6-chloro-7-phenylamino-5,8-phthalazinedione | 502584-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chloro-7-phenylamino-5,8-phthalazinedione
• 英文别名: 6-Anilino-7-chlorophthalazine-5,8-dione
• CAS: 502584-83-0
• 化学式: C₁₄H₈ClN₃O₂
• 分子量: 285.689
• InChiKey: IDKFTEQJVBIGIA-UHFFFAOYSA-N

物化性质

• 沸点：
  482.9±45.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-7-phenylamino-5,8-phthalazinedione 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以23%的产率得到Pyridazino[4,5-b]phenazine-5,12-dione
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of 6,11-dihydro-pyridazo- and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-diones

  摘要：

  The 6,11-dihydro-pyridazo[2,3-b]phenazine-6,11-dione and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-dione derivatives were synthesized from 6,7-dichloro-5,8-phthalazinedione and 6,7-dichloro-5,8-quinolinedione, respectively, producing a series of new anticancer drugs. The cytotoxic activities of the prepared compounds were evaluated by a SRB (Sulforhodamine B) assay against the following tumor cell lines: A459 (human lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Almost all the derivatives of the 6,11-dihydro-pyridazo[2[,3-b]phenazine-6,11-dione and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-dione, tetracyclic heteroquinone analogues with four or three nitrogen atoms, exhibited excellent cytotoxicity on almost all the human tumor cell lines tested. Specifically, 6,11-dihydro-pyridazo[2,3-b]phenazine-6,11-dione (4a) exhibited potent activity against all the tumor cell lines, and in particular, its cytotoxic effect against HCT 15 (ED50 = 0.004 mug/mL) was 25 times greater than that of doxorubicin (ED50 = 0.093 mug/mL). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.029
• 作为产物：
  描述：

  5-硝基酞嗪 在 palladium on activated charcoal 盐酸 、 sodium chlorate 、 氢氧化钾 、 氢气 、 羟胺 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0~65.0 ℃ 、20.68 kPa 条件下， 反应 11.0h， 生成 6-chloro-7-phenylamino-5,8-phthalazinedione
  参考文献：
  名称：

  Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones

  摘要：

  6-Arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones were synthesized and tested for in vitro antifungal activity against two pathogenic strains of fungi. Among those tested, many compounds showed good antifungal activity. The results suggest that phthalazine-5,8-diones would be potent antifungal agents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.003

文献信息

• Synthesis and cytotoxicity evaluation of 6,11-dihydro-pyridazo- and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-diones
  作者：Hyun-Jung Lee、Jin Sung Kim、Se-Young Park、Myung-Eun Suh、Hwa Jung Kim、Eun-Kyung Seo、Chong-Ock Lee

  DOI：10.1016/j.bmc.2004.01.029

  日期：2004.4

  The 6,11-dihydro-pyridazo[2,3-b]phenazine-6,11-dione and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-dione derivatives were synthesized from 6,7-dichloro-5,8-phthalazinedione and 6,7-dichloro-5,8-quinolinedione, respectively, producing a series of new anticancer drugs. The cytotoxic activities of the prepared compounds were evaluated by a SRB (Sulforhodamine B) assay against the following tumor cell lines: A459 (human lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Almost all the derivatives of the 6,11-dihydro-pyridazo[2[,3-b]phenazine-6,11-dione and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-dione, tetracyclic heteroquinone analogues with four or three nitrogen atoms, exhibited excellent cytotoxicity on almost all the human tumor cell lines tested. Specifically, 6,11-dihydro-pyridazo[2,3-b]phenazine-6,11-dione (4a) exhibited potent activity against all the tumor cell lines, and in particular, its cytotoxic effect against HCT 15 (ED50 = 0.004 mug/mL) was 25 times greater than that of doxorubicin (ED50 = 0.093 mug/mL). (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones
  作者：Chung-Kyu Ryu、Rae-Eun Park、Mi-Young Ma、Ji-Hee Nho

  DOI：10.1016/j.bmcl.2007.02.003

  日期：2007.5

  6-Arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones were synthesized and tested for in vitro antifungal activity against two pathogenic strains of fungi. Among those tested, many compounds showed good antifungal activity. The results suggest that phthalazine-5,8-diones would be potent antifungal agents. (c) 2007 Elsevier Ltd. All rights reserved.