阿扎胞苷杂质21 | 339091-26-8

• 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
• 中文名称: 阿扎胞苷杂质21
• 英文名称: 1,2,3,5-tetra-O-acetyl-L-xylofuranose
• 英文别名: [(2S,3R,4S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate
• CAS: 339091-26-8
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: IHNHAHWGVLXCCI-FXJUQPSGSA-N

物化性质

• 沸点：
  385.6±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  阿扎胞苷杂质21 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.08h， 生成 p-tolyl 2,3-di-O-benzyl-1-thio-β-L-xylofuranoside
  参考文献：
  名称：

  The 5-Deoxy-5-methylthio-xylofuranose Residue in Mycobacterial Lipoarabinomannan. Absolute Stereochemistry, Linkage Position, Conformation, and Immunomodulatory Activity

  摘要：

  Mycobacteria produce a cell-surface glycoconjugate, lipoarabinomannan (LAM), which has been shown to be a potent modulator of the immune response that arises from infection by these organisms. Recently, LAM from the human pathogens Mycobacterium tuberculosis and M. kansasii has been shown to contain an unusual 5-deoxy-5-methylthio-xylofuranose (MTX) residue as well as its corresponding oxidized counterpart, 5-deoxy-5-methylsulfoxy-xylofuranose (MSX). To date, the absolute configuration of these residues and their linkage position to the polysaccharide are unknown, as is their biological role. Through the combined use of chemical synthesis and NMR spectroscopy, we have established that the MTX/MSX residues in these glycoconjugates are of the D-configuration and that they are linked alpha-(1-4) to a mannopyranose residue in the mannan portion of the glycan. Conformational analysis of the MTX/MSX residue using NMR spectroscopy showed differences in ring conformation and as well as in the rotamer populations about the C-4-C-5 bond, as compared to the parent compound, methyl alpha-D-xylofuranoside. Two of the synthesized disaccharides, 3 and 34, were tested in cytokine induction assays, and neither led to the production of TNF-alpha or IL-12p70. In contrast, both demonstrated modest inhibitory properties when these same cytokines were induced using a preparation of Interferon-gamma and Staphylococcus aureus Cowan strain (SAC/IFN-gamma). These latter observations suggest that this motif may play a role in the immune response arising from mycobacterial infection.

  DOI：

  10.1021/ja057373q
• 作为产物：
  描述：

  L-xylopyranose 、 乙酸酐 在 硼酸 、 溶剂黄146 作用下， 反应 73.0h， 以99%的产率得到阿扎胞苷杂质21
  参考文献：
  名称：

  CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING LIVER CELL CANCER

  摘要：

  公开号：

  EP2636677B1

文献信息

• 2'-deoxy-L-nucleosides
  申请人：Watanabe Kyoichi

  公开号：US20050090660A1

  公开（公告）日：2005-04-28

  This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH 2 , NHR′, or NR′R″ Z is H, F, Cl, Br, I, CN, or NH 2 . R is hydrogen, halogen, lower alkyl of C 1 -C 6 or aralkyl, NO 2 , NH 2 , NHR′, NR′R″, OH, OR, SH, SR, CN, CONH 2 , CSNH 2 , CO 2 H, CO 2 R′, CH 2 CO 2 H, CH 2 CO 2 R′, CH═CHR, CH 2 CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C 1 -C 6 . R 13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

  这项发明提供了制备具有以下结构的化合物的方法： 其中 X和Y相同或不同，且H、OH、OR、SH、SR、NH2、NHR′或NR′R″ Z为H、F、Cl、Br、I、CN或NH2 R为氢、卤素、C1-C6的低碳烷基或芳基烷基、NO2、NH2、NHR′、NR′R″、OH、OR、SH、SR、CN、CONH2、CSNH2、CO2H、CO2R′、CH2CO2H、CH2CO2R′、CH═CHR、CH2CH═CHR或C═CR。 R′和R″相同或不同，且为C1-C6的低碳烷基。 R13为氢、烷基、酰基、磷酸酯（单磷酸酯、二磷酸酯、三磷酸酯或稳定磷酸酯）或硅基。
• IMMUNOMODULATORY SACCHARIDE COMPOUNDS
  申请人：Lowary L. Todd

  公开号：US20070219144A1

  公开（公告）日：2007-09-20

  Compounds comprising a saccharide molecule and a 5-deoxy-5-methylthio-xylofuranose (MTX) moiety or a 5-deoxy-5-methylsulfoxy-xylofuranose (MSX) moiety, and use of such compounds in methods for modulating inflammation and immune responses.

