7-tert-butyl-1,2,3,4-tetrahydroacridin-9(10H)-one | 444610-13-3

• 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: 7-tert-butyl-1,2,3,4-tetrahydroacridin-9(10H)-one
• 英文别名: 7-(1,1-Dimethylethyl)-9-hydroxy-1,2,3,4-tetrahydroacridine；7-tert-butyl-2,3,4,10-tetrahydro-1H-acridin-9-one
• CAS: 444610-13-3
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: ABWKRBGWUUJBSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-tert-butyl-1,2,3,4-tetrahydroacridin-9(10H)-one 在 9-chloro-7-1,1-dimethylethyl 作用下， 以 三氯氧磷 为溶剂， 反应 0.5h， 以Concentration of the organic phase gave 8.24 g of 9-chloro-7-1,1-dimethylethyl)-1,2,3,4-tetrahydroacridine的产率得到1,2,3,4-四氢吖啶
  参考文献：
  名称：

  Substituted 9-amino-tetrahydroacridines and related compounds

  摘要：

  公开了具有以下式子的化合物：##STR1## 其中n为1-4; X为3-18个碳原子的烷基，3-7个碳原子的环烷基或环烷基低烷基; R为氢，低烷基或低烷基羰基; R.sub.1为氢，低烷基，低烷基羰基，芳香族，二低烷基氨基低烷基，芳香基低烷基，二芳基低烷基，氧桥联芳香基低烷基或氧桥联二芳基低烷基; 其立体异构体和药学上可接受的酸加合盐，对增强记忆有用，制备它们的方法，以及包含有效增强记忆量的这种化合物的制药组合物。

  公开号：

  US05391553A1
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 对甲苯磺酸 作用下， 以 二苯醚 、 苯 为溶剂， 生成 7-tert-butyl-1,2,3,4-tetrahydroacridin-9(10H)-one
  参考文献：
  名称：

  Substituted 9-amino-tetrahydroacridines and related compounds

  摘要：

  披露了具有以下结构的化合物：其中n为1-4；X为3-18个碳原子的烷基，3-7个碳原子的环烷基或环烷基较低烷基；R为氢，较低烷基或较低烷基羰基；R.sub.1为氢，较低烷基，较低烷基羰基，芳基，二较低烷基氨基较低烷基，芳基较低烷基，二芳基较低烷基，氧桥芳基较低烷基或氧桥二芳基较低烷基；它们的立体异构体和药学上可接受的酸盐，这些化合物对增强记忆有用，合成它们的方法，以及包含有效的增强记忆量的这种化合物的药物组合物。

  公开号：

  US05391553A1

文献信息

• 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.
• Triazoquinolone derivatives as pest controllers
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP1364951B1

  公开（公告）日：2012-05-02
• US5391553A
  申请人：——

  公开号：US5391553A

  公开（公告）日：1995-02-21
• Substituted 9-amino-tetrahydroacridines and related compounds
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05391553A1

  公开（公告）日：1995-02-21

  There are disclosed compounds having the formula ##STR1## wherein n is 1-4; X is alkyl of 3-18 carbon atoms, cycloalkyl of 3-7 carbon atoms or cycloalkylloweralkyl; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl or oxygen-bridged diarylloweralkyl; stereo isomers thereof and pharmaceutically acceptable acid addition salts thereof, which are useful for enhancing memory, methods for synthesizing them, and pharmaceutical compositions comprising an effective memory enhancing amount of such a compound.

  披露了具有以下结构的化合物：其中n为1-4；X为3-18个碳原子的烷基，3-7个碳原子的环烷基或环烷基较低烷基；R为氢，较低烷基或较低烷基羰基；R.sub.1为氢，较低烷基，较低烷基羰基，芳基，二较低烷基氨基较低烷基，芳基较低烷基，二芳基较低烷基，氧桥芳基较低烷基或氧桥二芳基较低烷基；它们的立体异构体和药学上可接受的酸盐，这些化合物对增强记忆有用，合成它们的方法，以及包含有效的增强记忆量的这种化合物的药物组合物。