6-methyl-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one | 195379-42-1

• 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: 6-methyl-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one
• 英文别名: 6-methyl-2,3-dihydro-[1,4]-dioxino[2,3-b]acridin-11(6H)-one；6-methyl-6H-[1,4]dioxino[2,3-b]acridin-11-one；6-Methyl-2,3-dihydro-[1,4]dioxino[2,3-b]acridin-11-one
• CAS: 195379-42-1
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: FHBZUMQRAICACN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one 在 lithium aluminium tetrahydride 、 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以94%的产率得到6-methyl-2,3,6,11-tetrahydro-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 PPA 、 铜 作用下， 以 戊醇 为溶剂， 反应 19.0h， 生成 6-methyl-2,3,6,11-tetrahydro-1,4-dioxino[2,3-b]acridin-11-one
  参考文献：
  名称：

  Synthesis of New N-Alkyl- and N-Acyldioxinophenothiazine and Acridinone Derivatives

  摘要：

  DOI：

  10.3987/com-00-9013

文献信息

• Synthesis of 10-Methylacridin-9(10<i>H</i>)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp²)-H Amination of 2-(Methylamino)benzophenones
  作者：Jinbo Huang、Congqing Wan、Ming-Fang Xu、Qiang Zhu

  DOI：10.1002/ejoc.201201748

  日期：2013.4

  An efficient synthesis of a diverse set of 10-methylacridin-9(10H)-ones from 2-(methylamino)benzophenones has been developed. The reaction proceeds though Cu-catalyzed intramolecular aromatic C–H amination by using O2 as the sole oxidant to provide the desired products in moderate to good yields. In addition, 2-allylamino- and 2-(benzylamino)benzophenones as well as unprotected substrates can also

  已开发出一种从 2-(甲基氨基) 二苯甲酮中高效合成多种 10-methylacridin-9(10H)-ones 的方法。该反应通过使用 O2 作为唯一氧化剂通过 Cu 催化的分子内芳族 C-H 胺化进行，以中等至良好的产率提供所需的产物。此外，2-烯丙基氨基-和2-（苄基氨基）二苯甲酮以及未受保护的底物也可以进行C-H胺化反应，从而顺利地生成相应的环化产物。初步的机理研究表明，C-H 活化涉及限速步骤。
• 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.