2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea | 47537-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea
• 英文别名: tetra-O-acetyl-1-carbamimidoylthio-β-D-glucopyranose；S-(tetra-O-acetyl-β-D-glucopyranosyl)-isothiourea；S-(Tetra-O-acetyl-β-D-glucopyranosyl)-isothioharnstoff；2,3,4,6-tetra-O-acetyl-1-S-carbamimidoyl-1-thio-beta-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-carbamimidoylsulfanyloxan-2-yl]methyl acetate
• CAS: 47537-23-5
• 化学式: C₁₅H₂₂N₂O₉S
• 分子量: 406.414
• InChiKey: KFSDELSPBPIZQI-RGDJUOJXSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  490.9±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  190
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea 在 sodium dithionite 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 丁酮 为溶剂， 反应 2.0h， 生成 1-(tetra-O-acetyl-1-thio-β-D-glucopyranosyl)-8-(cholesten-3-α-yloxy)-3,6-dioxaoctane
  参考文献：
  名称：

  Design, Synthesis and In Vivo Evaluation of Sulfhydryl β-D-Glucose Cholesterols as Ligands for Brain Targeting Liposomes

  摘要：

  设计并合成了一种新型硫醇-β-D-葡萄糖胆固醇10a-10f作为脑靶向脂质体的配体。应用10e制备脂质体递送系统，旨在利用葡萄糖转运蛋白成员1（GLUT1）在 mice 中实现模型药物替加氟的脑靶向递送。结果表明，通过使用设计的化合物作为脂质体配体，可以增强脂质体向脑内递送药物的能力。

  DOI：

  10.2174/157018010790945788
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 三乙基硅烷 、 碘 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea
  参考文献：
  名称：

  Efficient synthesis of thioglycosylated kojic acid bys-glycosyl isothiouronium salts

  摘要：

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].

  DOI：

  10.1080/07328303.2016.1261881

文献信息

• Preparation of anomeric pairs of 1-thioglycosides: use of anomerization catalyzed by boron trifluoride
  作者：Daniel T. Connolly、Saul Roseman、Yuan C. Lee

  DOI：10.1016/s0008-6215(00)85209-x

  日期：1980.12

  Abstract Anomeric pairs of some alkyl 1-thioaldopyranosides of d -galactose, d -glucose, d -mannose, 2-acetamido-2-deoxy- d -glucose, 2-acetamido-2-deoxy- d -galactose, and l -fucose were prepared. The per- O -acetylated, 1,2- trans anomers of 6-(trifluoroacetamido)hexyl 1-thioaldopyranosides and 5-(methoxycarbonyl)pentyl 1-thioaldopyranosides were anomerized with boron trifluoride in dichloromethane. The

  摘要d-半乳糖，d-葡萄糖，d-甘露糖，2-乙酰氨基-2-脱氧-d-葡萄糖，2-乙酰氨基-2-脱氧-d-半乳糖和l-岩藻糖的一些烷基1-硫代醛吡喃糖苷的端基对准备好了。用三氟化硼在二氯甲烷中使6-（三氟乙酰胺基）己基1-硫代吡喃吡喃糖苷和5-（甲氧基羰基）戊基1-硫代吡喃吡喃糖苷的过-O-乙酰化的1，2-反式异构体。然后使用硅胶或离子交换树脂柱通过色谱分离异头混合物。分离的化合物的解封闭提供了6-氨基己基1-硫代吡喃二糖苷或5-羧基戊基1-硫代吡喃二糖苷的纯异构体。后一种糖苷的糖苷配基通过与氨基乙醛二乙缩醛反应而进一步延伸，在产物脱缩醛化后提供ω-醛基。
• Anodic Reactivity of Alkyl <i>S</i>-Glucosides
  作者：Bhavesh Deore、Joseph E. Ocando、Lan D. Pham、Carlos A. Sanhueza

  DOI：10.1021/acs.joc.2c00222

  日期：2022.5.6

  aglycone-derived thiyl radicals (RS•). In contrast, aryl glucosides’ Ep values exhibit excellent correlations with the aryl substituents’ Hammett parameters (σ+) and the ArS• RSEs, evidencing the inherent stability of the reactive radical intermediate as the primary factor controlling aryl glucoside’s electrochemical reactivity. The reactivity differences between alkyl and aryl S-glucosides also extend to the protective

