per-O-benzoyl-α-D-glucopyranosyl bromide | 828933-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per-O-benzoyl-α-D-glucopyranosyl bromide
• 英文别名: (2S,3R,4S,5S,6R)-2-bromo-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 828933-95-5
• 化学式: C₆H₁₁BrO₅
• 分子量: 243.054
• InChiKey: BDJLMNAHVITKNE-VFUOTHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dihydroartemisinin 、 per-O-benzoyl-α-D-glucopyranosyl bromide 在 四丁基硫酸氢铵 、 potassium hydroxide 、 sodium methylate 作用下， 以 二氯甲烷 、 水 、 甲醇 为溶剂， 反应 40.0h， 以24.5%的产率得到
  参考文献：
  名称：

  Synthesis and Study of Antitumor Activity of Artimisinin Glucoside

  摘要：

  糖基化已被广泛用于提高某些抗癌药物的疗效和生物利用度。本研究通过糖基化合成了青蒿素葡糖苷，并通过检测其抑制 U14 异种移植瘤增殖、诱导 Hela 细胞凋亡以及影响 p53、Bcl-2 和 Bax 表达的作用，对其体内和体外抗肿瘤作用进行了研究。在体内，青蒿素葡糖苷对肿瘤生长具有时间和剂量依赖性的抑制作用；在体外，青蒿素葡糖苷添加到 40 μM 甚至 20 μM 可诱导 Hela 细胞凋亡。通过分子对接和结构分析，详细研究了青蒿素葡糖苷与 galectin 相互作用的分子机制和结构基础。所有这些研究结果表明，青蒿素葡糖苷通过激活细胞色素 c 通路和诱导细胞凋亡而显示出强大的抗肿瘤活性。

  DOI：

  10.2174/157018012802652886

文献信息

• Method of fluorination
  申请人：Hara Shoji

  公开号：US20060014972A1

  公开（公告）日：2006-01-19

  A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200° C. where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides. When a complex compound comprising HF and a base is reacted under irradiation with microwave, fluorination at a specific position which is difficult in accordance with conventional methods proceeds highly selectively, efficiently in a short time and safely.

  一种氟化方法，包括通过热力学或微波辐射或波长在微波区域附近的电磁波与一种通式为(I)的氟化试剂反应，反应单糖，低聚糖，多糖，由这些糖与蛋白质和脂质结合形成的复合糖和具有多元醇，醛，酮和多元醇的酸以及这些化合物的衍生物和缩聚物。根据该方法，可以在150到200°C的温度范围内安全地进行选择性的氟化反应，而在传统方法中难以进行。上述方法包括使用微波或波长在微波区域附近的电磁波辐射，可应用于除糖类以外的基质。当HF和碱组成的复合物在微波辐射下反应时，难以在传统方法中进行的特定位置的氟化反应高度选择性，高效地在短时间内安全进行。
• 1(Beta-D-Glycopyranosyl)-3-Substituted Nitrogenous Heterocyclic Compound, Medicinal Composition Containing the Same, and Medicinal Use Thereof
  申请人：Teranishi Hirotaka

  公开号：US20080139484A1

  公开（公告）日：2008-06-12

  A compound having SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-(β-D-glycopyranosyl)-3-substituted nitrogen-containing heterocyclic compound represented by the general formula (I), a prodrug, or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof; an SGLT inhibitor containing the same; a pharmaceutical composition containing the same and a medicinal use thereof. In the formula, ring A represents optionally substituted aryl or heteroaryl; Q 1 to Q 5 independently represent a carbon atom having a hydrogen atom or substituent bonded thereto or a nitrogen atom; E represents a single bond, alkylene, —O—, —S— or —NH—; and R represents methyl, ethyl, fluoromethyl or hydroxymethyl.

