3β-O-(β-D-galactopyranosyl)olean-12-en-28-oic acid benzyl ester | 1229037-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-O-(β-D-galactopyranosyl)olean-12-en-28-oic acid benzyl ester
• CAS: 1229037-92-6
• 化学式: C₄₃H₆₄O₈
• 分子量: 708.976
• InChiKey: IKAHBYNVZAQFRV-HDZPLUCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  51.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  125.68
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3β-O-(β-D-galactopyranosyl)olean-12-en-28-oic acid benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到3-O-β-D-galactopyranosyloleanolic acid
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives

  摘要：

  Glucosidations of oleanolic acid (1) and its dihydroxy-olide derivatives (2) were carried out to provide eight glycosides. All synthesized compounds were evaluated by in vitro -glucosidase inhibitory activity assay. 3-Acetyl dihydroxy-olide oleanolic derivative 15 showed the most potent inhibitory effect. Structure-activity relationships within these compounds are discussed.

  DOI：

  10.1080/10286020903405456
• 作为产物：
  描述：

  benzyl oleanolate 3-O-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 以98%的产率得到3β-O-(β-D-galactopyranosyl)olean-12-en-28-oic acid benzyl ester
  参考文献：
  名称：

  Structure-activity relationships of 3-O-β-chacotriosyl oleanic acid derivatives as entry inhibitors for highly pathogenic H5N1 influenza virus

  摘要：

  Highly pathogenic H5N1 virus (H5N1) entry is a key target for the development of novel anti-influenza agents with new mechanisms of action. In our continuing efforts to identify novel potential anti-H5N1 entry inhibitors, a series of 3-O-beta-chacotriosyl oleanolic acid analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on two small molecule inhibitors 1 and 2 previously discovered by us. The anti-H5N1 entry activities were determined based on HA/HIV and VSVG/HIV entry assays. Compound 15 displayed the most promising anti-H5N1 entry activities with average IC50 values of 4.05 mu M and good selective index (22.9). Detailed structure-activity relationships (SARs) studies suggested that either the introduction of an additional oxo group to position 11 at OA or alteration of the C-3 configuration of OA from 3 beta- to 3 alpha-forms can significantly enhance the selective index while maintaining their antiviral activities in vitro. Molecular simulation analysis confirmed that the compounds exert their inhibitory activity through binding tightly to hemagglutinin (HA2) protein near the fusion peptide and prevent virus entry. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.025