4-(2-oxo-2-phenyl-ethylamino)-benzenesulfonamide | 906096-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-oxo-2-phenyl-ethylamino)-benzenesulfonamide
• 英文别名: 4-(2-oxo-2-phenylethylamino)benzenesulfonamide；4-(phenacylamino)benzenesulfonamide
• CAS: 906096-15-9
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: KEHQRQGECILSQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-oxo-2-phenyl-ethylamino)-benzenesulfonamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-(4-oxo-5-phenyl-3,4-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Ghorab, Moustafa M.; Noaman, Eman; Ismail, Magda M. F., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 6, p. 405 - 413

  摘要：

  DOI：
• 作为产物：
  描述：

  磺胺 、 2-溴苯乙酮 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以88%的产率得到4-(2-oxo-2-phenyl-ethylamino)-benzenesulfonamide
  参考文献：
  名称：

  Molecular modeling study and synthesis of novel pyrrolo[2,3-d]pyrimidines and pyrrolotriazolopyrimidines of expected antitumor and radioprotective activities

  摘要：

  Novel pyrrolo[2,3-d]pyrimidine derivatives 4a-e, 10, 14, 15, pyrazolopyrrolopyrimidine 13, pyrrolotriazolopyrimidine 5-9, 17 and pyrrolopyrimidotriazine 18 are reported herein. The design of these compounds was based upon the molecular modeling simulation of the fitting values and conformational energy values of the best-fitted conformers to VEGFRTK inhibitor hypothesis. This hypothesis was generated from its corresponding lead compounds using CATALYST software. The structures of these compounds were confirmed by microanalyses, IR, H-1 NMR, and mass spectral data. Compounds 6 and 15 showed interesting in vitro antitumor activity compared to doxorubicin as positive control. These results are nearly consistent with the molecular modeling studies. Docking studies were made on compound 15 to predict its binding mode. Moreover, compound 10 exhibited a significant radioprotective activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.072

文献信息

• Ismail, Magda M. F.; Ghorab, Mostafa M.; Noaman, Eman, Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 4, p. 301 - 308
  作者：Ismail, Magda M. F.、Ghorab, Mostafa M.、Noaman, Eman、Ammar, Yousry A.、Heiba, Helmy I.、Sayed, Marwa Y.

  DOI：——

  日期：——
• Synthesis and carbonic anhydrase I, II, IX and XII inhibition studies of 4-N,N-disubstituted sulfanilamides incorporating 4,4,4-trifluoro-3-oxo-but-1-enyl, phenacylthiourea and imidazol-2(3H)-one/thione moieties
  作者：Cenzo Congiu、Valentina Onnis、Gianfranco Balboni、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.02.030

  日期：2014.4

  A series of sulfonamides incorporating the sulfanilamide ( SA) scaffold were prepared. Reaction of the 4-amino moiety of SA with benzyl chlorides or substituted bromoacetophenones afforded the derivatives which were then reacted with 1,1,1-trifluoro-4-isobutoxybut-3-en-2-one leading to a series of 4-N,N-disubstituted SAs. The key intermediates were also reacted with ethoxycarbonyl isothiocyanate leading to thioureas or were cyclized in the presence of potassium cyanate/isothiocyanate to the corresponding imidazol-2(3H)-one/thiones. The new compounds were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and the transmembrane, tumor-associated CA IX and XII. These sulfonamides were ineffective CA I and II inhibitors but were nanomolar CA IX and XII inhibitors, making them of interest as clinical candidates for antitumor/antimetastasis applications. (C) 2014 Elsevier Ltd. All rights reserved.
• Molecular modeling study and synthesis of novel pyrrolo[2,3-d]pyrimidines and pyrrolotriazolopyrimidines of expected antitumor and radioprotective activities
  作者：Dalal A. Abou El Ella、Mostafa M. Ghorab、Eman Noaman、Helmy I. Heiba、Amira I. Khalil

  DOI：10.1016/j.bmc.2007.11.072

  日期：2008.3

  Novel pyrrolo[2,3-d]pyrimidine derivatives 4a-e, 10, 14, 15, pyrazolopyrrolopyrimidine 13, pyrrolotriazolopyrimidine 5-9, 17 and pyrrolopyrimidotriazine 18 are reported herein. The design of these compounds was based upon the molecular modeling simulation of the fitting values and conformational energy values of the best-fitted conformers to VEGFRTK inhibitor hypothesis. This hypothesis was generated from its corresponding lead compounds using CATALYST software. The structures of these compounds were confirmed by microanalyses, IR, H-1 NMR, and mass spectral data. Compounds 6 and 15 showed interesting in vitro antitumor activity compared to doxorubicin as positive control. These results are nearly consistent with the molecular modeling studies. Docking studies were made on compound 15 to predict its binding mode. Moreover, compound 10 exhibited a significant radioprotective activity. (C) 2007 Elsevier Ltd. All rights reserved.
• Ghorab, Moustafa M.; Noaman, Eman; Ismail, Magda M. F., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 6, p. 405 - 413
  作者：Ghorab, Moustafa M.、Noaman, Eman、Ismail, Magda M. F.、Heiba, Helmy I.、Ammar, Yousry A.、Sayed, Marwa Y.

  DOI：——

  日期：——