4,4'-(thiophene-2,5-diyl)dibenzonitrile | 55368-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-(thiophene-2,5-diyl)dibenzonitrile
• 英文别名: 4,4'-thiene-2,5-diyldibenzonitrile；2,5-Bis(p-cyanophenyl)thiophene；2,5-bis(4-cyanophenyl)thiophene；2,5-bis[4-cyanophenyl]thiophene；2,5-di(4-cyanophenyl)-thiophene；4,4'-thiophene-2,5-diyl-bis-benzonitrile；4-[5-(4-cyanophenyl)thiophen-2-yl]benzonitrile
• CAS: 55368-38-2
• 化学式: C₁₈H₁₀N₂S
• 分子量: 286.357
• InChiKey: HKDJGRLOXRXWOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4'-(thiophene-2,5-diyl)dibenzonitrile 在 lithium hexamethyldisilazane 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 以97%的产率得到2,5-bis-(4-amidinophenyl)thiophene hydrochloride
  参考文献：
  名称：

  The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease

  摘要：

  Botulinum neurotoxins (BoNTs), composed of a family of seven serotypes (categorized A-G), are the deadliest of known biological toxins. The activity of the metalloprotease, light chain (LC) component of the toxins is responsible for causing the life-threatening paralysis associated with the disease botulism. Herein we report significantly more potent analogs of novel, lead BoNT serotype A LC inhibitor 2,5-bis(4-amidinophenyl)thiophene (K-i = 10.881 mu M +/- 0.90 mu M). Specifically, synthetic modifications involved simultaneously replacing the lead inhibitor's terminal bis-amidines with secondary amines and the systematic tethering of 4-amino-7-chloroquinoline substituents to provide derivatives with K-i values ranging from 0.302 mu M (+/- 0.03 mu M) to 0.889 mu M (+/- 0.11 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.043
• 作为产物：
  描述：

  2,5-二溴噻吩 、 4-(4,4,5,5-四甲基-1,3,2-二恶硼)苯甲腈 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 4,4'-(thiophene-2,5-diyl)dibenzonitrile
  参考文献：
  名称：

  使用共价三嗪聚合物的无金属光催化加氢。

  摘要：

  生物质衍生的有机分子的光催化氢化将太阳能转化为高能密度化学键。本文报道了一种具有噻吩的共价三嗪聚合物作为光催化剂的制备方法，该聚合物具有独特的供体-受体单元，可用于不饱和有机分子的无金属光催化加氢。在可见光照射下，聚合光催化剂能够以约2 mmol g -1  h -1的生产率将马来酸转化为琥珀酸，并以约0.5 mmol g -1  h的速率将糠醛转化为糠醇。-1。还测量了催化剂的稳定性和可回收性。鉴于聚合物光催化剂的结构多样性及其易于调节的光学和电子特性，无金属光催化氢化代表了一种非常有前途的太阳能转化方法。

  DOI：

  10.1002/anie.202006618

文献信息

• Direct 2-Arylation of Thiophene Using Low Loading of a Phosphine-Free Palladium Catalyst
  作者：Souhila Bensaid、Julien Roger、Kassem Beydoun、David Roy、Henri Doucet

  DOI：10.1080/00397911.2010.518781

  日期：2011.12.1

  observed that through the use of only 0.2 mol% Pd(OAc)2 as the catalyst, a range of aryl bromides undergoes coupling via a C-H bond activation/functionalization reaction with thiophene to give 2-arylated thiophenes in good yields. In most cases, only traces of polyarylated thiophenes were detected when a large excess of thiophene was employed. This air-stable catalyst can be used with a wide variety of

