2-<(3'-acetylphenyl)amino>-3-chloro-1,4-naphthoquinone | 90510-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(3'-acetylphenyl)amino>-3-chloro-1,4-naphthoquinone
• 英文别名: 2-(3-acetylphenylamino)-3-chloronaphthalene-1,4-dione；2-(3-acetylphenylamino)-3-chloro-1,4-naphthoquinone；1,4-Naphthalenedione, 2-[(3-acetylphenyl)amino]-3-chloro-；2-(3-acetylanilino)-3-chloronaphthalene-1,4-dione
• CAS: 90510-67-1
• 化学式: C₁₈H₁₂ClNO₃
• 分子量: 325.751
• InChiKey: DARRDNGQIKRSKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 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：
  63.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<(3'-acetylphenyl)amino>-3-chloro-1,4-naphthoquinone 在 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 111.0h， 生成 4-[3-(3-acetylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]-1,1-dimethylpiperazinium iodide
  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
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 间氨基苯乙酮 以 乙醇 为溶剂， 以60%的产率得到2-<(3'-acetylphenyl)amino>-3-chloro-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives

  摘要：

  A series of 2-substituted amino-3-chloro-1,4-naphthoquinone derivatives (3-12) were synthesized as anticancer agents and tested against four cancer cell lines including HepG2, HuCCA-1, A549 and MOLT-3. The most potent cytotoxic activity against the HepG2, HuCCA-1 and A549 cell lines was found to be m-acetylphenylamino-1,4-naphthoquinone (8) affording IC50 values of 4.758, 2.364 and 12.279 μM, respectively. On the other hand, p-acetylphenylamino-1,4-naphthoquinone (9) exhibited the most potent cytotoxic activity against the MOLT-3 cell line with an IC50 of 2.118 μM. Quantitative structure-activity relationship (QSAR) investigations provided good predictive performance as observed from cross-validated R of 0.9177-0.9753 and RMSE of 0.0614-0.1881. The effects of substituents at the 2-amino position on the naphthoquinone core structure and its corresponding influence on the cytotoxic activity were investigated by virtually constructing additional 1,4-naphthoquinone compounds (13-36) for which cytotoxic activities were predicted using equations obtained from the previously constructed QSAR models. Interpretation of informative descriptors from QSAR models revealed pertinent knowledge on physicochemical properties governing the cytotoxic activities of tested cancer cell lines. It is anticipated that the QSAR models developed herein could provide guidelines for further development of novel and potent anticancer agents.

  DOI：

  10.1016/j.ejmech.2014.07.024

文献信息

• Parr, Rodney W.; Reiss, James A., Australian Journal of Chemistry, 1984, vol. 37, # 2, p. 389 - 394
  作者：Parr, Rodney W.、Reiss, James A.

  DOI：——

  日期：——
• PARR, R. W.;REISS, J. A., AUSTRAL. J. CHEM., 1984, 37, N 2, 389-394
  作者：PARR, R. W.、REISS, J. A.

  DOI：——

  日期：——
• Synthesis of photoactive 1-methyl-1-R-4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts
  作者：V. N. Berezhnaya、V. V. Shelkovnikov、S. V. Korotaev

  DOI：10.1134/s1070428011120086

  日期：2011.12

  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.
• Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives
  作者：Veda Prachayasittikul、Ratchanok Pingaew、Apilak Worachartcheewan、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.ejmech.2014.07.024

  日期：2014.9

  A series of 2-substituted amino-3-chloro-1,4-naphthoquinone derivatives (3-12) were synthesized as anticancer agents and tested against four cancer cell lines including HepG2, HuCCA-1, A549 and MOLT-3. The most potent cytotoxic activity against the HepG2, HuCCA-1 and A549 cell lines was found to be m-acetylphenylamino-1,4-naphthoquinone (8) affording IC50 values of 4.758, 2.364 and 12.279 μM, respectively. On the other hand, p-acetylphenylamino-1,4-naphthoquinone (9) exhibited the most potent cytotoxic activity against the MOLT-3 cell line with an IC50 of 2.118 μM. Quantitative structure-activity relationship (QSAR) investigations provided good predictive performance as observed from cross-validated R of 0.9177-0.9753 and RMSE of 0.0614-0.1881. The effects of substituents at the 2-amino position on the naphthoquinone core structure and its corresponding influence on the cytotoxic activity were investigated by virtually constructing additional 1,4-naphthoquinone compounds (13-36) for which cytotoxic activities were predicted using equations obtained from the previously constructed QSAR models. Interpretation of informative descriptors from QSAR models revealed pertinent knowledge on physicochemical properties governing the cytotoxic activities of tested cancer cell lines. It is anticipated that the QSAR models developed herein could provide guidelines for further development of novel and potent anticancer agents.