1,3-bis{(4-cyano)-phenoxymethyl}benzene | 53658-04-1

• 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-cyano)-phenoxymethyl}benzene
• 英文别名: 4-[[3-[(4-Cyanophenoxy)methyl]phenyl]methoxy]benzonitrile
• CAS: 53658-04-1
• 化学式: C₂₂H₁₆N₂O₂
• 分子量: 340.381
• InChiKey: PXZAKHHVDZRDNJ-UHFFFAOYSA-N

物化性质

• 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：

  1,3-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：
• 作为产物：
  描述：

  4-羟基苯甲腈 、 间二溴苄 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 以79%的产率得到1,3-bis{(4-cyano)-phenoxymethyl}benzene
  参考文献：
  名称：

  使用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结构-活性研究

  摘要：

  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。

  DOI：

  10.1021/acsinfecdis.1c00466

文献信息

• [EN] AMIDINES AND AMIDINE ANALOGS FOR THE TREATMENT OF BACTERIAL INFECTIONS AND POTENTIATION ANTIBIOTICS<br/>[FR] AMIDINES ET ANALOGUES D'AMIDINE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES ET D'ANTIBIOTIQUES DE POTENTIALISATION
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2019241566A1

  公开（公告）日：2019-12-19

  Compounds and methods for the treatment of a bacterial infection or the potentiation of an antibiotic in treating a bacterial infection are described herein.

  本文描述了用于治疗细菌感染或增强抗生素治疗细菌感染的化合物和方法。
• 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.
• Antitumor and Anti-Pneumocystis Carinii Activities of Novel Bisbenzamidines
  作者：Jean Jacques Vanden Eynde、Annie Mayence、Melissa T. Johnson、Tien L. Huang、Margaret S. Collins、Sandra Rebholz、Peter D. Walzer、Melanie T. Cushion、Isaac O. Donkor

  DOI：10.1007/s00044-005-0130-2

  日期：2005.4

  Among a library of 17 bisbenzamidines connected with various linkers, compounds with a flexible pentanediamide (10) or hexanediamide (12) linker were the most potent derivatives against rat Pneumocystis carinii (IC50 values of 3 and 2 nM, respectively) and had the highest selectivity index ratios (GI(50) of human tumor cells/IC50 of rat P. carinii cells) of > 10(4). Seven compounds caused 50% growth inhibition (GI(50)) of tumor cells at concentrations of < 100 mu M while the remaining ten were not cytotoxic. DNA binding affinity (Delta T-m) of the tested compounds did not correlate with either their anti-P. carinii activity or cytotoxicity.
• 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：——