11-chloro[1,4]dioxino[2,3-b]acridine | 154490-85-4

• 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: 11-chloro[1,4]dioxino[2,3-b]acridine
• 英文别名: 9-chloro-2,3-ethylenedioxyacridine；11-chloro-2,3-dihydro-1,4-dioxino[2,3-b]acridine；11-Chloro-2,3-dihydro-[1,4]dioxino[2,3-b]acridine
• CAS: 154490-85-4
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: WRYFXGLKCGAHFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 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：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-chloro[1,4]dioxino[2,3-b]acridine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以40%的产率得到9-bromo-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：

  6-氨基-1,4-苯并二氧杂环 在 铜 、 potassium carbonate 、 三氯氧磷 作用下， 反应 6.0h， 生成 11-chloro[1,4]dioxino[2,3-b]acridine
  参考文献：
  名称：

  cr啶衍生物。V †。新型9-苯胺基2,3-乙撑二氧ac啶的合成及P388的抗肿瘤活性

  摘要：

  已经合成了一类新型的插入脱氧核糖核酸（DNA）的抗肿瘤药，新型的9-苯胺基-2,3-乙二氧基ac啶（5种化合物），并评估了其在体内对P388白血病的活性。它们中的一些具有与氨水扁桃碱（m -AMSA）相同的抗肿瘤活性，后者是临床上重要的抗肿瘤剂。

  DOI：

  10.1002/jhet.5570300446

文献信息

• Synthesis of New N-Alkyl- and N-Acyldioxinophenothiazine and Acridinone Derivatives
  作者：Gérard Boyer、Florence Chatel、Sandrine Morel、Jean Pierre Galy

  DOI：10.3987/com-00-9013

  日期：——
• 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.
• Acridine derivatives.<b>V</b>. Synthesis and P388 antitumor activity of the novel 9-anilino-2,3-ethylenedioxyacridines
  作者：Michio Kimura、Ichizo Okabayashi、Akira Kato

  DOI：10.1002/jhet.5570300446

  日期：1993.7

  A new class of deoxyribonucleic acid (DNA)-intercalating antitumor agents, novel 9-anilino-2,3-ethylenedioxyacridines (five compounds) have been synthesized and evaluated for activity against P388 leukemia in vivo. A few of them possessed the same potency of antitumor activity as amsacrine (m-AMSA) which is an important antitumor agent in clinical use.

  已经合成了一类新型的插入脱氧核糖核酸（DNA）的抗肿瘤药，新型的9-苯胺基-2,3-乙二氧基ac啶（5种化合物），并评估了其在体内对P388白血病的活性。它们中的一些具有与氨水扁桃碱（m -AMSA）相同的抗肿瘤活性，后者是临床上重要的抗肿瘤剂。