cas 10034-20-5, 1,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCI

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Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34
A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.
Ahadi, Somayeh,Awan, Shahid I.,Werz, Daniel B.
supporting information

(2020/05/04)

Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives
Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-negative bacteria and fungi revealed potential antibacterial and antifungal activity. Hybrid compounds 9 (MIC 0.2668 ± 0.0001 mM), 10 (MIC 0.1358 ± 00025 mM) and 13 (MIC 0.0898 ± 0.0014 mM) had potential antimicrobial activity against a fluoroquinolone-resistant Escherichia coli clinical isolate, compared to ciprofloxacin (MIC 0.5098 ± 0.0024 mM) and norfloxacin (MIC 0.2937 ± 0.0021 mM) standard drugs. Interestingly, compound 10 also exerted potential antifungal activity against Candida albicans (MIC 0.0056 ± 0.0014 mM) and Penicillium chrysogenum (MIC 0.0453 ± 0.0156 mM). Novel derivatives and standard fluoroquinolone drugs exhibited near-identical cytotoxicity levels against L6 muscle cell-line, when measured using the MTT assay.
Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.
(2020/07/04)

GOLD COMPOSITIONS AND METHODS OF USE THEREOF
Gold compounds and pharmaceutically acceptable salts thereof are disclosed. Certain compounds and salts are active as antibacterial, antifungal, and/or anti-parasitic agents. The disclosure provides pharmaceutical compositions containing the gold compounds. Methods of using the gold compounds to treat bacterial infections are disclosed.
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Paragraph 0089; 0090

(2020/03/05)

1,8-NAPHTHYRIDINE GLUCOSAMINE DERIVATIVES, THEIR USE IN THE TREATMENT OF MICROBIAL INFECTIONS, AND A METHOD FOR PREPARATION
The present disclosure provides a compound of Formula (I) or any pharmaceutically acceptable salt thereof for use in treating a microbial infection in a subject, a method for preparing the same, and a pharmaceutical composition thereof: (I) wherein R
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Paragraph 049-050

(2020/06/10)

GLYCOSYLATED 3-SUBSTITUTED FLUOROQUINOLONE DERIVATIVES, PREPARATION METHODS THEREOF, AND THEIR USE IN THE TREATMENT OF ANTIMICROBIAL INFECTIONS
The present disclosure relates to 3-substituted fluoroquinolone derivatives, and more particularly to glycosylated 3-substitutred fluoroquinolone derivatives, methods of preparation thereof, and uses thereof for treating microbial infections.
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Paragraph 036; 037

(2020/10/20)

Design, synthesis, and biological evaluation of 1,8-naphthyridine glucosamine conjugates as antimicrobial agents
In the quest for discovering potent antimicrobial agents with lower toxicity, we envisioned the design and synthesis of nalidixic acid-D-(+)-glucosamine conjugates. The novel compounds were synthesized and evaluated for their in vitro antimicrobial activi
Mohammed, Aya A. M.,Suaifan, Ghadeer A. R. Y.,Shehadeh, Mayadah B.,Okechukwu, Patrick N.
p. 179 - 186
(2019/01/04)

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens
Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.
Wu, Bin,Yang, Xiaojian,Yan, Mingdi
supporting information
p. 7751 - 7768
(2019/09/10)

Synthesis, Optimization, and Evaluation of Glycosylated Naphthalimide Derivatives as Efficient and Selective Insect β- N-Acetylhexosaminidase OfHex1 Inhibitors
Insect chitinolytic β-N-acetylhexosaminidase OfHex1, from the agricultural pest Ostrinia furnacalis (Guenée), is considered as a potential target for green pesticide design. In this study, rational molecular design and optimization led to the synthesis of compounds 15r (Ki = 5.3 μM) and 15y (Ki = 2.7 μM) that had superior activity against OfHex1 than previously reported lead compounds. Both compounds 15r and 15y had high selectivity toward OfHex1 over human β-N-acetylhexosaminidase B (HsHexB) and human O-GlcNAcase (hOGA). In addition, to investigate the basis for the potency of glycosylated naphthalimides against OfHex1, molecular docking and molecular dynamics simulations were performed to study possible binding modes. Furthermore, the in vivo biological activity of target compounds with efficient OfHex1 inhibitory potency was assayed against Myzus persicae, Plutella xylostella, and O. furnacalis. This present work indicates that glycosylated naphthalimides can be further developed as potential pest control and management agents targeting OfHex1.
Shen, Shengqiang,Dong, Lili,Chen, Wei,Wu, Renjie,Lu, Huizhe,Yang, Qing,Zhang, Jianjun
p. 6387 - 6396
(2019/06/07)

Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen
Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.
Qin, Chunjun,Schumann, Benjamin,Zou, Xiaopeng,Pereira, Claney L.,Tian, Guangzong,Hu, Jing,Seeberger, Peter H.,Yin, Jian
supporting information
p. 3120 - 3127
(2018/03/08)

2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation
The Ugi four-component-reaction (Ugi 4CR) allowed synthesizing bisamide from carboxylic acid, aldehyde, amine, and isocyanide in one-pot operation. However, introducing 2-isocyano glucose into the Ugi 4CR and investigating the inhibitory effects of Ugi adducts against radical-induced oxidation of DNA remained technical challenges. We herein applied 2-isocyano glucose (acetylation of hydroxy groups) to perform a catalyst-free Ugi 4CR at room temperature. The gallic, ferulic, caffeic, or p-hydroxybenzoic acids, aniline (or benzylamine and p-aminophenol), and formaldehyde acted as reagents. In the case of inhibiting DNA oxidations induced by 2,2’-azobis(2-amidinopropane hydrochloride) (AAPH), hydroxy radical, and Cu2+/glutathione, the Ugi adduct containing glucose moiety exhibited higher antioxidative activities than the structural analog without glucose moiety involved. It was also proved that high antioxidative property was owing to hydroxy groups in glucose moiety. Therefore, sugar-appended Ugi adducts might hold promising inhibitors for DNA oxidation.
Zhao, Peng-Fei,Liu, Zai-Qun
p. 458 - 466
(2017/05/05)

Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors
Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N′-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2?mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein.
Biswas, Nripendra N.,Yu, Tsz Tin,Kimyon, ?nder,Nizalapur, Shashidhar,Gardner, Christopher R.,Manefield, Mike,Griffith, Renate,Black, David StC.,Kumar, Naresh
p. 1183 - 1194
(2017/02/18)

Glucosamide compound and preparation and application thereof
The invention relates to a glucosamide compound and a preparation method thereof. The glucosamide compound has a structure as shown in the formula (I). In the formula (I), R is methoxy group, nitro group, amino-group, hydroxyl group, C1-4 alkyl group or halogen, n is the number of substituent groups, and n is 1 or 2. The glucosamide compound is simple to prepare, has excellent plant induced resistance activity, and can be used as a plant induced resistance agent for controlling cucumber bacterial angular leaf spot, cucumber target leaf spot and tomato late blight. The invention also relates to a plant induced resistant agent containing the compound.
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(2017/06/21)

Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters
A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters fo
Carmona, José A.,Gonzalo, Gonzalo de,Serrano, Inmaculada,Crespo-Pe?a, Ana M.,?imek, Michal,Monge, David,Fernández, Rosario,Lassaletta, José M.
p. 2993 - 3005
(2017/04/10)

Acetyl glucosamine imidazolemethanol -2, 4, 5-Trion synthetic method of use with bacteriostatic
The invention discloses acetylglucosamine imidazol-2,4,5-trione, and further discloses a synthetic method of the acetylglucosamine imidazol-2,4,5-trione and antimicrobial application. The synthetic method is quick, efficient and high in productivity, and
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Paragraph 0030; 0031

(2017/02/23)

Design, synthesis and in vivo evaluation of novel glycosylated sulfonylureas as antihyperglycemic agents
Sulphonylurea compounds have versatile activities such as antidiabetic, diuretic, herbicide, oncolytic, antimalarial, antifungal and anticancer. The present study describes the design, synthesis and in vivo testing of novel glycosylated aryl sulfonylurea compounds as antihyperglycaemic agents in streptozocine-induced diabetic mice. The rational for the introduction of the glucosamine moiety is to enhance selective drug uptake by pancreatic β-cells in order to decrease the cardiotoxic side effect commonly associated with sulfonylurea agents. 2-Deoxy-2-(4-chlorophenylsulfonylurea)-D-glucopyranose was found to be the most potent antihyperglycaemic agents among the synthesized compounds in diabetic mice. This investigation indicates the importance of this novel class as potential antihyperglycaemic agents.
Suaifan, Ghadeer A. R. Y.,Shehadeh, Mayadah B.,Darwish, Rula M.,Al-Ijel, Hebah,Abbate, Vincenzo
p. 20063 - 20078
(2015/12/23)

Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases
Abstract β-N-Acetyl-d-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using d-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two β-N-acetyl-d-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 β-N-acetyl-d-hexosaminidase. Among the compounds tested, compounds 5a (IC50=12.6 μM, hOGA) and 5e (IC50=12.5 μM, OfOGA) proved to be a highly selective and potent inhibitor.
Kong, Hanchu,Chen, Wei,Lu, Huizhe,Yang, Qing,Dong, Yanhong,Wang, Daoquan,Zhang, Jianjun
p. 135 - 144
(2015/07/07)

Synthesis and characterisation of glucosamine-NSAID bioconjugates
Strategies to couple non-steroidal anti-inflammatory drugs (NSAIDs) to a glucosamine hydrochloride salt via an amino acid linker are investigated and a series of novel NSAID-glucosamine bioconjugates have been prepared. This journal is
Jones, Rachel A.,Thillier, Yann,Panda, Siva S.,Rivera Rosario, Nicole,Hall, C. Dennis,Katritzky, Alan R.
p. 8325 - 8335
(2015/01/08)

Synthesis and characterization of N-acyl-tetra-O-acyl glucosamine derivatives
Novel 1,3,4,6-tetra-O-acyl-N-acyl-d-glucosamine derivatives were synthesized from glucosamine hydrochloride (GlcN·HCl) by the acylation with pyridine as a catalyst. A derivative of tetra-O-acetyl glucosamine contained ketoprofen, a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects, was first synthesized. In analysis of the NMR spectra, the ratio of α:β-anomer showed that penta-acyl-d- glucosamine derivatives and N-acetylated glucosamines containing O-acyl groups have been only the α-anomer. Meanwhile, both the intermediates and the glucoconjugate compound of ketoprofen have only the β-anomer.
Dang, Chi-Hien,Nguyen, Cong-Hao,Nguyen, Thanh-Danh,Im, Chan
p. 6239 - 6245
(2014/01/23)

Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present in
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Page/Page column 27-28

(2014/09/03)

Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction
A convenient and efficient protocol for the synthesis of unnatural N-glycosyl α-amino acids was developed. Condensation of 1,3,4,6-tetra-O-actyl-β-d-glucosamine hydrochloride, alkenyl boronic acid, and glyoxylic acid was achieved in CH2Cl2
Tao, Chuan-Zhou,Zhang, Zhong-Tang,Wu, Jian-Wei,Li, Rong-Hua,Cao, Zhi-Ling
supporting information
p. 532 - 534
(2014/05/06)

Study on synthesis of 2-(substituted benzylidene)amino-2-deoxy-1,3,4,6- tetra-O-acetyl-β-D-glucopyranoses from D-glucosamine
The conditions in catalysts and in reaction time for the reaction of protected β-D-glucosamine hydrochloride with different substituted benzaldehydes have been investigated in the presence of various inorganic and organic bases. Based on obtained results,
Thanh, Nguyen Dinh,Quoc, Nguyen Van
p. 85 - 90
(2013/07/26)

PERMEABLE GLYCOSIDASE INHIBITORS AND USES THEREOF
Disclosed are compounds of Formula (I), wherein each substituent of Formula (I) is defined as in the specification, pharmaceutical formulations comprising these compounds which are useful as 0-linked N-acetylglucosaminidase (O-GlcNAcase) inhibitors, and thus are useful for the treatment of certain disorders such as Alzheimer' s disease including reducing NFTs and/or hyperphosphorylated tau. Also disclosed is the use of the compounds as O-GlcNAcase imaging agents.
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Page/Page column 28; 29

(2013/12/03)

PERMEABLE GLYCOSIDASE INHIBITORS AND USES THEREOF
The present invention is directed to compounds and pharmaceutical formulations comprising these compounds which are useful as O-linked N-acetylglucosaminidase (O-GlcNAcase) inhibitors, and thus may be useful for the treatment of certain disorders such as Alzheimer's disease including reducing NFTs and/or hyperphosphorylated tau. The invention is also directed to use of the compounds as O-GlcNAcase imaging agents.
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Page/Page column 28; 29

(2013/12/03)

Prednisolone succinate-glucosamine conjugate: Synthesis, characterization and in vitro cellular uptake by kidney cell lines
Prednisolone succinate-glucosamine (PSG) conjugate, a prodrug for prednisolone, was synthesized and confirmed by NMR and MS spectrum. The stabilities of the prodrug in PBS (pH 2.50, 5.00, 7.20, and 7.89) were studied. Cytotoxicity and uptake assay of the prodrug were perfomed on HK-2 and MDCK cell lines. The results showed that compared with prednisolone, the PSG not only did not increase the cytotoxicity but also improved the uptake to 2.2 times of prednisolone by the cells. Thus, it indicated that glucosamine might be a potential carrier for kidney-targeting delivery of prednisolone.
Lin, Yan,Sun, Xun,Gong, Tao,Zhang, Zhi Rong
p. 25 - 28
(2012/04/04)

SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.
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Page/Page column 35

(2012/05/31)

SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.
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Page/Page column 33

(2012/05/31)

PYRANO[3,2-D]THIAZOL DERIVATIVES AND USES THEREOF AS SELECTIVE GLYCOSIDASE INHIBITORS
Pyrano[3,2-d]thiazol derivatives of formula (I) for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds are disclosed. Methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc are also provided.
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Page/Page column 34; 35

(2012/05/31)

Steroid and bile acids amide conjugates with D-glucosamine
New type of amide conjugates of steroid and bile acids with D-glucosamine 1 and 2 were prepared. Title compounds are prepared via acid chloride or using N-[({[(1E)-1-cyano- 2-ethoxy-2-oxoethylidene]amino}oxy)(dimethylamino) methylidene]-N-methylmethanaminium tetrafluoroborate as condensation agent. They were examined for gelation properties with negative results. Per-O-acetylated D-glucosamine hydrochloride was prepared in one step procedure from D-glucosamine hydrochloride by acetylation in a mixture of acetyl chloride and acetic acid.
Novakova, Zdena,Tomanova, Jana,Sterbova, Lucie,Drasar, Pavel
experimental part
p. 65 - 74
(2011/09/21)

Synthesis of an Fmoc-threonine bearing core-2 glycan: A building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis
Selectins (L, E, and P) are vascular endothelial molecules that play an important role in the recruitment of leukocytes to inflamed tissue. In this regard, P-Selectin glycoprotein-1 (PSGL-1) has been identified as a ligand for P-Selectin. PSGL-1 binds to
Krishnamurthy, Venkata R.,Dougherty, Ann,Kamat, Medha,Song, Xuezheng,Cummings, Richard D.,Chaikof, Elliot. L.
experimental part
p. 1541 - 1547
(2010/08/20)

Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers
Fully protected tetra-, hexa- and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)- (1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D- glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.
Virlouvet, Mickael,Gartner, Michael,Koroniak, Katarzyna,Sleeman, Jonathan P.,Braese, Stefan
supporting information; experimental part
p. 2657 - 2662
(2011/01/05)

Nickel-catalyzed stereoselective glycosylation with C(2)- N-substituted benzylidene d-glucosamine and galactosamine trichloroacetimidates for the formation of 1,2-cis-2-amino glycosides. applications to the synthesis of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GalNAc
The 1,2-cis-2-amino glycosides are key components found within a variety of biologically important oligosaccharides and glycopeptides. Although there are remarkable advances in the synthesis of 1,2-cis-2-amino glycosides, disadvantages of the current state-of-the-art methods include limited substrate scope, low yields, long reaction times, and anomeric mixtures. We have developed a novel method for the synthesis of 1,2-cis-2-amino glycosides via nickel-catalyzed α-selective glycosylation with C(2)-N-substituted benzylidene d-glucosamine and galactosamine trichloroacetimidates. These glycosyl donors are capable of coupling to a wide variety of alcohols to provide glycoconjugates in high yields with excellent levels of α-selectivity. Additionally, only a substoichiometric amount of nickel (5-10 mol %) is required for the reaction to occur at 25 °C. The current nickel method relies on the nature of the nickel-ligand complex to control the α-selectivity. The reactive sites of the nucleophiles or the nature of the protecting groups have little effect on the α-selectivity. This methodology has also been successfully applied to both disaccharide donors and acceptors to provide the corresponding oligosaccharides in high yields and α-selectivity. The efficacy of the nickel procedure has been further applied toward the preparation of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GluNAc/GalNAc. Mechanistic studies suggest that the presence of the substituted benzylidene functionality at the C(2)-amino position of glycosyl donors is crucial for the high α-selectivity observed in the coupling products. Additionally, the α-orientation of the C(1)-trichloroacetimidate group on glycosyl donors is necessary for the coupling process to occur.
Mensah, Enoch A.,Yu, Fei,Nguyen, Hien M.
supporting information; experimental part
p. 14288 - 14302
(2010/12/19)

Synthesis of new optically active D-glucosamine-pyrrole derivatives
From D-glucosamine hydrochloride was synthesized, for the first time, three new optically active derivatives of D-glucosamine-pyrrole with the pyrrole group unsubstituted in the 2- and 5-positions. New N-benzylpyrrole-D-glucosamine derivatives were also prepared from the same substrate. Georg Thieme Verlag Stuttgart.
Frontana-Uribe, Bernardo A.,Escarcega-Bobadilla, Martha V.,Juarez-Lagunas, Jorge,Toscano, Ruben A.,De La Mora, Gustavo A. Garcia,Salmon, Manuel
scheme or table
p. 980 - 984
(2009/12/04)

MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF
The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin a
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Sheet 40

(2009/05/30)

A carbohydrate-linked hypericinic photosensitizing agent
With respect to an enhanced solubility under physiological conditions, a carbohydrate-containing hypericin-based second-generation photosensitizer was prepared. Its photochemical properties were tested by means of the light-sensitized destruction of bilir
Zuschrader, Joachim,Schoefberger, Wolfgang,Falk, Heinz
experimental part
p. 1387 - 1390
(2009/12/06)

Differently glycosidated 2-amino-2-deoxy-D-glucopyranosiduronic acids as building blocks in peptide synthesis
Seven differently glycosidated sugar amino acids (SSAs) derived from glucosamine have been prepared. Following standard solution-phase peptide-coupling procedures, the glycosidated 2-amino-2-deoxy-D- glucopyranosiduronic acids were condensed with natural
Kyas, Andreas,Feigel, Martin
p. 2375 - 2396
(2007/10/03)

NANOPARTICLES FOR DRUG-DELIVERY
This invention relates to a unique process for the preparation of polymeric nanoparticles with target molecules bonded to the surface of the particles and having sizes of up to 1000nm, preferably Inm to 400nm, more preferably Inm to 200nm, that are dispersed homogeneously in aqueous solution. To accomplish the above objective, the polymeric nanoparticles of the subject invention are prepared using a novel technique of microemulsion polymerization. The resulting aqueous solution of polymeric nanoparticles is comprised of about 1 to 100 parts per weight of water or buffer, about 1 to 80 parts per weight of polymeric nanoparticles, which the bio-active molecules are conjugated, about 0.001 to 10 parts per weight of emulsifier, and about 0.00001 to 5 parts per weight of radical initiator based on the weight of the solution. In the method of this invention, the target drug/target substance is covalently bonded to the polymeric nanoparticles to secure them from outer intervention in vivo or cell culture in vitro until they are exposed at the target site within the cell.
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Figure 47

(2008/06/13)

Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead
As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.
Chauvière, Gérard,Bouteille, Bernard,Enanga, Bertin,De Albuquerque, Cristina,Croft, Simon L.,Dumas, Michel,Périé, Jacques
p. 427 - 440
(2007/10/03)

Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride and its derivatives
2-Acetamido-2-deoxy-D-glucose hydrochloride (D-glucosamine hydrochloride) has been used for the preparation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β- (4) and 2-tetrachlorophthalimido-α,β-D-glucopyranose (6), which have been transformed into the appropriate bromides and the chloride. Both bromo and chloro sugars were used as a glycosyl donors for the glycosylation of diosgenin [(25R)-spirost-5-en-3β-ol]. These condensations were conducted under mild conditions, using silver triflate as a promoter, and gave diosgenyl glycosides 9 and 12. Each of them was converted into diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride (11) and N-acylamido derivatives. The structures of all new glycosides were established by 1H and 13C NMR spectroscopy. These diosgenyl glycosides are the first saponins containing the D-glucosamine residue that have been synthesized. These compounds show promising antitumor activities. The synthetic saponins increase the number of apoptotic B cells, in combination with cladribine (2-CdA), that are isolated from chronic lymphotic leukemia (B-CLL) patients.
Myszka, Henryk,Bednarczyk, Dorota,Najder, Maria,Kaca, Wiesllaw
p. 133 - 141
(2007/10/03)

