3-[4-(4-methoxyphenyl)piperazin-1-yl]-N-methylpropan-1-amine | 884738-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-[4-(4-methoxyphenyl)piperazin-1-yl]-N-methylpropan-1-amine
• CAS: 884738-52-7
• 化学式: C₁₅H₂₅N₃O
• 分子量: 263.383
• InChiKey: INPLXEUPBNOTLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(4-methoxyphenyl)piperazin-1-yl]-N-methylpropan-1-amine 、 (1R,3R,5S,6S,18S)-6-hydroxy-18-(methoxymethyl)-1,5-dimethyl-11,16-dioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate 以 二氯甲烷 为溶剂， 反应 0.5h， 以88.9%的产率得到[(1S,6E,9S,9aR,10R,11aS)-1,5-dihydroxy-9-(methoxymethyl)-6-[[3-[4-(4-methoxyphenyl)piperazin-1-yl]propyl-methylamino]methylidene]-9a,11a-dimethyl-4,7-dioxo-2,3,3a,9,10,11-hexahydro-1H-indeno[4,5-h]isochromen-10-yl] acetate
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Ring-Opened 17-Hydroxywortmannins: Potent Phosphoinositide 3-Kinase Inhibitors with Improved Properties and Anticancer Efficacy

  摘要：

  The phosphoinositide 3-kinase (PI3K) signaling pathway is frequently up-regulated in human cancer and is a promising target for the treatment of cancer. Wortmannin and its analogues are potent inhibitors of PI3K but suffer from inherent defects such as instability, insolubility, and toxicity. Opening of the reactive furan ring of 17-hydroxywortmannin with amines gives compounds with improved properties such as greater stability and aqueous solubility and a larger therapeutic index. Ring-opened analogues such as compound 13 containing basic amine groups have significantly increased PI3K inhibitory potency and greater efficacy in nude mouse xenograft assays.

  DOI：

  10.1021/jm7012858