5-methoxy-1,2,3,4-tetrahydro-acridin-9-ol | 855942-82-4

• 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: 5-methoxy-1,2,3,4-tetrahydro-acridin-9-ol
• 英文别名: 5-methoxy-2,3,4,10-tetrahydro-1H-acridin-9-one
• CAS: 855942-82-4
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD13477880
• 分子量: 229.279
• InChiKey: DRTNPMJEVFCBHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-1,2,3,4-tetrahydro-acridin-9-ol 在 三氯氧磷 作用下， 生成 9-chloro-5-methoxy-1,2,3,4-tetrahydro-acridine
  参考文献：
  名称：

  cr啶系列研究；衍生自5-和7-Bz-甲氧基-9-氯-1,2,3,4-四氢ac啶的二烷基氨基烷基胺。

  摘要：

  DOI：

  10.1021/jo01168a013
• 作为产物：
  描述：

  邻甲氧基苯胺 在 盐酸 、 paraffin oil 作用下， 生成 5-methoxy-1,2,3,4-tetrahydro-acridin-9-ol
  参考文献：
  名称：

  硼和碳原子中的全构型相互作用和多构型自旋密度

  摘要：

  通过与全构型相互作用 (FCI) 计算的结果进行比较，检验了使用几种广泛使用的高斯基组获得的原子自旋密度的自旋极化方法结果的可靠性。使用自旋极化模型和其他一些方法通过这些基组获得的自旋密度与 FCI 处理不一致。由于 FCI 波函数对于给定的基础是精确的，因此自旋极化模型是否普遍可靠尚不清楚。大型活动空间多配置 (CASSCF) 计算被证明不足以替代 FCI 处理。至少在一定程度上考虑基函数完整空间中所有轨道的激发的重要性可以通过 CASSCF 结果随着活动空间大小的增加而非常缓慢地收敛来说明。

  DOI：

  10.1063/1.1288377

文献信息

• Microwave-Assisted Preparation of Quinolone and Quinoline Derivatives
  作者：Markus Albrecht、Olga Osetska、Toni Rantanen、Roland Fröhlich、Carsten Bolm

  DOI：10.1055/s-0029-1219565

  日期：2010.4

  Quinolinone derivatives can be obtained in microwave-assisted syntheses by reaction of aniline derivatives with acetylene dicarboxylic esters, a malonic acid diester or β-keto ester derivatives. The reaction proceeds under mild conditions in short reaction times. Two of the quinolinones were transformed into the corresponding 4-chloroquinolines either by conventional heating or in a microwave-assisted

  通过苯胺衍生物与乙炔二羧酸酯、丙二酸二酯或β-酮酯衍生物的反应，可以在微波辅助合成中获得喹啉酮衍生物。该反应在温和的条件下在很短的反应时间内进行。通过常规加热或在微波辅助反应中，两种喹啉酮被转化为相应的 4-氯喹啉。进一步的修改导致硼加合物或附聚物的形成。后者通过 X 射线晶体结构分析表征。
• Optimization of 1,2,3,4-Tetrahydroacridin-9(10<i>H</i>)-ones as Antimalarials Utilizing Structure–Activity and Structure–Property Relationships
  作者：R. Matthew Cross、Jordany R. Maignan、Tina S. Mutka、Lisa Luong、Justin Sargent、Dennis E. Kyle、Roman Manetsch

  DOI：10.1021/jm200015a

  日期：2011.7.14

  Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine (1) in the 1970s and analogues thereof such as WR 243251 (2a) in the 1990s. These compounds failed just prior to clinical development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochemical liabilities of the THA scaffold. Several potent compounds (EC50 < 100 nM) were identified to be active against the clinically relevant isolates W2 and TM90-C2B while possessing good physicochemical properties and little to no cross-resistance.
• Stephen et al., Journal of the Chemical Society, 1947, p. 1034,1037
  作者：Stephen et al.

  DOI：——

  日期：——
• Bukhsh; Desai, Proceedings - Indian Academy of Sciences, Section A, 1939, vol. 10, p. 262,264
  作者：Bukhsh、Desai

  DOI：——

  日期：——