interactions of metal ions, especially those of Cu, Zn, and Fe, with the amyloid-β (Aβ) peptide are hypothesised to play an important role in the aetiology of AD, and disruption of these aberrant metal-peptide interactions via chelation therapy holds considerable promise as a therapeutic strategy. Tetrahydrosalens such as H2L1-5 have a significant affinity for metal ions, and thus should be able to compete with the Aβ peptide for Cu, Zn, and Fe in the brain. This activity was assayed in vitrovia a turbidity assay; H2L1 and H2L 3 were found to attenuate Aβ1-40 aggregation after exposure to Cu2+ and Zn2+. In addition, H 2L1-5 were determined to be potent antioxidants on the basis of an in vitro antioxidant assay. GL1-5 were prepared as metal binding prodrugs; glycosylation is intended to prevent systemic metal binding, improve solubility, and enhance brain uptake. Enzymatic (β-glucosidase) deprotection of the carbohydrate moieties was facile, with the exception of GL4, demonstrating the general feasibility of this prodrug approach. Finally, a representative prodrug, GL3, was determined to be non-toxic over a large concentration range in a cell viability assay.
Synthesis and evaluation of 5-benzylidene(thio)barbiturate-β-d-glycosides as mushroom tyrosinase inhibitors
Yan, Qin,Cao, Rihui,Yi, Wei,Yu, Liang,Chen, Zhiyong,Ma, Lin,Song, Huacan
supporting information; experimental part, p. 4055 - 4058 (2010/04/02)
A series of 5-benzylidene(thio)barbiturate-β-d-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that most of compounds had more potent inhibitory activities than arbutin (IC50 8.4 mmol/L). Compound 12b was found to be the most potent inhibitor with IC50 value of 0.05 mmol/L. SARs analysis suggested that (1) 5-benzylidenethiobarbiturate substructures were efficacious for the inhibitory activity; (2) the lipophilic property of acetylated sugar moiety facilitated the inhibitory potency; (3) the hydroxyl group of 3′-configuration contributed to the increase of inhibitory effects. In addition, the inhibition mechanism study revealed that 5-benzylidene(thio)barbiturate-β-d-glycosides were irreversible inhibitors.
2,2,2-Trichloro-N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2, 3-dihydro-1H-benzo[de]isoquinolin-5-yl}carbamoyl)acetamide (UNBS3157), a novel nonhematotoxic naphthalimide derivative with potent antitumor activity
Van Quaquebeke, Eric,Mahieu, Tine,Dumont, Patrick,Dewelle, Janique,Ribaucour, Fabrice,Simon, Gentiane,Sauvage, Sébastien,Gaussin, Jean-Fran?ois,Tuti, Jér?me,El Yazidi, Mohamed,Van Vynckt, Frank,Mijatovic, Tatjana,Lefranc, Florence,Darro, Francis,Kiss, Robert
, p. 4122 - 4134 (2008/02/12)
Amonafide (1), a naphthalimide which binds to DNA by intercalation and poisons topoisomerase IIα, has demonstrated activity in phase II breast cancer trials, but has failed thus far to enter clinical phase III because of dose-limiting bone marrow toxicity. Compound 17 (one of 41 new compounds synthesized) is a novel anticancer naphthalimide with a distinct mechanism of action, notably inducing autophagy and senescence in cancer cells. Compound 17 (2,2,2-trichloro-N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H- benzo[de]isoquinolin-5-yl}carbamoyl)acetamide (UNBS3157)) was found to have a 3-4-fold higher maximum tolerated dose compared to amonafide and not to provoke hematotoxicity in mice at doses that display significant antitumor effects. Furthermore, 17 has shown itself to be superior to amonafide in vivo in models of (i) L1210 murine leukemia, (ii) MXT-HI murine mammary adenocarcinoma, and (iii) orthotopic models of human A549 NSCLC and BxPC3 pancreatic cancer. Compound 17, therefore, merits further investigation as a potential anticancer agent.
NAPHTHALIMIDE DERIVATIVES, METHODS FOR THEIR PRODUCTION AND PHARMACEUTICAL COMPOSITIONS THEREFROM
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Page/Page column 59-60, (2008/06/13)
Novel substituted naphthalimide derivatives, pharmaceutically acceptable salts thereof and solvates thereof, are useful for making pharmaceutical compositions for the treatment of cell proliferative diseases such as cancer. The invention also provides methods for making such derivatives.
Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts
Pavlov,Sokolov,Zakharov
, p. 1811 - 1814 (2007/10/03)
A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols. 2001 MAIK "Nauka/Interperiodica".
Synthesis, Spectroscopy, and Photocytotoxicity of Glycosylated Amino Acid Porphyrin Derivatives as Promising Molecules for Cancer Phototherapy
Sol,Blais,Carre,Granet,Guilloton,Spiro,Krausz
, p. 4431 - 4444 (2007/10/03)
To obtain molecules that can target malignant cells, two series of new meso glucosylporphyrins bearing amino acid residues are synthesized in four steps. The first series contained n meso glycosyl moieties and (4 -n) alanyl groups on the ortho or para positions of the meso phenyl. In the second series, the carbohydrate moiety is separated from the aryl substituent by a serine unit. Starting from p- or o-nitrobenzaldehyde, p- or o-acetylbenzaldehyde or -tolualdehyde, and pyrrole, the glycosylnitrophenylporphyrins 3-6 and tritolylporphyrins 8a,b are synthesized under optimized conditions tailored from Lindsey's method. The nitro function is then reduced and N-Fmoc-L-alanine or acetylglycosylated N-Fmoc-serine are coupled on the amino function. A detailed 1H and 13C NMR study allows complete structural elucidation. The UV-visible fluorescence and MALDI mass spectra are presented. Compounds 19-22 produced 1O2, and photocytotoxicities against the K562 leukemia cell line are compared to hematoporphyrin. As a result of their sensitizing abilities, these resultant compounds are of considerable interest for photodynamic therapy.
