1-苯磺酰基苯并咪唑-2-胺 | 173374-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯磺酰基苯并咪唑-2-胺
• 中文别名: 2-(4-硝基苯氧基)乙醛二乙基缩醛
• 英文名称: 1-(phenylsulfonyl)-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-benzenesulfonyl-1H-benzimidazol-2-amine；1-(Phenylsulfonyl)-1H-benzimidazol-2-amine；1-(benzenesulfonyl)benzimidazol-2-amine
• CAS: 173374-91-9
• 化学式: C₁₃H₁₁N₃O₂S
• 分子量: 273.315
• InChiKey: KNZWBHGWTXXRTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯磺酰基苯并咪唑-2-胺 在 N-碘代丁二酰亚胺 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 生成 6-iodo-1-(phenylsulfonyl)-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  [EN] BENZIMIDAZOLE DERIVATIVES AS ANTIVIRAL AGENTS
  [FR] DÉRIVÉS DE BENZIMIDAZOLE EN TANT QU'AGENTS ANTIVIRAUX

  摘要：

  公开号：

  WO2012174312A3
• 作为产物：
  描述：

  甲基1H-苯并咪唑-2-基氨基甲酸酯 在 三乙胺 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 6.0h， 生成 1-苯磺酰基苯并咪唑-2-胺
  参考文献：
  名称：

  Benzazoles: I. Regioselective arylsulfonylation of benzimidazol-2-amine

  摘要：

  Benzimidazol-2-amine reacted with arenesulfonyl chlorides in the presence of triethylamine in regioselective fashion at the endocyclic nitrogen atom, the exocyclic amino group remaining intact. The yields of 1-arylsulfonylbenzimidazol-2-amines depend on the electronic properties of substituents in the benzene ring of arenesulfonyl chlorides. DOI: 10.1134/S1070428013010181

  DOI：

  10.1134/s1070428013010181

文献信息

• Efficient Transposition of the Sandmeyer Reaction from Batch to Continuous Process
  作者：Joseph D’Attoma、Titi Camara、Pierre Louis Brun、Yves Robin、Stéphane Bostyn、Frédéric Buron、Sylvain Routier

  DOI：10.1021/acs.oprd.6b00318

  日期：2017.1.20

  The transposition of Sandmeyer chlorination from a batch to a safe continuous-flow process was investigated. Our initial approach was to develop a cascade method using flow chemistry which involved the generation of a diazonium salt and its quenching with copper chloride. To achieve this safe continuous process diazotation, a chemometric approach (Simplex method) was used and extrapolated to establish

  研究了桑德迈尔氯化法从批次到安全连续流过程的转换。我们最初的方法是开发一种使用流化学的级联方法，该方法涉及重氮盐的生成并用氯化铜淬灭。为了实现这种安全的连续过程重氮化，使用了化学计量方法（Simplex方法）并外推以建立完全连续流方法。还通过合成几种（杂）芳基氯来检查反应范围。还对过程进行了验证和放大。在提高安全性的同时获得了更高的生产率。
• Identification of Inhibitors of NOD1-Induced Nuclear Factor-κB Activation
  作者：Pasha M. Khan、Ricardo G. Correa、Daniela B. Divlianska、Satyamaheshwar Peddibhotla、E. Hampton Sessions、Gavin Magnuson、Brock Brown、Eigo Suyama、Hongbin Yuan、Arianna Mangravita-Novo、Michael Vicchiarelli、Ying Su、Stefan Vasile、Layton H. Smith、Paul W. Diaz、John C. Reed、Gregory P. Roth

  DOI：10.1021/ml200158b

  日期：2011.10.13

  NOD1 (nucleotide-binding oligomerization domain 1) protein is a member of the NLR (NACHT and leucine rich repeat domain containing proteins) protein family, which plays a key role in innate immunity as a sensor of specific microbial components derived from bacterial peptidoglycans and induction of inflammatory responses. Mutations in NOD proteins have been associated with various inflammatory diseases that affect NF-kappa B (nuclear factor kappa B) activity, a major signaling pathway involved in apoptosis, inflammation, and immune response. A luciferase-based reporter gene assay was utilized in a high-throughput screening program conducted under the NIH-sponsored Molecular Libraries Probe Production Center Network program to identify the active scaffolds. Herein, we report the chemical synthesis, structure-activity relationship studies, downstream counterscreens, secondary assay data, and pharmacological profiling of the 2-aminobenzimidazole lead (compound 1c, ML130) as a potent and selective inhibitor of NOD 1-induced NF-kappa B activation.
• Benvenuti, Stefania; Severi, Fabio; Vampa, Gabriella, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1613 - 1620
  作者：Benvenuti, Stefania、Severi, Fabio、Vampa, Gabriella、Malmusi, Luca、Antolini, Luciano

  DOI：——

  日期：——