olivamide | 1353052-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: olivamide
• CAS: 1353052-12-6
• 化学式: C₅₉H₈₈N₂O₂₄
• 分子量: 1209.35
• InChiKey: TVPGNAWUEDMIMH-TXAUWYQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  85.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  334.15
• 氢给体数：
  7.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  olivamide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 olivamide hydrochloride
  参考文献：
  名称：

  Development of a Dosage Form of the New Antitumor Antibiotic Olivamide

  摘要：

  GINA开发了抗肿瘤抗生素奥利维霉素A（OA）的选择性化学修饰方法。从一系列OA类似物中选出了具有优势的化合物奥利维酰胺。目前工作的目标是开发一种抗肿瘤半合成抗生素奥利维酰胺的剂型，确保奥利维酰胺药物的稳定性和高特异性活性，并用于进一步的临床前综合研究。

  DOI：

  10.1007/s11094-019-01928-x
• 作为产物：
  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 、 N1,N1-dimethylethane-1,2-diamine hydrochloride 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 以82%的产率得到olivamide
  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