- Ice recrystallization inhibitor
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【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
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Paragraph 0089-0094
(2021/12/07)
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- SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes
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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.
- Zhou, Guan,Deng, Xingwang,Pan, Chenyu,Goh, Eunice Tze Leng,Lakshminarayanan, Rajamani,Srinivasan, Rajavel
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p. 12546 - 12549
(2020/11/02)
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- Synthesis and antimicrobial activity of glycosylated 2-Aryl?5?amidinobenzimidazoles
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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.
- 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.
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p. 1304 - 1317
(2018/05/07)
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- Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D
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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.
- Yan, Shiqiang,Ren, Sumei,Ding, Ning,Li, Yingxia
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- Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides
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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.
- St-Pierre, Gabrielle,Dafik, Laila,Klegraf, Ellen,Hanessian, Stephen
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p. 3575 - 3588
(2016/10/17)
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- Synthesis of Glycosylated Chrysin Derivatives Via Ester Linkers
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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.
- Fei, Gaishun,Fan, Xiaofei,Ma, Huiping,Fan, Pengchang,Jia, Zhengping,Jing, Linlin
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p. 602 - 610
(2016/08/31)
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- Synthesis of a sugar-based thiosemicarbazone series and structure-activity relationship versus the parasite cysteine proteases rhodesain, cruzain, and Schistosoma mansoni cathepsin B1
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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.
- 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
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p. 2666 - 2677
(2015/06/23)
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- Remarkable enhancement in photocytotoxicity and hydrolytic stability of curcumin on binding to an oxovanadium(iv) moiety
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Oxovanadium(iv) complexes of polypyridyl and curcumin-based ligands, viz. [VO(cur)(L)Cl] (1, 2) and [VO(scur)(L)Cl] (3, 4), where L is 1,10-phenanthroline (phen in 1 and 3), dipyrido[3,2-a:2′,3′-c]phenazine (dppz in 2 and 4), Hcur is curcumin and Hscur is
- Banerjee, Samya,Pant, Ila,Khan, Imran,Prasad, Puja,Hussain, Akhtar,Kondaiah, Paturu,Chakravarty, Akhil R.
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p. 4108 - 4122
(2015/04/14)
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- Enhancing the photocytotoxic potential of curcumin on terpyridyl lanthanide(iii) complex formation
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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.
- Hussain, Akhtar,Somyajit, Kumar,Banik, Bhabatosh,Banerjee, Samya,Nagaraju, Ganesh,Chakravarty, Akhil R.
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p. 182 - 195
(2013/02/26)
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- Synthesis and biological evaluation of glycosylated psoralen derivatives
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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
- Chen, Chao-Yue,Sun, Jian-Guo,Liu, Fei-Yan,Fung, Kwok-Pui,Wu, Ping,Huang, Zhi-Zhen
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experimental part
p. 2598 - 2606
(2012/05/20)
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- An efficient synthesis of D-galactose-based multivalent neoglycoconjugates
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In this work, the synthesis of dimeric, trimeric and tetrameric D-galactose-based neoglycoconjugates is reported. The monosaccharide ligand was prepared in 5 straightforward steps from D-galactose using the Doebner modification of the Knoevenagel reaction for chain elongation. The ligand was coupled to 1,4-butanediamine, tris-(2-ethylamino)amine, pentaerythrityltetramine and PAMAM dendrimers (1,4-butanodiamine core G0 and 1,12-dodecanediamine core G0). The unprotected glycodendrimers were purified by size-exclusion chromatography (SEC). This was the only step in which a chromatographic method was employed throughout the synthetic route. This is a new and efficient strategy for the preparation of neoglycoconjugates.
- De Andrade, Saulo F.,Figueiredo, Rute C.,De Souza Filho, Jose? D.,Alves, Ricardo J.
