5-溴苯并呋喃-2-甲腈 | 35351-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 5-溴苯并呋喃-2-甲腈
• 英文名称: 5-bromo-2-cyanobenzo[b]furan
• 英文别名: 5-bromobenzofuran-2-carbonitrile；5-bromo-2-cyanobenzofuran；5-Brombenzofuran-2-carbonitril；5-bromobenzo[b]furan-2-carbonitrile；5-bromo-3-cyanobenzo[b]furan；5-bromo-1-benzofuran-2-carbonitrile
• CAS: 35351-45-2
• 化学式: C₉H₄BrNO
• mdl: MFCD11574570
• 分子量: 222.041
• InChiKey: SBGMVGYYYFGZJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴苯并呋喃-2-甲腈 以45%的产率得到
  参考文献：
  名称：

  DANN O.; FICK H.; PIETZNER B.; WALKENHORST E.; FERNBACH R.; ZEH D., J. LIEBIGS ANN. CHEM. , 1975, NO 1, 160-194

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴苯并呋喃-2-羧酸 在 ammonium hydroxide 、 氯化亚砜 、 三氯氧磷 作用下， 以 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 5.0h， 生成 5-溴苯并呋喃-2-甲腈
  参考文献：
  名称：

  Benzofuranyl-2-imidazoles as imidazoline I2 receptor ligands for Alzheimer's disease

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113540

文献信息

• Structure-In Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents
  作者：Maurizio Del Poeta、Wiley A. Schell、Christine C. Dykstra、Susan Jones、Richard R. Tidwell、Agnieszka Czarny、Miroslav Bajic、Marina Bajic、Arvind Kumar、David Boykin、John R. Perfect

  DOI：10.1128/aac.42.10.2495

  日期：1998.10

  Twenty analogues of pentamidine, 7 primary metabolites of pentamidine, and 30 dicationic substituted bis-benzimidazoles were screened for their inhibitory and fungicidal activities against Candida albicans and Cryptococcus neoformans . A majority of the compounds had MICs at which 80% of the strains were inhibited (MIC ₈₀ s) comparable to those of amphotericin B and fluconazole. Unlike fluconazole, many of these compounds were found to have potent fungicidal activity. The most potent compound against C. albicans had an MIC ₈₀ of ≤0.09 μg/ml, and the most potent compound against C. neoformans had an MIC ₈₀ of 0.19 μg/ml. Selected compounds were also found to be active against Aspergillus fumigatus , Fusarium solani , Candida species other than C. albicans , and fluconazole-resistant strains of C. albicans and C. neoformans . It is clear from the data presented here that further studies on the structure-activity relationships, mechanisms of action and toxicities, and in vivo efficacies of these compounds are warranted to determine their clinical potential.

  摘要：对于20种戊二胺类似物、7种戊二胺的主要代谢产物以及30种二阳离子取代的双苯并咪唑类化合物进行了筛选，评估它们对念珠菌和隐球菌的抑制和杀真菌活性。大多数化合物的MIC（80%菌株被抑制的最小抑菌浓度）与两性霉素B和氟康唑相当。与氟康唑不同，许多这些化合物表现出强效的杀真菌活性。对于念珠菌而言，最有效的化合物的MIC80为≤0.09μg/ml，对于隐球菌而言，最有效的化合物的MIC80为0.19μg/ml。选择的化合物也对曲霉、索兰镰孢霉、除念珠菌外的其他种类的念珠菌，以及氟康唑耐药菌株的活性。从这里呈现的数据清楚地表明，有必要进行进一步的研究，以确定这些化合物的结构活性关系、作用机制和毒性，以及它们在体内的疗效，以确定它们的临床潜力。
• A highly efficient one-pot reaction of 2-(gem-dibromovinyl)phenols(thiophenols) with K4Fe(CN)6 to 2-cyanobenzofurans(thiophenes)
  作者：Wei Zhou、Wei Chen、Lei Wang

  DOI：10.1039/c2ob25356a

  日期：——

  2-Cyanobenzofurans and 2-cyanobenzothiophenes were prepared through an efficient one-pot Ullmann-reaction/cyanation reaction. In the presence of CuI/Na2CO3–Pd(OAc)2/PPh3 in DMF, the reaction of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)thiophenols with K4Fe(CN)6, as non-toxic and user-friendly cyanating reagent, proceeded smoothly to generate the corresponding 2-cyanobenzofurans and 2-cyanobenzothiophenes

