4-(4'-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one | 244241-77-8

• 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: 4-(4'-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one
• 英文别名: 4-(4-methylphenylthio)pyrido[2,3,4-kl]acridin-6-one；4-[(4-Methylphenyl)sulfanyl]-6H-pyrido[2,3,4-kl]acridin-6-one；12-(4-methylphenyl)sulfanyl-8,14-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,11,13,15-octaen-10-one
• CAS: 244241-77-8
• 化学式: C₂₂H₁₄N₂OS
• 分子量: 354.432
• InChiKey: NXDFBOPJSSHYHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4'-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以64%的产率得到4-aminobenzo[de][3,6]phenanthrolin-6(6H)-one
  参考文献：
  名称：

  A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

  摘要：

  4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.

  DOI：

  10.1080/00397919908086428
• 作为产物：
  描述：

  2-(p-tolylthio)cyclohexa-2,5-diene-1,4-dione 在 cerium(III) chloride 、 硫酸 、 氯化铵 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 192.25h， 生成 4-(4'-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one
  参考文献：
  名称：

  A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

  摘要：

  4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.

  DOI：

  10.1080/00397919908086428

文献信息

• anti-Tuberculosis natural products: synthesis and biological evaluation of pyridoacridine alkaloids related to ascididemin
  作者：David R. Appleton、A. Norrie Pearce、Brent R. Copp

  DOI：10.1016/j.tet.2010.05.033

  日期：2010.7

  novel therapeutics possessing new modes of action to treat tuberculosis (TB) infections. In this study we report on the synthesis and biological evaluation of a series of pyrido[2,3,4-kl]acridin-6-one alkaloids related to the anti-TB (MIC 0.35 μM) but cytotoxic (IC50 <0.14 μM) marine natural product ascididemin (1). The most interesting compounds identified were 21 and 24, which were found to inhibit

  迫切需要具有新的作用方式以治疗结核病（TB）感染的新型疗法。在这项研究中，我们报告了一系列与抗-TB（MIC 0.35μM）但具有细胞毒性（IC 50 < 0.14μM）相关的吡啶并[2,3,4- kl ] acridin-6-one生物碱的合成和生物学评估。）海洋天然产物ascididemin（1）。鉴定出的最有趣的化合物为21和24，发现它们以MIC 2.0μM抑制结核分枝杆菌（Mtb）H 37 Rv的生长，但对Vero和P388细胞的细胞毒性却微不足道（IC 50 > 25μM）。另一个类似物（10）针对一系列Mtb的单药耐药菌株进行了评估），发现没有交叉耐药性。这些结果表明，吡啶并[2,3,4- KL ]吖-6-一个骨架可以提供针对未来可能的研究有用的支架抗-TB药物。
• A Convenient New Route to 4-Substituted Benzo[<i>de</i>][3,6]Phenanthrolin-6(6<i>H</i>)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin
  作者：Brent R. Copp、Richard P. Hansen、David R. Appleton、Brent S. Lindsay、Chris J. Squire、George R. Clark、Cliff E. F. Rickard

  DOI：10.1080/00397919908086428

  日期：1999.8.1

  4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.