methyl 2,3,4-tri-O-benzyl-6-deoxy-6-isocyano-α-D-mannopyranoside | 857466-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-isocyano-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-(isocyanomethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 857466-10-5
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: TYRPZURYEJDHGY-PNHLWVRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-isocyano-α-D-mannopyranoside 在 Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 18.0 ℃ 、344.75 kPa 条件下， 反应 26.0h， 生成
  参考文献：
  名称：

  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

  摘要：

  A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of D-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.001
• 作为产物：
  描述：

  methyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside 在 乙酸酐 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-isocyano-α-D-mannopyranoside
  参考文献：
  名称：

  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

  摘要：

  A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of D-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.001

文献信息

• [EN] GLYCOSAMINOGLYCAN (GAG) MIMETICS<br/>[FR] COMPOSES MIMETIQUES DU GLYCOSAMINOGLYCANE (GAG)
  申请人：PROGEN IND LTD

  公开号：WO2005061523A1

  公开（公告）日：2005-07-07

  The invention relates to compounds that are designed to mimic the structure of GAGs; methods for the preparation of the compounds; compositions comprising the compounds; and use of the compounds and compositions thereof for the anti-angiogenic, anti-metastatic, anti-inflammatory, anticoagulant, antithrombotic, and/or antimicrobial treatment of a mammalian subject.

  本发明涉及旨在模仿GAGs结构的化合物；制备这些化合物的方法；包含这些化合物的组合物；以及将这些化合物及其组合物用于哺乳动物主体的抗血管生成、抗转移、抗炎、抗凝血、抗血栓和/或抗微生物治疗的用途。
• GLYCOSAMINOGLYCAN (GAG) MIMETICS
  申请人：Progen Industries Limited

  公开号：EP1699806A1

  公开（公告）日：2006-09-13