5-bromo-2,2-dimethyl-2H-benzimidazole-1,3-dioxide | 63087-06-9

• 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-bromo-2,2-dimethyl-2H-benzimidazole-1,3-dioxide
• 英文别名: 5-bromo-2,2-dimethyl-2H-benzoimidazole 1,3-dioxide；5-Bromo-2,2-dimethyl-3-oxidobenzimidazol-1-ium 1-oxide
• CAS: 63087-06-9
• 化学式: C₉H₉BrN₂O₂
• 分子量: 257.087
• InChiKey: ZNIPTDGCMYWPTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2,2-dimethyl-2H-benzimidazole-1,3-dioxide 以71%的产率得到
  参考文献：
  名称：

  LATHAM D. W. S.; METH-COHN O.; SUSCHITZKY H.; HERBERT J. A. L., J. CHEM. SOC. PERKIN TRANS., PART 1 , 1977, NO 5, 470-478

  摘要：

  DOI：
• 作为产物：
  描述：

  6-溴苯并[c][1,2,5]噁二唑1-氧化物 以82%的产率得到
  参考文献：
  名称：

  LATHAM D. W. S.; METH-COHN O.; SUSCHITZKY H.; HERBERT J. A. L., J. CHEM. SOC. PERKIN TRANS., PART 1 , 1977, NO 5, 470-478

  摘要：

  DOI：

文献信息

• Synthesis and activity of benzimidazole-1,3-dioxide inhibitors of separase
  作者：Ha T. Do、Nenggang Zhang、Debananda Pati、Scott R. Gilbertson

  DOI：10.1016/j.bmcl.2016.07.080

  日期：2016.9

  other alkyl chains at the C2 moderately improves the effects on the inhibitory activity of those compounds. Modifications on 2H-benzimidazole-1,3-dioxide or the skeleton have variable effect on inhibition of separase enzymatic activity. Density-functional theory (DFT) calculations suggest there may be a correlation between the charges on the oxide moieties on these compounds and their activity in inhibiting

  由于粘蛋白蛋白酶，separase在人癌细胞中的致癌活性，对separase酶活性的调节可能构成靶向抗性，separase过表达的非整倍性肿瘤的新治疗策略。在这里，我们报告了基于铅分子2,2-二甲基-5-硝基-2H-苯并咪唑-1,3-二氧化物（称为Sepin）的修饰，分离酶抑制剂的合成，结构信息和构效关系（SAR） -1，（1）从高通量屏幕中识别。用其他官能团取代C5处的-NO2会降低Separase酶法测定中的抑制活性。两个甲基在C2处被其他烷基链取代可适度改善对这些化合物的抑制活性的影响。对2H-苯并咪唑-1的修饰 3-二氧化物或骨架对Separase酶活性的抑制作用不同。密度泛函理论（DFT）计算表明，这些化合物上的氧化物部分上的电荷与其抑制Separase酶的活性之间可能存在相关性。
• Benzofurazan N-oxides as synthetic precursors. Part 2. Conversion of benzofurazan N-oxides into 2H-benzimidazoles and some unusual reactions of 2H-benzimidazoles
  作者：D. W. S. Latham、O. Meth-Cohn、H. Suschitzky、J. A. L. Herbert

  DOI：10.1039/p19770000470

  日期：——

  Benzofurazan N-oxides react with primary nitroalkanes to give 1-hydroxybenzimidazole 3-oxides; with secondary nitroalkanes, red 2,2-dialkyl-2H-benzimidazole 1,3-dioxides are formed. The 2H-benzimidazole oxides react as bis-1,3-dipolar nitrones with acetylenic dipolarophiles (methyl acetylenedicarboxylate and benzyne) but undergo a complex series of redox reactions with tetracyanoethylene giving purple

  苯并呋喃氮氧化物与伯硝基链烷反应生成1-羟基苯并咪唑3-氧化物; 与仲硝基烷烃一起，形成红色的2,2-二烷基-2 H-苯并咪唑1,3-二氧化物。2 H-苯并咪唑氧化物以双1,3-双极性硝酮与炔属双极性亲和剂（乙炔二羧酸甲酯和苯炔）反应，但与四氰基乙烯发生一系列复杂的氧化还原反应，生成紫色醌类二氰基亚甲基衍生物，也由丙二腈阴离子的作用形成。2 H-苯并咪唑氧化物的O-烷基化与氟代硫酸甲酯发生，并且辐射导致重排为O -2-硝基苯基羟胺衍生物。
• 2<i>H</i>-Benzimidazole 1,3-Dioxide Derivatives:  A New Family of Water-Soluble Anti-Trypanosomatid Agents
  作者：Mariana Boiani、Lucía Boiani、Ana Denicola、Susana Torres de Ortiz、Elva Serna、Ninfa Vera de Bilbao、Luis Sanabria、Gloria Yaluff、Héctor Nakayama、Antonieta Rojas de Arias、Celeste Vega、Miriam Rolan、Alicia Gómez-Barrio、Hugo Cerecetto、Mercedes González

  DOI：10.1021/jm0600343

  日期：2006.6.1

  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.
• LATHAM D. W. S.; METH-COHN O.; SUSCHITZKY H.; HERBERT J. A. L., J. CHEM. SOC. PERKIN TRANS., PART 1 <JCPK-BH>, 1977, NO 5, 470-478
  作者：LATHAM D. W. S.、 METH-COHN O.、 SUSCHITZKY H.、 HERBERT J. A. L.

  DOI：——

  日期：——