bromo 2,3,4-tri-O-acetyl-α-D-xylofuranoside | 55057-30-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bromo 2,3,4-tri-O-acetyl-α-D-xylofuranoside
• 英文别名: tri-O-acetyl-α-D-xylofuranoside bromide；2,3,5-tri-O-acetyl-α-D-xylofuranosyl bromide；[(2R,3S,4R,5R)-3,4-diacetyloxy-5-bromooxolan-2-yl]methyl acetate
• CAS: 55057-30-2
• 化学式: C₁₁H₁₅BrO₇
• 分子量: 339.14
• InChiKey: WIDXXHUKKJXPEP-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bromo 2,3,4-tri-O-acetyl-α-D-xylofuranoside 在 氨 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.0h， 生成 4-mesityl-1-(β-D-xylofuranosylthio)phthalazine
  参考文献：
  名称：

  Synthesis and antimicrobial activities of S-nucleosides of 4-mesitylphthalazine-1-thiol and some new selenium-containing nucleoside analogues

  摘要：

  A new series of selenium-containing nucleoside analogues, S-nucleosides and S-alkyl derivatives of 4-mesitylphthalazine-1(2H)-selenone and 4-mesitylphthalazine-1(2H)-thione is prepared using different halo compounds. Spectral (IR, H-1 NMR, C-13 NMR) data, and elemental analyses confirmed the structures of the newly synthesized compounds. The antimicrobial and analytical activities of the new compounds have been investigated. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.103
• 作为产物：
  描述：

  β-D-xylofuranose tetraacetate 在 氢溴酸 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 bromo 2,3,4-tri-O-acetyl-α-D-xylofuranoside
  参考文献：
  名称：

  Synthesis and evaluation of a series of 6-chloro-4-methylumbelliferyl glycosides as fluorogenic reagents for screening metagenomic libraries for glycosidase activity

  摘要：

  Screening of large enzyme libraries such as those derived from metagenomic sources requires sensitive substrates. Fluorogenic glycosides typically offer the best sensitivity but typically must be used in a stopped format to generate good signal. Use of fluorescent phenols of pKa < 7, such as halogenated coumarins, allows direct screening at neutral pH. The synthesis and characterisation of a set of nine different glycosides of 6-chloro-4-methylumbelliferone are described. The use of these substrates in a pooled format for screening of expressed metagenomic libraries yielded a "hit rate" of 1 in 60. Hits were then readily deconvoluted with the individual substrates in a single plate to identify specific activities within each clone. The use of such a collection of substrates greatly accelerates the screening process. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.12.010

文献信息

• Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid
  作者：Zhangjian Huang、Yihua Zhang、Li Zhao、Yongwang Jing、Yisheng Lai、Luyong Zhang、Qinglong Guo、Shengtao Yuan、Jianjun Zhang、Li Chen、Sixun Peng、Jide Tian

  DOI：10.1039/b918846k

  日期：——

  A series of nitric oxide (NO)-releasing glycosyl derivatives (2–14) of oleanolic acid were synthesized to improve the aqueous solubility and cytotoxicity of the parent compound 1. Derivative 3 exhibited better solubility and strong cytotoxicity against human hepatocellular carcinoma (HCC) in vitro. Furthermore, 3 displayed low acute toxicity to mice and significantly inhibited the growth of HCC tumors

  一系列 一氧化氮 （NO）释放 糖基的导数（2–14）齐墩果酸合成以改善母体化合物1的水溶性和细胞毒性。衍生物3对人肝细胞癌具有更好的溶解性和较强的细胞毒性（肝癌）体外。此外，3对小鼠的急性毒性较低，并显着抑制了小鼠的生长。肝癌体内肿瘤，表明3可能是治疗人类的有前途的候选药物肝癌。
• Synthesis, antitumor and antimicrobial activities of 4-(4-chlorophenyl)-3-cyano-2-(β-O-glycosyloxy)-6-(thien-2-yl)-nicotinonitrile
  作者：Hassan A. El-Sayed、Ahmed H. Moustafa、Abd El-Fattah Z. Haikal、Rajab Abu-El-Halawa、El Sayed H. El Ashry

  DOI：10.1016/j.ejmech.2011.04.019

  日期：2011.7

  4-(4-Chlorophenyl)-3-cyano-6-(thien-2-yl)-1H-pyridin-2-one (2) was obtained by reaction of 2-acetyl thiophene with 4-chlorobenzaldehyde and ethyl cyanoacetate in presence of ammonium acetate or by the reaction of α,β-unsaturated compound 1 with ethyl cyanoacetate in the presence of ammonium acetate. 4-(4-Chlorophenyl)-2-(2′,3′,4′,6′-tetra-O-acetyl-β-d-gluco/galactopyranosyloxy)-6-(thien-2-yl)nicotinonitrile

  通过2-乙酰基噻吩与4-氯苯甲醛和氰基乙酸乙酯的反应，制得4-（4-氯苯基）-3-氰基-6-（噻吩-2-基）-1 H-吡啶-2-一（2）。存在乙酸铵或在乙酸铵存在下通过α，β-不饱和化合物1与氰基乙酸乙酯反应。4-（4-氯苯基）-2-（2'，3'，4'，6'-四-O-乙酰基-β - d-葡萄糖/吡喃半乳糖基氧基）-6-（噻吩-2-基）烟腈（5a和5b），核糖苷11，木糖苷12和乳糖苷16是通过反应制备的。2与糖基/半乳糖/木糖/乳糖溴化物和全乙酰化木糖/下常规和微波辐射的方法核糖。反应已经区域选择性地产生了O-糖苷而不是N-糖苷。苷图5a，b，核糖核苷11，木糖苷12和乳糖苷16在Et的存在下脱乙酰化3 N / MeOH和几滴水，得到图7a，b，13，14和17。新合成的化合物的结构通过IR，1 H，13 C NMR光谱和微量分析。筛选这些化合物的选定成员的抗肿瘤和抗菌活性。
• Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New Se-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity
  作者：I. E. El-Shamy、E. Hleli、A. A. Alsheikh、M. A. Yawer、M. A. El-Hashash、J. Dybal、A. M. Abdel-Mohsen

