2-(3-hydroxypropyl)-6-(methylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 258271-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(3-hydroxypropyl)-6-(methylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 4-methylaminonaphthalic acid N-(3-hydroxypropyl)imide；N-(3-propanol)-4-methylamino-1,8-naphthalimide；2-(3-Hydroxypropyl)-6-(methylamino)benzo[de]isoquinoline-1,3-dione
• CAS: 258271-08-8
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: NCJTXVPZGIDKLD-UHFFFAOYSA-N

物化性质

• 沸点：
  534.0±40.0 °C(predicted)
• 密度：
  1.368±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxypropyl)-6-(methylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 四丁基溴化铵 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以73%的产率得到2-(3-bromopropyl)-6-(methylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Antiproliferative and apoptosis-inducing activities of novel naphthalimide–cyclam conjugates through dual topoisomerase (topo) I/II inhibition

  摘要：

  A novel series of naphthalimide-cyclam conjugates were designed and synthesized. Among them, compounds 4c, 4d, 8c and 8d which bearing long lipophilic alkyl chains, displayed comparable or more potent cytotoxic activities against human tumor cell lines than amonafide. Furthermore, the four compounds were proved to possess strong inhibition against both topoisomerase I and II. The representative compound 8c exhibited moderate DNA intercalation activity. Molecular modeling studies identified the possible interaction of compound 8c with the molecular target by forming topoisomerase/DNA/drug ternary complex. Finally, derivatives with long lipophilic alkyl chains could efficiently induce apoptosis. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2015.07.011
• 作为产物：
  描述：

  4-氯-1,8-萘二甲酸酐 以 乙二醇乙醚 为溶剂， 反应 9.0h， 生成 2-(3-hydroxypropyl)-6-(methylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  4-取代萘酸含羟基N-酰亚胺的合成

  摘要：

  DOI：

  10.1007/bf02324650

文献信息

• Synthesis of ODNs Containing 4-Methylamino-1,8-naphthalimide as a fluorescence probe in DNA
  作者：Kiyohiko Kawai、Kazuhiro Kawabata、Sachiko Tojo、Tetsuro Majima

  DOI：10.1016/s0960-894x(02)00404-3

  日期：2002.9

  Synthesis and fluorescence properties of oligodeoxynucleotides containing 4-methylamino-1,8-naphthalimide (NI) have been described. NI was successfully incorporated into DNA without significant destabilization of DNA whilst retaining its high fluorescence quantum yield. The attachment site of the NI greatly affected its property as an energy acceptor in FRET analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.