1,4-bis(4-cyano-phenoxymethyl)benzene | 53658-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(4-cyano-phenoxymethyl)benzene
• 英文别名: 4,4'-[1,4-Phenylenebis(methyleneoxy)]dibenzonitrile；4-[[4-[(4-cyanophenoxy)methyl]phenyl]methoxy]benzonitrile
• CAS: 53658-03-0
• 化学式: C₂₂H₁₆N₂O₂
• 分子量: 340.381
• InChiKey: KISAWPXPYQSTQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C
• 沸点：
  572.6±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-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50%的产率得到1,4-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：
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 sodium 4-cyanophenolate 在 乙醇 作用下， 生成 1,4-bis(4-cyano-phenoxymethyl)benzene
  参考文献：
  名称：

  Ashley et al., Journal of the Chemical Society, 1942, p. 103,107

  摘要：

  DOI：

文献信息

• Structure–Activity Studies with Bis-Amidines That Potentiate Gram-Positive Specific Antibiotics against Gram-Negative Pathogens
  作者：Charlotte M. J. Wesseling、Cornelis J. Slingerland、Shanice Veraar、Samantha Lok、Nathaniel I. Martin

  DOI：10.1021/acsinfecdis.1c00466

  日期：2021.12.10

  observed synergistic activity reported for pentamidine, while further assessing the capacity for structurally similar bis-amidines to also potentiate Gram-positive specific antibiotics against Gram-negative pathogens. Among the bis-amidines prepared, a number of them were found to exhibit synergistic activity greater than pentamidine. These synergists were shown to effectively potentiate the activity of

  喷他脒是一种 FDA 批准的抗寄生虫药，最近被鉴定为一种外膜破坏增效剂，可增强红霉素、利福平和新生霉素对革兰氏阴性菌的作用。同一项研究还描述了使用市售喷他脒类似物的初步构效关系。我们在这里报告了受喷他脒启发的更广泛的双脒组的设计、合成和评估。本研究既验证了先前观察到的喷他脒的协同活性，同时进一步评估了结构相似的双脒增强革兰氏阳性特异性抗生素对抗革兰氏阴性病原体的能力。在制备的双脒中，发现其中一些表现出比喷他脒更大的协同活性。鲍曼不动杆菌、肺炎克雷伯菌、铜绿假单胞菌和大肠杆菌，包括耐多粘菌素和碳青霉烯的菌株。
• 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.
• Novel bisbenzamidines as potential drug candidates for the treatment of Pneumocystis carinii pneumonia
  作者：Jean Jacques Vanden Eynde、Annie Mayence、Tien L Huang、Margaret S Collins、Sandra Rebholz、Peter D Walzer、Melanie T Cushion

  DOI：10.1016/j.bmcl.2004.06.034

  日期：2004.9

  A series of pentamidine congeners has been synthesized and screened for their in vitro activity against Pneumocystis carinii. Among the tested compounds, bisbenzamidines linked by a flexible pentanediamide or hexanediamide chain (7 and 9) emerged as exceptionally potent agents that were more effective and less toxic than pentamidine in the assays described in this study. (C) 2004 Elsevier Ltd. All rights reserved.
• 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：——
• Ashley et al., Journal of the Chemical Society, 1942, p. 103,107
  作者：Ashley et al.

  DOI：——

  日期：——