1,3-Bis(4-amidoximinophenoxymethyl)benzene | 118499-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-Bis(4-amidoximinophenoxymethyl)benzene
• 英文别名: 1,3-bis[(4-{N2-hydroxy}amidino)phenoxymethyl]benzene；N'-hydroxy-4-[[3-[[4-(N'-hydroxycarbamimidoyl)phenoxy]methyl]phenyl]methoxy]benzenecarboximidamide
• CAS: 118499-85-7
• 化学式: C₂₂H₂₂N₄O₄
• 分子量: 406.441
• InChiKey: BXFZFJYOFCSYLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-Bis(4-amidoximinophenoxymethyl)benzene 、 硫酸二甲酯 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以59%的产率得到1,3-bis[4-(N2-methoxyamidino)phenoxymethyl]benzene
  参考文献：
  名称：

  Synthesis and antiprotozoal activities of dicationic bis(phenoxymethyl)benzenes, bis(phenoxymethyl)naphthalenes, and bis(benzyloxy)naphthalenes

  摘要：

  A series of 37 dicationically substituted bis(phenoxymethyl)benzene bis(phenoxymethyl)naphthalene, and bis(benzyloxy)naphthalene analogues of pentamidine was prepared and evaluated for antiprotozoal activities and cytotoxicity in in vitro. 1,3-Bis(4-amidinophenoxymethyl)benzene (1) was the most active against Trypanosoma brucei rhodesiense (IC50 = 2.1 nM). 1,3-Bis[4-(N-isopropylamidino) phenoxymethyl]benzene (2) was most active against Plasmodium falciparum (IC50 = 3.6 nM) and displayed a selectivity index more than 50 times greater than that of pentamidine. Several other compounds displayed lower antiplasmodial IC50 values and higher selectivity indices relative to pentamidine. 1,4-Bis(4-amidinophenoxymethyl)benzene (14) was the most active against Leishmania donovani (IC50 = 1.3 mu M). Compound 2 displayed the greatest activity against T b. rhodesiense in vivo, curing three of four infected mice dosed intraperitoneally at 5 mg/kg x 4 days. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.014
• 作为产物：
  描述：

  1,3-bis{(4-cyano)-phenoxymethyl}benzene 在 吡啶 、 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以65%的产率得到1,3-Bis(4-amidoximinophenoxymethyl)benzene
  参考文献：
  名称：

  Chauhan, P. M. S.; Niyer, R.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 38 - 42

  摘要：

  DOI：

文献信息

• Chauhan, P. M. S.; Niyer, R.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 38 - 42
  作者：Chauhan, P. M. S.、Niyer, R.、Bhakuni, D. S.、Shankhdhar, V.、Guru, P.Y.、Sen, A. B.

  DOI：——

  日期：——
• CHAUHAN, P. M. S.;IYER, R. N.;BHAKUNI, D. S.;SHANKHDHAR, V.;GURU, P. Y.;S+, INDIAN J. CHEM. B, 27,(1988) N 1, 38-42
  作者：CHAUHAN, P. M. S.、IYER, R. N.、BHAKUNI, D. S.、SHANKHDHAR, V.、GURU, P. Y.、S+

  DOI：——

  日期：——
• Synthesis and antiprotozoal activities of dicationic bis(phenoxymethyl)benzenes, bis(phenoxymethyl)naphthalenes, and bis(benzyloxy)naphthalenes
  作者：Donald A. Patrick、Stanislav A. Bakunov、Svetlana M. Bakunova、E.V.K. Suresh Kumar、Heidi Chen、Susan Kilgore Jones、Tanja Wenzler、Todd Barzcz、Karl A. Werbovetz、Reto Brun、Richard R. Tidwell

  DOI：10.1016/j.ejmech.2009.03.014

  日期：2009.9

  A series of 37 dicationically substituted bis(phenoxymethyl)benzene bis(phenoxymethyl)naphthalene, and bis(benzyloxy)naphthalene analogues of pentamidine was prepared and evaluated for antiprotozoal activities and cytotoxicity in in vitro. 1,3-Bis(4-amidinophenoxymethyl)benzene (1) was the most active against Trypanosoma brucei rhodesiense (IC50 = 2.1 nM). 1,3-Bis[4-(N-isopropylamidino) phenoxymethyl]benzene (2) was most active against Plasmodium falciparum (IC50 = 3.6 nM) and displayed a selectivity index more than 50 times greater than that of pentamidine. Several other compounds displayed lower antiplasmodial IC50 values and higher selectivity indices relative to pentamidine. 1,4-Bis(4-amidinophenoxymethyl)benzene (14) was the most active against Leishmania donovani (IC50 = 1.3 mu M). Compound 2 displayed the greatest activity against T b. rhodesiense in vivo, curing three of four infected mice dosed intraperitoneally at 5 mg/kg x 4 days. (C) 2009 Elsevier Masson SAS. All rights reserved.