2-acetyl-7,8,10-trimethoxy-9-methyl-6-phthalimidomethyl-2,3-dihydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione | 863290-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-acetyl-7,8,10-trimethoxy-9-methyl-6-phthalimidomethyl-2,3-dihydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione
• 英文别名: 2-acetyl-6-[(1,3-dioxoisoindol-2-yl)methyl]-7,8,10-trimethoxy-9-methyl-3,6-dihydropyrazino[1,2-b]isoquinoline-1,4-dione
• CAS: 863290-02-2
• 化学式: C₂₇H₂₅N₃O₈
• 分子量: 519.511
• InChiKey: AULAJPAJSHPENQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  122.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-7,8,10-trimethoxy-9-methyl-6-phthalimidomethyl-2,3-dihydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione 在 硫酸 、 三氟乙酸 作用下， 反应 16.0h， 以93%的产率得到7,8,10-trimethoxy-9-methyl-6-phthalimidomethyl-2,3-dihydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione
  参考文献：
  名称：

  Pyrazino[1,2-b]isoquinolines: Synthesis and study of their cytostatic and cytotoxic properties

  摘要：

  The in vitro antitumor potential of novel pyrazino[1,2-b]-isoquinoline-4-ones that contain a half portion of significant natural products was explored in three cancer cell lines: MDA-MB 231 human breast carcinoma, A-549 human lung carcinoma, and HT-29 human colon carcinoma. In general, these compounds show mid to low mu M GI(50)s, but LC(50)s over 100 mu M with the exceptions of compounds 3b and 31 that are moderately toxic in all cell lines, while compound 4a is highly toxic and selective for HT-29 cells with LC50 values in the high nanomolar range. Experiments directed to elucidate possible mechanisms of action with compounds 3a, 29, and 31 showed that compound 3a is able to efficiently induce apoptosis triggered directly from the G2/M phase of cell cycle, while compounds 29 and 31 are potentially cytostatic agents that induce the G1/S arrest of cell cycle. All three compounds do not act through DNA damage, since they do not activate this signaling at the level of sensors, transducers, and executers. Furthermore, the apoptosis induction of 3a is not mediated by activation of pro-apoptotic kinases JNK and p38 or by activation of AKT. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.083
• 作为产物：
  描述：

  N-(2,2-二甲氧基乙基)邻苯二甲酰亚胺 在 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 偶氮二异丁腈 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2-acetyl-7,8,10-trimethoxy-9-methyl-6-phthalimidomethyl-2,3-dihydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione
  参考文献：
  名称：

  邻苯二酚类似物的合成

  摘要：

  我们报告了一种获得邻苯二酚类似物的新方法。6- Phthalimidomethylpyrazino [1,2 b ]异喹啉-1,4-二酮（5A）在一锅得到Ñ烷基化相应的1-乙酰基-3-芳甲基-2,5-哌嗪二酮与/环化Ñ -邻苯二甲酰乙醛二甲基乙缩醛。对3-芳基甲基-11,11a-脱氢衍生物9a中的C（1）-羰基进行化学选择性还原，然后将酰基中间体中间体环化，得到6,15-亚氨基-7-氧代-14,14a-脱氢异喹啉[3，2 - b ] 3-苯扎佐星11a。或者，八环化合物13a 通过对C（1）-羰基和一个邻苯二甲酰亚胺羰基进行了还原的前体进行新型双环化反应，得到了α-烯烃。

  DOI：

  10.1016/j.tet.2005.05.068