Category: 604-69-3

A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning was written by Da Silva, Ophelie;Probst, Nicolas;Landry, Christophe;Hanak, Anne-Sophie;Warnault, Pierre;Coisne, Caroline;Calas, Andre-Guilhem;Gosselet, Fabien;Courageux, Charlotte;Gastellier, Anne-Julie;Trancart, Marilene;Baati, Rachid;Dehouck, Marie-Pierre;Jean, Ludovic;Nachon, Florian;Renard, Pierre-Yves;Dias, Jose. And the article was included in Journal of Medicinal Chemistry in 2022.COA of Formula: C16H22O11 The following contents are mentioned in the article:

Recent events demonstrated that organophosphorus nerve agents are a serious threat for civilian and military populations. The current therapy includes a pyridinium aldoxime reactivator to restore the enzymic activity of acetylcholinesterase located in the central nervous system and neuro-muscular junctions. One major drawback of these charged acetylcholinesterase reactivators is their poor ability to cross the blood-brain barrier. In this study, we propose to evaluate glucoconjugated oximes devoid of permanent charge as potential central nervous system reactivators. We determined their in vitro reactivation efficacy on inhibited human acetylcholinesterase, the crystal structure of two compounds in complex with the enzyme, their protective index on intoxicated mice, and their pharmacokinetics. We then evaluated their endothelial permeability coefficients with a human in vitro model. This study shed light on the structural restrains of new sugar oximes designed to reach the central nervous system through the glucose transporter located at the blood-brain barrier. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3COA of Formula: C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. COA of Formula: C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Property of alkyltri(oxyethyl) β-D-glucopyranosides was written by Fan, Yulin;Fu, Fang;Chen, Langqiu;Li, Jiping;Zhang, Jing;Zhang, Guochao;Liao, Jingyi. And the article was included in Journal of Molecular Liquids in 2021.Electric Literature of C16H22O11 The following contents are mentioned in the article:

Based on reconstructing conventional alkyl β-D-glucopyranosides, alkyltri(oxyethyl) β-D-glucopyranosides (4a-4h, n = 6-16) were prepared by introducing a tri(oxyethyl) group ((-OCH₂CH₂-)₃) as a hydrophilic spacer to improve effectively the related water solubility Their foaming performance, emulsifying property, hygroscopicity, solubility, and thermotropic phase transitions were further investigated. The exptl. results showed that the phase transition temperature (T_iso) increased with increasing their alkyl chain length. Such β-D-glucopyranosides (4b-4h, n = 7-16) showed a smectic focal conic-shaped texture. Their water solubility, surface tension, CMC value, and hygroscopicity decreased with increasing their alkyl chain length. Meanwhile, 4e (n = 10) had the best foamability. In the rapeseed oil/water system, 4f (n = 12) had excellent emulsifying property. Furthermore, 4 (n = 8, 10, 12) and SDS or CTAC had the synergistic effect because their exptl. CMC value was smaller than their ideal CMC value (CMC^id). This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Electric Literature of C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Electric Literature of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation was written by Andreeva, Olga V.;Garifullin, Bulat F.;Sharipova, Radmila R.;Strobykina, Irina Yu.;Sapunova, Anastasiya S.;Voloshina, Alexandra D.;Belenok, Mayya G.;Dobrynin, Alexey B.;Khabibulina, Leysan R.;Kataev, Vladimir E.. And the article was included in Journal of Natural Products in 2020.COA of Formula: C16H22O11 The following contents are mentioned in the article:

Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds exhibited high selective cytotoxic activity against M-HeLa cells (IC₅₀ = 1.7-1.9μM) that corresponded to the activity of the anticancer drug doxorubicin (IC₅₀ = 3.0μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC₅₀ > 100μM), whereas doxorubicin was cytotoxic to this cell line (IC₅₀ = 3.0μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3COA of Formula: C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.COA of Formula: C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Discovery of Salidroside Glycoside Analogs as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia was written by Liu, Caiping;Han, Jingxuan;Marcelina, Olivia;Nugrahaningrum, Dyah Ari;Huang, Song;Zou, Meijuan;Wang, Guixue;Miyagishi, Makoto;He, Yun;Wu, Shourong;Kasim, Vivi. And the article was included in Journal of Medicinal Chemistry in 2022.Related Products of 604-69-3 The following contents are mentioned in the article:

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-mol. drugs capable of inducing it at the clin. level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and drug angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and non-diabetic HLI mice. Together, this study offers a novel, promising small-mol.-based therapeutic strategy for treating HLI. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Related Products of 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Related Products of 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Biodegradable Surface Active D-Glucose Based Quaternary Ammonium Ionic Liquids in the Solventless Synthesis of Chloroprene was written by Erfurt, Karol;Markiewicz, Marta;Siewniak, Agnieszka;Lisicki, Dawid;Zalewski, Mariusz;Stolte, Stefan;Chrobok, Anna. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.Product Details of 604-69-3 The following contents are mentioned in the article:

Five ionic liquids based on a quaternary ammonium core substituted with a D-glucose moiety and alkyl chains of varying length were synthesized as prospective phase-transfer catalysts. The catalytic activity of the obtained ionic liquids was tested in the dehydrochlorination of 3,4-dichloro-1-butene to chloroprene. The reaction proceeded in a two-phase system in the presence of an aqueous solution of sodium hydroxide. The results showed that the longer the alkyl chain in the cation, the higher the activity of the ionic liquid as a phase-transfer catalyst. The tested ionic liquids gave an easily recyclable system compared to classical phase-transfer catalysts that were soluble in the reaction system, with no leaching observed over five cycles (chloroprene yield >99%). The cytotoxicity and biodegradability of a series of synthesized ionic liquids based on D-glucose were determined so that a preliminary hazard assessment could be undertaken. Solvent-free synthesis of chloroprene in the presence of biodegradable surface-active D-glucose-based quaternary ammonium ionic liquids This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Product Details of 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Product Details of 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Monosaccharide Analogues of Anticancer Peptide R-Lycosin-I: Role of Monosaccharide Conjugation in Complexation and the Potential of Lung Cancer Targeting and Therapy was written by Zhang, Peng;Ma, Jing;Zhang, Qianqian;Jian, Shandong;Sun, Xiaoliang;Liu, Bobo;Nie, Liqin;Liu, Meiyan;Liang, Songping;Zeng, Youlin;Liu, Zhonghua. And the article was included in Journal of Medicinal Chemistry in 2019.Computed Properties of C16H22O11 The following contents are mentioned in the article:

Glycoconjugation is a promising modification strategy for the optimization of peptide drugs. In this study, five different monosaccharide derivatives (7a-e) were covalently linked to the N-terminal of R-lycosin-I, which yielded five glycopeptides (8a-e). They demonstrated increased or reduced cytotoxicity depending on monosaccharide types, which might be explained by the changes of physicochem. properties. Among all synthesized glycopeptides, only 8a exhibited increased cytotoxicity (IC₅₀ = 9.6 ± 0.3 μM) and selectivity (IC₅₀ = 37.4 ± 5.9 μM). The glucose transporter 1 (GLUT1) with high expression in cancer cells was approved to be involved in the cytotoxicity and selectivity enhancement of 8a. Furthermore, 8a but not R-lycosin-I inhibited tumor growth in the nude mice xenograft model without generating side effects i.p. Taken together, this study reveals the different monosaccharide roles in peptide modification and also provides an optimized anticancer peptide with high activity and selectivity, i.e., 8a might be a promising lead for developing anticancer drugs. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Computed Properties of C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Computed Properties of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis and antibacterial profiles of targeted triclosan derivatives was written by Howse, Gemma L.;Bovill, Richard A.;Stephens, Peter J.;Osborn, Helen M. I.. And the article was included in European Journal of Medicinal Chemistry in 2019.Electric Literature of C16H22O11 The following contents are mentioned in the article:

There is an ongoing urgent need for new targeted antibacterial compounds with novel mechanisms of action for the treatment of infections caused by bacteria that are resistant to currently available materials. Herein we report the synthesis and characterization of four α-D-glycopyranosides, e.g. I, and three β-D-glycopyranosides of the broad antibacterial agent triclosan, in generally good synthetic yields, and with excellent purity. Each triclosan glycoside was analyzed to determine its ability to inhibit the growth of a wide range of Gram-neg. and Gram-pos. organisms, including many of clin. significance. All of the triclosan glycosides that were synthesized demonstrated antibacterial activity against many of the organisms that were examined Two Bacillus strains could be identified from various strains of Bacillus and Staphylococcus after inoculation onto nutrient agar Number 2 with 0.25 μg/mL triclosan-α-D-glucopyranoside I. This glucoside may, therefore, be of use for the isolation and identification of the food-poisoning organism Bacillus cereus. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Electric Literature of C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Electric Literature of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy was written by Murray, Akilah B.;Quadri, Marta;Li, Haoxi;McKenna, Robert;Horenstein, Nicole A.. And the article was included in Carbohydrate Research in 2019.Related Products of 604-69-3 The following contents are mentioned in the article:

Carbonic anhydrase IX (CA IX) has been identified as a biomarker and drug target for several malignant tumors due to its role in cancer cell growth and proliferation. Simple cyclic sulfonamides, like saccharin (SAC), have shown up to a 60-fold selectivity towards CA IX over other ubiquitous CA isoforms, with greater selectivity obtained applying the “tail-approach” to derivatize SAC with a methylene triazole linker that connected to a “tail” beta glucoside. These modifications of SAC led to an increased selectivity of more than 1000-fold towards CA IX, whereas clin. available CA inhibitors show little to no isoform selectivity. As part of our interest in the development of new CA inhibitors, we found the existing synthetic protocol, which relies on a N-tert-Bu saccharin intermediate, to be problematic in the final deprotection steps. We therefore describe an alternative approach to the synthesis of these compounds featuring a gentle “one pot” deprotection/cyclization as the final synthetic step, and report new galactosyl and glucosyl conjugates with low to mid nM inhibition of CA IX. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Related Products of 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Related Products of 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Cu^II and Au^III complexes with glycoconjugated dithiocarbamato ligands for potential applications in targeted chemotherapy was written by Pettenuzzo, Nicolo;Brustolin, Leonardo;Coltri, Elisa;Gambalunga, Alberto;Chiara, Federica;Trevisan, Andrea;Biondi, Barbara;Nardon, Chiara;Fregona, Dolores. And the article was included in ChemMedChem in 2019.COA of Formula: C16H22O11 The following contents are mentioned in the article:

This work is focused on the synthesis, characterization, and preliminary biol. evaluation of bio-conjugated Au^III and Cu^II complexes with the aim of overcoming the well-known side effects of chemotherapy by improving the selective accumulation of an anticancer metal payload in malignant cells. For this purpose, carbohydrates were chosen as targeting agents, exploiting the Warburg effect that accounts for the over expression of glucose-transporter proteins (in particular GLUTs) in the phospholipid bilayer of most neoplastic cells. We linked the dithiocarbamato moiety to the C1 position of three different monosaccharides: D-glucose, D-galactose, and D-mannose. Altogether, six complexes with a 1:2 metal-to-ligand stoichiometry were synthesized and in vitro tested as anticancer agents. One of them showed high cytotoxic activity toward the HCT116 colorectal human carcinoma cell line, paving the way to future in vivo studies aimed at evaluating the role of carbohydrates in the selective delivery of whole mols. into cancerous cells. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3COA of Formula: C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.COA of Formula: C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Uptake and release of species from carbohydrate containing organogels and hydrogels was written by Pan, Abhishek;Roy, Saswati G.;Haldar, Ujjal;Mahapatra, Rita D.;Harper, Garry R.;Low, Wan Li;De, Priyadarsi;Hardy, John G.. And the article was included in Gels in 2019.Formula: C16H22O11 The following contents are mentioned in the article:

Hydrogels are used for a variety of tech. and medical applications capitalizing on their three-dimensional (3D) crosslinked polymeric structures and ability to act as a reservoir for encapsulated species (potentially encapsulating or releasing them in response to environmental stimuli). In this study, carbohydrate-based organogels were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization of a β-D-glucose pentaacetate containing methacrylate monomer (Ac-glu-HEMA) in the presence of a di-vinyl crosslinker; these organogels could be converted to hydrogels by treatment with sodium methoxide (NaOMe). These materials were studied using solid state 13C cross-polarization/magic-angle spinning (CP/MAS) NMR, Fourier transform IR (FTIR) spectroscopy, and field emission SEM (FE-SEM). The swelling of the gels in both organic solvents and water were studied, as was their ability to absorb model bioactive mols. (the cationic dyes methylene blue (MB) and rhodamine B (RhB)) and absorb/release silver nitrate, demonstrating such gels have potential for environmental and biomedical applications. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Formula: C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Formula: C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics