N-(3-chlorobenzyl)benzimidazole | 838880-77-6

• 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: N-(3-chlorobenzyl)benzimidazole
• 英文别名: 1‑(3‑chlorobenzyl)benzimidazole；1-[(3-Chlorophenyl)methyl]benzimidazole
• CAS: 838880-77-6
• 化学式: C₁₄H₁₁ClN₂
• mdl: MFCD06643510
• 分子量: 242.708
• InChiKey: QHYIRANSSQXDBU-UHFFFAOYSA-N

物化性质

• 沸点：
  417.3±47.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

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：

  N-(3-chlorobenzyl)benzimidazole 在 palladium diacetate 、 copper (I) acetate 、 copper(II) acetate monohydrate 、 cesium pivalate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以15%的产率得到2-chloro-11H-isoindolo[2,1-a]benzimidazole
  参考文献：
  名称：

  Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling

  摘要：

  Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a fused polycyclic motif. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.103
• 作为产物：
  描述：

  N1-[(3-氯苯基)甲基]-1,2-乙二胺 在 N,N-二甲基甲酰胺二甲基缩醛 作用下， 反应 2.0h， 以86%的产率得到N-(3-chlorobenzyl)benzimidazole
  参考文献：
  名称：

  苯并咪唑衍生物取代的[Mn（CO）3（bpy）L] PF6型新型锰配合物的结构，CO释放性能，电化学，DFT计算和抗氧化活性

  摘要：

  摘要羰基金属配合物由于在工业和制药化学中的应用而成为主要的有机金属化合物。近年来，羰基金属配合物已被广泛用于一氧化碳的存储和运输，一氧化碳是在某些疾病的发病机理中重要的重要信号分子。因此，我们设计并合成了通式[Mn（CO）3（bpy）L] PF 6（bpy = 2,2-联吡啶基，L = N-（2-氯苄基）苯并咪唑，N -（2-甲氧基苄基）苯并咪唑，N-（2-甲基苄基）苯并咪唑）。通过LC-MS，1 H-NMR，13 C-NMR，IR光谱法和元素分析对复合物分子进行表征。研究了这些配合物的CO释放特性，抗氧化活性和氧化还原特性。

  DOI：

  10.1016/j.ica.2016.05.027

文献信息

• Design, Synthesis and Anticancer Activity of 4-Morpholinothieno[3,2-<i>d</i>]pyrimidine Derivatives Bearing Arylmethylene Hydrazine Moiety
  作者：Wufu Zhu、Xin Zhai、Qiangqiang Fu、Fei Guo、Mei Bai、Jianqiang Wang、Haiyan Wang、Ping Gong

  DOI：10.1248/cpb.c12-00342

  日期：——

  Three series of 4-morpholinothieno[3,2-d]pyrimidine derivatives containing arylmethylene hydrazine moiety (11a–f, 13a–k and 15a–h) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. The synthesized compounds were evaluated for their cytotoxicity against three cancer cell lines (H460, HT-29, MDA-MB-231). Most of them exhibited moderate to significant cytotoxicity and high-selectivity against one or more cell lines, especially compounds 11c, 13b, 15f and 15g possessing dramatically increased cytotoxicity as compared with the positive controls, which were further evaluated for six other cancer cell lines and one normal cell line. The most promising compound 11c, bearing 3,4-methylenedioxy phenyl group, showed remarkable cytotoxicity against H460, HT-29 and MDA-MB-231 cell lines with IC50 values of 0.003 µM, 0.42 µM and 0.74 µM, which was 1.6- to 290-fold more potent than GDC-0941.

  合成了三系列含有芳基亚甲基肼部分的4-吗啉硫烯并[3,2-d]嘧啶衍生物（11a–f, 13a–k 和 15a–h），并确认了它们的化学结构以及相对立体化学。合成的化合物对三种癌细胞系（H460, HT-29, MDA-MB-231）的细胞毒性进行了评估。大多数化合物表现出中等到显著的细胞毒性，并对一种或多种细胞系展现出高选择性，特别是化合物11c、13b、15f和15g与阳性对照相比显示出显著提高的细胞毒性，后者进一步在另外六种癌细胞系和一种正常细胞系中进行了评估。最有前景的化合物11c，含有3,4-亚甲基二氧苯基基团，对H460、HT-29和MDA-MB-231细胞系显示出显著细胞毒性，IC50值分别为0.003 µM、0.42 µM和0.74 µM，比GDC-0941的效力提高了1.6到290倍。
• Benzimidazole bearing Pd–PEPPSI complexes catalyzed direct C2‐arylation/heteroarylation of<i>N</i>‐substituted benzimidazoles
  作者：Anusha Gokanapalli、Venkata Krishna Reddy Motakatla、Vasu Govardhana Reddy Peddiahgari

  DOI：10.1002/aoc.5869

  日期：2020.10

  A convenient and highly efficient palladium‐catalyzed direct C2‐arylation/heteroarylation of N‐substituted benzimidazole derivatives such as N‐benzyl/3‐chlorobenzyl/2,4,6‐trimethylbenzyl/2,4,6‐triisopropylbenzyl/aryl benzimidazoles with various aryl/heteroaryl bromides in the presence of Pd–PEPPSI (palladium‐pyridine enhanced pre‐catalyst preparation stabilization and initiation) complexes is reported

