6-脱氧-6-氟葡萄糖 | 4536-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-脱氧-6-氟葡萄糖
• 英文名称: 6-fluoro-6-deoxyglucosse
• 英文别名: 6-fluoro-D-6-deoxy-glucose；6-fluoro-6-deoxy-D-glucose；D-gluco-6-Fluor-2,3,4,5-tetrahydroxy-hexanal；6-Fluor-6-desoxy-D-glucose；6-deoxy-6-fluoro-D-glucose；(2R,3S,4S,5S)-6-fluoro-2,3,4,5-tetrahydroxyhexanal
• CAS: 4536-08-7
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: LFIUMOHGAWHPEA-JGWLITMVSA-N

物化性质

• 熔点：
  120-126°C
• 沸点：
  459.5±45.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)
• 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：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  6-脱氧-6-氟葡萄糖 在 吡啶 作用下， 生成 1,2,3,4-四-o-乙酰基-6-脱氧-6-氟-alpha-d-吡喃葡萄糖
  参考文献：
  名称：

  氟化碳水化合物。十一。6-脱氧-6-氟-D-葡萄糖：一种改进的合成方法和糖基氟衍生物。

  摘要：

  DOI：

  10.1016/s0008-6215(00)80310-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 6-脱氧-6-氟葡萄糖
  参考文献：
  名称：

  Helferich; Vock, Chemische Berichte, 1941, vol. 74, p. 1807,1811

  摘要：

  DOI：

文献信息

• N-glycosylated carboxamide derivatives as growth-promoters in livestock
  申请人：Bayer Aktiengesellschaft

  公开号：US04680287A1

  公开（公告）日：1987-07-14

  Growth of animals is promoted by inclusion in their feed of compounds of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical having up to 30 Carbon atoms optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical having up to 30 Carbon atoms optionally interrupted by O or substituted by groups containing oxygen or by halogen, with the proviso that COR.sub.1 is not an acyl group having 1-5 Carbon atoms when R.sub.2 is an alkyl group having 10-20 Carbon atoms.

  动物生长可以通过在其饲料中添加以下化合物的形式得到促进：其中Z是通过异头碳原子连接的糖基自由基，R1是氢或者是一个最多含有30个碳原子，可以选择性地被O、N或S原子隔断的，也可以选择性地被取代的烃基团，而R2是氢或者是一个最多含有30个碳原子的烷基或芳烷基团，可以选择性地被O原子隔断或被含氧基团或卤素取代，条件是当R2是一个含有10-20个碳原子的烷基团时，COR1不能是一个含有1-5个碳原子的酰基团。
• N-glycosylated carboxylic acid derivatives as agents for combating
  申请人：Troponwerke GmbH & Co., KG

  公开号：US04710491A1

  公开（公告）日：1987-12-01

  A method of combating rheumatic diseases which comprises administering to a patient afflicted therewith an amount effective to combat such disease of a compound of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical with up to 30 C atoms, which hydrocarbon radical is optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical with up to 30 C atoms, which is optionally interrupted by O, N or S or substituted by an oxygen-containing group or halogen, with the proviso that COR.sub.1 is not an acyl group with 1-5 C atoms if R.sub.2 is alkyl with 10-20 C atoms.

  一种治疗风湿病的方法，包括给患者施用有效治疗该疾病的量的以下化合物的公式：##STR1## 其中Z是通过异构碳原子连接的糖基自由基，R1是氢或最多有30个碳原子的可选取代的烃基，该烃基可被O、N或S隔断，R2是氢或最多有30个碳原子的烷基或芳烷基，该基团可被O、N或S隔断或被含氧基团或卤素取代，条件是如果R2是10-20个碳原子的烷基，则COR1不是1-5个碳原子的酰基。
• Efficient bioconjugation of 5-fluoro-5-deoxy-ribose (FDR) to RGD peptides for positron emission tomography (PET) imaging of αvβ3 integrin receptor
  作者：Sergio Dall'Angelo、Qingzhi Zhang、Ian N. Fleming、Monica Piras、Lutz F. Schweiger、David O'Hagan、Matteo Zanda

