1,2-dipalmitoyl-3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol | 1192755-05-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-dipalmitoyl-3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol
• 英文别名: [(2S)-3-[(2S,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
• CAS: 1192755-05-7
• 化学式: C₆₂H₉₅N₃O₉
• 分子量: 1026.45
• InChiKey: WJBGNRWGHKONIF-HLVREVBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.6
• 重原子数：
  74
• 可旋转键数：
  47
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2-dipalmitoyl-3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以95%的产率得到1,2-dipalmitoyl-3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol
  参考文献：
  名称：

  6'-氨基-6'-脱氧葡萄糖甘油脂类似物的合成和抗甲型流感病毒活性。

  摘要：

  已经合成了一系列氨基葡萄糖甘油脂衍生物，包括6'-酰基酰胺基-葡萄糖甘油脂1a-1f和相应的带有不同脂肪酸的2'-酰基酰胺基-葡萄糖甘油脂2a-2c，在C-6'处带有不同官能团的葡糖基甘油二酸酯3a-3e和带有双尾烷基醇的醚连接的葡萄糖甘油脂4a-4c。通过细胞病变效应（CPE）抑制试验评估了抗甲型流感病毒（IAV）的活性。结果表明，氨基糖甘油脂的完整结构对于抑制MDCK细胞中的IAV是必不可少的。此外，口服化合物1d能够显着提高IAV感染小鼠的存活率并降低其肺病毒滴度，

  DOI：

  10.3390/md14060116
• 作为产物：
  描述：

  甲基-6-O-三苯基甲基-alpha-D-吡喃葡萄糖苷 在 sodium azide 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 1,2-dipalmitoyl-3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol
  参考文献：
  名称：

  Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay

  摘要：

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.007

文献信息

• First total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol—a glycoglycerolipid of a marine alga with a high inhibitor activity against human Myt1-kinase
  作者：Christiane Göllner、Claudia Philipp、Bodo Dobner、Wolfgang Sippl、Matthias Schmidt

  DOI：10.1016/j.carres.2009.05.022

  日期：2009.9

  The first total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-alpha-D-glucosyl)-sn-glycerol, a glycoglycerolipid isolated from a marine alga extract, is described. Starting from alpha-methylglucopyranoside the multistep strategy allows the stereoselective synthesis of the final compound using various protective group procedures as well as derivatization of partial molecule domains. The latter offers the development of lead structures for inhibitors of human Myt1-kinase. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and Anti-Influenza A Virus Activity of 6′-amino-6′-deoxy-glucoglycerolipids Analogs
  作者：Li Ren、Jun Zhang、Haizhen Ma、Linlin Sun、Xiaoshuang Zhang、Guangli Yu、Huashi Guan、Wei Wang、Chunxia Li

  DOI：10.3390/md14060116

  日期：——

  A series of aminoglucoglycerolipids derivatives had been synthesized, including 6'-acylamido-glucoglycerolipids 1a-1f and corresponding 2'-acylamido-glucoglycerolipids 2a-2c bearing different fatty acids, glucosyl diglycerides 3a-3e bearing different functional groups at C-6' and ether-linked glucoglycerolipids 4a-4c with double-tailed alkyl alcohol. The anti-influenza A virus (IAV) activity was evaluated

  已经合成了一系列氨基葡萄糖甘油脂衍生物，包括6'-酰基酰胺基-葡萄糖甘油脂1a-1f和相应的带有不同脂肪酸的2'-酰基酰胺基-葡萄糖甘油脂2a-2c，在C-6'处带有不同官能团的葡糖基甘油二酸酯3a-3e和带有双尾烷基醇的醚连接的葡萄糖甘油脂4a-4c。通过细胞病变效应（CPE）抑制试验评估了抗甲型流感病毒（IAV）的活性。结果表明，氨基糖甘油脂的完整结构对于抑制MDCK细胞中的IAV是必不可少的。此外，口服化合物1d能够显着提高IAV感染小鼠的存活率并降低其肺病毒滴度，
• Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay
  作者：Alexander Rohe、Christiane Göllner、Kanin Wichapong、Frank Erdmann、Ghassab M.A. Al-Mazaideh、Wolfgang Sippl、Matthias Schmidt

  DOI：10.1016/j.ejmech.2012.06.007

  日期：2013.3

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.