Synthesis of 4-acyl-1H-1,2,3-triazolic nucleosides
Two simple regiospecific methodologies based on triazolic ring construction in the course of synthesis were applied for the synthesis of 1,2,3-triazolic nucleoside analogues. The cycloaddition reactions between diazomalonaldehyde and appropriate glycosylamine derivatives were rather effective, producing the desired nucleosides 11, 17 and 24. Diazotization of enamines 21a and 21b led to the corresponding triazolic ribonucleoside derivatives 22a and 22b, in good yields. Deprotection reaction of 22a, 22b and 24 was easily achieved by Lewis acid catalysis, producing the corresponding ribonucleosides 23a, 23b and 25.
Cunha,Pereira,De Souza,De Souza,Ferreira
p. 1555 - 1569
(2007/10/03)

Stereospecific solution- and solid-phase glycosylations. Synthesis of β-linked saccharides and construction of disaccharide libraries using phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides as glycosyl donors
An efficient strategy to construct β-O-2-amino-2-deoxyglycopyranosidic linkages using glycosyl sulfoxides is demonstrated. Phenylsulfenyl 2-deoxy- 2-trifluoroacetamido glycopyranosides were found to be reactive glycosyl donors in both solid- and solution-phase glycosylations, affording the corresponding β-glycosides exclusively and in high yield. The trifluoroacetamido group was removed under mild conditions, allowing orthogonal derivatization of multiple protected amino groups on an oligosaccharide or glycoconjugate. On the basis of the results with these glycosyl donors, a solid-phase β-linked disaccharide library was constructed. The scope and flexibility of this approach will be discussed.
Silva, Domingos J.,Wang, Huiming,Allanson, Nigel M.,Jain, Rakesh K.,Sofia, Michael J.
p. 5926 - 5929
(2007/10/03)

Glycosylation of threonine of the repeating unit of RNA polymerase II with β-linked N-acetylglucosame leads to a turnlike structure
Two models of the repeating C-terminal domain of RNA polymerase II (Ac- SYSPTSPSYS-NH2; Ac-SYSPT(β-O-GlcNAc)SPSYS-NH2) were prepared and their conformations in water studied using 1-D and 2-D 1H NMR spectroscopies, CD spec
Simanek, Eric E.,Huang, Dee-Hua,Pasternack, Laura,Machajewski, Timothy D.,Seitz, Oliver,Millar, David S.,Jane Dyson,Wong, Chi-Huey
p. 11567 - 11575
(2007/10/03)

Synthesis of the monosaccharide units of the O-specific polysaccharide of Shigella sonnei
The monosaccharide components of the O-specific polysaccharide 1 of the lipopolysaccharide of the enteropathogenic bacterium Shigella sonnei were synthesized as their methyl glycosides 2 and 3 in their natural anomeric form. The key intermediate to the diaminotrideoxygalactose derivative 2 was ethyl-3-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D- glucopyranoside (9) that was converted to its ditosylate 10. Regioselective deoxygenation at C-6 followed by nucleophilic displacement of the secondary tosyloxy group by azide afforded the 4-azido thioglycoside 13. Methyl trifluoromethanesulfonate-assisted methanolysis of 13 gave the O-glycoside 14. Replacement of the phthalimido by an acetamido group followed by catalytic reduction of the azido group led to the diamino-trideoxygalactose derivative 2. The precursor to the L-altruronic acid derivative 3 was methyl α-L-glucopyranoside (19) that was routinely converted to the benzylidene-protected 2,3-anhydro-allopyranoside 22. Regioselective opening of the epoxide ring by NaN3 afforded the 2-azido derivative 23 that was benzylated at HO-3. Hydrolytic removal of the benzylidene group followed by TEMPO oxidation of C-6 and subsequent esterification with MeI gave the key L-azido-altruronic acid intermediate 29 that was transformed to the acetamido-altruronic acid derivative 3. High resolution NMR data of the altruronic acid derivatives indicate that the conformation of their pyranose ring is crucially dependent on the substitution pattern: the 2-azido altruronic acid derivatives prefer the 4C1 conformation whereas the 2-acetamido congeners exist preferentially in the 1C4 conformation.
Medgyes, Adel,Farkas, Erzsebet,Liptak, Andras,Pozsgay, Vince
p. 4159 - 4178
(2007/10/03)

The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose as donors in glycosylation reactions
1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-β-D-glucopyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-α-D-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity.An oxazolidone was formed as the main product from the reaction of some of the glucopyranosylbromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.
Boullanger, Paul,Jouineau, Martine,Bouammali, Boufelja,Lafont, Dominique,Descotes, Gerard
p. 151 - 164
(2007/10/02)