  N取代的苯并咪唑衍生物（如N-苄基/ 3-氯苄基/ 2,4,6-三甲基苄基/ 2,4,6-三异丙基苄基/芳基苯并咪唑）的便捷，高效的钯催化的直接C2芳基化/杂芳基化据报道，在Pd-PEPPSI（钯-吡啶增强的前催化剂制剂的稳定和引发）复合物中存在芳基/杂芳基溴化物。为此，我们准备了一系列不同的对称和不对称的N，N'-二重烷基苯并咪唑Pd-PEPPSI复合物。在所有准备好的络合物中，Pd–PEPPSI- 3在乙醇-水系统中，在温和的反应条件下，可以相对较高的速率有效地调节反应。另外，催化过程避免了使用外部配体和添加剂。进一步将反应性与市售的铜-N-杂环卡宾催化剂进行了比较，但反应不太成功。在优化的反应条件下，通过Csp 2 -H / Csp 2 -X联芳基交叉偶联以良好至极好的收率合成了范围广泛的2-芳基/杂芳基-N-取代的苯并咪唑。
• Water-soluble N-heterocyclic carbene precursors bearing benzimidazole core: synthesis, characterization, in vitro antioxidant and anticancer studies
  作者：Öznur Doğan Ulu、Ali Kuruçay、İsmail Özdemir

  DOI：10.1007/s00706-023-03041-y

  日期：2023.4

  13C NMR spectroscopy, LC–MS, and elemental analysis. The compounds were used for their antioxidant capacity by commercial kit assay. Further, these were screened for their cytotoxic effect against cell lines including MCF-7, A-549, and L929 using cisplatin as a reference drug. It resulted that the total antioxidant capacity values of the compounds were found to be quite low compared to the trolox equivalent

  苯并咪唑是含氮杂环系统的重要成员，因为它在药物化学（例如抗癌药物应用）中具有令人惊讶的良好生物学特性。牢记这一点，设计并报道了一系列新的不对称 1,3-二取代苯并咪唑盐。这些化合物是通过 1-烷基苯并咪唑与 2-(2-溴乙基)-1,3-二恶烷的反应合成的。所有化合物的结构均使用 FT-IR、1 H 和13C NMR 光谱、LC-MS 和元素分析。通过商业试剂盒测定使用化合物的抗氧化能力。此外，使用顺铂作为参考药物筛选它们对包括 MCF-7、A-549 和 L929 在内的细胞系的细胞毒性作用。结果发现，与 trolox 等效物相比，这些化合物的总抗氧化能力值非常低。另一方面，最重要的是，与顺铂（IC 50 = 83.11 和 87.80 µg/厘米3). 此外，与癌细胞相比，大多数化合物被发现对正常 L929 成纤维细胞是安全的（健康成纤维细胞的 IC 50值为 142.70–268.37
• Synthesis, antimicrobial activity and molecular docking study of benzyl functionalized benzimidazole silver(I) complexes
  作者：Erkan Arı、Neslihan Şahin、Elvan Üstün、Muhammed Dündar、Hüseyin Karcı、İlknur Özdemir、Ahmet Koç、Nevin Gürbüz、İsmail Özdemir

  DOI：10.1007/s00775-023-02024-y

  日期：——

  In this study, a series of N-functionalized benzimidazole silver(I) complexes were prepared and characterized by FT-IR, 1H, 13C1H} NMR spectroscopy, and elemental analysis. Synthesized N-benzylbenzimidazole silver(I) complexes were evaluated for their antimicrobial activities against bacteria Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and the fungal strains Candida albicans and

  在本研究中，制备了一系列N-官能化苯并咪唑银(I)配合物，并通过FT-IR、 1H 、 13C 1H }NMR光谱和元素分析对其进行了表征。评估了合成的N-苄基苯并咪唑银(I)复合物对大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌以及真菌菌株白色念珠菌和光滑念珠菌的抗菌活性。结果表明，与N-烷基苯并咪唑衍生物相比， N-烷基苯并咪唑银(I)配合物表现出良好的抗菌活性。特别是，复合物2e比其他复合物表现出完美的抗菌活性。通过基于DFT的计算方法对表征的分子进行优化，并通过针对细菌DNA旋转酶和CYP51的分子对接方法对优化后的分子进行详细分析。检测到的两个目标分子的氨基酸残基与预期一致，计算出的结合亲和力和抑制常数有利于进一步的研究。  图文摘要 合成了一系列N-烷基苯并咪唑银(I)配合物，并通过1H NMR、13C NMR和FT-IR光谱进行了充分表征。研究了合成的N-烷基苯并咪唑银 (I)
• Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents
  作者：Wufu Zhu、Yajing Liu、Xin Zhai、Xiao Wang、Yan Zhu、Di Wu、Hongyu Zhou、Ping Gong、Yanfang Zhao

  DOI：10.1016/j.ejmech.2012.09.002

  日期：2012.11

  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.