N-[2-(1'-piperidinyl)ethyl]-4-methoxybenzenesulfonamide | 209968-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(1'-piperidinyl)ethyl]-4-methoxybenzenesulfonamide
• 英文别名: 4-methoxy-N-(2-piperidin-1-ylethyl)benzenesulfonamide
• CAS: 209968-37-6
• 化学式: C₁₄H₂₂N₂O₃S
• 分子量: 298.406
• InChiKey: XFXNKYQSRSSRAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(1'-piperidinyl)ethyl]-4-methoxybenzenesulfonamide 在 碘 、 三氟乙酸 、 thallium(III) trifluoroacetate 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以83%的产率得到N-[2-(1'-piperidinyl)ethyl]-3-iodo-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  Substituted Halogenated Arylsulfonamides:  A New Class of σ Receptor Binding Tumor Imaging Agents

  摘要：

  The discovery of a series of novel halogenated arylsulfonamides (HAS) as new sigma receptor binding tumor imaging agents is described. Several substituted halogenated sulfonamides have been prepared and characterized. Target compounds were examined for their affinity for sigma(1) and sigma(2) receptor subtypes using guineapig brain membranes and rat liver membranes, respectively. A number of substituted halogenated sulfonamides displayed subnanomolar affinities for sigma(1) sites add low nanomolar affinities for sigma(2) subtype receptors. A limited structure-activity relationship study of this chemical series is discussed. The radioiodination (I-125) of one congener member (4-[I-125]iodo-N-[2-(1'-piperidinyl)ethyl]benzenesulfonamide 4-[I-125]IPBS) was accomplished in high yields. The in vitro competition binding studies of 4-[I-125]IPBS in guinea pig brain membranes with sigma receptor binding ligands confirmed its sigma pharmacology. The rank order of potency was BD1008 [N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)- ethylamine)> 4-IPBS > haloperidol > (+)-pentazocine > DTG (1,3-di-o-tolylguanidine) > (-)-pentazocine. The inhibition constants (IC50) were 0.70, 1.46, 6.28, 10.4, 87.2, and 152 nM, respectively, and are consistent with labeling of sigma(1) receptors. The tumor imaging potential of 4-[I-125]IPBS was studied in C57 black mice bearing B16 melanoma xenograft. A high tumor uptake of 4-[I-125]IPBS was observed (7.40% ID/g) at 1 h postinjection. The wash out of activity from the tumor was slow at 6 h postinjection (7.22% ID/g). The tumor also had the highest amount of radioactivity (1.54% ID/g) at 24 h postinjection. These results demonstrate that radiohalogenated benzenesulfonamides could be a potentially useful class of compounds in nuclear oncologic scintigraphy.

  DOI：

  10.1021/jm9800447
• 作为产物：
  描述：

  1-(2-氨乙基)哌啶 、 对甲氧基苯磺酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 以94%的产率得到N-[2-(1'-piperidinyl)ethyl]-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  Substituted Halogenated Arylsulfonamides:  A New Class of σ Receptor Binding Tumor Imaging Agents

  摘要：

  The discovery of a series of novel halogenated arylsulfonamides (HAS) as new sigma receptor binding tumor imaging agents is described. Several substituted halogenated sulfonamides have been prepared and characterized. Target compounds were examined for their affinity for sigma(1) and sigma(2) receptor subtypes using guineapig brain membranes and rat liver membranes, respectively. A number of substituted halogenated sulfonamides displayed subnanomolar affinities for sigma(1) sites add low nanomolar affinities for sigma(2) subtype receptors. A limited structure-activity relationship study of this chemical series is discussed. The radioiodination (I-125) of one congener member (4-[I-125]iodo-N-[2-(1'-piperidinyl)ethyl]benzenesulfonamide 4-[I-125]IPBS) was accomplished in high yields. The in vitro competition binding studies of 4-[I-125]IPBS in guinea pig brain membranes with sigma receptor binding ligands confirmed its sigma pharmacology. The rank order of potency was BD1008 [N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)- ethylamine)> 4-IPBS > haloperidol > (+)-pentazocine > DTG (1,3-di-o-tolylguanidine) > (-)-pentazocine. The inhibition constants (IC50) were 0.70, 1.46, 6.28, 10.4, 87.2, and 152 nM, respectively, and are consistent with labeling of sigma(1) receptors. The tumor imaging potential of 4-[I-125]IPBS was studied in C57 black mice bearing B16 melanoma xenograft. A high tumor uptake of 4-[I-125]IPBS was observed (7.40% ID/g) at 1 h postinjection. The wash out of activity from the tumor was slow at 6 h postinjection (7.22% ID/g). The tumor also had the highest amount of radioactivity (1.54% ID/g) at 24 h postinjection. These results demonstrate that radiohalogenated benzenesulfonamides could be a potentially useful class of compounds in nuclear oncologic scintigraphy.

