6-氯-6-脱氧-alpha-d-吡喃葡萄糖 | 28528-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-氯-6-脱氧-alpha-d-吡喃葡萄糖
• 英文名称: 6-chloro-6-deoxy-α-D-glucopyranose
• 英文别名: 6-chloro-α-D-6-deoxy-glucopyranose；6-chloro-D-quinovopyranose；6-Chloro-6-deoxy-alpha-d-glucopyranose；(2S,3R,4S,5S,6S)-6-(chloromethyl)oxane-2,3,4,5-tetrol
• CAS: 28528-86-1
• 化学式: C₆H₁₁ClO₅
• 分子量: 198.603
• InChiKey: QMWDIHPSUCUMFU-DVKNGEFBSA-N

物化性质

• 熔点：
  48-53°C
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  6-氯-6-脱氧-alpha-d-吡喃葡萄糖 、 3,4,5-tris(benzyloxy)benzoyl chloride 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 [(2S,3S,4S,5R,6R)-2-(chloromethyl)-4,5,6-tris[[3,4,5-tris(phenylmethoxy)benzoyl]oxy]oxan-3-yl] 3,4,5-tris(phenylmethoxy)benzoate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Study of Antidiabetic Penta-O-galloyl-d-glucopyranose and Its Analogues

  摘要：

  The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the alpha- and beta-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-alpha-D-glucopyranose (43) and tetra-O-galloyl-alpha-D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy- 1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.

  DOI：

  10.1021/jm060087k
• 作为产物：
  描述：

  a-无水葡萄糖酯 生成 6-氯-6-脱氧-alpha-d-吡喃葡萄糖
  参考文献：
  名称：

  Baratova; Ibragimov; Konstantinova, Russian Journal of Organic Chemistry, 1997, vol. 33, # 4, p. 575 - 576

  摘要：

  DOI：

文献信息

• [EN] PREPARATION FOR APPLICATION OF ACTIVE SUBSTANCES IN THE FORM OF MINIMUM-SIZED DROPLETS
  申请人：CEVC, Gregor

  公开号：WO1992003122A1

  公开（公告）日：1992-03-05

  (DE) Die Erfindung betrifft ein Präparat zur Applikation von Wirkstoffen in Form kleinster, insbesondere mit einer membranartigen Hülle aus einer oder wenigen Lagen amphiphiler Moleküle bzw. mit einer amphiphilen Trägersubstanz versehenen Flüssigkeitströpfchen, insbesondere zum Transport des Wirkstoffes in und durch natürliche Barrieren und Konstruktionen wie Häute und dergleichen. Das Präparat weist einen Gehalt einer randaktiven Substanz auf, der bis zu 99 Mol.-% des Gehaltes dieser Substanz entspricht, durch den der Solubilisierungspunkt der Tröpfchen erreicht wird. Das Präparat eignet sich zur nichtinvasiven Verabreichung von Antidiabetica, insbesondere von Insulin. Die Erfindung betrifft außerdem ein Verfahren zur Herstellung solcher Präparate.(EN) The invention concerns a preparation for the application of active substances in the form of minimum-sized droplets, in particular in the form of minimum-sized droplets provided with a membrane-type sheath consisting of one or more layers of amphiphilic molecules or minimum-sized droplets provided with an amphiphilic carrier substance, in particular for transporting the active substance into and across natural barriers and constrictions such as skin and the like. The preparation contains up to 99 mol% of an edge-active substance for obtaining the solubilization point of the droplets. The preparation is suitable for non-invasive administration of antidiabetics, in particular insulin. The invention also concerns a process for producing these preparations.(FR) Une composition permet d'appliquer de fines gouttelettes de substances actives, notamment pourvues d'une enveloppe similaire à une membrane formée d'une ou plusieurs couches de molécules amphiphiles ou pourvues d'une substance porteuse amphiphile, utiles notamment pour transporter la substance active dans et à travers des barrières et des étranglements naturels, tels que la peau et similaire. La composition contient une substance à activité marginale qui représente jusqu'à 99% en moles de la teneur de cette substance, qui permet d'atteindre le point de solubilisation des gouttelettes. Cette composition est utile pour administrer de manière non invasive des agents anti-diabétiques, notamment l'insuline. L'invention concerne en outre un procédé de production de ces compositions.

  (法文)该发明涉及一种用于以最小尺寸呈递活性物质的装置，特别是具备由单一或多个 amphiphilic 分子层或 amphiphilic 承载物质组成的膜状外衣的最小尺寸液滴，尤其适于将活性物质运输到和穿过天然屏障和structures，如皮肤等等。该装置含有高达 99 摩尔百分率的一种边缘活性物质，以使液滴的溶解点得以实现。该装置可用于非侵入性地管理抗糖尿病药剂，尤其是胰岛素。该发明还涉及一种制备上述装置的方法。（英文同上）
• [EN] METHODS AND COMPOSITIONS FOR TREATING HYPERGLYCEMIC, HYPERLIPIDEMIC, OR HYPERINSULINEMIC DISORDERS<br/>[FR] PROCEDES ET COMPOSITIONS POUR LE TRAITEMENT DE TROUBLES HYPERGLYCEMIQUES, HYPERLIPIDEMIQUES, OU HYPERINSULINEMIQUES
  申请人：UNIV OHIO

  公开号：WO2006034468A3

  公开（公告）日：2006-04-20
• DERIVATIVES OF POLYENE MACROLIDES AND PREPARATION AND USE THEREOF
  申请人：IntraBiotics Pharmaceuticals, Inc.

  公开号：EP1278527A1

  公开（公告）日：2003-01-29
• EP1278527A4
  申请人：——

  公开号：EP1278527A4

  公开（公告）日：2003-04-09
• Preparation for the application of agents in mini-droplets
  申请人：Cevc Gregor

  公开号：US20070042030A1

  公开（公告）日：2007-02-22

  The invention relates to a preparation for the application of agents in the form of minuscule droplets of fluid, in particular provided with membrane-like structures consisting of one or several layers of amphiphilic molecules, or an amphiphilic carrier substance, in particular for transporting the agent into and through natural barriers such as skin and similar materials. The preparation contains a concentration of edge active substances which amounts to up to 99 mol-% of the agent concentration which is required for the induction of droplet solubilization. Such preparations are suitable, for example, for the non-invasive applications of antidiabetics, in particular of insulin. The invention, moreover, relates to the methods for the preparation of such formulations.