2-(3-methoxyphenylamino)-3-chloro-1,4-naphthoquinone | 64505-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-methoxyphenylamino)-3-chloro-1,4-naphthoquinone
• 英文别名: 3-chloro-2-(3-methoxyphenylamino)-1,4-dihydronaphthalene-1,4-dione；2-Chloro-3-(3-methoxyanilino)naphthalene-1,4-dione
• CAS: 64505-79-9
• 化学式: C₁₇H₁₂ClNO₃
• 分子量: 313.74
• InChiKey: ABBVBLZNAGCFNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenylamino)-3-chloro-1,4-naphthoquinone 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以41%的产率得到2-methoxybenzo[b]phenazine-6,11-dione
  参考文献：
  名称：

  Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives

  摘要：

  6,11-Dihydro-pyrido[2,3-b]phenazine-6,11-diones and 6,11 -dihydro-benzo[2,3-b]phenazine-6,11-diones were synthesized from 6,7-dichloro-5,8-quinolinedione and 2,3-dichloro-1,4-naphthoquinone. The study on the cytotoxicity on these products revealed that the pyridophenazinediones, tetracyclic heteroquinone analogues with three nitrogen atoms exhibited a high cytotoxicity on several human tumor cell lines. Compound 9c and 9e showed in vitro antitumor activity comparable or superior to doxorubicin against the human ovarian tumor cells (SK-OV-3) and the human CNS cells (XF 498). The IC50 value for compound 9e,was 0.06 muM against the human CNS cells (XF 498), which was 2.6 times higher than that (0.16 muM) of doxorubicin. In addition, the X-ray crystallographic analysis of two phenazinedione derivatives (9b,c) showed clearly the exact position of the nucleophilic substitution of 6,7-dichloro-5,8-quinolinedione. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00028-2
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 间氨基苯甲醚 在 N,N-二乙基苯胺 作用下， 反应 5.0h， 以85%的产率得到2-(3-methoxyphenylamino)-3-chloro-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of photoactive 1-methyl-1-R-4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts

  摘要：

  Photoactive 4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts were synthesized by alkylation of 3-chloro-2-(piperazin-1-yl)-and 2-arylamino-3-(4-methylpiperazin-1-yl)-1,4-naphthoquinones. Light sensitivities of materials obtained by adsorption of the synthesized piperazinium salts from solution onto oxidized aluminum support were estimated.

  DOI：

  10.1134/s1070428011120086