23598-07-4Relevant academic research and scientific papers
Coniferin dimerisation in lignan biosynthesis in flax cells
Beejmohun, Vickram,Fliniaux, Ophelie,Hano, Christophe,Pilard, Serge,Grand, Eric,Lesur, David,Cailleu, Dominique,Lamblin, Frederic,Laine, Eric,Kovensky, Jose,Fliniaux, Marc-Andre,Mesnard, Francois
, p. 2744 - 2752 (2007)
[13C2]-Coniferin was provided to a flax (Linum usitatissimum L.) cell suspension to monitor subsequent dimerisation by MS and NMR. The label was mainly incorporated into a 8-8′-linked lignan, lariciresinol diglucoside, a 8-5′-linked
Enhancing the photocytotoxic potential of curcumin on terpyridyl lanthanide(iii) complex formation
Hussain, Akhtar,Somyajit, Kumar,Banik, Bhabatosh,Banerjee, Samya,Nagaraju, Ganesh,Chakravarty, Akhil R.
, p. 182 - 195 (2013)
Lanthanide(iii) complexes [Ln(R-tpy)(cur)(NO3)2] (Ln = La(iii) in 1, 2; Gd(iii) in 5, 6) and [Ln(R-tpy)(scur)(NO3) 2] (Ln = La(iii) in 3, 4; Gd(iii) in 7, 8), where R-tpy is 4′-phenyl-2,2′:6′,2′′-terpyridine (ph-tpy in 1, 3, 5, 7), 4′-(1-pyrenyl)-2,2′:6′,2′′-terpyridine (py-tpy in 2, 4, 6, 8), Hcur is curcumin (in 1, 2, 5, 6) and Hscur is diglucosylcurcumin (in 3, 4, 7, 8), were prepared and their DNA photocleavage activity and photocytotoxicity studied. Complexes [La(ph-tpy)(cur)(NO 3)2] (1) and [Gd(ph-tpy)(cur)(NO3)2] (5) were structurally characterized. The complexes in aqueous-DMF showed an absorption band near 430 nm and an emission band near 515 nm when excited at 420 nm. The complexes are moderate binders to calf-thymus DNA. They cleave plasmid supercoiled DNA to its nicked circular form in UV-A (365 nm) and visible light (454 nm) via1O2 and OH pathways. The complexes are remarkably photocytotoxic in HeLa cells in visible light (λ = 400-700 nm) and are non-toxic in the dark. FACScan analysis of the HeLa cells treated with 2 and 4 showed cell death via an apoptotic pathway. Nuclear localization of 1-4 is evidenced from confocal imaging on HeLa cells. The hydrolytic instability of curcumin gets significantly reduced upon binding to the lanthanide ions while retaining its photocytotoxic potential. The Royal Society of Chemistry 2013.
Synthesis and purification of [1,2-13C2]coniferin
Beejmohun, Vickram,Grand, Eric,Lesur, David,Mesnard, Francois,Fliniaux, Marc-Andre,Kovensky, Jose
, p. 463 - 470 (2006)
The double labelled lignan precursors [1,2-13C 2]coniferin and the glucoside of [1,2-13C 2]ferulic acid were prepared by classical synthetic methods. Pure double labelled lignan precursors could only be obtained
Ice recrystallization inhibitor
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Paragraph 0089-0094, (2021/12/07)
【Challenge】Provide a small molecule ice recrystallization inhibitor with high IRI activity even in small quantities.Solution: The ice recrystallization inhibitor according to one aspect of the present invention includes a compound represented by the following chemical formula (1) as an active ingredient.【Chemical 1】 In the chemical formula (1), R1 is an alkyl group or hydrogen, R2 is an unsaturated hydrocarbon group or acyl group, and R3 is a monosaccharide or polysaccharide.【Selection Figure】Figure 2
SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes
Zhou, Guan,Deng, Xingwang,Pan, Chenyu,Goh, Eunice Tze Leng,Lakshminarayanan, Rajamani,Srinivasan, Rajavel
supporting information, p. 12546 - 12549 (2020/11/02)
Herein, we disclose the first set of unique selenium-containing SLAP (SiLicon Amine Protocol) reagents for the direct synthesis of C3/C5-substituted selenomorpholines and 1,4-selenazepanes fromdiverse (hetero)aldehydes under mild photocatalytic conditions. Enantiomerically pure 1,2-amino alcohol/α-amino acid versions of these heterocycles were also synthesized. Further, we have shown the late-stage modification of certain biologically active agents using the developed seleno-SLAPreagents.