  摘要 芳基卤化物与噻吩的直接偶联对于可持续发展将是一个相当大的优势，因为只有 HBr 与作为副产物的碱结合形成，并且制备这些化合物的步骤数量少于更经典的偶联反应。我们观察到，通过仅使用 0.2 mol% Pd(OAc)2 作为催化剂，一系列芳基溴化物通过 CH 键活化/官能化反应与噻吩发生偶联，以良好的产率得到 2-芳基化噻吩。在大多数情况下，当使用大量过量的噻吩时，只能检测到痕量的多芳基噻吩。这种空气稳定的催化剂可与多种芳基溴化物一起使用。
• Synthesis and evaluation of thiophene-based guanylhydrazones (iminoguanidines) efficient against panel of voriconazole-resistant fungal isolates
  作者：Vladimir Ajdačić、Lidija Senerovic、Marija Vranić、Marina Pekmezovic、Valentina Arsic-Arsnijevic、Aleksandar Veselinovic、Jovana Veselinovic、Bogdan A. Šolaja、Jasmina Nikodinovic-Runic、Igor M. Opsenica

  DOI：10.1016/j.bmc.2016.01.058

  日期：2016.3

  inhibited C. albicans yeast to hyphal transition, essential for its biofilm formation, while 11 and 18 were able to disperse preformed Candida biofilms. All guanylhydrazones showed the equal potential to interact with genomic DNA of C. albicans in vitro, thus indicating a possible mechanism of their action, as well as possible mechanism of observed cytotoxic effects. Tested compounds did not have significant

  使用简单的两步程序以高收率合成了一系列新的基于噻吩的胍基hy​​dr（亚氨基胍）。与临床使用的药物伏立康唑相比，针对多种医学上重要的真菌菌株（包括酵母，霉菌和皮肤真菌）对化合物的抗真菌活性进行了评估。还使用人肺成纤维细胞系和溶血测定法测定了化合物的细胞毒性。所有鸟嘌呤showed均显示出对多种临床上重要的念珠菌，烟曲霉，尖孢镰刀菌，犬小孢子菌和毛癣菌的广谱活性。，在某些情况下与伏立康唑的活性相当或更好。更重要的是，化合物10，11，13，14，18和21表现出对耐伏立康唑，优异的活性白色念珠菌CA5具有非常低的最低抑菌浓度（MIC）值<2微克毫升-1。苯环上带有溴的衍生物14是最有效的化合物，MIC的范围为0.25至6.25μgmL -1。然而，双脒腙18在治疗指数值方面显示出更好的选择性。对斑马鱼的体内胚胎毒性（斑马鱼）显示的改进的毒性谱11，14和18相比，该伏立康唑。大多数胍hydr
• Asymmetric Covalent Triazine Framework for Enhanced Visible‐Light Photoredox Catalysis via Energy Transfer Cascade
  作者：Wei Huang、Jeehye Byun、Irina Rörich、Charusheela Ramanan、Paul W. M. Blom、Hao Lu、Di Wang、Lucas Caire da Silva、Run Li、Lei Wang、Katharina Landfester、Kai A. I. Zhang

  DOI：10.1002/anie.201801112

  日期：2018.7.2

  design of an asymmetric covalent triazine framework as an efficient organic single‐component semiconductor photocatalyst. Four different molecular donor–acceptor domains are obtained within the network, leading to enhanced photogenerated charge separation via an intramolecular energy transfer cascade. The photocatalytic efficiency of the asymmetric covalent triazine framework is superior to that of

  可以构建复杂的多组分半导体光催化剂，该催化剂通过多次电荷和能量转移表现出增强的催化效率，从而模仿自然界中的光系统。相反，单组分半导体光催化剂的效率通常由于光生激子的快速重组而受到限制。在这里，我们报告了一种不对称共价三嗪骨架的设计，该骨架是一种有效的有机单组分半导体光催化剂。在网络中获得了四个不同的分子供体-受体域，从而通过分子内能量转移级联增强了光生电荷的分离。不对称共价三嗪骨架的光催化效率优于其对称对应物。
• Palladium-catalysed direct arylation of thiophenes tolerant to silyl groups
  作者：Lu Chen、Julien Roger、Christian Bruneau、Pierre H. Dixneuf、Henri Doucet

  DOI：10.1039/c0cc04302h

  日期：——

  The palladium catalysed 5-arylation of 2-(trimethylsilyl)thiophene with aryl bromides via C–H bond functionalisation allows the synthesis of arylated silylthiophenes in only one step.