  一系列烷基和芳基S-葡糖苷的伏安研究揭示了烷基S-葡糖苷对阳极氧化的反应模式，并发现与芳基衍生物的趋势存在显着差异。烷基S-葡糖苷的氧化电位，本文由方波伏安峰电位( E p )估计，取决于苷元的空间特性。被大体积基团取代的糖苷在电压比带有小糖苷配基的那些的值更正的电压下表现出E p值。在所有分析的烷基系列中观察到的这种关系由E p之间的良好线性相关性证明和各个烷基取代基的 Taft 空间参数 ( ES )。此外，苷元的空间特性作为主要反应性调节剂的作用得到了E p与苷元衍生的硫基自由基 (RS•) 的自由基稳定能 (RSE) 之间较差相关性的支持。相比之下，芳基葡糖苷的E p值与芳基取代基的 Hammett 参数 (σ+) 和 ArS• RSE 表现出极好的相关性，证明了活性自由基中间体的固有稳定性是控制芳基葡糖苷电化学反应性的主要因素。烷基和芳基S-葡糖苷之间的反应性差异也延伸到保护基团对EP
• Developing Bi-Gold Compound BGC2a to Target Mitochondria for the Elimination of Cancer Cells
  作者：Qingbin Cui、Wenwen Ding、Panpan Liu、Bingling Luo、Jing Yang、Wenhua Lu、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.3390/ijms232012169

  日期：——

  Reactive oxygen species (ROS) homeostasis and mitochondrial metabolism are critical for the survival of cancer cells, including cancer stem cells (CSCs), which often cause drug resistance and cancer relapse. Auranofin is a mono-gold anti-rheumatic drug, and it has been repurposed as an anticancer agent working by the induction of both ROS increase and mitochondrial dysfunction. Hypothetically, increasing auranofin’s positive charges via incorporating more gold atoms to enhance its mitochondria-targeting capacity could enhance its anti-cancer efficacy. Hence, in this work, both mono-gold and bi-gold compounds were designed and evaluated to test our hypothesis. The results showed that bi-gold compounds generally suppressed cancer cells proliferation better than their mono-gold counterparts. The most potent compound, BGC2a, substantially inhibited the antioxidant enzyme TrxR and increased the cellular ROS. BGC2a induced cell apoptosis, which could not be reversed by the antioxidant agent vitamin C, implying that the ROS induced by TrxR inhibition might not be the decisive cause of cell death. As expected, a significant proportion of BGC2a accumulated within mitochondria, likely contributing to mitochondrial dysfunction, which was further confirmed by measuring oxygen consumption rate, mitochondrial membrane potential, and ATP production. Moreover, BGC2a inhibited colony formation and reduced stem-like side population (SP) cells of A549. Finally, the compound effectively suppressed the tumor growth of both A549 and PANC-1 xenografts. Our study showed that mitochondrial disturbance may be gold-based compounds’ major lethal factor in eradicating cancer cells, providing a new approach to developing potent gold-based anti-cancer drugs by increasing mitochondria-targeting capacity.

  活性氧（ROS）平衡和线粒体代谢对包括癌症干细胞（CSCs）在内的癌细胞的存活至关重要，而癌症干细胞往往会导致耐药性和癌症复发。奥拉诺芬是一种单金抗风湿药，它已被重新用作抗癌药，通过诱导 ROS 增加和线粒体功能障碍发挥作用。根据推测，通过加入更多的金原子来增加乌拉诺芬的正电荷，从而提高其线粒体靶向能力，可以增强其抗癌功效。因此，本研究设计并评估了单金和双金化合物，以验证我们的假设。结果表明，双金化合物抑制癌细胞增殖的效果普遍优于单金化合物。最有效的化合物 BGC2a 能显著抑制抗氧化酶 TrxR，增加细胞的 ROS。BGC2a 可诱导细胞凋亡，而抗氧化剂维生素 C 无法逆转细胞凋亡，这意味着抑制 TrxR 所诱导的 ROS 可能不是细胞死亡的决定性原因。正如预期的那样，相当一部分 BGC2a 聚集在线粒体内，很可能会导致线粒体功能障碍，这一点通过测量耗氧率、线粒体膜电位和 ATP 产量得到了进一步证实。此外，BGC2a 还能抑制 A549 的集落形成并减少干样侧群（SP）细胞。最后，该化合物还能有效抑制 A549 和 PANC-1 异种移植的肿瘤生长。我们的研究表明，线粒体干扰可能是金基化合物消灭癌细胞的主要致命因素，这为通过提高线粒体靶向能力开发强效金基抗癌药物提供了一种新方法。
• Reaction of 1,2-trans-glycosyl acetates with thiourea: a new entry to 1-thiosugars
  作者：Farid M. Ibatullin、Konstantin A. Shabalin、Janne V. Jänis、Alexander G. Shavva

  DOI：10.1016/j.tetlet.2003.08.120

  日期：2003.10

  The reaction of 1,2-trans-glycosyl acetates with thiourea Under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethylamine and Subsequent alkylation or acylation of the in situ formed 1-thioaldose. (C) 2003 Elsevier Ltd. All rights reserved.
• Cerny et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 64,67
  作者：Cerny et al.

  DOI：——

  日期：——