  包含糖分子和5-去氧-5-甲硫氧基-木糖呋喃糖（MTX）基团或5-去氧-5-甲基磺氧基-木糖呋喃糖（MSX）基团的化合物，以及在调节炎症和免疫反应方法中使用这些化合物。
• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20050065139A1

  公开（公告）日：2005-03-24

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

  一种合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，可能用作糖苷酶抑制剂。本发明的化合物可能具有一般式(I)或(II)：合成方案包括将环状硫酸酯与含有杂原子(X)的5元环糖反应。杂原子优选包括硫、硒或氮。环状硫酸酯和环糖试剂可以从碳水化合物前体（如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖）中轻松制备。目标化合物是通过杂原子对5元环糖的亲核攻击打开环状硫酸酯来制备的。所得的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸酯阴离子。合成方案以中等至良好的产率产生目标化合物的各种立体异构体，副反应有限。
• CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING HEPATOCELLULAR CARCINOMA
  申请人：Lee Seung Ki

  公开号：US20130237495A1

  公开（公告）日：2013-09-12

  The present invention relates to a CDK-inhibiting pyrrolopyrimidinone carboxamide derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing same as an active ingredient for preventing or treating liver cell cancer, and the composition containing the pyrrolopyrimidinone carboxamide derivative of the present invention suppresses the cell growth of SNU-354 cell, which is a liver cancer stem cell in humans, by inhibiting CDK1 and CDK2, and induces cell apoptosis of the cell by inhibiting CDK7 and CDK 7, and thus can be effective in use for preventing or treating liver cell cancer.

  本发明涉及一种CDK抑制吡咯吡嘧啶酮羧酰胺衍生物或其药用可接受的盐，以及含有该衍生物作为活性成分的药物组合物，用于预防或治疗肝细胞癌，本发明的吡咯吡嘧啶酮羧酰胺衍生物组合物通过抑制CDK1和CDK2抑制SNU-354细胞（人类肝癌干细胞）的细胞生长，并通过抑制CDK7和CDK7诱导细胞凋亡，从而可有效用于预防或治疗肝细胞癌。
• Efficient Synthesis of the Glucosidase Inhibitor Blintol, the Selenium Analogue of the Naturally Occurring Glycosidase Inhibitor Salacinol
  作者：Hui Liu、B. Mario Pinto

  DOI：10.1021/jo048058+

  日期：2005.1.1

  An efficient synthesis of blintol, the selenium congener of the naturally occurring glycosidase inhibitor salacinol, and a potent glucosidase inhibitor itself, is described. Unlike our previously reported synthesis, this improved route makes use of p-methoxybenzyl ether protecting groups in the synthesis of one of the two key intermediates, 2,3,5-tri-O-p-methoxybenzyl-1,4-anhydro-4-seleno-d-arabinitol

  描述了blintol，天然存在的糖苷酶抑制剂salacinol的硒同类物以及有效的葡萄糖苷酶抑制剂本身的有效合成。与我们先前报道的合成方法不同，这种改进的途径在合成两个关键中间体之一2,3,5-tri- O - p-甲氧基苄基-1,4-脱水-4中利用了对甲氧基苄基醚保护基-seleno- d -arabinitol，从升木糖。另一关键中间体，2,4- ö -benzylidene-升-赤-1,3-环硫酸酯，成功地从制备d -葡萄糖代替昂贵升-葡萄糖。用三氟乙酸除去所得加合物中的所有保护基，得到立体异构体的混合物，从而避免了氢解引起苄基醚脱保护的问题。然后通过分步结晶获得主要的立体异构体blintol。