  DOI：10.1039/c3ob40550h

  日期：——

  The utility of 5-fluoro-5-deoxyribose (FDR) as an efficient bioconjugation agent for radiolabelling of the RGD peptides c(RGDfK) and c(RGDfC) is demonstrated. The bioconjugation is significantly superior to that achieved with 2-fluoro-2-deoxyglucose (FDG) and benefits from the location of the fluorine at C-5, and that ribose is a 5-membered ring sugar rather than a 6-membered ring. Both features favour ring opening to the aldehydic form of the sugar to promote smooth oxime ligation with aminooxy ether functionalised peptides. [18F]FDR was prepared in this study by synthesis from fluoride-18 using an automated synthesis protocol adapting that used routinely for [18F]FDG. c(RGDfK) was functionalised with an aminooxyacetyl group (Aoa) via its lysine terminus, while c(RGDfC) was functionalised with an aminooxyhexylmaleimide (Ahm) through a cysteine–maleimide conjugation. Bioconjugation of [18F]FDR to c(RGDfC)-Ahm proved to be more efficient than c(RGDfK)-Aoa (92% versus 65%). The unlabelled (19F) bioconjugates c(RGDfK)-Aoa-FDR and c(RGDfC)-Ahm-FDR were prepared and their in vitro affinity to purified integrin αvβ3 was determined. c(RGDfK)-Aoa-FDR showed the greater affinity. Purified “hot” bioconjugates c(RGDfK)-Aoa-[18F]FDR and c(RGDfC)-Ahm-[18F]FDR were assayed by incubation with MCF7, LNCaP and PC3 cell lines. In both cases the conjugated RGD peptides showed selectivity for PC3 cells, which express αvβ3 integrin, with the c(RGDfK)-Aoa-[18F]FDR demonstrating better binding, consistent with its higher in vitro affinity. The study demonstrates that [18F]FDR is an efficient bioconjugation ligand for RGD bioactive peptides.

  研究表明，5-氟-5-脱氧核糖（FDR）作为RGD肽c(RGDfK)和c(RGDfC)的放射标记高效生物偶联剂具有实用性。与2-氟-2-脱氧葡萄糖（FDG）相比，生物偶联效果显著优越，这得益于氟原子位于C-5位置，以及核糖是五元环糖而非六元环糖的特点。这两个特性有利于糖环开环形成醛式，促进与氨基氧乙基功能化肽的顺利肟连接。在本研究中，[18F]FDR通过从氟-18开始，采用适应常规[18F]FDG合成方法的自动化合成协议制备。c(RGDfK)通过其赖氨酸末端与氨基氧乙酰基（Aoa）功能化，而c(RGDfC)通过半胱氨酸-马来酰亚胺连接与氨基氧己基马来酰亚胺（Ahm）功能化。[18F]FDR与c(RGDfC)-Ahm的生物偶联证明比c(RGDfK)-Aoa更高效（92%对65%）。制备了未标记的（19F）生物偶联物c(RGDfK)-Aoa-FDR和c(RGDfC)-Ahm-FDR，并测定了它们对纯化整合素αvβ3的体外亲和力。c(RGDfK)-Aoa-FDR显示出更高的亲和力。纯化的“热”生物偶联物c(RGDfK)-Aoa-[18F]FDR和c(RGDfC)-Ahm-[18F]FDR通过与MCF7、LNCaP和PC3细胞系共孵育进行检测。两种情况下，结合的RGD肽均显示出对表达αvβ3整合素的PC3细胞的选择性，其中c(RGDfK)-Aoa-[18F]FDR显示出更好的结合效果，与其更高的体外亲和力一致。该研究表明，[18F]FDR是RGD生物活性肽的高效生物偶联配体。
• [EN] GLYCOSIDE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] COMPOSÉS DE GLYCOSIDE ET COMPOSITIONS PHARMACEUTIQUES DE CEUX-CI
  申请人：CT SE LLC

  公开号：WO2010017480A1

  公开（公告）日：2010-02-11

  The present invention provides glycoside compounds, methods of preparing such compounds, pharmaceutical compositions comprising such compounds, and a method for the treatment of hyperproliferative diseases using the same.

  本发明提供了糖苷化合物、制备这种化合物的方法、包含这种化合物的药物组合物，以及使用这种化合物治疗过度增殖性疾病的方法。
• [EN] NEOGLYCORANDOMIZATION AND DIGITOXIN ANALOGS<br/>[FR] ALEATOIRISATION DES NEOGLYCOSIDES ET ANALOGUES DE LA DIGITOXINE
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2006002381A1

  公开（公告）日：2006-01-05

  The present invention provides methods of producing libraries of compounds with enhanced desirable properties and diminished side effects as well as the compounds produced by the methods. In preferred embodiments, methods of the present invention use a universal chemical glycosylation method that employs reducing sugars and requires no protection or activation. In a preferred embodiment, the invention provides a library of neoglycoside digitoxin analogs that includes compounds with significantly enhanced cytotoxic potency toward human cancer cells and tumor-specificity, but are less potent Na+/K+-ATPase inhibitors in a human cell line than digitoxin.

  本发明提供了一种生产具有增强理想性能和减少副作用的化合物库的方法，以及通过这些方法生产的化合物。在优选实施例中，本发明的方法使用一种通用的化学糖基化方法，该方法采用还原糖，无需保护或激活。在优选实施例中，本发明提供了一种新糖苷地高辛类似物库，其中包括对人类癌细胞具有显著增强的细胞毒性活性和肿瘤特异性的化合物，但在人类细胞系中对Na+/K+-ATPase的抑制作用较地高辛要弱。