3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol | 1446098-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol
• CAS: 1446098-78-7
• 化学式: C₃₃H₃₉N₃O₇
• 分子量: 589.689
• InChiKey: XNFYGLLTOFAEAN-BUOONKCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  113.37
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 palladium(II) hydroxide 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0~65.0 ℃ 、2.0 MPa 条件下， 反应 97.0h， 生成 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-β-D-galactopyranosyl)-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
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(methylsulfonyl)-α-D-galactopyranoside 在 sodium azide 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-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

• Synthesis of 6′-acylamido-6′-deoxy-α-d-galactoglycerolipids
  作者：Chunxia Li、Yihua Sun、Jun Zhang、Zhimin Zhao、Guangli Yu、Huashi Guan

  DOI：10.1016/j.carres.2013.02.008

  日期：2013.7

  Aminoglycoglycerolipid 1a isolated from an algal extract showed activity against the enzyme Myt1 kinase with an IC50 value of 0.12 mu g/mL. Its analogues, 6'-acylamido-6'-deoxy-alpha-D-galactoglycerolipids (2a-g) were synthesized in an efficient way with high stereoselectivity. The key step was to employ a 4-OAc protecting group of the galactosyl donor 14 as a remote neighboring participation group to give the glycoside with high alpha-anomeric selectivity (alpha:beta = 32:1) in the glycosylation. The preliminary bioactivity screening showed that compound 2g exhibited good inhibition against Myt1 kinase. (C) 2013 Elsevier Ltd. All rights reserved.