  具有SGLT1和/或SGLT2抑制活性的化合物，可用作预防或治疗糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症、肥胖等的药物。该化合物是一种1-(β-D-葡萄糖苷基)-3-取代的含氮杂环化合物，由通式(I)表示，是一种前药、药学上可接受的盐或其水合物或溶剂化物；还包括含有该化合物的SGLT抑制剂、含有该化合物的药物组合物和药用。在式中，环A代表可选取代的芳基或杂环基；Q1至Q5独立地表示具有氢原子或配基键合的碳原子或氮原子；E代表单键，烷基，-O-，-S-或-NH-；R代表甲基，乙基，氟甲基或羟甲基。
• 1-( -D-GLYCOPYRANOSYL)-3-SUBSTITUTED NITROGENOUS HETEROCYCLIC COMPOUND, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1803729A1

  公开（公告）日：2007-07-04

  A compound having SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-(β-D-glycopyranosyl)-3-substituted nitrogen-containing heterocyclic compound represented by the general formula (I), a prodrug, or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof; an SGLT inhibitor containing the same; a pharmaceutical composition containing the same and a medicinal use thereof. In the formula, ring A represents optionally substituted aryl or heteroaryl; Q1 to Q5 independently represent a carbon atom having a hydrogen atom or substituent bonded thereto or a nitrogen atom; E represents a single bond, alkylene, -O-, -S- or -NH-; and R.represents methyl, ethyl, fluoromethyl or hydroxymethyl.

  一种具有 SGLT1 和/或 SGLT2 抑制活性的化合物，可用作预防或治疗糖尿病、餐后高血糖症、糖耐量受损、糖尿病并发症、肥胖症等的药物。它是由通式（I）代表的1-（β-D-吡喃甘露糖基）-3-取代的含氮杂环化合物、其原药或药学上可接受的盐，或其水合物或溶液；含有相同物质的SGLT抑制剂；含有相同物质的药物组合物及其药用用途。式中，环A代表任选取代的芳基或杂芳基；Q1至Q5独立地代表具有氢原子或取代基键合的碳原子或氮原子；E代表单键、亚烷基、-O-、-S-或-NH-；R.代表甲基、乙基、氟甲基或羟甲基。
• Evaluation of glucose-linked nitroxide radicals for use as an in vivo spin-label probe
  作者：Shingo Sato、Masaki Yamaguchi、Akio Nagai、Ryo Onuma、Misaki Saito、Rina Sugawara、Sayaka Shinohara、Eriko Okabe、Tomohiro Ito、Tateaki Ogata

  DOI：10.1016/j.saa.2014.01.047

  日期：2014.4

  In vivo incorporation and reduction abilities of 4-carboxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4-carboxy-TEMPO) (1), 3-carboxy-2,2,5,5-tetramethylpyrroline-1-oxyl (3-carboxy-dehydro-PROXYL, 3-carboxy-DPRO) (2), 4-hydroxy-TEMPO and 3-hydroxymethyl-DPRO O-beta-o-glucosides (3 and 5), and newly designed forms of 6-O-(TEMPO-4-carbonyl and DPRO-3-carbonyl)-D-glucose (4 and 6) were evaluated using white radish sprouts. For each of these compounds, electron spin resonance (ESR) spectrometry was used to measure two effects: the rate of in vitro reduction via the addition of ascorbic acid; and, the rate of successful incorporation into radish sprouts for a reduction to the corresponding hydroxyl amine. DPRO-radicals 2, 5, and 6 were detected significantly more than TEMPO-radicals 1, 3, and 4 in vitro and in vivo for both experiments. Four glucose-linked nitroxide radicals were reduced faster than the glucose-non-linked ones in the in vitro experiment, but were nonetheless detected more each time in radish sprouts due to the absorbability. Glucose ester-linked radicals 4 and 6 were detected more than glycosides 3 and 5, which suggests that glucose ester-linked DPRO-radical 6 is the best for use as a spin-label probe that a plant will incorporate. (C) 2014 Elsevier B.V. All rights reserved.
• REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS
  申请人：ISIS INNOVATION LIMITED

  公开号：EP1644390A2

  公开（公告）日：2006-04-12