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experimental part
p. 1062 - 1069
(2012/09/10)
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- Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo- β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols
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We report here the stereoconvergent formylation of (E/Z)-β-bromo- β-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-α-fluorocinnamaldehydes in g
- Zemmouri, Rajae,Kajjout, Mohammed,Castanet, Yves,Eddarir, Said,Rolando, Christian
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scheme or table
p. 7691 - 7698
(2011/12/02)
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- Molecular interactions between Barley and Oat β-glucans and phenolic derivatives
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Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available β-glucan preparations, Glucagel and PromOat, from barley and oats. The two β-glucan products showed very similar binding properties. It was demonstrated that the two β-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the β-glucans. When the barley β-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.
- Simonsen, Henrik Toft,Nielsen, Mette S.,Christensen, Niels J.,Christensen, Ulla,Cour, Thomas V. La,Motawia, Mohammed Saddik,Jespersen, Birthe P.M.,Engelsen, Soren B.,Moller, Birger Lindberg
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experimental part
p. 2056 - 2064
(2010/07/02)
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- Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives
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New curcumin derivatives are synthesized in order to improve chemical properties of curcumin. The aromatic ring glycosylation of curcumin provides more water-soluble compounds with a greater kinetic stability which is a fundamental feature for drug bioavailability. The glycosylation reaction is quite simple, low cost, with high yield and minimum waste. NMR data show that the ability of curcumin to coordinate metal ion, in particular Ga(III), is maintained in the synthesized products. Although the binding of glucose to curcumin reduces the cytotoxicity of the derivatives towards cisplatin (cDDP)-sensitive and -resistant human ovarian carcinoma cell lines, the compounds display a good selectivity since they are much less toxic against non-tumourigenic Vero cells. The combination of cDDP with the most active glycosyl-curcuminoid drug against both cDDP-sensitive and -resistant as well as against Vero cell lines is tested. The results show an improvement of cDDP efficacy with higher selectivity towards cancer cells than non-cancer cells. These studies indicate the need for developing new valid components of drug treatment protocols to cDDP-resistant cells as well.
- Ferrari, Erika,Lazzari, Sandra,Marverti, Gaetano,Pignedoli, Francesca,Spagnolo, Ferdinando,Saladini, Monica
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experimental part
p. 3043 - 3052
(2009/09/30)
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- Synthesis, chemical and biological studies on new Fe3+-glycosilated β-diketo complexes for the treatment of iron deficiency
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A simple synthetic pathway to obtain glycosilated β-diketo derivatives is proposed. These compounds show a good iron(III) affinity therefore we may suggest the use of their Fe3+-complexes as oral iron supplements in the treatment of anaemia. The glycosilated compounds (6-GlcH, 6-GlcOH and 6-GlcOCH3) are characterized by means of spectroscopic (UV, 1H and 13C NMR) and potentiometric techniques; they have a good water solubility, are kinetically stable in physiological condition (t1/2 > 100 h) and show a low cytotoxicity also in high concentrations (IC50 > 400 μM). They are able to bind Fe3+ ion in acid condition (pH ~ 2) forming complex species thermodynamically more stable than those of other ligands commonly used in the treatment of iron deficiency. The iron complexes show also a good kinetic stability both in acidic and physiological pH and have a good lypophilicity (log P > -0.7) that suggests an efficient gastrointestinal absorption in view of their possible use in oral therapy. In addition they demonstrate a poor affinity for competitive biological metal ion such as Ca2+, and in particular 6-GlcOCH3 is able to inhibit lipid peroxidation.
- Arezzini, Beatrice,Ferrali, Marco,Ferrari, Erika,Frassineti, Chiara,Lazzari, Sandra,Marverti, Gaetano,Spagnolo, Ferdinando,Saladini, Monica
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p. 2549 - 2556
(2008/12/23)
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- Study on glycosylated prodrugs of toxoflavins for antibody-directed enzyme tumor therapy
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Eight novel toxoflavin glycosides, which are potential prodrugs in antibody directed enzyme prodrug therapy (ADEPT), were synthesized. The structures of all toxoflavin glycosides were characterized by 13C NMR spectroscopy, elemental analysis, and MS. Their enzymatic hydrolysis activities were tested against β-glucosidase (EC.3.2.1.21).
