2-(萘-1-甲基)-1H-苯并[d]咪唑 | 42268-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(萘-1-甲基)-1H-苯并[d]咪唑
• 中文别名: 2-(萘-1-基甲基)-1H-苯并[D]咪唑
• 英文名称: 2-(1-naphthyl)methylbenzimidazole
• 英文别名: 2-(Naphthalen-1-ylmethyl)-1H-benzo[d]imidazole；2-(naphthalen-1-ylmethyl)-1H-benzimidazole
• CAS: 42268-60-0
• 化学式: C₁₈H₁₄N₂
• mdl: MFCD00754353
• 分子量: 258.323
• InChiKey: VJRPHCDQRJAVSR-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C(Solv: ethanol (64-17-5))
• 沸点：
  542.7±29.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.055
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(萘-1-甲基)-1H-苯并[d]咪唑 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.0h， 生成 2-[2-(naphthalen-1-ylmethyl)-1H-benzimidazol-1-yl]acetohydrazide
  参考文献：
  名称：

  Synthesis, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline

  摘要：

  2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-{5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10(-5) M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).

  DOI：

  10.1007/s00044-014-1308-2
• 作为产物：
  描述：

  1-萘乙酸 在 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(萘-1-甲基)-1H-苯并[d]咪唑
  参考文献：
  名称：

  Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators

  摘要：

  Design, synthesis and structure-activity relationships of beU:/AP/DTD501/BMC/4818nzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure activity relationships are being described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.028

文献信息

• Simple inorganic base promoted C–N and C–C formation: synthesis of benzo[4,5]imidazo[1,2-<i>a</i>]pyridines as functional AIEgens used for detecting picric acid
  作者：Kai Yang、Shi-He Luo、Si-Hong Chen、Xi-Ying Cao、Yong-Jun Zhou、Yan-Lan Lin、Yan-Ping Huo、Zhao-Yang Wang

  DOI：10.1039/d1ob01424b

  日期：——

  Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We

  无金属催化分子间串联迈克尔加成/环化已被开发用于从 α-溴肉桂醛和 2-取代苯并咪唑合成苯并[4,5]咪唑并[1,2- a ]吡啶。由简单的无机碱促进的反应显示出中等至良好的产率和良好的官能团耐受性。研究了一些典型产品的光学特性。我们发现，由于苯并[4,5]咪唑并[1,2- a ]吡啶的C1位存在限制分子内运动的苯环，作为一种新型的聚集诱导发射（AIE） luminogen (AIEgen)，它们显示出非常好的固态荧光，量子产率高达 88.80%。重要的是，化合物3b的 AIE 性能可用于检测硝基芳香炸药苦味酸 (PA)，检测限和淬灭常数分别为 42.5 nM 和 7.27 × 10 4 M -M。
• 一种苯并[4,5]咪唑并[1,2-a]吡啶类衍生物及其制备方法与应用
  申请人：华南师范大学

  公开号：CN113512038B

  公开（公告）日：2022-08-05

  本发明公开了一种苯并[4,5]咪唑并[1,2‑a]吡啶类衍生物及其制备方法与应用。本发明公开了一种苯并[4,5]咪唑并[1,2‑a]吡啶类衍生物，其结构为R1选自氢、烷基、卤素、烷氧基；R2选自氢、取代或未取代的烷基、取代或未取代的芳基、取代或未取代的杂芳基；Ar选自取代或未取代的芳基和取代或未取代的杂芳基。本发明提供的苯并[4,5]咪唑并[1,2‑a]吡啶类衍生物具有优良的荧光性能和聚集诱导发光性能，且其制备方法具有简单易行、原料易得、底物适用范围广、产率高等优点。这种苯并[4,5]咪唑并[1,2‑a]吡啶类衍生物在化学和生物荧光探针领域具有良好的应用前景。
• N-Alkylation of benzimidazoles with ketonic Mannich bases and the reduction of the resulting 1-(3-oxopropyl)benzimidazoles
  作者：Gheorghe Roman

  DOI：10.2478/s11532-012-0062-x

  日期：2012.10.1

  position 2, and 5,6-dimethylbenzimidazole have been alkylated at N 1 with ketonic Mannich bases derived from acetophenones, acetylnaphthalenes, 2-acetylthiophene and 1-tetralone to afford a series of novel 1-(3-oxopropyl)benzimidazoles. The reduction of these transamination products with NaBH4 in methanol produced the corresponding 1-(3-hydroxypropyl)benzimidazoles in excellent yields.

  苯并咪唑，在2位被不同取代的苯并咪唑和5,6-二甲基苯并咪唑已在 N 1被衍生自苯乙酮，乙酰萘，2-乙酰基噻吩和1-四氢萘酮的酮基曼尼希碱烷基化， 从而制得一系列新型的1-（3-氧代丙基） ）苯并咪唑 在甲醇中用NaBH 4还原这些氨基转移产物可产生相应的1-（3-羟丙基）苯并咪唑类，产率很高。
• One‐pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies
  作者：Ronak Haj Ersan、Ahmet Yuksel、Tugba Ertan‐Bolelli、Aylin Dogen、Serdar Burmaoglu、Oztekin Algul

  DOI：10.1002/jccs.202000125

  日期：2021.2

  design a greener approach for the synthesis of a potent class of antimicrobials, 1,2‐phenylenediamine derivatives were reacted with various 1/2‐carboxylic acid‐substituted naphthalene derivatives to generate a series of naphthyl‐substituted benzimidazole derivatives (11–19) using polyphosphoric acid as catalyst under microwave irradiation and conventional synthesis method. This is an eco‐friendly and

  为了设计一种更绿色的方法来合成强大的抗菌剂，将1,2-苯二胺衍生物与各种1 / 2-羧酸取代的萘衍生物反应，生成了一系列萘基取代的苯并咪唑衍生物（11 – 19）在微波辐射和常规合成方法下，使用多磷酸作为催化剂。这是一种环保，快速的反应方法，适用于多种苯并咪唑的合成方法。根据光谱数据确定合成化合物的结构，并筛选其抗菌活性。化合物18在所有革兰氏阳性和革兰氏阴性细菌菌株中显示最大效价，最小抑菌浓度（MIC）值在7.81–62.50μg/ ml范围内。发现仅化合物17对所有真菌菌株最具活性，其MIC值为15.62μg/ ml。在这项研究中，我们进行了分子对接实验，以了解化合物17和18与大肠杆菌拓扑异构酶I之间的相互作用，并将我们获得的结果与2-（3,4-二甲氧基苯基）-5- [5-（ 4-甲基哌嗪-1-基）-1H-苯并咪唑-2-基] -1H-苯并咪唑（DMA）。化合物17和18与重要的活性位
• Composition for treating copper and copper alloy surfaces and method for the surface treatment
  申请人：MEC CO., Ltd.

  公开号：EP0643154A2

  公开（公告）日：1995-03-15

  A composition for treating surfaces of copper and copper alloys comprising a specific imidazole derivative and water, and an acid or a water-soluble solvent. The composition can produce a heat resistant organic film with superior solderability when applied to surfaces of copper or copper alloys. It is particularly useful as a rust preventing agent for printed-wiring boards.

  一种用于处理铜和铜合金表面的组合物，由特定的咪唑衍生物和水、酸或水溶性溶剂组成。当该组合物用于铜或铜合金表面时，可产生一层耐热的有机薄膜，具有极佳的可焊性。作为印刷线路板的防锈剂，它尤其有用。