  DOI：

  10.1021/jm9800447

文献信息

• Discovery of CGS 27023A, a Non-Peptidic, Potent, and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits
  作者：Lawrence J. MacPherson、Erol K. Bayburt、Michael P. Capparelli、Brian J. Carroll、Robert Goldstein、Michael R. Justice、Lijuan Zhu、Shou-ih Hu、Richard A. Melton、Lynn Fryer、Ron L. Goldberg、John R. Doughty、Salvatore Spirito、Vincent Blancuzzi、Doug Wilson、Elizabeth M. O'Byrne、Vishwas Ganu、David T. Parker

  DOI：10.1021/jm960871c

  日期：1997.8.1

  Structure-activity relationships of a lead hydroxamic acid inhibitor of recombinant human stromelysin were systematically defined by taking advantage of a concise synthesis that allowed diverse functionality to be explored at each position in a template. An ex vivo rat model and an in vivo rabbit model of stromelysin-induced cartilage degradation were used to further optimize these analogs for oral activity and duration of action. The culmination of these modifications resulted in CGS 27023A, a potent, orally active stromelysin inhibitor that blocks the erosion of cartilage matrix.
• Substituted Halogenated Arylsulfonamides:  A New Class of σ Receptor Binding Tumor Imaging Agents
  作者：Christy S. John、Benjamin B. Lim、Bertold J. Vilner、Brian C. Geyer、Wayne D. Bowen

  DOI：10.1021/jm9800447

  日期：1998.7.1

  The discovery of a series of novel halogenated arylsulfonamides (HAS) as new sigma receptor binding tumor imaging agents is described. Several substituted halogenated sulfonamides have been prepared and characterized. Target compounds were examined for their affinity for sigma(1) and sigma(2) receptor subtypes using guineapig brain membranes and rat liver membranes, respectively. A number of substituted halogenated sulfonamides displayed subnanomolar affinities for sigma(1) sites add low nanomolar affinities for sigma(2) subtype receptors. A limited structure-activity relationship study of this chemical series is discussed. The radioiodination (I-125) of one congener member (4-[I-125]iodo-N-[2-(1'-piperidinyl)ethyl]benzenesulfonamide 4-[I-125]IPBS) was accomplished in high yields. The in vitro competition binding studies of 4-[I-125]IPBS in guinea pig brain membranes with sigma receptor binding ligands confirmed its sigma pharmacology. The rank order of potency was BD1008 [N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)- ethylamine)> 4-IPBS > haloperidol > (+)-pentazocine > DTG (1,3-di-o-tolylguanidine) > (-)-pentazocine. The inhibition constants (IC50) were 0.70, 1.46, 6.28, 10.4, 87.2, and 152 nM, respectively, and are consistent with labeling of sigma(1) receptors. The tumor imaging potential of 4-[I-125]IPBS was studied in C57 black mice bearing B16 melanoma xenograft. A high tumor uptake of 4-[I-125]IPBS was observed (7.40% ID/g) at 1 h postinjection. The wash out of activity from the tumor was slow at 6 h postinjection (7.22% ID/g). The tumor also had the highest amount of radioactivity (1.54% ID/g) at 24 h postinjection. These results demonstrate that radiohalogenated benzenesulfonamides could be a potentially useful class of compounds in nuclear oncologic scintigraphy.