5-cyano-2-(4-methoxyphenyl)-1H-benzimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-cyano-2-(4-methoxyphenyl)-1H-benzimidazole
• 英文别名: 2-(4-methoxyphenyl)-3H-benzimidazole-5-carbonitrile
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: JTDTWUAEZBPWDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-cyano-2-(4-methoxyphenyl)-1H-benzimidazole 在 aluminum nickel 甲酸 作用下， 以 硝基苯 为溶剂， 反应 4.0h， 生成 2'-(4-Methoxy-phenyl)-1H,3'H-[2,5']bibenzoimidazolyl-5-carbonitrile
  参考文献：
  名称：

  Synthesis and Evaluation of Terbenzimidazoles as Topoisomerase I Inhibitors

  摘要：

  The synthesis and pharmacological activity of a series of terbenzimidazoles are described. The ability of these derivatives to induce DNA cleavage in the presence of topoisomerase I was evaluated in vitro. These analogs were also assayed for their cytotoxicity in RPMI 8402 cells and the camptothecin-resistant CPT-K5 cells. In addition the potential for these compounds to serve as substrates for MDR1 was also determined. Several terbenzimidazoles exhibited similar cytotoxicity against variants of human tumor cells that either overexpress MDR1 or are camptothecin-resistant.

  DOI：

  10.1021/jm00018a024
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲腈 在 palladium on activated charcoal sodium disulfite 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 130.0 ℃ 、275.79 kPa 条件下， 反应 4.0h， 生成 5-cyano-2-(4-methoxyphenyl)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against candida species

  摘要：

  New 2-substituted-phenyl-1H-benzimidazole-5-carboxylic acids (35, 38), ethyl-5-carboxylate (36), -5-carboxamides (37, 39),-5-carboxaldeliyde (42), -5-chloro (40), -5-trifluoromethyl (41), and -5-carbonitriles (44-53, 55-67), -6-carbonitrilc (54) were prepared and evaluated in vitro against Candida species. The cyano substituted compounds 53, 57, 58 and 61 exhibited the greatest activity with MIC values of 3.12 mug/mL, values similar to that of fluconazole. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00103-7

文献信息

• New route for the synthesis of benzimidazoles by a one-pot multistep process with mono and bifunctional solid catalysts
  作者：Violeta R. Ruiz、Avelino Corma、María J. Sabater

  DOI：10.1016/j.tet.2009.11.048

  日期：2010.1

  One-pot multistep reactions involving a new environmentally friendly catalytic procedure have been developed for the synthesis of benzimidazoles. Benzimidazole derivatives with biological and pharmaceutical interest have been prepared by a one-pot four step process with a solid catalyst containing basic and oxidation sites. The four steps refer to: (a) oxidation of the alcohol; (b) cyclocondensation

  已开发出涉及新型环境友好催化程序的一锅多步反应，用于合成苯并咪唑。具有生物学和药学意义的苯并咪唑衍生物已经通过一锅四步法用含有碱性和氧化位点的固体催化剂制备。这四个步骤涉及：（a）醇的氧化；（b）与邻苯二胺形成的醛的环缩合；（c）碳氮键的氧化；（d）N烷基化反应。通过合成具有抗病毒活性的1,2-二取代的苯并咪唑衍生物可以说明这一过程。
• DNA sequence-selective monoheterocyclic analog of Hoechst 33258: cytotoxicity and antiparasitic properties
  作者：Sameer Chavda、Kristen Dittenhafer、Kristy Wu、Curtis Merrick、Dereje Desta、Emily Cordes、Balaji Babu、Samuel Tzou、Olivia Brockway、Robert Sjoholm、Moses Lee

  DOI：10.1515/hc.2010.004

  日期：2010.1.1

  Abstract The biophysical and biological evaluations of DNA minor groove binding AT sequence selective benzimidazole analogs of Hoechst 33258 which contain a p-anisyl, a p-[bis(2-chloroethyl)amino]phenyl or a p-anisyl and an amidine moiety are discussed. The preference for all three compounds for the 5′-AAATTT-3′ sequence was ascertained by thermal denaturation and circular dichroism studies. The mustard-containing

