6,7-二氯喹唑啉-5,8-二酮 | 102072-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6,7-二氯喹唑啉-5,8-二酮
• 英文名称: 6,7-dichloroquinazoline-5,8-dione
• 英文别名: DA 3045；6,7-Dichloro-5,8-quinazolinedione
• CAS: 102072-83-3
• 化学式: C₈H₂Cl₂N₂O₂
• 分子量: 229.022
• InChiKey: RLWGCMZFKSBELN-UHFFFAOYSA-N

物化性质

• 沸点：
  345.2±42.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-二氯喹唑啉-5,8-二酮 在 ammonium hydroxide 、 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 5.17h， 生成 Ethyl 2-amino-5-hydroxy-4-(4-methoxyphenyl)sulfanyl-furo[2,3-f]quinazoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and antifungal activity of 6,7-bis(arylthio)-quinazoline-5,8-diones and furo[2,3-f]quinazolin-5-ols

  摘要：

  6,7-Bis(arylthio)-quinazoline-5,8-dione and furo[2,3-f]quinazolin-5-ol derivatives were synthesized and tested for in vitro antifungal activity against Candida, Aspergillus species, and Cryptococcus neoformans. Among them tested, many of furo[2,3-f]quinazolin-5-ols and 6,7-bis(arylthio)-quinazoline-5,8-diones showed good antifungal activity. The compounds 4a and 4e completely inhibited the growth of all against Candida and Aspergillus species tested at the MIC level of 12.5 mu g/mL. The results suggest that furo[2,3-f]quinazolin-5-ols and 6,7-bis(arylthio)-quinazoline-5,8-diones would be promising antifungal agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.099
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 盐酸 、 硝酸 、 silica gel 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 3.92h， 生成 6,7-二氯喹唑啉-5,8-二酮
  参考文献：
  名称：

  Synthesis and antiproliferative activity of new cytotoxic tri- and tetraazabenzo[3,2-a]fluorene-5,6-dione derivatives

  摘要：

  A new series of substituted tri-/tetraazabenzo[3,2-alpha] fluorene-5,6-diones and their corresponding oxime derivatives have been synthesized and spectroscopically characterized. The antiproliferative activities of all compounds were evaluated on at least three different cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.021

文献信息

• Synthesis and Cytotoxic Activity of 6-(Substituted-Phenyl)Amino-5,8-Quinazolinediones
  作者：Chung-Kyu Ryu、You-Jin Yi、Ik Hwa Choi、Mi Jin Chae、Ja-Young Han、Ok-Jai Jung、Chong-Ock Lee

  DOI：10.1007/s00044-004-0032-8

  日期：2004.6

  6-Arylamino-5,8-quinazolinediones were synthesized and evaluated for in vitro cytotoxic activity against human solid tumor cell lines A549, SK-OV-3, SK-MEL-2, XF498 and HCT-15. Most of the 6-arylamino-5,8-quinazolinediones exhibited potent activity against the cell lines HCT-15 and SK-MEL-2.
• Streptonigrin. 1. Structure-activity relationships among simple bicyclic analogs. Rate dependence of DNA degradation on quinone reduction potential
  作者：Iftikhar A. Shaikh、Francis Johnson、Arthur P. Grollman

  DOI：10.1021/jm00158a002

  日期：1986.8

  A series of simple aza and diaza bicyclic quinones related to the AB ring system of streptonigrin (1) have been synthesized and tested in vitro for their ability to degrade DNA under conditions similar to those used with the parent drug. The results obtained from a study of 22 quinones indicate that there is a quantitative linear relationship between their reduction potentials and the rate at which they degrade DNA under identical conditions in vitro. Almost all of the synthetic substances were superior to 1 in their DNA-degrading ability.
• 6-Arylamino-7-chloro-quinazoline-5,8-diones as novel cytotoxic and DNA topoisomerase inhibitory agents
  作者：Hyen Joo Park、Young-Shin Kim、Jin Sung Kim、Eun-Jin Lee、You-Jin Yi、Hye Jin Hwang、Myung-Eun Suh、Chung-Kyu Ryu、Sang Kook Lee

  DOI：10.1016/j.bmcl.2004.04.094

  日期：2004.7

  A series of 6-arylamino-7-chloro-quinazoline-5,8-diones were prepared and evaluated for their in vitro cytotoxicity in cultured human cancer cell lines A549 (lung cancer), Col2 (colon cancer), and SNU-638 (stomach cancer). The preliminary structure-activity relationship has been described for providing further development of potent antitumor agents. To further investigate the cytotoxic mechanism, the effects of test compounds on DNA topoisomerase I and II activities have been assessed. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and antiproliferative activity of new cytotoxic tri- and tetraazabenzo[3,2-a]fluorene-5,6-dione derivatives
  作者：Theerachart Leepasert、Manochehr Shahabi、Karem Shanab、Eva Schirmer、Wolfgang Holzer、Helmut Spreitzer、Babette Aicher、Gilbert Müller、Eckhard Günther

  DOI：10.1016/j.bmcl.2013.08.021

  日期：2013.10

  A new series of substituted tri-/tetraazabenzo[3,2-alpha] fluorene-5,6-diones and their corresponding oxime derivatives have been synthesized and spectroscopically characterized. The antiproliferative activities of all compounds were evaluated on at least three different cell lines. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activity of 6,7-bis(arylthio)-quinazoline-5,8-diones and furo[2,3-f]quinazolin-5-ols
  作者：Chung-Kyu Ryu、Yang Hui Kim、Hyun Ah Im、Ji Young Kim、Joo Hee Yoon、Aram Kim

  DOI：10.1016/j.bmcl.2011.10.099

  日期：2012.1

  6,7-Bis(arylthio)-quinazoline-5,8-dione and furo[2,3-f]quinazolin-5-ol derivatives were synthesized and tested for in vitro antifungal activity against Candida, Aspergillus species, and Cryptococcus neoformans. Among them tested, many of furo[2,3-f]quinazolin-5-ols and 6,7-bis(arylthio)-quinazoline-5,8-diones showed good antifungal activity. The compounds 4a and 4e completely inhibited the growth of all against Candida and Aspergillus species tested at the MIC level of 12.5 mu g/mL. The results suggest that furo[2,3-f]quinazolin-5-ols and 6,7-bis(arylthio)-quinazoline-5,8-diones would be promising antifungal agents. (C) 2011 Elsevier Ltd. All rights reserved.