N-9H-芴-9-基-2,2,2-三氟-乙酰胺 | 1493-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-9H-芴-9-基-2,2,2-三氟-乙酰胺
• 英文名称: N-(9-fluorenyl)trifluoroacetamide
• 英文别名: N-Fluorenyl-(9)-trifluoracetamid；N-9-Fluorenyl-trifluoracetamid；n-(9h-Fluoren-9-yl)-2,2,2-trifluoroacetamide
• CAS: 1493-54-5
• 化学式: C₁₅H₁₀F₃NO
• 分子量: 277.246
• InChiKey: AGVIFRIDPJTZJF-UHFFFAOYSA-N

物化性质

• 熔点：
  252-253 °C
• 沸点：
  160 °C(Press: 0.001 Torr)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-9H-芴-9-基-2,2,2-三氟-乙酰胺 在 氢氧化钾 、 copper(II) sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.5h， 生成 2-(3,4-dimethoxyphenyl)-6-[9H-fluoren-9-yl(methyl)amino]-2-propan-2-ylhex-4-ynenitrile
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range

  摘要：

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.

  DOI：

  10.1021/jm980440p
• 作为产物：
  描述：

  9-氨基芴 、 三氟乙酸酐 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.25h， 生成 N-9H-芴-9-基-2,2,2-三氟-乙酰胺
  参考文献：
  名称：

  Oxygen sensitization of electron capture response to isomers of polycyclic aromatic amines and hydroxides

  摘要：

  DOI：

  10.1021/ac00259a034

文献信息

• Bestimmung von prim�ren und sekund�ren Aminen in Form von Amiden mit Hilfe der Gaschromatographie auf gepackten und Kapillar-S�ulen
  作者：M. Pailer、W. J. H�bsch

  DOI：10.1007/bf00901432

  日期：——
• Oxygen sensitization of electron capture response to isomers of polycyclic aromatic amines and hydroxides
  作者：J. A. Campbell、E. P. Grimsrud、L. R. Hageman

  DOI：10.1021/ac00259a034

  日期：1983.7.1
• Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range
  作者：Elisabetta Teodori、Silvia Dei、Patricia Quidu、Roberta Budriesi、Alberto Chiarini、Arlette Garnier-Suillerot、Fulvio Gualtieri、Dina Manetti、Maria Novella Romanelli、Serena Scapecchi

  DOI：10.1021/jm980440p

  日期：1999.5.1

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.