1,3-dimethyl-5-nitrobenzimidazolium iodide | 52142-81-1

• 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: 1,3-dimethyl-5-nitrobenzimidazolium iodide
• 英文别名: 1,3-Dimethyl-5-nitro-benzimidazolium; Jodid；1,3-Dimethyl-5-nitro-1H-benzo[d]imidazol-3-ium iodide；1,3-dimethyl-5-nitrobenzimidazol-1-ium;iodide
• CAS: 52142-81-1
• 化学式: C₉H₁₀N₃O₂*I
• 分子量: 319.102
• InChiKey: ADLOZNVXSDXHRU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.08
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.95
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  bis[iodido(η²,η²-cycloocta-1,5-diene)rhodium-(I)] 、 1,3-dimethyl-5-nitrobenzimidazolium iodide 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以38%的产率得到(η²,η²-cycloocta-1,5-diene)iodido(5-nitro-1,3-dimethylbenzimidazol-2-ylidene)rhodium(I)
  参考文献：
  名称：

  Rhodium(I) N-Heterocyclic Carbene Bioorganometallics as in Vitro Antiproliferative Agents with Distinct Effects on Cellular Signaling

  摘要：

  Organometallics with N-heterocyclic carbene (NHC) ligands have triggered major interest in inorganic medicinal chemistry. Complexes of the type Rh(I)(NHC)(COD)X (where X is Cl or I, COD is cyclooctadiene, and NHC is a dimethylbenzimidazolylidene) represent a promising type of new metallodrugs that have been explored by advanced biomedical methods only recently. In this work, we have synthesized and characterized several complexes of this type. As observed by mass spectrometry, these complexes remained stable over at least 3 h in aqueous solution, after which hydrolysis of the halido ligands occurred and release of the NHC ligand was evident. Effects against mitochondria and general cell tumor metabolism were noted at higher concentrations, whereas phosphorylation of HSP27, p38, ERK1/2, FAK, and p70S6K was induced substantially already at lower exposure levels. Regarding the antiproliferative activity in tumor cells, a clear preference for iodido over chlorido secondary ligands was noted, as well as effects of the substituents of the NHC ligand.

  DOI：

  10.1021/acs.jmedchem.5b01159
• 作为产物：
  描述：

  苯并咪唑 在 甲醇 、 硫酸 、 硝酸 作用下， 生成 1,3-dimethyl-5-nitrobenzimidazolium iodide
  参考文献：
  名称：

  Fischer,O.; Hess, Chemische Berichte, 1903, vol. 36, p. 3972

  摘要：

  DOI：

文献信息

• Rhodium(I) N-Heterocyclic Carbene Bioorganometallics as in Vitro Antiproliferative Agents with Distinct Effects on Cellular Signaling
  作者：Luciano Oehninger、Sarah Spreckelmeyer、Pavlo Holenya、Samuel M. Meier、Suzan Can、Hamed Alborzinia、Julia Schur、Bernhard K. Keppler、Stefan Wölfl、Ingo Ott

  DOI：10.1021/acs.jmedchem.5b01159

  日期：2015.12.24

  Organometallics with N-heterocyclic carbene (NHC) ligands have triggered major interest in inorganic medicinal chemistry. Complexes of the type Rh(I)(NHC)(COD)X (where X is Cl or I, COD is cyclooctadiene, and NHC is a dimethylbenzimidazolylidene) represent a promising type of new metallodrugs that have been explored by advanced biomedical methods only recently. In this work, we have synthesized and characterized several complexes of this type. As observed by mass spectrometry, these complexes remained stable over at least 3 h in aqueous solution, after which hydrolysis of the halido ligands occurred and release of the NHC ligand was evident. Effects against mitochondria and general cell tumor metabolism were noted at higher concentrations, whereas phosphorylation of HSP27, p38, ERK1/2, FAK, and p70S6K was induced substantially already at lower exposure levels. Regarding the antiproliferative activity in tumor cells, a clear preference for iodido over chlorido secondary ligands was noted, as well as effects of the substituents of the NHC ligand.
• Fischer,O.; Hess, Chemische Berichte, 1903, vol. 36, p. 3972
  作者：Fischer,O.、Hess

  DOI：——

  日期：——