3,5-diamino-4-(dibutylamino)-N-phenylbenzenesulfonamide | 949571-13-5

• 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: 3,5-diamino-4-(dibutylamino)-N-phenylbenzenesulfonamide
• CAS: 949571-13-5
• 化学式: C₂₀H₃₀N₄O₂S
• 分子量: 390.55
• InChiKey: PVWVSPGNEFJKCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-diamino-4-(dibutylamino)-N-phenylbenzenesulfonamide 在 盐酸 、 sodium nitrite 、 copper(l) chloride 作用下， 以 水 为溶剂， 反应 3.25h， 以23%的产率得到3,5-dichloro-4-(dibutylamino)-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling of 3,5-substituted-N1-phenyl-N4,N4-di-n-butylsulfanilamides as antikinetoplastid antimicrotubule agents

  摘要：

  Dinitroanilines are of interest as antiprotozoal lead compounds because of their selective activity against the tubulin of these organisms, but concern has been raised due to the potentially mutagenic nitro groups. Analogues of N-1 -phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (GB-II-150, compound 2b), a selective antimitotic agent against African trypanosomes and Leishmania. have been prepared where the nitro groups are replaced with amino, chloro, cyano, carboxylate, methyl ester, amide, and methyl ketone moieties. Dicyano compound 5 displays IC50 values that are comparable to 2b against purified leishmanial tubulin assembly (6.6 vs 7.4 mu M) Trvpanosoma brucei brucei growth in vitro (0.26 vs 0.18 mu M), Leishmania donovani axenic amastigote growth in vitro (4.4 vs 2.3 mu M), and in vitro toxicity against Vero cells (16 vs 9.7 mu M). Computational studies provide a rationale or the antiparasitic order of activity of these analogues and further insight into the role of the substituents at the 3 and 5 positions of the sulfanilamide ring. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.042
• 作为产物：
  描述：

  4-(二丁基氨基)-3,5-二硝基-N-苯基苯磺酰胺 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以98%的产率得到3,5-diamino-4-(dibutylamino)-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling of 3,5-substituted-N1-phenyl-N4,N4-di-n-butylsulfanilamides as antikinetoplastid antimicrotubule agents

  摘要：

  Dinitroanilines are of interest as antiprotozoal lead compounds because of their selective activity against the tubulin of these organisms, but concern has been raised due to the potentially mutagenic nitro groups. Analogues of N-1 -phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (GB-II-150, compound 2b), a selective antimitotic agent against African trypanosomes and Leishmania. have been prepared where the nitro groups are replaced with amino, chloro, cyano, carboxylate, methyl ester, amide, and methyl ketone moieties. Dicyano compound 5 displays IC50 values that are comparable to 2b against purified leishmanial tubulin assembly (6.6 vs 7.4 mu M) Trvpanosoma brucei brucei growth in vitro (0.26 vs 0.18 mu M), Leishmania donovani axenic amastigote growth in vitro (4.4 vs 2.3 mu M), and in vitro toxicity against Vero cells (16 vs 9.7 mu M). Computational studies provide a rationale or the antiparasitic order of activity of these analogues and further insight into the role of the substituents at the 3 and 5 positions of the sulfanilamide ring. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.042

文献信息

• Synthesis, biological evaluation, and molecular modeling of 3,5-substituted-N1-phenyl-N4,N4-di-n-butylsulfanilamides as antikinetoplastid antimicrotubule agents
  作者：Tesmol G. George、Molla M. Endeshaw、Rachel E. Morgan、Kiran V. Mahasenan、Dawn A. Delfín、Mitali S. Mukherjee、Adam J. Yakovich、Jean Fotie、Chenglong Li、Karl A. Werbovetz

  DOI：10.1016/j.bmc.2007.06.042

  日期：2007.9

  Dinitroanilines are of interest as antiprotozoal lead compounds because of their selective activity against the tubulin of these organisms, but concern has been raised due to the potentially mutagenic nitro groups. Analogues of N-1 -phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (GB-II-150, compound 2b), a selective antimitotic agent against African trypanosomes and Leishmania. have been prepared where the nitro groups are replaced with amino, chloro, cyano, carboxylate, methyl ester, amide, and methyl ketone moieties. Dicyano compound 5 displays IC50 values that are comparable to 2b against purified leishmanial tubulin assembly (6.6 vs 7.4 mu M) Trvpanosoma brucei brucei growth in vitro (0.26 vs 0.18 mu M), Leishmania donovani axenic amastigote growth in vitro (4.4 vs 2.3 mu M), and in vitro toxicity against Vero cells (16 vs 9.7 mu M). Computational studies provide a rationale or the antiparasitic order of activity of these analogues and further insight into the role of the substituents at the 3 and 5 positions of the sulfanilamide ring. (c) 2007 Elsevier Ltd. All rights reserved.