1-(4-chlorobenzyl)benzimidazole | 107456-42-8

• 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: 1-(4-chlorobenzyl)benzimidazole
• 英文别名: 1-(4-chlorobenzyl)-1H-benzo[d]imidazole；N-(4-chlorobenzyl)benzimidazole；1-(4-chlorobenzyl)-1H-benzimidazole；1‑(4‑chlorobenzyl)benzimidazole；1-[(4-Chlorophenyl)methyl]benzimidazole
• CAS: 107456-42-8
• 化学式: C₁₄H₁₁ClN₂
• mdl: MFCD00435969
• 分子量: 242.708
• InChiKey: UFLCBIQQTOCIHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C(Solv: methanol (67-56-1))
• 沸点：
  417.3±47.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)
• 溶解度：
  27 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)benzimidazole 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 1.5h， 生成 N-[(E)-[1-[(4-chlorophenyl)methyl]benzimidazol-2-yl]methylideneamino]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-amine
  参考文献：
  名称：

  Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

  摘要：

  A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4-morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q(2) = 0.436, r(2) = 0.937) and CoMSIA (q(2) = 0.706, r(2) = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.002
• 作为产物：
  描述：

  2-溴苯胺 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 1-(4-chlorobenzyl)benzimidazole
  参考文献：
  名称：

  通过 Pd 催化的 C-N 键形成和环化方便合成 N-1-烷基苯并咪唑

  摘要：

  摘要 N -1-烷基-2-未取代的苯并咪唑通过甲酰亚胺与苄胺的分子间偶联直接合成；合成由 Pd(OAc) 2在一锅中催化，产生中等至良好的产率。由相应的苯胺和N,N-二甲基甲酰胺二甲基乙缩醛的反应可以很容易地以高产率制备具有各种取代基的芳族甲脒作为原料。

  DOI：

  10.1080/00397911.2021.1939056

文献信息

• Synthesis of New 1,4-Diarylimidazoles and 1-Aryl-4-(5-Nitrofuran-2-il)imidazoles and Study of Their Anti-Infective Activity
  作者：T. A. Kuzmenko、L. N. Divaeva、A. S. Morkovnik、Yu. V. Koshchienko、A. A. Zubenko、Yu. D. Drobin、L. N. Fetisov、A. N. Bodryakov

  DOI：10.1134/s1068162018050096

  日期：2018.11

  1-R-3-acylmethylbenzimidazolium salts have been obtained which transformed under the action of ammonium acetate into the previously undescribed 1,4-diarylimidazoles and 1-aryl-4- (5-nitrofuran-2-il)imidazoles. The antiprotozoal, fungistatic, and antimicrobial activities of these compounds have been tested.

  使用 1-R-苯并咪唑和 ω-溴苯乙酮或 2-溴乙酰-5-硝基呋喃，已获得相应的 1-R-3-酰基甲基苯并咪唑季盐，其在乙酸铵的作用下转化为先前未描述的 1,4-二芳基咪唑和 1-芳基-4-(5-硝基呋喃-2-il)咪唑。已经测试了这些化合物的抗原生动物、抑真菌和抗微生物活性。
• Benzimidazolium salts prevent and disrupt methicillin-resistant <i>Staphylococcus aureus</i> biofilms
  作者：Jérémie Tessier、Andreea R. Schmitzer

  DOI：10.1039/d0ra00738b

  日期：——

  resistance they acquire. One of the defense mechanisms of resistant bacteria is the formation of biofilms. Herein we show that benzimidazolium salts with various flexible or rigid side chains act as strong antibiotic and antibiofilm agents. We show that their antibiofilm activity is due to their capacity to destroy the biofilm matrix and the bacterial cellular membranes. These compounds are able to avoid

  耐药细菌的出现鼓励我们开发新的抗生素和策略来补偿它们获得的不同耐药机制。耐药细菌的防御机制之一是生物膜的形成。在这里，我们展示了具有各种柔性或刚性侧链的苯并咪唑盐可作为强抗生素和抗生物膜剂。我们表明它们的抗生物膜活性是由于它们破坏生物膜基质和细菌细胞膜的能力。这些化合物能够避免生物膜的形成并分散成熟的生物膜，显示出在治疗生物膜相关感染中的普遍用途。
• Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of <scp>d</scp>-Glucose with <i>o</i>-Phenylenediamines in Water
  作者：Dineshkumar Raja、Abigail Philips、Pushbaraj Palani、Wei-Yu Lin、Sundaramurthy Devikala、Gopal Chandru Senadi

  DOI：10.1021/acs.joc.0c01053

  日期：2020.9.4

  d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a

  d-葡萄糖已被确定为通过氧化环化策略由邻苯二胺合成苯并咪唑的有效C1合成子。用13 C 6 - d-葡萄糖和D 2 O进行的同位素研究明确证实了次甲基的来源。该方法的显着特征包括：宽泛的官能团耐受性，可生物再生的次甲基来源，优异的反应收率，较短的反应时间，水作为环境友好的溶剂以及以克为单位的维生素B 12组分的合成。
• Benzimidazolium sulfonate ligand precursors and application in ruthenium-catalyzed aromatic amine alkylation with alcohols
  作者：Nazan Kaloglu、Ismail Özdemir、Nevin Gürbüz、Mathieu Achard、Christian Bruneau

  DOI：10.1016/j.catcom.2015.10.028

  日期：2016.1

  New benzimidazolium sulfonate salts have been prepared and fully characterized. They have been associated in situ with [RuCl2(p-cymene)]2 to generate efficient catalytic systems operating at 120 °C under neat conditions in the presence of potassium tert-butylate for selective N-alkylation of primary aromatic amines into secondary amines.

  已经制备并充分表征了新的苯并咪唑磺酸盐。它们已与[RuCl 2（p- cymene）] 2原位缔合，以产生有效的催化体系，在叔丁酸钾存在下于纯条件下在120°C的条件下运行，用于将伯芳族胺选择性N-烷基化为仲胺。 。
• Metal-catalyzed direct heteroarylation of C–H (<i>meso</i>) bonds in porphyrins: facile synthesis and photophysical properties of novel <i>meso</i>-heteroaromatic appended porphyrins
  作者：Santosh B. Khandagale、Meenakshi Pilania、V. Arun、Dalip Kumar

  DOI：10.1039/c8ob00174j

  日期：——

  A simple and rapid microwave-assisted synthesis of heteroaromatic appended porphyrins using the Pd/Cu-catalyzed C–C coupling of meso-bromoporphyrins with various five- and six-membered heteroaromatic azoles has been successfully developed. The prepared heteroaromatic porphyrins 7a-lNi were found to exhibit slightly red-shifted (∼5–10 nm) Soret and Q bands. The developed reaction conditions are useful

  已成功开发了一种介孔溴卟啉与各种五元和六元杂芳族吡咯的Pd / Cu催化C-C偶合的简单快速的微波辅助合成杂芳族附加卟啉的方法。发现制备的杂芳族卟啉7a-1Ni表现出轻微的红移（〜5-10 nm）Soret和Q谱带。所开发的反应条件可用于制备不同取代的杂芳族卟啉（A 3 B型和A 2 B 2型）。