N,N-diethylamino-1-sulfonic acid [3-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-pyrazol-1-yl]-methylsulfanyl-methyleneamide | 505031-21-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N,N-diethylamino-1-sulfonic acid [3-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-pyrazol-1-yl]-methylsulfanyl-methyleneamide
• 英文别名: methyl 3-(4-chlorophenyl)-N-[(diethylamino)sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carbimidothioate；methyl 5-(4-chlorophenyl)-N-(diethylsulfamoyl)-4-phenyl-3,4-dihydropyrazole-2-carboximidothioate
• CAS: 505031-21-0
• 化学式: C₂₁H₂₅ClN₄O₂S₂
• 分子量: 465.04
• InChiKey: GTFKFUMVIZFSMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-diethylamino-1-sulfonic acid [3-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-pyrazol-1-yl]-methylsulfanyl-methyleneamide 、 异丙胺 以 甲醇 为溶剂， 反应 2.0h， 生成 5-(4-chlorophenyl)-N-(diethylsulfamoyl)-4-phenyl-N'-propan-2-yl-3,4-dihydropyrazole-2-carboximidamide
  参考文献：
  名称：

  Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity

  摘要：

  Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (K-i = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA(2) = 8.8) and a high CB1/CB2 subtype selectivity (similar to 147-fold). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.054
• 作为产物：
  描述：

  (ethyl(isothiocyanatosulfonyl)amino)ethane 在 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 N,N-diethylamino-1-sulfonic acid [3-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-pyrazol-1-yl]-methylsulfanyl-methyleneamide
  参考文献：
  名称：

  Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity

  摘要：

  Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (K-i = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA(2) = 8.8) and a high CB1/CB2 subtype selectivity (similar to 147-fold). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.054

文献信息

• Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity
  作者：Jos H.M. Lange、Herman H. van Stuivenberg、Willem Veerman、Henri C. Wals、Bob Stork、Hein K.A.C. Coolen、Andrew C. McCreary、Tiny J.P. Adolfs、Chris G. Kruse

  DOI：10.1016/j.bmcl.2005.07.054

  日期：2005.11

  Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (K-i = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA(2) = 8.8) and a high CB1/CB2 subtype selectivity (similar to 147-fold). (c) 2005 Elsevier Ltd. All rights reserved.