5'-溴-[2,2'-联噻吩]-5-甲腈 | 176787-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 中文名称: 5'-溴-[2,2'-联噻吩]-5-甲腈
• 英文名称: 5'-bromo-2,2'-bithiophene-5-carbonitrile
• 英文别名: 5-bromo-2,2’-bithiophene-5’-carbonitrile；5'-Bromo-[2,2'-bithiophene]-5-carbonitrile；5-(5-bromothiophen-2-yl)thiophene-2-carbonitrile
• CAS: 176787-96-5
• 化学式: C₉H₄BrNS₂
• 分子量: 270.173
• InChiKey: OHVCHDZJRUEOKH-UHFFFAOYSA-N

物化性质

• 熔点：
  161.0 to 165.0 °C
• 沸点：
  352.0±42.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  80.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-溴-[2,2'-联噻吩]-5-甲腈 在 四(三苯基膦)钯 六正丁基二锡 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到[2,2':5',2'':5'',2'''-quaterthiophene]-5,5'''-dicarbonitrile
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 在 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 乙酸酐 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 5'-溴-[2,2'-联噻吩]-5-甲腈
  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。
• Synthesis, Characterisation of (Arene)tricarbonylchromium Complexes Linked to Cationic Fe and Ru Derivatives and Studies of First Hyperpolarisabilities by Hyper‐Rayleigh Scattering
  作者：Maria Helena Garcia、Sophie Royer、Maria Paula Robalo、Alberto Romão Dias、Jean‐Philippe Tranchier、René Chavignon、Damien Prim、Audrey Auffrant、Françoise Rose‐Munch、Eric Rose、Jacqueline Vaissermann、André Persoons、Inge Asselberghs

  DOI：10.1002/ejic.200300190

  日期：2003.11

  Ru organometallic π-donor fragments were linked by an extended π system to the acceptor Cr(CO)3 fragment. The effect of π back-donation involving the second Fe or Ru metal centre and the π* orbitals of the N≡C-coordinated group, was probed by the ν(N≡C) stretching bands on the IR spectra and also by NMR spectroscopic data. The planarity, largely due to the π-electron resonance, found on the solid state

  为了研究非线性光学性质，特别是双核有机金属配合物的二阶效应，一系列新的阳离子双核 [MCp(DPPE)N≡C−(spacer)−C≡C−C6H5Cr(CO)3 ]+[PF6]- 化合物和单核前体 [N≡C-(spacer)-C≡ C-C6H5Cr(CO)3] 已经合成 [其中 M = FeII 或 RuII; Cp = η5-C5H5 和间隔基 = 苯环 (C6H4)、噻吩、(C4H2S) 或联噻吩 (C4H2S)2]。Fe 或 Ru 有机金属 π 供体片段通过扩展的 π 系统连接到受体 Cr(CO)3 片段。涉及第二个 Fe 或 Ru 金属中心和 N≡C 配位基团的 π* 轨道的 π 回馈效应通过 ν(N≡C) 拉伸带对 IR 光谱以及核磁共振光谱进行了探测数据。平面性，主要是由于 π 电子共振，在单核配合物的固态结构上发现 [N≡C-C6H5-C≡C-(η6-C6H5)Cr(CO)3]
• Toward the Rational Design of Conjugated Oligomers and Polymers: Systematic Study of the Substituent Effect in Oligothiophenes
  作者：Natalia Zamoshchik、Yana Sheynin、Michael Bendikov

  DOI：10.1002/ijch.201400010

  日期：2014.6

  A systematic study of substituent electronic effects on a number of oligothiophene properties was performed using well‐defined oligothiophenes of various chain lengths that were monosubstituted with classical electron‐withdrawing or ‐donating groups. The main focus was to understand how the effect of a substituent on one thiophene ring was transmitted through the other thiophene rings in the oligomer

  系统地研究了取代基电子对许多低聚噻吩性质的影响，使用了定义明确的，具有不同链长的低聚噻吩，它们被经典的吸电子或供电子基团单取代。主要焦点是了解低聚物中取代基对一个噻吩环的影响如何通过另一个噻吩环传递。通过光学吸收和发射光谱以及通过循环伏安法研究了物理和电化学性质。实验数据得到HOMOLUMO间隙，电荷分布，键长交替和13的理论计算的补充1 H NMR谱。我们表明，取代对取代的环具有重要的电子效应；但是，这种效果在共轭作用下会大大降低。首次使用Hammett方程对定义明确的长共轭体系中的取代基效应进行了半定量评估。
• 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.
• Dicationic phenyl-2,2′-bichalcophenes and analogues as antiprotozoal agents
  作者：Mohamed A. Ismail、Serry A. El Bialy、Reto Brun、Tanja Wenzler、Rupesh Nanjunda、W. David Wilson、David W. Boykin

  DOI：10.1016/j.bmc.2010.11.047

  日期：2011.1

  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.