7-(4-hydroxybutoxy)-4-methyl-2H-chromen-2-one | 1469911-65-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(4-hydroxybutoxy)-4-methyl-2H-chromen-2-one
• 英文别名: 7-(3-hydroxybutyl)-4-methyl-2H-chromen-2-one
• CAS: 1469911-65-6
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: IVTMEYJCTSXDIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-(4-hydroxybutoxy)-4-methyl-2H-chromen-2-one 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.08h， 生成 7-[4-[2-Methoxy-5-(trifluoromethyl)pyridin-1-ium-1-yl]butoxy]-4-methylchromen-2-one;trifluoromethanesulfonate
  参考文献：
  名称：

  Reversible inhibition of human acetylcholinesterase by methoxypyridinium species

  摘要：

  The irreversible inhibition of acetylcholinesterase (AChE) by organophosphorous chemical warfare agents necessitates that antidotes be administered for effective treatment. Currently no antidote is known that resurrects the phosphyl-AChE complex once aging has occurred. This report characterizes the affinities of over 30 new AChE inhibitors which could act as resurrecting agents for the aged AChE-OP adduct. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.09.008
• 作为产物：
  描述：

  羟甲香豆素 、 4-氯丁醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到7-(4-hydroxybutoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Hybrids of Phenylsulfonylfuroxan and Coumarin as Potent Antitumor Agents

  摘要：

  Sixteen furoxan-based nitric oxide (NO) releasing coumarin derivatives (6ac, 8ag, 10a, 13a,b, 15, and 17a,b) were designed, synthesized, and evaluated against the A549, HeLa, A2780, A2780/CDDP, and HUVEC cell lines. Most derivatives displayed potent antiproliferation activities. Among them, 8b exhibited the strongest antiproliferation activity on the four sensitive cell lines mentioned above and three drug resistant tumor cell lines A2780/CDDP, MDA-MB-231/Gem, and SKOV3/CDDP with IC50 values from 14 to 53 nM and from 62 to 140 nM, respectively. Furthermore, 8b inhibited the growth of A2780 in vivo and displayed lower toxicity on nontumorigenesis T29, showing good selectivity against malignant cells in vitro. Preliminary pharmacological studies showed that 8b induces apoptosis, arrests the cell cycle at the G2/M phase in the A2780 cell line, and disrupts the phosphorylation of MEK1 and ERK1. Overall, the NO-releasing capacity and the inhibition of ERK/MAPK pathway signaling may explain the potent antineoplastic activity of these compounds.

  DOI：

  10.1021/jm500613m