1,3-dibenzyl-4,5-dichloroimidazolium bromide | 1038692-15-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1,3-dibenzyl-4,5-dichloroimidazolium bromide
• 英文别名: 4,5-dichloro-1,3-dibenzylimidazolium bromide；4,5-dichloro-1,3-dibenzylimidazoliumbromide；1,3-dibenzyl-4,5-dichloro-1H-imidazol-3-ium bromide；1,3-dibenzyl-4,5-dichloroimidazol-1-ium;bromide
• CAS: 1038692-15-7
• 化学式: Br*C₁₇H₁₅Cl₂N₂
• 分子量: 398.13
• InChiKey: DVJQSOSMQINNDH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dibenzyl-4,5-dichloroimidazolium bromide 以 乙腈 为溶剂， 生成 1-benzyl-4,5-dichloro-3-(naphthalen-2-ylmethyl)imidazolium bromide
  参考文献：
  名称：

  Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

  摘要：

  The anti-tumor activity of imidazolium salts is highly dependent upon the substituents on the nitrogen atoms of the imidazolium cation. We have synthesized and characterized a series of naphthalene-substituted imidazolium salts and tested them against a variety of non-small-cell lung cancer cell lines. Several of these complexes displayed anticancer activity comparable to cisplatin. These compounds induced apoptosis in the NCI-H460 cell line as determined by Annexin V staining, caspase-3, and PARP cleavage. These results strongly suggest that this class of compounds can serve as potent chemotherapeutic agents.

  DOI：

  10.1007/s00044-015-1330-z
• 作为产物：
  描述：

  溴甲苯 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 1,3-dibenzyl-4,5-dichloroimidazolium bromide
  参考文献：
  名称：

  Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

  摘要：

  The anti-tumor activity of imidazolium salts is highly dependent upon the substituents on the nitrogen atoms of the imidazolium cation. We have synthesized and characterized a series of naphthalene-substituted imidazolium salts and tested them against a variety of non-small-cell lung cancer cell lines. Several of these complexes displayed anticancer activity comparable to cisplatin. These compounds induced apoptosis in the NCI-H460 cell line as determined by Annexin V staining, caspase-3, and PARP cleavage. These results strongly suggest that this class of compounds can serve as potent chemotherapeutic agents.

  DOI：

  10.1007/s00044-015-1330-z

文献信息

• [EN] AZOLIUM AND PURINIUM SALT ANTICANCER AND ANTIMICROBIAL AGENTS<br/>[FR] ANTIMICROBIENS ET ANTINÉOPLASIQUES DE SELS D'AZOLIUM ET DE PURINIUM
  申请人：UNIV AKRON

  公开号：WO2012149523A1

  公开（公告）日：2012-11-01

  Singly and multiply charged imidazolium cations (ICs) have been identified as a class of chemical compositions that possess potent antineoplastic, antibacterial and antimicrobial properties. The imidazolium cations disclosed demonstrate greater or equivalent potency towards cancerous cells as the current clinical standard, cisplatin. These imidazolium cations, however, achieve this efficacy without any of the known toxic side effects caused by heavy metal-based antineoplastic drugs such as cisplatin.

  单电荷和多电荷咪唑阳离子（ICs）已被确认为一类具有强效抗肿瘤、抗菌和抗微生物特性的化学成分。所披露的咪唑阳离子对癌细胞表现出比当前临床标准顂铂更高或相等的效力。然而，这些咪唑阳离子在不引起类似顂铂等重金属抗肿瘤药物已知的毒副作用的情况下实现了这种功效。
• Synthesis, Cytotoxicity and Antibacterial Studies of <i>p</i> ‐Methoxybenzyl‐Substituted and Benzyl‐Substituted N‐Heterocyclic Carbene–Silver Complexes
  作者：Siddappa Patil、James Claffey、Anthony Deally、Megan Hogan、Brendan Gleeson、Luis Miguel Menéndez Méndez、Helge Müller‐Bunz、Francesca Paradisi、Matthias Tacke

  DOI：10.1002/ejic.200900889

  日期：2010.3

  zol-2-ylidene]silver(I) acetate (4a), [4,5-dichloro-1,3-bis(4-methoxybenzyl)imidazol-2-ylidene]silver(I) acetate (4b), [1,3-bis(4-methoxybenzyl)benzimidazol-2-ylidene]-silver(I) acetate (4c), (1,3-dibenzylimidazol-2-ylidene)silver(I) acetate (7a), (1,3-dibenzyl-4,5-dichloroimidazol-2-ylidene)-silver(I) acetate (7b), and (1,3-dibenzylbenzimidazol-2-ylidene)silver(I) acetate (7c), respectively. The NHC

