(7S,8R)-7-benzoylamino-8-hydroxylcheliensisin A | 1334592-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (7S,8R)-7-benzoylamino-8-hydroxylcheliensisin A
• 英文别名: [(2S,3S)-2-[(1R,2R)-1-benzamido-2-hydroxy-2-phenylethyl]-6-oxo-2,3-dihydropyran-3-yl] acetate
• CAS: 1334592-37-8
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: FBDBKXCAYMPEJZ-OYNPSCLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4R,5R)-2-phenyl-4-[(5'S,6'S)-5'-acetoxyl-5',6'-dihydro-2'H-pyran-2'-one-6'-yl]-5-phenyl-(5H,6H)-oxazoline 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 以46%的产率得到(7S,8R)-7-benzoylamino-8-hydroxylcheliensisin A
  参考文献：
  名称：

  Development of novel conformation-constrained cytotoxic derivatives of cheliensisin A by embedment of small heterocycles

  摘要：

  Cheliensisin A is a natural styryl-lactone isolated from Goniothalamus cheliensis Hu in considerably large quantity with putative anticancer activities. However, its poor water solubility and chemical instability have precluded cheliensisin A as a potential drug candidate. To explore the strategy to overcome these problems, 21 novel derivatives of cheliensisin A with different substitutions at C-7 and C-8 positions were designed and synthesized. Inhibition of proliferation against five tumors cell lines indicates that eight new derivatives with embedment of oxazole or oxazoline exhibit improved cytotoxicity on SK-BR-3 and PANC-1, and compounds 2d and 2g show 5-8 folds higher potency than cisplatin. HPLC investigation of representative compounds indicates that oxazole and oxazoline analogs exhibit much improved chemical stability than their natural parent. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.028