5-chloro-2-[(4-chlorophenoxy)methyl]-1H-benzimidazole | 1621-01-8

• 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: 5-chloro-2-[(4-chlorophenoxy)methyl]-1H-benzimidazole
• 英文别名: 5-chloro-2-((4-chlorophenoxy)methyl)benzimidazole；5-chloro-2-((4-chlorophenoxy)methyl)-1H-benzo[d]imidazole；6-chloro-2-[(4-chlorophenoxy)methyl]-1H-benzimidazole
• CAS: 1621-01-8
• 化学式: C₁₄H₁₀Cl₂N₂O
• 分子量: 293.152
• InChiKey: AOVFOFHJYXPODM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯氧乙酸 、 4-氯-1,2-苯二胺 在 盐酸 作用下， 以 水 为溶剂， 生成 5-chloro-2-[(4-chlorophenoxy)methyl]-1H-benzimidazole
  参考文献：
  名称：

  2-苯基取代的苯并咪唑衍生物：其抗增殖和抗菌活性的设计、合成和评价

  摘要：

  无法达到抗癌治疗的预期结果以及细菌和真菌感染治疗成功率的下降加速了这些领域的研究。我们的研究小组进行了大量研究，特别是苯并咪唑环系统的抗增殖和抗菌活性。在这项研究中，通过 MTT 法测试了苯并咪唑化合物对 A549、A498、HeLa、A375 和 HepG2 癌细胞系的抗增殖活性。所有化合物对所有测试的癌细胞系均表现出良好至强效的抗增殖活性。化合物 6-chloro-2-(4-fluorobenzyl)-1 H - benzo[d]imidazole (30)和 6-chloro-2-phenethyl-1 H - benzo[d]imidazole (46)对 HeLa 和 A375 癌细胞系特别有效，IC 50值在 0.02–0.04 µM 范围内。相反，化合物 6-chloro-2-((p-tolyloxy)methyl)-1 H - benzo[d]imidazole (67)和

  DOI：

  10.1007/s00044-022-02900-3

文献信息

• Synthesis and structure–activity relationships of new antimicrobial active multisubstituted benzazole derivatives
  作者：Ilkay Yildiz-Oren、Ismail Yalcin、Esin Aki-Sener、Nejat Ucarturk

  DOI：10.1016/j.ejmech.2003.11.014

  日期：2004.3

  benzothiazole ring system enhanced the antimicrobial activity against Staphylococcus aureus. In these sets of non-nucleoside fused heterocyclic compounds electron withdrawing groups at position 5 of the benzazoles increased the activity against C. albicans.

  合成了一系列多取代的苯并恶唑，苯并咪唑和苯并噻唑（5-7）作为非核苷稠合的等排杂环化合物，并测试了它们对各种革兰氏阳性和革兰氏阴性细菌的抗菌活性以及对白色念珠菌的抗菌活性。微生物学结果表明，所合成的化合物在MIC值为100至3.12 microg / ml的范围内具有针对被测微生物的广谱活性。结构-活性关系（SAR）研究表明，苯并噻唑环系统增强了对金黄色葡萄球菌的抗菌活性。在这些非核苷稠合的杂环化合物中，苯并恶唑的5位吸电子基团增加了对白色念珠菌的活性。
• Benzimidzolyl neuropeptide Y receptor antagonists
  申请人：——

  公开号：US20020007071A1

  公开（公告）日：2002-01-17

  This invention provides a series of substituted benzimidazoles which are useful in treating or preventing a condition associated with an excess of neuropeptide Y. This invention also provides methods employing these substituted benzimidazoles as well as pharmaceutical formulations with comprise as an active ingredient one or more of these compounds.

  这项发明提供了一系列替代苯并咪唑，这些化合物可用于治疗或预防与神经肽Y过量有关的疾病。此外，该发明还提供了使用这些替代苯并咪唑的方法以及包含这些化合物中的一种或多种作为活性成分的制药配方。
• Akbay, Ayseguel; Oeren, Ilkay; Temiz-Arpaci, Oezlem, Arzneimittel-Forschung/Drug Research, 2003, vol. 53, # 4, p. 266 - 271
  作者：Akbay, Ayseguel、Oeren, Ilkay、Temiz-Arpaci, Oezlem、Aki-Sener, Esin、Yalcin, Ismail

  DOI：——

  日期：——
• Theoretical investigations on the molecular structure, vibrational spectra, HOMO–LUMO and NBO analysis of 5-chloro-2-((4-chlorophenoxy)methyl)benzimidazole
  作者：Y. Shyma Mary、P.J. Jojo、C. Yohannan Panicker、Christian Van Alsenoy、Sanaz Ataei、Ilkay Yildiz

  DOI：10.1016/j.saa.2013.11.025

  日期：2014.3

  The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-chloro-2-((4-chlorophenoxy)methyl)benzimidazole have been investigated experimentally and theoretically using Gaussian09 software package. The energy and oscillator strength calculated by time dependent density functional theory results almost compliments with experimental findings. Gauge-including atomic orbital H-1 NMR chemical shifts calculations were carried out and compared with experimental data. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. Molecular electrostatic potential was performed by the DFT method and the infrared intensities and Raman activities are reported. Mulliken's net charges have been calculated and compared with the atomic natural charges. Fist hyperpolarizability is calculated in order to find its role in non-linear optics. (C) 2013 Elsevier B.V. All rights reserved.
• GUMUS, F.;ALTUNTAS, T. G.;SAYGUN, N.;OZDEN, T.;OZDEN, S., J. PHARM. BELG., 44,(1989) N, C. 398-402
  作者：GUMUS, F.、ALTUNTAS, T. G.、SAYGUN, N.、OZDEN, T.、OZDEN, S.

  DOI：——

  日期：——