8-hydrazinocarbonyloctyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 70761-84-1

• 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: 8-hydrazinocarbonyloctyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• CAS: 70761-84-1
• 化学式: C₂₁H₄₀N₂O₁₂
• 分子量: 512.555
• InChiKey: GSLVTLSGCKVGDR-ZJSKFKIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.65
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  233.65
• 氢给体数：
  9.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 sodium methylate 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 8-hydrazinocarbonyloctyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors

  摘要：

  A beta-lactosyl residue was linked to the amino groUpS Of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C-9) to give trivalent beta-lactosyl clusters in order to increase the inhibitory activity of the beta-lactosyl group against tumor cell colonization. Thus, O-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-acetyl-glucopyranosyl trichloroacetimidate was treated with methyl or benzyl hydroxyethanoate, methyl or benzyl 4-hydroxybutanoate, and methyl 9-hydroxynonanoate, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate to give the corresponding beta-lactosides. These were coupled to L-lysyl-L-lysine, after conversion to the N-hydroxysuccinimide esters, to yield the corresponding trivalent beta-lactosyl-L-lysyl-L-lysine conjugates in good yields. The beta-lactosyl group with a C4 spacer arm was also coupled similarly to poly(L-lysine) (M(r) 3800) to form a polyvalent beta-lactosyl cluster. Coinjection of the trivalent (with C2 and C4 spacer arms) and polyvalent beta-lactosyl clusters with the highly metastatic B16 murine melanoma cells inhibited the formation of lung colonies in C57/BL mice, whereas the trivalent cluster with a C-9 spacer arm displayed no activity.

  DOI：

  10.1016/0008-6215(93)80071-l