phenyl 3,4-di-O-acetyl-2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside | 1331825-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-di-O-acetyl-2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside
• 英文别名: phenyl-3,4-diacetyl-2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranose
• CAS: 1331825-38-7
• 化学式: C₁₆H₁₈N₆O₅S
• 分子量: 406.422
• InChiKey: XGMSQVKOIHKXBN-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  159.35
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-acetyl-2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside 、 (1R,2R,4S,5S)-2,4-diazido-N-((1S,2S,4R,5R)-2,4-diamino-5-methoxycyclohexyl)-5-hydroxycyclohexanecarboxamide 在 二甲基二硫 、 三氟甲磺酸酐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (2R,3R,5R,6S)-5-azido-2-(azidomethyl)-6-(((1S,2S,4R,5R)-2,4-diazido-5-(((1S,2S,4R,5R)-2,4-diazido-5-methoxycyclohexyl)carbomoyl)cyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 (2R,3R,5R,6S)-5-azido-2-(azidomethyl)-6-(((1S,2S,4R,5R)-2,4-diazido-5-(((1S,2S,4R,5R)-2,4-diazido-5-methoxycyclohexyl)carbomoyl)cyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Conjugate of neamine and 2-deoxystreptamine mimic connected by an amide bond

  摘要：

  An amino-functionalized 2-deoxystreptamine (2-DOS) mimic was conjugated by an amide bond to a neamine moiety containing a carboxylic acid in ring II. A library of A-site RNA and its mutants was prepared to examine RNA binding characteristics of the additional 2-DOS moiety attached to neamine. The 2-DOS mimic conjugated to the neamine increased binding affinity up to 200-folds compared to that of neamine. The conjugate binds to native A-site RNA and its mutants with up to 6-fold difference in sequence selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.084
• 作为产物：
  描述：

  乙酸酐 、 (2R,3S,4R,5R)-5-azido-2-(azidomethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4-diol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 18.0h， 以8%的产率得到
  参考文献：
  名称：

  设计，合成和评估双氨基糖基化抗肿瘤醚脂质对癌细胞和癌细胞干细胞的细胞毒性特性† ‡

  摘要：

  糖基化抗肿瘤醚脂质（GAEL）是一类通过非凋亡途径杀死癌细胞的两亲性抗肿瘤药。以前的研究已经表明，2-氨基-2-脱氧d -葡萄糖为基础的盖尔如α-GLN和β-GLN显示出大大改善的抗上皮癌细胞的抗肿瘤活性和干细胞。为了进一步优化生物活性，我们制备了一系列二氨基的d -葡糖基础的盖尔和它们的类似物，并筛选它们免受人类上皮癌细胞系和癌症干细胞的一个面板。大多数新的GAEL类似物比苯丁酸氮芥，顺铂和沙利霉素更有效。最有效的基于双胺的GAEL类似物1，与β-GLN相比，图2，图4和图8显示出对各种癌细胞系的细胞毒性提高了2-3倍，这表明添加第二个氨基基团增强了细胞毒性作用。活性最高的GAEL 1和4对分离自乳腺癌（BT-474）和前列腺（DU-145）细胞系的癌症干细胞的影响表明，两种GAEL抑制肿瘤球的形成并导致> 95％的损失5μM时癌症干细胞的活力 GAEL 1对BT-474癌症干细胞的活性优于沙利霉素。

  DOI：

  10.1039/c6md00328a

文献信息

• [EN] DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS<br/>[FR] ETHERS LIPIDIQUES ANTITUMORAUX GLYCOSYLÉS DI- ET TRICATIONIQUES, GAEL L-GLYCOSYLÉS ET GAEL LIÉS À DU RHAMNOSE UTILISABLES EN TANT QU'AGENTS CYTOTOXIQUES DIRIGÉS CONTRE DES CELLULES ÉPITHÉLIALES CANCÉREUSES ET DES CELLULES SOUCHES CANCÉREUSES
  申请人：UNIV MANITOBA

  公开号：WO2015179983A1

  公开（公告）日：2015-12-03

  Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

  糖基化抗肿瘤醚脂质（GAELs）通过一种非凋亡途径杀灭癌细胞，这是一种吸引人的策略，可以避免抗药性。为了进一步优化抗肿瘤效果，我们制备了不同的双-和三-阳离子GAEL类似物，其糖的性质（D-葡萄糖或L-葡萄糖）、缩醛键以及甘油脂类团的位置不同。合成了双-和三-阳离子GAEL类似物，并评估了它们对人类乳腺、前列腺、胰腺和卵巢癌衍生的耐药和快速生长的癌细胞系的体外抗癌性能。最有效的双阳离子GAEL类似物也针对从乳腺BT 474、前列腺DU145和卵巢A2780cp细胞系中获得的癌干细胞进行了研究。我们的结果表明，阳离子数量、氨基取代物的位置和糖的性质对这些化合物的抗癌活性有显著影响。最活跃的类似物在浓度范围为0.5-5μΜ时杀死50%的细胞，在浓度为1-10μΜ时杀死90%的细胞，具体取决于癌细胞类型。