3'-chloropropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 16977-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-chloropropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-chloropropoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(3-chloropropoxy)oxan-2-yl]methylacetate；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(3-chloropropoxy)oxan-2-yl]methyl acetate
• CAS: 16977-80-3
• 化学式: C₁₇H₂₅ClO₁₀
• 分子量: 424.832
• InChiKey: VQNCUDCIONDRHQ-NQNKBUKLSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  473.0±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3'-chloropropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-chloropropyl β-d-glucopyranoside
  参考文献：
  名称：

  Polyvalent effect enhances diglycosidic antiplasmodial activity

  摘要：

  An efficient and facile total synthesis of diglycoside Matayoside D isolated from the root bark of Matayba guiattensis with antiplasmodial activity have been accomplished in 11 steps with 5% overall yields starting from commercially available glucose and rhamnose. Furthermore, a class of the diglycosidic derivatives with different lengths of the linker and valences were also prepared and evaluated for their antiplasmodial activities against chloroquine-susceptible (3D7) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Low valent and short linker attached diglycoside show no enhancement of the antiplasmodial activity while polyvalent conjugates showed enhanced antiplasmodial activity with IC50 value at least 20 fold better than that of the corresponding diglycosidic monomer. The polyvalent diglycoside were non-cytotoxic against normal mammalian cells under 50,000 g/L. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.05.069
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3'-chloropropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation ofd-glucose-based cationic glycolipids for gene delivery

  摘要：

  合成了两个阳离子环糖脂类新系列，并研究了这些糖脂类对基因转染的效率。

  DOI：

  10.1039/c5ob02107c

文献信息

• Monosaccharide Analogues of Anticancer Peptide R-Lycosin-I: Role of Monosaccharide Conjugation in Complexation and the Potential of Lung Cancer Targeting and Therapy
  作者：Peng Zhang、Jing Ma、Qianqian Zhang、Shandong Jian、Xiaoliang Sun、Bobo Liu、Liqin Nie、Meiyan Liu、Songping Liang、Youlin Zeng、Zhonghua Liu

  DOI：10.1021/acs.jmedchem.9b00634

  日期：2019.9.12

  promising modification strategy for the optimization of peptide drugs. In this study, five different monosaccharide derivatives (7a-e) were covalently linked to the N-terminal of R-lycosin-I, which yielded five glycopeptides (8a-e). They demonstrated increased or reduced cytotoxicity depending on monosaccharide types, which might be explained by the changes of physicochemical properties. Among all synthesized

  糖缀合是用于肽药物优化的有希望的修饰策略。在这项研究中，五个不同的单糖衍生物（7a-e）与R-lycosin-I的N端共价连接，产生了五个糖肽（8a-e）。他们显示出取决于单糖类型的细胞毒性增加或减少，这可以用理化性质的变化来解释。在所有合成的糖肽中，只有8a表现出增加的细胞毒性（IC50 = 9.6±0.3μM）和选择性（IC50 = 37.4±5.9μM）。癌细胞中高表达的葡萄糖转运蛋白1（GLUT1）被批准参与8a的细胞毒性和选择性增强。此外，在裸鼠异种移植模型中，8a抑制R-lycosin-I抑制肿瘤生长，而不会在腹膜内产生副作用。
• 葡萄糖衍生物阳离子脂质体纳米颗粒的制备 方法
  申请人：湖南师范大学