  通过有效的一锅Ullmann反应/氰化反应制备2-氰基苯并呋喃和2-氰基苯并噻吩。在DMF中CuI / Na 2 CO 3 -Pd（OAc）2 / PPh 3的存在下，2-（宝石-二溴乙烯基）苯酚和2-（宝石-二溴乙烯基）苯硫酚与K 4 Fe（CN）6的反应作为无毒且对用户友好的氰化试剂，该试剂可顺利进行，以高收率生成相应的2-氰基苯并呋喃和2-氰基苯并噻吩。
• Antifungal activity of dicationic molecules
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1685836A2

  公开（公告）日：2006-08-02

  Methods of treating fungal infections comprise administering a therapeutically effective amount of a compound described by Formulas [(I)-(II)]. Examples of fungal infections include Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Fusarium solani, and combinations thereof.

  治疗真菌感染的方法包括施用治疗有效量的式[(I)-(II)]所述化合物。真菌感染的例子包括白色念珠菌、新生隐球菌、烟曲霉、梭菌及其组合。
• Efficient Synthesis of a Benzo[<i>b</i>]furan Building Block
  作者：Jaekyoo Lee、Subhash P. Khanapure、Hwa-Ok Kim、Raj (S. B.) Rajur、Bing Li、John D. Williams、Ramdas Pai、Norton P. Peet

  DOI：10.1080/00397910903419902

  日期：2010.10.20

  Unexpected difficulty in the conversion of a bromobenzofuran to the corresponding formylbenzofuran led us to develop a new synthesis for 5-formylbenzo[b]furan-2-carbonitrile (1).
• Synthesis and antifungal evaluation of head-to-head and head-to-tail bisamidine compounds
  作者：Son T. Nguyen、Steven M. Kwasny、Xiaoyuan Ding、John D. Williams、Norton P. Peet、Terry L. Bowlin、Timothy J. Opperman

  DOI：10.1016/j.bmc.2015.07.006

  日期：2015.9

  Herein, we describe the antifungal evaluation of 43 bisamidine compounds, of which 26 are new, having the scaffold [Am]-[HetAr]-[linker]-[HetAr]-[Am], in which [Am] is a cyclic or acyclic amidine group, [linker] is a benzene, pyridine, pyrimidine, pyrazine ring, or an aliphatic chain of two to four carbon, and [HetAr] is a 5,6-bicyclic heterocycle such as indole, benzimidazole, imidazopyridine, benzofuran, or benzothiophene. In the head-to-head series the two [HetAr] units are oriented such that the 5-membered rings are connected through the linker, and in the head-to-tail series, one of the [HetAr] systems is connected through the 6-membered ring; additionally, in some of the head-to-tail compounds, the [linker] is omitted. Many of these compounds exhibited significant antifungal activity against Candida albicans, Candida krusei, Candida glabrata, Candida parapsilosis, and Cryptococcus neoformans (MIC <= 4 mu g/ml). The most potent compounds, for example, P10, P19 and P34, are comparable in antifungal activities to amphotericin B (MIC 0.125 mu g/ml). They exhibited rapid fungicidal activity (>3 log(10) decrease in cfu/ml in 4 h) at concentrations equivalent to 4x the MIC in time kill experiments. The bisamidines strongly inhibited DNA, RNA and cell wall biosynthesis in C. albicans in macromolecular synthesis assays. However, the half-maximal inhibitory concentration for DNA synthesis was approximately 30-fold lower than those for RNA and cell wall biosynthesis. Fluorescence microscopy of intact cells of C. albicans treated with a bisamidine exhibited enhanced fluorescence in the presence of DNA, demonstrating that the bisamidine was localized to the nucleus. The results of this study show that bisamidines are potent antifungal agents with rapid fungicidal activity, which is likely to be the result of their DNA-binding activity. Although it was difficult to obtain a broad-spectrum antifungal compound with low cytotoxicity, some of the compounds (e.g., P9, P14 and P43) exhibited favorable CC50 values against HeLa cells and maintained considerable antifungal activity. (C) 2015 Elsevier Ltd. All rights reserved.