2,2,5-trimethyl-2Н-benzimidazole 1,3-dioxide

• 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: 2,2,5-trimethyl-2Н-benzimidazole 1,3-dioxide
• 英文别名: 2,2,5-trimethyl-2H-benzimidazole 1,3-dioxide；2,2,5-Trimethyl-3-oxidobenzimidazol-1-ium 1-oxide
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: DWYOMHDIRWJAFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲基苯并呋喃-1-氧化物 、 2-硝基丙烷 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到2,2,5-trimethyl-2Н-benzimidazole 1,3-dioxide
  参考文献：
  名称：

  2H-Benzimidazole 1,3-Dioxide Derivatives:  A New Family of Water-Soluble Anti-Trypanosomatid Agents

  摘要：

  Three series of benzimidazole N-oxide derivatives were developed and were examined for their activity against trypanosomatid parasites (Trypanosoma cruzi and Leishmania spp.). 2H-Benzimidazole 1,3-dioxides displayed remarkable in vitro activities against both parasites, with derivatives 28, 29, and 32 being the most potent (IC50 < 5 mu M) against the epimastigote form of T. cruzi and 28, 33, and 35 the most potent against the promastigote form of Leishmania spp. Unspecific cytotoxicity was evaluated using murine macrophages, and derivative 33 was not toxic at a concentration 30 times that of its IC50 against T. cruzi that was completely toxic for Leishmania spp., implying that the series of 2H-benzimidazole 1,3-dioxides is selective toward both trypanosomatid parasites. Derivatives 33 and 35 were submitted to an in vivo assay using an acute model of Chagas' disease and a short-term treatment (30 mg/kg/day orally administrated as aqueous solution, during 10 days). While in the control (untreated) and Benznidazole (50 mg/kg/day) groups survival fraction was 60.0% and 87.5%, respectively, none of the animals treated with derivatives 33 and 35 died. From the preliminary structure-activity relationship studies reduction potential and electrophilicity were found relevant to anti-T. cruzi activity. Active compounds are better electrophiles and more easily reduced than inactive ones.

  DOI：

  10.1021/jm0600343

文献信息

• Synthesis of 2H-benzimidazole 1,3-dioxides, separase inhibitors, by reaction of o-benzoquinone dioximes with ketones
  作者：Elena Chugunova、Vladimir Samsonov、Nurgali Akylbekov、Dmitrii Mazhukin

  DOI：10.1016/j.tet.2017.05.078

  日期：2017.7

  The synthesis of novel 2H-benzimidazole 1,3-dioxides on the basis of o-benzoquinone dioximes interaction with ketones in the presence of acids is described. Nitration of these compounds by nitric acid in acetic acid yields the 5-nitro derivatives of 2H-benzimidazole 1,3-dioxide.

  描述了在酸存在下，基于邻苯醌二肟与酮的相互作用，合成新颖的2 H-苯并咪唑1,3-二氧化物。用硝酸在乙酸中硝化这些化合物，得到2 H-苯并咪唑1，3-二氧化物的5-硝基衍生物。
• Synthesis and some properties of 2 H -benzimidazole 1,3-dioxides
  作者：Elena Chugunova、Vladimir Samsonov、Tatiana Gerasimova、Tatiana Rybalova、Irina Bagryanskaya

  DOI：10.1016/j.tet.2015.03.096

  日期：2015.9

  The synthesis of novel 2H-benzimidazole 1,3-dioxides on the basis of benzofuroxans interaction with alcohols in acids is described. The formation of a stable secondary carbocation from alcohol is necessary for formation of 2H-benzimidazole 1,3-dioxide while substituents in benzofuroxans don't prevent the reaction. Under heating 2H-benzimidazole 1,3-dioxides are rearranged to 3H-[2,1,4]benzoxadiazine

  描述了基于苯并呋喃类与酸中的醇相互作用的新型2 H-苯并咪唑1,3-二氧化物的合成。由醇形成稳定的仲碳阳离子对于形成2 H-苯并咪唑1,3-二氧化物是必要的，而苯并呋喃类中的取代基不会阻止反应。在加热下，将2 H-苯并咪唑1，3-二氧化物重排为3 H- [2,1,4]苯并恶二嗪4-氧化物，其稳定性取决于芳环中的取代基。在辐射下，恶二嗪被转化回2 H-苯并咪唑1，3-二氧化物。