5'-bromo-2,2'-bifuran-5-carbonitrile | 1020847-50-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5'-bromo-2,2'-bifuran-5-carbonitrile
• 英文别名: 5-(5-Bromofuran-2-yl)furan-2-carbonitrile；5-(5-bromofuran-2-yl)furan-2-carbonitrile
• CAS: 1020847-50-0
• 化学式: C₉H₄BrNO₂
• 分子量: 238.04
• InChiKey: ROEMXCYGWUZXEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-bromo-2,2'-bifuran-5-carbonitrile 在 四(三苯基膦)钯 、 盐酸羟胺 、 potassium tert-butylate 、 sodium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 16.0h， 生成 N-acetoxy-5'-[4-(N-acetoxyamidino)-phenyl]-2,2'-bifuran-5-carboxamidine
  参考文献：
  名称：

  Dicationic phenyl-2,2′-bichalcophenes and analogues as antiprotozoal agents

  摘要：

  A series of phenyl-2,2'-bichalcophene diamidines 1a-h were synthesized from the corresponding dinitriles either via a direct reaction with LiN(TMS)(2), followed by deprotection with ethanolic HCl or through the bis-O-acetoxyamidoxime followed by hydrogenation in acetic acid and EtOH over Pd-C. These diamidines show a wide range of DNA affinities as judged from their Delta T-m values which are remarkably sensitive to replacement of a furan unit with a thiophene one. These differences are explained in terms of the effect of subtle changes in geometry of the diamidines on binding efficacy. Five of the eight compounds were highly active (below 6 nM IC50) in vitro against Trypanosoma brucei rhodesiense (T. b. r.) and four gave IC(50)values less than 7 nM against Plasmodium falciparum (P. f.). Only one of the compounds was as effective as reference compounds in the T. b. r. mouse model for the acute phase of African trypanosomiasis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.047
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 乙酸酐 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5'-bromo-2,2'-bifuran-5-carbonitrile
  参考文献：
  名称：

  Ismail, Mohamed A., Journal of Chemical Research, 2006, # 11, p. 733 - 737

  摘要：

  DOI：

文献信息

• Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity
  作者：Abdelbasset A. Farahat、Mohamed A. Ismail、Arvind Kumar、Tanja Wenzler、Reto Brun、Ananya Paul、W. David Wilson、David W. Boykin

  DOI：10.1016/j.ejmech.2017.10.056

  日期：2018.1

  with the DNA minor groove and generally show excellent in vitro antitrypanosomal activity. The diamidino-indole derivatives also showed excellent in vitro antimalarial activity while their benzimidazole counterparts were generally less active. Compound 7c was highly active in vivo and cured all mice infected with Trypanosoma brucei rhodesiense, a model that mimics the acute stage of African sleeping sickness

  制备了一系列新的吲哚和苯并咪唑二氟噻吩二am衍生物，以研究它们对引起非洲昏睡病和疟疾的热带寄生虫的抗菌活性。合成目标二am所需的二氰基吲哚是通过Stille偶联反应获得的，而双氰基苯并咪唑中间体是通过不同醛与4-氰基1,2-二氨基苯胺的缩合/环化反应制得的。使用不同的am合成方法，即双三甲基甲硅烷基氨基锂（LiN [Si（CH3）3 ] 2）和Pinner方法制备二am。新的二am类化合物的两种类型（吲哚和苯并咪唑）衍生物都与DNA小沟紧密结合，通常显示出优异的体外抗锥虫活性。二mid基吲哚衍生物还显示出优异的体外抗疟活性，而它们的苯并咪唑对应物通常活性较低。化合物7c在体内具有很高的活性，可治愈所有感染了布氏锥虫的小鼠，该小鼠模仿非洲昏睡病的急性期，剂量低至4×5 mg / kg ip，因此7c在体内比在体内更有效喷他idine。
• Green Fluorescent Diamidines as Diagnostic Probes for Trypanosomes
  作者：Federica Giordani、Manoj Munde、W. David Wilson、Mohamed A. Ismail、Arvind Kumar、David W. Boykin、Michael P. Barrett

  DOI：10.1128/aac.02024-13

  日期：2014.3

  Light-emitting diode (LED) fluorescence microscopy offers potential benefits in the diagnosis of human African trypanosomiasis and in other aspects of diseases management, such as detection of drug-resistant strains. To advance such approaches, reliable and specific fluorescent markers to stain parasites in human fluids are needed. Here we describe a series of novel green fluorescent diamidines and their suitability as probes with which to stain trypanosomes.

  摘要 发光二极管（LED）荧光显微镜为诊断人类非洲锥虫病和疾病管理的其他方面（如检测耐药菌株）提供了潜在的益处。要推进这些方法，需要可靠而特异的荧光标记物来染色人体液中的寄生虫。在此，我们介绍了一系列新型绿色荧光二脒及其作为探针对锥虫进行染色的适用性。
• Anticancer activity, dual prooxidant/antioxidant effect and apoptosis induction profile of new bichalcophene-5-carboxamidines
  作者：Mohamed A. Ismail、Amr Negm、Reem K. Arafa、Ehab Abdel-Latif、Wael M. El-Sayed

  DOI：10.1016/j.ejmech.2019.02.062

  日期：2019.5

  A series of thirteen new aryl/hetarylbichalcophene-5-carboxamidines was prepared and screened for an in vitro anti-proliferative activity against sixty cancer cell lines. The tested monocationic bichalcophenes displayed promising potent anticancer activity against most cancer cell lines with GI(50) values of 1.34 -3.09 mu M. The most potent compound was derivative 8 (median GI(50) and TGI values of 1.34 and 3.23 mu M, respectively), being also the least cytotoxic in this bichalcophene series with an LC50 of 77.6 mu M. The most responsive cancer cell lines were leukemia (SR and K-562) and colon (HCT-15 and HT29) with GI(50) in the sub-micromolar range. The effect of the tested bichalcophenes on normal human lung fibroblast (WI-38) cell line showed that they exerted their antiproliferative activity outside the realms of causing any toxicity in normal cells. To study apoptotic profiles of representatives of this class, compounds 4h, 4i, and 8 were found to cause significant reductions in cdk1 expression in HCT-116 colon cells by 46, 79, and 84%, respectively versus 52% reduction by 5- Flourouracil (5-FU). These three compounds were also unique being the only derivatives that significantly elevated the expression of p53 by similar to 2, 4, and 5 folds, respectively. The tested bichalcophenes exhibited moderate to potent antioxidant activity in DPPH and ABTS as well as hydroxyl radical scavenging assays. Moreover, compounds IIIb, IIIc, 4c, and 4i, showed the highest pro-oxidant activity. Finally, to aid future endeavors for optimization of this series, a 5 descriptor 2D-QSAR model was derived from the common physicochemical parameters of these bichalcophenes and the external validation proved the model's good predictive efficiency. (C) 2019 Elsevier Masson SAS. All rights reserved.