1-(2-prop-1-ynyl)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 182688-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-prop-1-ynyl)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: propargyl hepta-O-acetyl-β-D-maltopyranoside
• CAS: 182688-43-3
• 化学式: C₂₉H₃₈O₁₈
• 分子量: 674.61
• InChiKey: NXVPJXKDYQZVDU-WLIRAPOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1-(2-prop-1-ynyl)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 copper(ll) sulfate pentahydrate 、 sodium methylate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 甲醇 、 重水 、 叔丁醇 为溶剂， 反应 0.5h， 生成 1-octyl-4-(propargyl-β-D-maltopyranosidyl) triazole
  参考文献：
  名称：

  Controlling the Kinetics of Self-Reproducing Micelles by Catalyst Compartmentalization in a Biphasic System

  摘要：

  Compartmentalization of reactions is ubiquitous in biochemistry. Self-reproducing lipids are widely studied as chemical models of compartmentalized biological systems. Here, we explore the effect of catalyst location on copper-catalyzed azide-alkyne cycloadditions which drive the self-reproduction of micelles from phase-separated components. Tuning the hydrophilicity of the copper-ligand complex, so that hydro-phobic or -philic catalysts are used in combination with hydro-philic and -phobic coupling partners, provides a wide range of reactivity patterns. Analysis of the kinetic data shows that reactions with a hydrophobic catalyst are faster than with a hydrophilic catalyst. Diffusion-ordered spectroscopy experiments suggest compartmentalization of the hydrophobic catalyst inside micelles while the hydrophilic catalyst remains in the bulk aqueous phase. The autocatalytic effects observed can be tuned by varying reactant structure and coupling a hydrophilic alkyne and hydrophobic azide results in a more pronounced autocatalytic effect. We propose and test a model that rationalizes the observations in terms of the phase behavior of the reaction components and catalysts.

  DOI：

  10.1021/acs.joc.8b03149
• 作为产物：
  描述：

  peracetylated α-maltosyl trichloroacetimidate 、 2-丙炔-1-醇 在 乙烯 、 三氟甲磺酸三甲基硅酯 作用下， 以53%的产率得到1-(2-prop-1-ynyl)-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  ortho-Carboranyl Glycosides for the Treatment of Cancer by Boron Neutron Capture Therapy

  摘要：

  Distinct biological properties of the ortho-carboranyl (1,2-dicarba-closo-dodecaboranyl) glycosides 1, 2 and 3 were evaluated to estimate the suitability of these compounds for cancer treatment by boron neutron capture therapy. The boron uptake into B16-Melanoma cells was significantly higher by incubating the cells with aqueous solutions of carboranyl glucoside 1 (11.2 ppm after 3 h), lactoside 2 (13.2 ppm after 12 h) and maltoside 3 (20.0 ppm after 24 h) compared with solutions of clinically used p-boronophenylalanine (BPA) 5 (3.1 ppm after 34 h), Carboranyl maltoside 3 was more effective than boron-10 enriched 5 in killing C-6 rat glioma cells by incubating the cells with the compound and subsequent treatment with thermal neutrons. 3 was also administrated iv, in concentrations of 25 mg boron/kg body weight to rats bearing brain tumors. After a period of 4 h after administration the concentration of boron in the tumor tissue was 3.0 ppm. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00061-x

文献信息

• Water soluble luminescent platinum terpyridine complexes with glycosylated acetylide and arylacetylide ligands: photoluminescent properties and cytotoxicities
  作者：Dik-Lung Ma、Tina Yuen-Ting Shum、Fuyi Zhang、Chi-Ming Che、Mengsu Yang

  DOI：10.1039/b507114c

  日期：——

  Platinum(II) terpyridine complexes with glycosylated acetylide and arylacetylide ligands bind to DNA with binding constants ∼105 mol−1 dm3; the glycosylated arylacetylide complexes exhibit emission at λmax ≈ 620 nm in water and are up to ∼100-times higher in potency than the clinical cisplatin drug in killing cancer cells.

