1,3-bis(2-(4-nitrophenyl)acetamido)propan-2-yl α-D-mannopyranoside | 1581270-45-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,3-bis(2-(4-nitrophenyl)acetamido)propan-2-yl α-D-mannopyranoside
• 英文别名: 2-(4-nitrophenyl)-N-[3-[[2-(4-nitrophenyl)acetyl]amino]-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl]acetamide；2-(4-nitrophenyl)-N-[3-[[2-(4-nitrophenyl)acetyl]amino]-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl]acetamide
• CAS: 1581270-45-2
• 化学式: C₂₅H₃₀N₄O₁₂
• 分子量: 578.533
• InChiKey: UBIHBPGKTMFBDP-CPSSSWKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  249
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 148.0h， 生成 1,3-bis(2-(4-nitrophenyl)acetamido)propan-2-yl α-D-mannopyranoside
  参考文献：
  名称：

  Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor

  摘要：

  Dendritic cell-specific, intercellular adhesion molecule-3-grabbing non-integrin (DC-SIGN) is a C-type lectin expressed specifically on dendritic cells. It is a primary site for recognition and binding of various pathogens and thus a promising therapeutic target for inhibition of pathogen entry and subsequent prevention of immune defense cell infection. We report the design and synthesis of D-mannose-based DC-SIGN antagonists bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties incorporated to target the hydrophobic groove of the receptor. The designed glycomimetics were evaluated by in vitro assay of the isolated DC-SIGN extracellular domain for their ability to compete with HIV-1 gp120 for binding to the DC-SIGN carbohydrate recognition domain. Compounds 14d and 14e, that display IC50 values of 40 mu M and 50 mu M, are among the most potent monovalent DC-SIGN antagonists reported. The antagonistic effect of all the synthesized compounds was further evaluated by a one-point in vitro assay that measures DC adhesion. Compounds 14d, 14e, 18d and 18e were shown to act as functional antagonists of DC-SIGN-mediated DC adhesion. The binding mode of 14d was also studied by molecular docking and molecular dynamics simulation, which revealed flexibility of 14d in the binding site and provides a basis for further optimization. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.047