4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino-N-((4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino)phenyl)benzamide | 1615763-09-1

• 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: 4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino-N-((4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino)phenyl)benzamide
• 英文别名: 4-[[(E)-N'-tetrahydropyran-2-yloxycarbamimidoyl]amino]-N-[4-[[(Z)-N'-tetrahydropyran-2-yloxycarbamimidoyl]amino]phenyl]benzamide；4-[[amino-(oxan-2-yloxyamino)methylidene]amino]-N-[4-[[amino-(oxan-2-yloxyamino)methylidene]amino]phenyl]benzamide
• CAS: 1615763-09-1
• 化学式: C₂₅H₃₃N₇O₅
• 分子量: 511.581
• InChiKey: WTMOBKUFONYTEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  167
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino-N-((4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino)phenyl)benzamide 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.0h， 以69%的产率得到4-(2-hydroxyguanidino)-N-(4-(2-hydroxyguanidino)phenyl)benzamide dihydrochloride
  参考文献：
  名称：

  Antiprotozoal activity and DNA binding of N-substituted N-phenylbenzamide and 1,3-diphenylurea bisguanidines

  摘要：

  Two series of N-alkyl, N-alkoxy, and N-hydroxy bisguanidines derived from the N-phenylbenzamide and 1,3-diphenylurea scaffolds were synthesised in three steps from the corresponding 4-amino-N-(4aminophenyl)benzamide and 1,3-bis(4-aminophenyl)urea, respectively. All of the new compounds were evaluated in vitro against T. b. rhodesiense (STIB900) trypomastigotes and Plasmodium falciparum NF54 parasites (erythrocytic stage). N-alkoxy and N-hydroxy derivatives showed weak micromolar range IC50 values against T b. rhodesiense and P. falciparum whereas the N-alkyl analogues displayed submicromolar and low nanomolar IC50 values against R falciparum and Trypanosoma brucei, respectively. Two compounds, 4-(2-ethylguanidino)-N-(4-(2-ethylguanidino)phenyl)benzamide dihydrochloride (7b) and 4-(2-isopropylguanidino)-N-(4-(2-isopropylguanidino)phenyl)benzamide dihydrochloride (7c), which showed favourable drug-like properties and in vivo efficacy (100% cures) in the STIB900 mouse model of acute human African trypanosomiasis represent interesting leads for further in vivo studies. The binding of these compounds to AT-rich DNA was confirmed by surface plasmon resonance (SPR) biosensor experiments. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.083
• 作为产物：
  描述：

  4-(3-ethoxycarbonyl-2-((tetrahydro-2H-pyran-2-yl)oxy)guanidino)-N-(4-(3-ethoxycarbonyl-2-((tetrahydro-2H-pyran-2-yl)oxy)guanidino)phenyl)benzamide 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以85%的产率得到4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino-N-((4-(2-(tetrahydro-2H-pyran-2-yl)oxy)guanidino)phenyl)benzamide
  参考文献：
  名称：

  Antiprotozoal activity and DNA binding of N-substituted N-phenylbenzamide and 1,3-diphenylurea bisguanidines

  摘要：

  Two series of N-alkyl, N-alkoxy, and N-hydroxy bisguanidines derived from the N-phenylbenzamide and 1,3-diphenylurea scaffolds were synthesised in three steps from the corresponding 4-amino-N-(4aminophenyl)benzamide and 1,3-bis(4-aminophenyl)urea, respectively. All of the new compounds were evaluated in vitro against T. b. rhodesiense (STIB900) trypomastigotes and Plasmodium falciparum NF54 parasites (erythrocytic stage). N-alkoxy and N-hydroxy derivatives showed weak micromolar range IC50 values against T b. rhodesiense and P. falciparum whereas the N-alkyl analogues displayed submicromolar and low nanomolar IC50 values against R falciparum and Trypanosoma brucei, respectively. Two compounds, 4-(2-ethylguanidino)-N-(4-(2-ethylguanidino)phenyl)benzamide dihydrochloride (7b) and 4-(2-isopropylguanidino)-N-(4-(2-isopropylguanidino)phenyl)benzamide dihydrochloride (7c), which showed favourable drug-like properties and in vivo efficacy (100% cures) in the STIB900 mouse model of acute human African trypanosomiasis represent interesting leads for further in vivo studies. The binding of these compounds to AT-rich DNA was confirmed by surface plasmon resonance (SPR) biosensor experiments. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.083