  对甲氧基苄基取代和苄基取代的 N-杂环卡宾 (NHC) [(3a-c) 和 (6a-c)] 前体由 1H-咪唑 (1a)、4,5-二氯-1H 的反应合成-咪唑 (1b) 和 1H-苯并咪唑 (1c) 与对甲氧基苄基溴 (2) 和苄基溴 (5)。然后将这些 NHC 前体用乙酸银 (I) 处理以产生 NHC-银复合物 [1,3-双 (4-甲氧基苄基)-咪唑-2-亚基] 乙酸银 (I) (4a), [4,5 -二氯-1,3-双(4-甲氧基苄基)咪唑-2-亚基]银(I)醋酸盐(4b)，[1,3-双(4-甲氧基苄基)苯并咪唑-2-亚基]-银(I)醋酸盐 (4c), (1,3-dibenzylimidazol-2-ylidene) 银 (I) 醋酸盐 (7a), (1,3-dibenzyl-4,5-dichloroimidazol-2-ylidene)-银 (I) 醋酸盐 (7b) ) 和 (1,3-二苄基苯并咪唑-2-亚基)
• Rhodium(I), a Carbene-Transfer Transition-Metal Ion and a Synthetic Route to Symmetrical and Asymmetrical Substituted <i>trans</i>-RhCl(CO)(NHC)(NHC) Complexes
  作者：Agnes Bittermann、Eberhardt Herdtweck、Peter Härter、Wolfgang A. Herrmann

  DOI：10.1021/om900785p

  日期：2009.12.28

  Group IX element Rh(I) was shown to be able to transfer N-heterocyclic carbenes. The dimerization process of RhCl(CO)2(NHC) to [RhCl(CO)(NHC)]2, followed by a rearrangement step to trans-RhCl(CO)(NHC)2, is one possible mechanism for the loss of activity of Rh(I) species in various catalytic reactions. Utilizing this methodology symmetrical and asymmetrical trans-RhCl(CO)(NHC)(NHC) complexes were synthesized

  显示第IX族元素Rh（I）能够转移N-杂环卡宾。RhCl（CO）2（NHC）到[RhCl（CO）（NHC）] 2的二聚过程，然后重排为反式-RhCl（CO）（NHC）2，是活性降低的一种可能机制各种催化反应中Rh（I）种类的变化 利用该方法，合成并表征了对称和不对称的反式-RhCl（CO）（NHC）（NHC）配合物。
• Carbene Complexes Made Easily: Decomposition of Reissert Compounds and Further Synthetic Approaches
  作者：Agnes Bittermann、Denys Baskakov、Wolfgang A. Herrmann

  DOI：10.1021/om900354v

  日期：2009.9.14

  New methods for the preparation of NHC-metal complexes have been developed. It was shown that a nitrile group in Reissert analogous compounds can act as a good leaving group in thermal elimination, resulting in carbene formation. Moreover potassium carbonate was introduced as a highly efficient and mild reagent for the generation of N-heterocyclic carbene complexes in good to excellent yields, even

  已经开发了用于制备NHC-金属配合物的新方法。结果表明，Reissert类似化合物中的腈基可在热消除中充当良好的离去基团，从而形成卡宾。此外，引入碳酸钾作为一种高效温和的试剂，即使在水中也能以极高的产率获得N-杂环卡宾络合物，这是最环保的介质。
• AZOLIUM AND PURINIUM SALT ANTICANCER AND ANTIMICROBIAL AGENTS
  申请人：Youngs Wiley

  公开号：US20140142307A1

  公开（公告）日：2014-05-22

  Singly and multiply charged imidazolium cations (ICs) have been identified as a class of chemical compositions that possess potent antineoplastic, antibacterial and antimicrobial properties. The imidazolium cations disclosed demonstrate greater or equivalent potency towards cancerous cells as the current clinical standard, cisplatin. These imidazolium cations, however, achieve this efficacy without any of the known toxic side effects caused by heavy metal-based antineoplastic drugs such as cisplati.

  单电荷和多电荷咪唑阳离子（ICs）已被确定为一类具有强效抗肿瘤、抗菌和抗微生物特性的化学成分。所公开的咪唑阳离子在对癌细胞的作用上表现出与当前临床标准药物顺铂相当或更强的效力。然而，这些咪唑阳离子在不像顺铂这样的重金属抗肿瘤药物所知的毒性副作用下，就能实现这种功效。