  钯催化的2-(三甲基硅基)噻吩与芳基溴化物的C-H键官能化的5-芳基化反应允许仅通过一步合成芳基化硅基噻吩。
• Antileishmanial Activities of Several Classes of Aromatic Dications
  作者：James J. Brendle、Abram Outlaw、Arvind Kumar、David W. Boykin、Donald A. Patrick、Richard R. Tidwell、Karl A. Werbovetz

  DOI：10.1128/aac.46.3.797-807.2002

  日期：2002.3

  Aromatic dicationic molecules possess impressive activity against a broad spectrum of microbial pathogens, including Pneumocystis carinii , Cryptosporidium parvum , and Candida albicans . In this work, 58 aromatic cations were examined for inhibitory activity against axenic amastigote-like Leishmania donovani parasites. In general, the most potent of the compounds were substituted diphenyl furan and thiophene dications. 2,5-Bis-(4-amidinophenyl)thiophene was the most active compound. This agent displayed a 50% inhibitory concentration (IC ₅₀ ) of 0.42 ± 0.08 μM against L. donovani and an in vitro antileishmanial potency 6.2-fold greater than that of the clinical antileishmanial dication pentamidine and was 155-fold more toxic to the parasites than to a mouse macrophage cell line. 2,4-Bis-(4-amidinopheny)furan was twice as active as pentamidine (IC ₅₀ , 1.30 ± 0.21 μM), while 2,5-bis-(4-amidinopheny)furan and pentamidine were essentially equipotent in our in vitro antileishmanial assay. Carbazoles, dibenzofurans, dibenzothiophenes, and benzimidazoles containing amidine or substituted amidine groups were generally less active than the diphenyl furans and thiophenes. In all cases, aromatic dications possessing strong antileishmanial activity were severalfold more toxic to the parasites than to a cultured mouse macrophage cell line. These structure-activity relationships demonstrate the potent antileishmanial activity of several aromatic dications and provide valuable information for the future design and synthesis of more potent antiparasitic agents.

  摘要 芳香族二阳离子分子对多种微生物病原体具有令人印象深刻的活性，包括 卡氏肺囊虫 , 副猪隐孢子虫 和 白色念珠菌 .在这项工作中，研究了 58 种芳香族阳离子对轴突吸虫类 利什曼原虫 寄生虫的抑制活性。一般来说，最有效的化合物是取代的二苯基呋喃和噻吩二阳离子。2,5-双（4-脒基苯基）噻吩是活性最强的化合物。这种药剂显示出 50%的抑制浓度（IC 50 ）为 0.42 ± 0.08 μM 多诺万 体外抗利什曼药效是临床抗利什曼药喷他脒的 6.2 倍，对寄生虫的毒性是小鼠巨噬细胞系的 155 倍。2,4-双（4-脒苯基）呋喃的活性是喷他脒的两倍（IC 50 1.30 ± 0.21 μM），而在体外抗利什曼病试验中，2,5-双（4-脒苯基）呋喃和喷他脒的活性基本相当。含有脒基或取代脒基的咔唑、二苯并呋喃、二苯并噻吩和苯并咪唑的活性通常低于二苯基呋喃和噻吩。在所有情况下，具有较强抗利什曼活性的芳香族二元酸盐对寄生虫的毒性比对培养的小鼠巨噬细胞系的毒性高出数倍。这些结构-活性关系证明了几种芳香族配位化合物具有很强的抗利什曼病活性，并为今后设计和合成更强的抗寄生虫药物提供了宝贵的信息。