9-nitro-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one | 891191-81-4

• 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: 9-nitro-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one
• 英文别名: 9-nitro-3,6-dihydro-2H-[1,4]dioxino[2,3-b]acridin-11-one
• CAS: 891191-81-4
• 化学式: C₁₅H₁₀N₂O₅
• 分子量: 298.255
• InChiKey: UQOMZWUHMNWIMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-nitro-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one 在 三氯氧磷 作用下， 反应 3.0h， 以57%的产率得到9-nitro-11-chloro-2,3-dihydro-1,4-dioxino[2,3-b]acridine
  参考文献：
  名称：

  Synthesis and biological evaluation of modified acridines: the effect of N- and O- substituent in the nitrogenated ring on antitumor activity

  摘要：

  A series of new acridines has been prepared by cyclodehydration of N-(2,3-dihydro-1,4-berizodioxin-6-yl)anthranilic acid in acidic media following classical procedures. All these compounds have in common a dioxygenated ring fused to the acridine. The tetracyclic system possesses a linear or angular structure formed by intramolecular cyclisation. The last ring and the substituent of the system modify, in an interesting way, the antitumor activity of acridines. Several of the studied compounds displayed significant cytotoxic activity (inhibition of L 12 10 and HT-29 cell proliferation). The most cytotoxic compound 13a, shows more activity than m-AMSA in inhibiting L1210 and HT-29 cell proliferation and this compound has been selected as a development candidate for further evaluation. The activity results also indicate that the new 11-O-substituted compounds are of considerable interest with high levels of cytotoxic activity. The angular or non-linear dioxinoacridine 10 was equiactive with the linear structure 7. Pentacyclic analogues (14 and 15) were more cytotoxic than the tetracyclic compounds (up to twofold). (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.006
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 铜 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 28.0h， 生成 9-nitro-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one
  参考文献：
  名称：

  Synthesis and biological evaluation of modified acridines: the effect of N- and O- substituent in the nitrogenated ring on antitumor activity

  摘要：

  A series of new acridines has been prepared by cyclodehydration of N-(2,3-dihydro-1,4-berizodioxin-6-yl)anthranilic acid in acidic media following classical procedures. All these compounds have in common a dioxygenated ring fused to the acridine. The tetracyclic system possesses a linear or angular structure formed by intramolecular cyclisation. The last ring and the substituent of the system modify, in an interesting way, the antitumor activity of acridines. Several of the studied compounds displayed significant cytotoxic activity (inhibition of L 12 10 and HT-29 cell proliferation). The most cytotoxic compound 13a, shows more activity than m-AMSA in inhibiting L1210 and HT-29 cell proliferation and this compound has been selected as a development candidate for further evaluation. The activity results also indicate that the new 11-O-substituted compounds are of considerable interest with high levels of cytotoxic activity. The angular or non-linear dioxinoacridine 10 was equiactive with the linear structure 7. Pentacyclic analogues (14 and 15) were more cytotoxic than the tetracyclic compounds (up to twofold). (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.006

文献信息

• Synthesis and biological evaluation of modified acridines: the effect of N- and O- substituent in the nitrogenated ring on antitumor activity
  作者：Isabel Sánchez、Rosa Reches、Daniel Henry Caignard、Pierre Renard、Maria Dolors Pujol

  DOI：10.1016/j.ejmech.2005.11.006

  日期：2006.3

  A series of new acridines has been prepared by cyclodehydration of N-(2,3-dihydro-1,4-berizodioxin-6-yl)anthranilic acid in acidic media following classical procedures. All these compounds have in common a dioxygenated ring fused to the acridine. The tetracyclic system possesses a linear or angular structure formed by intramolecular cyclisation. The last ring and the substituent of the system modify, in an interesting way, the antitumor activity of acridines. Several of the studied compounds displayed significant cytotoxic activity (inhibition of L 12 10 and HT-29 cell proliferation). The most cytotoxic compound 13a, shows more activity than m-AMSA in inhibiting L1210 and HT-29 cell proliferation and this compound has been selected as a development candidate for further evaluation. The activity results also indicate that the new 11-O-substituted compounds are of considerable interest with high levels of cytotoxic activity. The angular or non-linear dioxinoacridine 10 was equiactive with the linear structure 7. Pentacyclic analogues (14 and 15) were more cytotoxic than the tetracyclic compounds (up to twofold). (c) 2006 Elsevier SAS. All rights reserved.