  公开号：CN105585597B

  公开（公告）日：2019-02-19

  本发明公开了葡萄糖衍生物阳离子脂质体纳米颗粒的制备方法。以葡萄糖为原料，合成了一系列不同结构的葡萄糖衍生物阳离子脂质：di‑C12‑Glu‑TMA、di‑C12‑Glu‑TMA、di‑C12‑Glu‑TMA、di‑C12‑Glu‑TMA、Glu‑DiC12MA、Glu‑DiC14MA、Glu‑DiC16MA和Glu‑DiC18MA。上述脂质体经水分散后得到一系列具有结构稳定性好、粒度尺寸适中、粒径分布窄、表面电荷适中、制备成本低廉的葡萄糖衍生物阳离子脂质体纳米颗粒，能实现核酸药物从胞外到胞内的转运，亦可用于非核酸药物的转运载体。
• Glycosylated platinum(<scp>iv</scp>) prodrugs demonstrated significant therapeutic efficacy in cancer cells and minimized side-effects
  作者：Jing Ma、Qingpeng Wang、Xiande Yang、Wenpei Hao、Zhonglv Huang、Jiabao Zhang、Xin Wang、Peng George Wang

  DOI：10.1039/c6dt02207c

  日期：——

  Conjugates (A1–A5) of the Pt(iv) derivative (A6) with amino groups from peracetyl glucose, rhamnose and mannose with a propyl amino or ethyl amino linker at the reducing end were synthesized and exhibited significant therapeutic efficacy in tumour cells, especially for prostate cancer (PCa).

  使用从过乙酰葡萄糖、鼠李糖和甘露糖的氨基团合成的铂（IV）衍生物（A6）的共轭物（A1-A5），在还原端具有丙基氨基或乙基氨基连接剂，表现出显著的治疗效果对于肿瘤细胞，尤其是前列腺癌（PCa）。
• Mono-functionalized glycosylated platinum(IV) complexes possessed both pH and redox dual-responsive properties: Exhibited enhanced safety and preferentially accumulated in cancer cells in vitro and in vivo
  作者：Jing Ma、Xiande Yang、Wenpei Hao、Zhonglv Huang、Xin Wang、Peng George Wang

  DOI：10.1016/j.ejmech.2017.01.032

  日期：2017.3

  agents in vitro and in vivo. The conjugates possessing both pH and redox dual-responsive properties exhibited more potent cytotoxicity in seven different human cancer cell lines and lower toxicity to the normal 3T3 cells than cisplatin, oxaliplatin and even the reported bis-functionalized glycosylated platinum(IV) complexes indicating the enhanced safety of the sugar conjugates. Cellular drug uptake and

  一个严重的糖缀合铂（IV）在形成复合物的Pt（L2）（A2）（OH）基于临床药物顺铂和奥沙利铂R的设计，合成和评价作为抗肿瘤剂的体外和体内。与顺铂，奥沙利铂甚至报道的双功能化糖基化铂（IV）配合物相比，具有pH和氧化还原双重响应特性的结合物在七个不同的人类癌细胞系中表现出更强的细胞毒性，对正常3T3细胞的毒性更低。糖缀合物的安全性。细胞药物吸收和DNA铂化也优于顺铂，奥沙利铂和已报道的双功能化药物。B7和B8的峰值电流在0.08mM浓度下200mv / s的扫描速率在pH 6.4时比pH 7.4高5倍，这表明碳水化合物缀合的单官能化铂（IV）配合物在pH值下同时具有pH和氧化还原双重响应特性。癌细胞。在体内试验表明，铂（IV）化合物能抑制MCF-7肿瘤的生长和比奥沙利铂施加更多的安全性。
• Glycosidase activated release of fluorescent 1,8-naphthalimide probes for tumor cell imaging from glycosylated ‘pro-probes’
  作者：Elena Calatrava-Pérez、Sandra A. Bright、Stefan Achermann、Claire Moylan、Mathias O. Senge、Emma B. Veale、D. Clive Williams、Thorfinnur Gunnlaugsson、Eoin M. Scanlan

  DOI：10.1039/c6cc06451e

  日期：——

  Glycosylated 4-amino-1,8-naphthalimide derivatives can be selectively hydrolysed in situ by glycosidase enzymes to release the naphthalimide as a fluorescent imaging agent.

  糖基化的4-氨基-1,8-萘酰亚胺衍生物可以被糖苷酶酶选择性地水解，释放萘酰亚胺作为荧光成像试剂。