  摘要 讨论了 Hoechst 33258 的 DNA 小沟结合 AT 序列选择性苯并咪唑类似物的生物物理学和生物学评价，该类似物含有对茴香基、对[双（2-氯乙基）氨基]苯基或对茴香基和脒部分。 . 通过热变性和圆二色性研究确定了所有三种化合物对 5'-AAATTT-3' 序列的偏好。发现含芥末化合物4比不含芥末化合物的化合物对培养物中生长的鼠癌细胞具有更高的细胞毒性。DNA烷基化不是抗利什曼原虫活性所必需的。
• A Versatile Method for the Synthesis of Benzimidazoles from <i>o</i>-Nitroanilines and Aldehydes in One Step via a Reductive Cyclization
  作者：Donglai Yang、Demosthenes Fokas、Jingzhou Li、Libing Yu、Carmen Baldino

  DOI：10.1055/s-2004-834926

  日期：——

  versatile method for the synthesis of benzimidazoles was achieved in one step via the Na 2 S 2 O 4 reduction of o-nitroanilines in the presence of aldehydes. Heating a solution of o-nitroaniline (1c) and an aldehyde in EtOH or another appropriate solvent, in the presence of aqueous or solid Na 2 S 2 O 4 , provided facile access to a series of 2-substituted N-H benzimidazoles 5a-m containing a wide range of

  通过在醛的存在下通过Na 2 S 2 O 4 还原邻硝基苯胺，一步实现了一种高效且通用的苯并咪唑合成方法。在存在水性或固体 Na 2 S 2 O 4 的情况下，加热邻硝基苯胺 (1c) 和醛在 EtOH 或其他合适溶剂中的溶液，可轻松获得一系列 2-取代的 NH 苯并咪唑 5a-m，其中含有广泛的官能团并不总是与现有的合成方法兼容。该方法也已分别通过相应的 N-取代的硝基苯胺 13a-e 的环化应用于 N-烷基和 N-芳基苯并咪唑 6a-f 的区域选择性合成。此外，该方法成功地应用于合成其他含咪唑杂环体系如1H-咪唑[4,
• Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons
  作者：Jung Sun Kim、Qun Sun、Barbara Gatto、Chiang Yu、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/0968-0896(96)00047-8

  日期：1996.4

  the highest activity and was significantly more active than the 4-nitro positional isomer. The 5- and 6-nitro derivatives of 2-(4-methoxyphenyl) benzoxazole, 2-(4-methoxyphenyl)benzothiazole, and 2-(4-methoxyphenyl)indole were synthesized and their relative activity as topoisomerase I inhibitors determined. None of these heterocyclic analogues were effective in significantly inhibiting cleavable-complex

  合成了一系列取代的2-（4-甲氧基苯基）-1H-苯并咪唑类，并作为拓扑异构酶I的抑制剂进行了评估。存在5-甲酰基-，5-（氨基羰基）-或5-硝基（即取代基）能够充当氢键受体的分子）与选择的衍生物抑制拓扑异构酶I的潜力相关。与联苯并咪唑和叔苯并咪唑相反，作为拓扑异构酶I毒物具有活性的取代苯并咪唑显示出最低的DNA亲和力或没有DNA亲和力。5-硝基-2-（4-甲氧基苯基）-1H-苯并咪唑显示出最高的活性，并且比4-硝基位置异构体具有更高的活性。2-（4-甲氧基苯基）苯并恶唑，2-（4-甲氧基苯基）苯并噻唑的5-和6-硝基衍生物 合成了2-（4-甲氧基苯基）吲哚和2-（4-甲氧基苯基）吲哚，它们作为拓扑异构酶I抑制剂的相对活性。这些杂环类似物在DNA和拓扑异构酶I的存在下均不能有效地抑制可裂解复合物的形成，这表明与这些取代的苯并咪唑与酶或酶-DNA复合物的相互作用相关的高度结构特异性。在评估它们
• Efficient heterogeneous silver nanoparticles catalyzed one-pot synthesis of 5-substituted 1H-tetrazoles
  作者：Pavnesh Mani、Chiranjeev Sharma、Satyanand Kumar、Satish Kumar Awasthi

  DOI：10.1016/j.molcata.2014.05.008

  日期：2014.10

  Silver nanoparticles (AgNPs), characterized by TEM, EDX and UV studies were used as an efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles from various nitriles possessing different functional groups in excellent yields. All title compounds were characterized by spectroscopy (H-1 NMR, C-13 NMR and IR) and crystallography. (C) 2014 Published by Elsevier B.V.