3-C-(3S)-6-{[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-2-{[4-O-isobutyroyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl]oxy}-8,9-dihydroxy-(1-oxo-1,2,3,4-tetra-hydroanthracen-2-yl)-2-O-methyl-acetic acid | 1355700-80-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-(3S)-6-{[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-2-{[4-O-isobutyroyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl]oxy}-8,9-dihydroxy-(1-oxo-1,2,3,4-tetra-hydroanthracen-2-yl)-2-O-methyl-acetic acid
• 英文别名: olivomycin SA
• CAS: 1355700-80-9
• 化学式: C₅₅H₇₈O₂₅
• 分子量: 1139.21
• InChiKey: KJANJNVYTTVHFT-IJKQITFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  80.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  339.11
• 氢给体数：
  7.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  3-C-(3S)-6-{[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-2-{[4-O-isobutyroyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl]oxy}-8,9-dihydroxy-(1-oxo-1,2,3,4-tetra-hydroanthracen-2-yl)-2-O-methyl-acetic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氯化铵 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Modification of olivomycin A at the side chain of the aglycon yields the derivative with perspective antitumor characteristics

  摘要：

  A novel way of chemical modification of the antibiotic olivomycin A (1) at the side chain of the aglycon moiety was developed. Interaction of olivomycin A with the sodium periodate produced the key acid derivative olivomycin SA (2) in 86% yield. This acid was used in the reactions with different amines in the presence of benzotriazol-1-yl-oxy-trispyrrolidino-phosphonium hexafluorophosphate (PyBOP) or diphenylphosphoryl azide (DPPA) to give corresponding amides. Whereas olivomycin SA was two orders of magnitude less cytotoxic than the parent antibiotic, the amides of 2 demonstrated a higher cytotoxicity. In particular, N,N-dimethylaminoethylamide of olivomycin SA showed a pronounced antitumor effect against transplanted experimental lymphoma and melanoma and a remarkably high binding constant to double stranded DNA. The therapeutic effects of this derivative were achievable at tolerable concentrations, suggesting that modifications of the aglycon's side chain, namely, its shortening to methoxyacetic residue and blocking of free carboxyl group, are straightforward for the design of therapeutically applicable derivatives of olivomycin A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.055
• 作为产物：
  描述：

  橄榄霉素 在 sodium periodate 、 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到3-C-(3S)-6-{[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-2-{[4-O-isobutyroyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl-(1->3)-β-D-arabino-hexopyranosyl]oxy}-8,9-dihydroxy-(1-oxo-1,2,3,4-tetra-hydroanthracen-2-yl)-2-O-methyl-acetic acid
  参考文献：
  名称：

  Modification of olivomycin A at the side chain of the aglycon yields the derivative with perspective antitumor characteristics

  摘要：

  A novel way of chemical modification of the antibiotic olivomycin A (1) at the side chain of the aglycon moiety was developed. Interaction of olivomycin A with the sodium periodate produced the key acid derivative olivomycin SA (2) in 86% yield. This acid was used in the reactions with different amines in the presence of benzotriazol-1-yl-oxy-trispyrrolidino-phosphonium hexafluorophosphate (PyBOP) or diphenylphosphoryl azide (DPPA) to give corresponding amides. Whereas olivomycin SA was two orders of magnitude less cytotoxic than the parent antibiotic, the amides of 2 demonstrated a higher cytotoxicity. In particular, N,N-dimethylaminoethylamide of olivomycin SA showed a pronounced antitumor effect against transplanted experimental lymphoma and melanoma and a remarkably high binding constant to double stranded DNA. The therapeutic effects of this derivative were achievable at tolerable concentrations, suggesting that modifications of the aglycon's side chain, namely, its shortening to methoxyacetic residue and blocking of free carboxyl group, are straightforward for the design of therapeutically applicable derivatives of olivomycin A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.055