  DOI：10.3390/molecules28010317

  日期：——

  A highly efficient and versatile synthetic approach for the synthesis of 4-(pyren-1-ylmethyl)-1-(d-glycosyloxy) phthalazine nucleosides 11a,b, 13, β-S-nucleosides 16, 18, 20, and acyclo C-nucleosides 23a,b, 24, 25 and 27a-f was described and fully characterized. Furthermore, a series of desired new nucleoside analogues containing Se of 4-(pyren-1-ylmethyl) phthalazine-1(2H)-selenone 28-33 were synthesized

  一种高效且通用的合成方法，用于合成 4-(pyren-1-ylmethyl)-1-(d-glycosyloxy) phthalazine nucleosides 11a,b, 13, β-S-nucleosides 16, 18, 20, and acyclo C - 描述并充分表征了核苷 23a、b、24、25 和 27a-f。此外，合成了一系列所需的新核苷类似物，其中含有 Se of 4-(pyren-1-ylmethyl) phthalazine-1(2H)-selenone 28-33。所有报道化合物的结构均通过IR、1H-NMR、13C-NMR、MS和元素分析确证。所有化合物都经过抗菌和抗真菌活性筛选。与具有较低毒性的标准药物相比，20 和 33a 显示出最大活性。测量并评估了所选化合物的细胞毒性。使用理论计算计算最高占据分子轨道和最低未占据分子轨道之间的能隙，以反映合成化合物的
• Electrochemically Mediated S-Glycosylation of 1-Thiosugars with Xanthene Derivatives
  作者：Rui-Qi Wang、Qing-Hui Jiang、Hui-Xiang Wang、Xiao-Wei Zhang、Nan Yan

  DOI：10.1021/acs.orglett.3c01185

  日期：2023.6.16

  electrochemical dehydrogenative cross-coupling of benzylic C–H bonds with 1-thiosugars at room temperature is described. The direct S-glycosylation protocol avoids using any oxidant, which provides facile access to various glycosylated xanthene derivatives with up to 91% yield. This current electrooxidative reaction is characterized by high atom economy, high efficiency, mild reaction conditions, being

  描述了室温下苄基 C-H 键与 1-硫糖的有效电化学脱氢交叉偶联。直接 S-糖基化方案避免使用任何氧化剂，可以轻松获得各种糖基化呫吨衍生物，收率高达 91%。目前的电氧化反应具有原子经济性高、效率高、反应条件温和、环境友好、官能团耐受性好等特点。此外，初步的机理研究表明该反应涉及自由基过程。
• &lt;p&gt;Novel purine thioglycoside analogs: synthesis, nanoformulation and biological evaluation in in vitro human liver and breast cancer models&lt;/p&gt;
  作者：Mamdouh A. Abu-Zaied、Samah A Loutfy、Ashraf E. Hassan、Galal H Elgemeie

  DOI：10.2147/dddt.s201249

  日期：——

  Background: A series of novel pyrazolopyrimidine and pyrazololpyridine thioglycosides were synthesized and confirmed via their spectral analyses.Purpose: To evaluate the effect of these anti-metabolic compounds against proliferation of Huh-7 and Mcf-7 as in vitro models of human liver and breast cancers, respectively. Vero cells were used as an example of normal green monkey kidney cells.Methods: The most promising compound was subjected to a nanoformulation by its encapsulation into chitosan nanoparticles to increase its anti-cancerous activity. Nanoformulation was confirmed by TEM and FT-IR to ensure encapsulation and screened for their cytotoxicity against Huh-7 and Mcf-7 cells using MTT colorimetric assay and morphological examination. Genotoxic effect was performed by cellular DNA fragmentation assay. Simulated CompuSyn software (linear interaction effect) was conducted to predict the possible synergistic effect of nanocomposite as anticancerous activity. Apoptotic effect was further analyzed by detection of apoptotic proteins using ELISA assay.Results: The nano preparation was successfully prepared by encapsulation of compound 14 into chitosan nanoparticles, controlled to a size at 105 nm and zeta charges at 40.2 mV. Treatment of Huh-7 and Mcf-7 showed that compound 14 was the most cytotoxic compound on both cancer cell lines where IC50 was 24.59 (9.836 mu g/mL) and 12.203 (4.8812 mu g/mL) on Huh-7 and Mcf-7 respectively. But IC50 of the nano preparation was 37.19 and 30.68 mu g/mL on Huh-7 and Mcf-7, respectively, indicating its aggressiveness on human breast cancer cells as confirmed by DNA fragmentation assay and theoretically by CompuSyn tool.Conclusion: A novel series of pyrazolopyrimidine thioglycosides and pyrazolopyridine thioglycosides were synthesized. Nanoformulation of compound 14 into chitosan nanoparticles demonstrated anticancer activity and can be used as a drug delivery system, but further studies are still required.