  含糖基化乙炔和芳基乙炔配体的铂(II)三联吡啶配合物与DNA的结合常数约为10^5 mol−1 dm^3；糖基化芳基乙炔配合物在水中发射波长λmax约为620 nm，在杀死癌细胞方面，其效力比临床用药顺铂高出约100倍。
• Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols
  作者：Senthil Narayanaperumal、Rodrigo César da Silva、Julia L. Monteiro、Arlene G. Corrêa、Márcio W. Paixão

  DOI：10.1590/s0103-50532012005000070

  日期：——

  condicoes de reacao nao perigosas, quantidade de catalisador baixa, bom rendimento e seletividade anomerico elevada. In this work, the use of ferric chloride as an efficient catalyst in glycosylation reactions of sugars in the presence of allyl and alkynyl alcohols is described. The corresponding glycosides were obtained with moderate to good yields. This new procedure presented greater selectivity when compared

  Neste trabalho，高级企业的加泰罗尼亚人，加泰罗尼亚州的加尔各答，加利福利亚州的加尔各答，加利福利亚州的加尔各答，加利福利亚州的加尔各答，加利福利亚州的加泰罗尼亚人，加泰罗尼亚的加泰罗尼亚人。Os glicosidios通讯员for a obtidos com rendimentos de Moderados a bons。Este novo procedimento apresenta maior seletividade quando comparado a metodos classicos encontrados na literatura。作为基本原理，包括共性罪犯，白化罪犯，叛逃罪犯。在这项工作中，描述了在烯丙基和炔醇存在下，氯化铁作为糖的糖基化反应中的有效催化剂的用途。以中等至良好的产率获得了相应的糖苷。与文献中的经典方法相比，这种新方法具有更高的选择性。这种简单
• Amino-OPE glycosides and blue light: a powerful synergy in photodynamic therapy
  作者：Andrea Lara-Pardo、Aurora Mancuso、Silvia Simón-Fuente、Paola M. Bonaccorsi、Chiara M. A. Gangemi、María Ángeles Moliné、Fausto Puntoriero、Maria Ribagorda、Anna Barattucci、Francisco Sanz-Rodriguez

  DOI：10.1039/d2ob01742c

  日期：——

  Herein we report the synthesis and biological properties of sugar-conjugated oligophenylene ethynylene (OPE) dyes, used as novel photosensitizers (PSs) for photodynamic treatment (PDT) under blue light. The OPE-bearing glycosides at both ends are successfully prepared by a Pd-catalyzed Sonogashira cross-coupling reaction. The live-cell imaging studies have shown that these OPE glycosides (including

  在此，我们报告了糖共轭低聚亚苯基乙炔 (OPE) 染料的合成和生物学特性，用作蓝光下光动力治疗 (PDT) 的新型光敏剂 (PS)。通过 Pd 催化的 Sonogashira 交叉偶联反应成功制备了两端带有 OPE 的糖苷。活细胞成像研究表明，这些 OPE 糖苷（包括葡萄糖、甘露糖和麦芽糖衍生物）可有效穿透培养的 HeLa 癌细胞的细胞质。没有观察到暗毒性，但在蓝光下照射细胞后，在低浓度（10 -6 –10 -8 M）下观察到非凡的光动力效应。定位研究表明 OPE-葡萄糖1和 OPE-甘露糖2具有高尔基体模式，而 OPE-麦芽糖3可能位于溶酶体中。对用亚致死剂量的 PS 1-3处理的 HeLa 细胞进行的 PDT 和形态学研究表明，细胞死亡是由坏死引起的。
• Photocleavable Molecule for Laser Desorption Ionization Mass Spectrometry
  作者：Toshihide Maki、Koji Ishida

  DOI：10.1021/jo070621b

  日期：2007.8.1

  A new photocleavable molecule for laser desorption ionization mass spectrometry (LDI-MS) was designed and synthesized. The molecule exhibited high sensitivity for negative mode MS detection with good chemical stability. The molecule was successfully applied to molecular tag for (LDI-MS). Kinetic measurement of the amidation reaction and monitoring of aminolysis of acetylated sugars were demonstrated with the molecular tag.
• Carbonic Anhydrase Inhibitors:  Inhibition of Isozymes I, II, and IX with Triazole-Linked <i>O</i>-Glycosides of Benzene Sulfonamides
  作者：Brendan L. Wilkinson、Laurent F. Bornaghi、Todd A. Houston、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm061320h

  日期：2007.4.1

  We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low-nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 and 9.7-107 nM, respectively, was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (K-i = 9.7 nM); this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.