3-(4-Nitro-phenyl)-3,4-dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracene | 909910-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(4-Nitro-phenyl)-3,4-dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracene
• 英文别名: 3-(4-nitrophenyl)-3,4-dihydro-1H-[1,3]oxazino[4,5-c]acridine
• CAS: 909910-67-4
• 化学式: C₂₁H₁₅N₃O₃
• 分子量: 357.368
• InChiKey: PJTRLRACXVEWHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Nitro-phenyl)-3,4-dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracene 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 以100%的产率得到4-hydroxymethyl-3-aminoacridine
  参考文献：
  名称：

  3,4-Dihydro-1H-[1,3]oxazino[4,5-c]acridines as a new family of cytotoxic drugs

  摘要：

  A series of [1,3]oxazino fused acridines has been prepared as precursors of cytotoxic 3-amino-4-bydroxymethylacridine 2. Their cytotoxic activity has been evaluated against HT29 colon carcinoma cell line and was shown to be dependent on the nature of the substituent located on position 2 of the oxazine ring. Additionally, the nitrophenyl derivative 3f is activated by nitroreductase, indicating its potency as prodrug for either gene-directed or antibody-directed enzyme prodrug therapies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.101
• 作为产物：
  描述：

  对硝基苯甲醛 、 4-hydroxymethyl-3-aminoacridine 在 盐酸 作用下， 以58%的产率得到3-(4-Nitro-phenyl)-3,4-dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracene
  参考文献：
  名称：

  3,4-Dihydro-1H-[1,3]oxazino[4,5-c]acridines as a new family of cytotoxic drugs

  摘要：

  A series of [1,3]oxazino fused acridines has been prepared as precursors of cytotoxic 3-amino-4-bydroxymethylacridine 2. Their cytotoxic activity has been evaluated against HT29 colon carcinoma cell line and was shown to be dependent on the nature of the substituent located on position 2 of the oxazine ring. Additionally, the nitrophenyl derivative 3f is activated by nitroreductase, indicating its potency as prodrug for either gene-directed or antibody-directed enzyme prodrug therapies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.101

文献信息

• 3,4-Dihydro-1H-[1,3]oxazino[4,5-c]acridines as a new family of cytotoxic drugs
  作者：Myriam Ouberai、Christian Asche、Danièle Carrez、Alain Croisy、Pascal Dumy、Martine Demeunynck

  DOI：10.1016/j.bmcl.2006.05.101

  日期：2006.9

  A series of [1,3]oxazino fused acridines has been prepared as precursors of cytotoxic 3-amino-4-bydroxymethylacridine 2. Their cytotoxic activity has been evaluated against HT29 colon carcinoma cell line and was shown to be dependent on the nature of the substituent located on position 2 of the oxazine ring. Additionally, the nitrophenyl derivative 3f is activated by nitroreductase, indicating its potency as prodrug for either gene-directed or antibody-directed enzyme prodrug therapies. (c) 2006 Elsevier Ltd. All rights reserved.