- Wang, Shusheng,Liu, Dan,Zhang, Xu,Li, Shengyu,Sun, Yongxu,Li, Jia,Zhou, Yifa,Zhang, Liping
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p. 1254 - 1260
(2008/02/02)
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- Coniferin dimerisation in lignan biosynthesis in flax cells
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[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
- 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
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p. 2744 - 2752
(2008/09/18)
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- Synthesis and purification of [1,2-13C2]coniferin
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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
- Beejmohun, Vickram,Grand, Eric,Lesur, David,Mesnard, Francois,Fliniaux, Marc-Andre,Kovensky, Jose
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p. 463 - 470
(2007/10/03)
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- First synthesis of (1,2-13C2)-monolignol glucosides
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The monolignol glucosides (1,2-13C2)-p-glucocoumaryl alcohol, (1,2-13C2)-coniferin and (1,2-13C 2)-syringin, and the glucosides of (1,2-13C 2)-p-coumaric, (1,2-13C2)-ferulic and (1,2-13C2)-sinapic acids were synthesized by condensation of the corresponding aldehydes with (1,2,3-13C3)-malonic acid. The free acids were converted to the acyl chlorides prior to their reduction to alcohols.
- Beejmohun, Vickram,Grand, Eric,Mesnard, Fran?ois,Fliniaux, Marc-André,Kovensky, José
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p. 8745 - 8747
(2007/10/03)
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- Synthesis of glycosylcurcuminoids.
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Condensation of glycosylated arylaldehyde with acetylacetone-B(2)O(3) complex gave a corresponding diglycosylcurcuminoid, and a similar reaction using a mixture of arylaldehyde and glycosylarylaldehyde gave an unsymmetrical monoglycosylcurcuminoid, both as boron-complexes. The boron was removed from the complexes by heating in methanol, thus achieving the synthesis of di- and mono-glycosylcurcuminoids.
- Mohri, Kunihiko,Watanabe, Yuhya,Yoshida, Yuki,Satoh, Mitsuru,Isobe, Kimiaki,Sugimoto, Naoki,Tsuda, Yoshisuke
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p. 1268 - 1272
(2007/10/03)
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- Synthesis and antitumor activity of new D-galactose-containing derivatives of doxorubicin
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A general scheme of synthesis of antibiotic doxorubicin derivatives is based on the 13-dimethyl ketal of 14-bromodaunorubicin (4). The interaction of 4 with melibiose (5), lactose (6), 3-methoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4- oxybenz
- Olsufyeva, Eugenia N.,Tevyashova, Anna N.,Trestchalin, Ivan D.,Preobrazhenskaya, Maria N.,Platt, David,Klyosov, Anatole
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p. 1359 - 1367
(2007/10/03)
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- Coniferin and derivatives: A fast and easy synthesis via the aldehyde series using phase-transfer catalysis
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Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig- type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.
- Daubresse, Nicolas,Francesch, Charlette,Mhamdi, Farida,Rolando, Christian
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p. 157 - 161
(2007/10/03)
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- Synthesis and Antiinflammatory Activity of Some Glycosidated 3-Methylpyrazolin-5-(4H)-one-4-benzylidenes
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The substituted hydroxybenzaldehyde 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides (IIA-H), obtained by the stereospecific synthesis using phase transfer catalysis, on condensation with 3-methylpyrazolin-5-(4H)-one in the presence of piperidine yield the title compounds (IIIA-H).The effect of various phase transfer catalysts has been studied during the preparation of II.Compounds III have been tested for their antiinflammatory activity.
- Jain, S. M.,Devi, Sunita,Bani, S.,Singh, Surjit,Singh, G. B.
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p. 1019 - 1023
(2007/10/02)
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