3-stearamidopropyl α-D-glucopyranosyl-(1-4)-α-D-glucopyranosyl-(1-4)-β-D-glucopyranoside | 1144493-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-stearamidopropyl α-D-glucopyranosyl-(1-4)-α-D-glucopyranosyl-(1-4)-β-D-glucopyranoside
• CAS: 1144493-14-0
• 化学式: C₃₉H₇₃NO₁₇
• 分子量: 828.005
• InChiKey: GFNNPDUWMGRNDT-WUHYWKRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  57.0
• 可旋转键数：
  28.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  286.78
• 氢给体数：
  11.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  3-stearamidopropyl α-D-glucopyranosyl-(1-4)-α-D-glucopyranosyl-(1-4)-β-D-glucopyranoside 在 三氧化硫吡啶 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 1.0h， 以40%的产率得到3-stearamidopropyl 2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-sulfo-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside decasodium salt
  参考文献：
  名称：

  [EN] NOVEL SULFATED OLIGOSACCHARIDE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS D'OLIGOSACCHARIDES SULFATÉS

  摘要：

  这项发明涉及具有作为肝素硫酸结合蛋白抑制剂的效用的新化合物；包含这些化合物的组合物；以及利用这些化合物和组合物对哺乳动物主体进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗的用途。

  公开号：

  WO2009049370A1
• 作为产物：
  描述：

  3-stearamidopropyl (2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 、 acidic resin 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以91%的产率得到3-stearamidopropyl α-D-glucopyranosyl-(1-4)-α-D-glucopyranosyl-(1-4)-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] NOVEL SULFATED OLIGOSACCHARIDE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS D'OLIGOSACCHARIDES SULFATÉS

  摘要：

  这项发明涉及具有作为肝素硫酸结合蛋白抑制剂的效用的新化合物；包含这些化合物的组合物；以及利用这些化合物和组合物对哺乳动物主体进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗的用途。

  公开号：

  WO2009049370A1

文献信息

• Discovery of PG545: A Highly Potent and Simultaneous Inhibitor of Angiogenesis, Tumor Growth, and Metastasis
  作者：Vito Ferro、Ligong Liu、Ken D. Johnstone、Norbert Wimmer、Tomislav Karoli、Paul Handley、Jessica Rowley、Keith Dredge、Cai Ping Li、Edward Hammond、Kat Davis、Laura Sarimaa、Job Harenberg、Ian Bytheway

  DOI：10.1021/jm201708h

  日期：2012.4.26

  Increasing the aglycone lipophilicity of a series of polysulfated oligosaccharide glycoside heparan sulfate (HS) mimetics via attachment of a steroid or long chain alkyl group resulted in compounds with significantly improved in vitro and ex vivo antiangiogenic activity. The compounds potently inhibited heparanase and HS-binding angiogenic growth factors and displayed improved antitumor and antimetastatic activity in vivo compared with the earlier series. Preliminary pharmacokinetic analyses also revealed significant increases in half-life following iv dosing, ultimately supporting less frequent dosing regimens in preclinical tumor models compared with other HS mimetics. The compounds also displayed only mild anticoagulant activity, a common side effect usually associated with HS mimetics. These efforts led to the identification of 3 beta-cholestanyl 2,3,4,6-tetra-O-sulfo-alpha-D-glucopyranosyl- (1 -> 4)-2,3,6-tri-O-sulfo-alpha-D-glucopyranosyl-(1 -> 4)-2,3,6-tri-O-sulfo-alpha-D-glucopyranosyl-(1 -> 4)-2,3,6-tri-O-sulfo-beta-D-glucopyranoside, tridecasodium salt (PG545, 18) as a clinical candidate. Compound 18 was recently evaluated in a phase I clinical trial in cancer patients.