Synthesis and antimicrobial activity of glycosylated 2-Aryl?5?amidinobenzimidazoles
de Souza, Thiago B.,Oliver, Josidel C.,Gomes, Ana Paula B.,Arag?o, Cícero Flávio S.,Ferreira, Leandro S.,Nogueira, Fernando Henrique A.,Dias, Amanda Latércia T.,Alves, Ricardo J.
, p. 1304 - 1317 (2018/05/07)
A series of new glycosylated 2-aryl-5-amidinobenzimidazoles derived from four different carbohydrates (D-glucose, D-galactose, N-acetyl-D-glucosamine and lactose) were synthesized by the condensation of the appropriate 4-formyl-3-methoxyphenyl glycoside with 4-amidino- or 4-N-isopropylamidino-ortho-phenylenediamine hydrochloride. All the compounds were properly characterized by high resolution mass spectrometry, uni- and bidimensional1H and13C nuclear magnetic resonance and then were evaluated for their antibacterial and antifungal potential. Considering the antifungal potential of them, two derivatives were active against Candida parapsilosis at 96.4 μmol L-1 and another was active against this same strain at 83.5 μmol L-1. In addition, one benzamidine showed activity against Candida glabrata at 97 μmol L-1. Considering the antibacterial potential of these compounds, six of them showed better activity against three different stains: three of them with IC50 of 96.4, 97 and 83.5 μmol L-1 against Gram-positive Micrococcus luteus, the other two with IC50 96.5 and 96.4 μmol L-1 against Gram-positive Enterococcus faecalis and one against Gram-negative Escherichia coli at 90.5 μmol L-1. These findings suggest this structural pattern can be employed for design of more potent agents for discovery of new antimicrobial drug candidates.
Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D
Yan, Shiqiang,Ren, Sumei,Ding, Ning,Li, Yingxia
, p. 41 - 46 (2018/03/09)
Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.
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.
Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides
St-Pierre, Gabrielle,Dafik, Laila,Klegraf, Ellen,Hanessian, Stephen
supporting information, p. 3575 - 3588 (2016/10/17)
Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.
Synthesis of a sugar-based thiosemicarbazone series and structure-activity relationship versus the parasite cysteine proteases rhodesain, cruzain, and Schistosoma mansoni cathepsin B1
Fonseca, Nayara Cristina,Da Cruz, Luana Faria,Da Silva Villela, Filipe,Do Nascimento Pereira, Glaécia Aparecida,De Siqueira-Neto, Jair Lage,Kellar, Danielle,Suzuki, Brian M.,Ray, Debalina,De Souza, Thiago Belarmino,Alves, Ricardo José,Júnior, Policarpo Ademar Sales,Romanha, Alvaro José,Murta, Silvane Maria Fonseca,McKerrow, James H.,Caffrey, Conor R.,De Oliveira, Renata Barbosa,Ferreira, Rafaela Salgado
, p. 2666 - 2677 (2015/06/23)
The pressing need for better drugs against Chagas disease, African sleeping sickness, and schistosomiasis motivates the search for inhibitors of cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1), the major cysteine proteases from Trypanosoma cruzi, Trypanosoma brucei, and S. mansoni, respectively. Thiosemicarbazones and heterocyclic analogues have been shown to be both antitrypanocidal and inhibitory against parasite cysteine proteases. A series of compounds was synthesized and evaluated against cruzain, rhodesain, and SmCB1 through biochemical assays to determine their potency and structure-activity relationships (SAR). This approach led to the discovery of 6 rhodesain, 4 cruzain, and 5 SmCB1 inhibitors with 50% inhibitory concentrations (IC50s) of ≤10 μM. Among the compounds tested, the thiosemicarbazone derivative of peracetylated galactoside (compound 4i) was discovered to be a potent rhodesain inhibitor (IC50 = 1.2 ± 1.0 μM). The impact of a range of modifications was determined; removal of thiosemicarbazone or its replacement by semicarbazone resulted in virtually inactive compounds, and modifications in the sugar also diminished potency. Compounds were also evaluated in vitro against the parasites T. cruzi, T. brucei, and S. mansoni, revealing active compounds among this series.
