N,N-Diethyl 4-N,N-Dimethylamino-2-[3-(N,N-dimethylamino)-phenylthio]benzamide | 705964-32-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N,N-Diethyl 4-N,N-Dimethylamino-2-[3-(N,N-dimethylamino)-phenylthio]benzamide
• 英文别名: 4-(dimethylamino)-2-[3-(dimethylamino)phenyl]sulfanyl-N,N-diethylbenzamide
• CAS: 705964-32-5
• 化学式: C₂₁H₂₉N₃OS
• 分子量: 371.547
• InChiKey: VCUVGJQJDQUTHX-UHFFFAOYSA-N

物化性质

• 沸点：
  553.2±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-Diethyl 4-N,N-Dimethylamino-2-[3-(N,N-dimethylamino)-phenylthio]benzamide 在 lithium diisopropyl amide 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以13%的产率得到3,6-Bis(dimethylamino)thioxanthon
  参考文献：
  名称：

  Novel chalcogenoxanthylium dyes for purging blood pathogens and for photodynamic therapy

  摘要：

  提供了硫、硒和碲氧杂芴阳离子化合物，可有效用作光动力疗法的增敏剂、光动力抗微生物化疗的病毒灭活剂以及癌细胞Pgp功能的逆转剂。还提供了一种制备硫、硒和碲氧杂芴阳离子化合物的通用方法。

  公开号：

  US20060040908A1
• 作为产物：
  描述：

  3-溴-N,N-二甲基苯胺 在 四甲基乙二胺 、 双氧水 、 仲丁基锂 、 magnesium 、 di-n-hexyl telluride 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 6.0h， 生成 N,N-Diethyl 4-N,N-Dimethylamino-2-[3-(N,N-dimethylamino)-phenylthio]benzamide
  参考文献：
  名称：

  Synthesis, properties, and photodynamic properties in vitro of heavy-chalcogen analogues of tetramethylrosamine

  摘要：

  Thio and seleno analogues of tetramethylrosamine were prepared by the directed-metalation/cyclization of the corresponding N,N-diethyl 2-(3-dimethylaminophenylchalcogeno)-4-dimethylaminobenzamide to the 2,7-bis-(N,N-dimethylaniiiio)-9H-chalcoaenoxanthen-9-one followed by the addition of phenylmagnesium bromide, dehydration, and ion exchange to the chloride salt. The thio and seleno tetramethylrosamines had longer wavelengths of absorption and higher quantum yields for the generation of singlet oxygen than tetramethylrosamine. Both the thio and selenoanalogues of tetramethylrosamine were efficient photosensitizers against R3230AC rat mammary adenocarcinoma cells in vitro. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.029

文献信息

• Novel chalcogenoxanthylium dyes for purging blood pathogens and for photodynamic therapy
  申请人：Detty R. Michael

  公开号：US20060040908A1

  公开（公告）日：2006-02-23

  Provided are chalcogenoxanthylium compounds which can effectively be used as sensitizers in photodynamic therapy, virucides in photodynamic antimicrobial chemotherapy and reversal agents of Pgp function in cancer cells. Further provided is a general method for the preparation of chalcogenoxanthylium compounds.

  提供了硫、硒和碲氧杂芴阳离子化合物，可有效用作光动力疗法的增敏剂、光动力抗微生物化疗的病毒灭活剂以及癌细胞Pgp功能的逆转剂。还提供了一种制备硫、硒和碲氧杂芴阳离子化合物的通用方法。
• Synthesis, properties, and photodynamic properties in vitro of heavy-chalcogen analogues of tetramethylrosamine
  作者：Michael R Detty、Paras N Prasad、David J Donnelly、Tymish Ohulchanskyy、Scott L Gibson、Russell Hilf

  DOI：10.1016/j.bmc.2004.03.029

  日期：2004.5

  Thio and seleno analogues of tetramethylrosamine were prepared by the directed-metalation/cyclization of the corresponding N,N-diethyl 2-(3-dimethylaminophenylchalcogeno)-4-dimethylaminobenzamide to the 2,7-bis-(N,N-dimethylaniiiio)-9H-chalcoaenoxanthen-9-one followed by the addition of phenylmagnesium bromide, dehydration, and ion exchange to the chloride salt. The thio and seleno tetramethylrosamines had longer wavelengths of absorption and higher quantum yields for the generation of singlet oxygen than tetramethylrosamine. Both the thio and selenoanalogues of tetramethylrosamine were efficient photosensitizers against R3230AC rat mammary adenocarcinoma cells in vitro. (C) 2004 Elsevier Ltd. All rights reserved.
• Structure–activity studies of uptake and phototoxicity with heavy-chalcogen analogues of tetramethylrosamine in vitro in chemosensitive and multidrug-resistant cells
  作者：Scott L. Gibson、Jason J. Holt、Mao Ye、David J. Donnelly、Tymish Y. Ohulchanskyy、Youngjae You、Michael R. Detty

  DOI：10.1016/j.bmc.2005.06.056

  日期：2005.12

  Several thio and seleno analogues of tetramethylrosamine (TMR) were prepared. Thio derivatives of TMR have absorption maxima near 570 nm, while seleno derivatives of TMR have absorption maxima near 580 nm. The 3- or 4-N,N-dimethylaminophenyl substituent in the 9-position greatly increases internal conversion, which lowers quantum yields for fluorescence and the generation of singlet oxygen. Thio and seleno analogues of TMR are effective photosensitizers against chemosensitive AUXB1 cells in vitro and against multidrug-resistant CRI R 12 cells in vitro, which have been treated with verapamil. The CR1R12 cells accumulated significantly lower concentrations of the photosensitizers relative to the AUXB1 cells presumably due to the expression of P-glycoprotein (Pgp) in the CR1R12 cells. Following treatment with 5 x 10(-5) M verapamil, the uptake in CR1R12 cells of several fluorescent thio analogues of TMR is comparable to that observed for the chemosensitive AUXB1 cells. (c) 2005 Elsevier Ltd. All rights reserved.