1-己基苯并咪唑-2-胺 | 141211-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-己基苯并咪唑-2-胺
• 英文名称: 1-hexyl-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-Hexyl-1H-benzimidazol-2-amine；1-hexylbenzimidazol-2-amine
• CAS: 141211-32-7
• 化学式: C₁₃H₁₉N₃
• 分子量: 217.314
• InChiKey: DAUBVHYSFXTNAX-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±25.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-硝基糠醛 、 1-己基苯并咪唑-2-胺 以60%的产率得到(1-Hexyl-1H-benzoimidazol-2-yl)-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine
  参考文献：
  名称：

  Vlaovic, Djordje; Canadanovic-Brunet, Jasna; Balaz, Jelica, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 2.3.4., p. 199 - 206

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二胺 在 potassium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 1-己基苯并咪唑-2-胺
  参考文献：
  名称：

  Human Toll-Like Receptor 8-Selective Agonistic Activities in 1-Alkyl-1H-benzimidazol-2-amines

  摘要：

  Toll-like receptor (TLR)-8 agonists strongly induce the production of T helper 1-polarizing cytokines and may therefore serve as promising candidate vaccine adjuvants, especially for the very young and the elderly. Earlier structure-based ligand design led to the identification of 3-pentyl-quinoline-2-amine as a novel, human TLR8-specific agonist. Comprehensive structure-activity relationships in ring-contracted 1-alkyl-1H-benzimidazol-2-amines were undertaken, and the best-in-class compound, 4-methyl-1-pentyl-1H-benzo[d]imidazol-2-amine, was found to be a pure TLR8 agonist, evoking strong proinflammatory cytokine and Type II interferon responses in human PBMCs, with no attendant CD69 upregulation in natural lymphocytic subsets. The 1-alkyl-1H-benzimidazol-2-amines represent a novel, alternate chemotype with pure TLR8-agonistic activities and will likely prove useful not only in understanding TLR8 signaling but also perhaps as a candidate vaccine adjuvant.

  DOI：

  10.1021/jm500701q

文献信息

• [EN] TOLL-LIKE RECEPTOR AGONISTS<br/>[FR] AGONISTES DE RÉCEPTEURS DE TYPE TOLL
  申请人：UNIV KANSAS

  公开号：WO2015023958A1

  公开（公告）日：2015-02-19

  Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivatives thereof, prodrugs thereof, salts thereof, or stereoisomers thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines, as well as for other therapeutic purposes described herein.

  本文描述的化合物可用于治疗目的。这些化合物可以是TLR激动剂，例如TLR7或TLR8激动剂。这些化合物可以包含在药物组合物中，并用于需要作为TLR激动剂有用的治疗中。药物组合物可以包括任何成分，如载体、稀释剂、赋形剂、填料或类似的在药物组合物中常见的成分。这些化合物可以是本文所示或描述的化合物，以及其衍生物、前药、盐、立体异构体，或在任何手性中心具有任何手性，或互变异构体、多晶形、溶剂化合物，或其组合。因此，这些化合物可以用作疫苗的佐剂，以及用于本文描述的其他治疗目的。
• TOLL-LIKE RECEPTOR AGONISTS
  申请人：DAVID Sunil Abraham

  公开号：US20160166681A1

  公开（公告）日：2016-06-16

  Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivative thereof, prodrug thereof, salt thereof, or stereoisomer thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines as well as for other therapeutic purposes described herein. The compounds can have any one of the formulae. Examples of the compounds can be reviewed in Table 1 and Table A1 for activates.

  本文所描述的化合物可用于治疗目的。这些化合物可以是TLR激动剂，例如TLR7或TLR8激动剂。这些化合物可以包含在制药组合物中，并用于需要TLR激动剂的治疗中。制药组合物可以包括任何常见于制药组合物中的成分，例如载体、稀释剂、辅料、填充剂或类似物。这些化合物可以是本文所示或描述的化合物，以及其衍生物、前药、盐、立体异构体或在任何手性中心具有任何手性，互变异构体、多晶形、溶剂化物或其组合。因此，这些化合物可以用作疫苗佐剂以及本文中描述的其他治疗目的。这些化合物可以具有以下任何一个式子。化合物的例子可以在表1和表A1中查看。
• Novel Biologically Active N-Substituted Benzimidazole Derived Schiff Bases: Design, Synthesis, and Biological Evaluation
  作者：Anja Beč、Maja Cindrić、Leentje Persoons、Mihailo Banjanac、Vedrana Radovanović、Dirk Daelemans、Marijana Hranjec

  DOI：10.3390/molecules28093720

  日期：——

  benzimidazole-derived Schiff bases, and the evaluation of their antiviral, antibacterial, and antiproliferative activity. The impact on the biological activity of substituents placed at the N atom of the benzimidazole nuclei and the type of substituents attached at the phenyl ring were examined. All of the synthesized Schiff bases were evaluated in vitro for their antiviral activity against different viruses

  在此，我们介绍了新型 N-取代苯并咪唑衍生的席夫碱的设计和合成，以及它们的抗病毒、抗菌和抗增殖活性的评估。检测了位于苯并咪唑核 N 原子上的取代基对生物活性的影响以及连接在苯环上的取代基类型。所有合成的席夫碱都在体外评估了它们对不同病毒的抗病毒活性、对一组细菌菌株的抗菌活性以及对几种人类癌细胞系的抗增殖活性，从而能够研究结构-活性关系。注意到一些轻微的抗病毒作用，尽管与包含的参考药物相比浓度更高。此外，一些衍生物显示出适度的抗菌活性，前体 23 对大多数测试的细菌菌株具有广泛的活性。最后，席夫碱 40，一种 4-N,N-二乙氨基-2-羟基取代的衍生物，在苯并咪唑核的 N 原子上带有一个苯环，对几种癌细胞系表现出很强的抗增殖活性（IC50 1.1–4.4 μM ). 对急性髓性白血病 (HL-60) 观察到最强的抗肿瘤作用。
• Synthesis and characterization of asymmetric oxyacetamide bridged porphyrin conjugates embedded with N-containing heterocycles
  作者：Ayman M. K. Sweed、Sherif S. Ragab、Yasser M. Shaker

  DOI：10.1142/s108842462250047x

  日期：2022.10

  In the search for photosensitizers based on 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin (m-THPP, 1), a novel series of asymmetric A₃B porphyrin molecules with oxyacetamide linkers have been synthesized. A facile synthetic route was followed through the reaction of m-THPP derived porphyrin monoacid with amino-heterocyclic molecules in the presence of HBTU/DIPEA coupling reagent to obtain the respective porphyrin conjugates 7-10, 16, 18 in satisfactory yields 30–76%. The structures of all compounds were confirmed by the means of ¹H, [Formula: see text]C NMR and by mass spectrometry (MALDI-TOF). The absorption and emission spectra of the synthesized porphyrin conjugates were displayed in methanol and showed high extension coefficient values. These preliminary studies could qualify these new candidates in being added to the porphyrin library for photomedicine applications.

  为了寻找基于 5,10,15,20-四（3-羟基苯基）卟啉（m-THPP，1）的光敏剂，我们合成了一系列带有氧乙酰胺连接体的新型不对称 A3B 卟啉分子。在 HBTU/DIPEA 偶联试剂存在下，通过 m-THPP 衍生的卟啉单酸与氨基杂环分子的反应，采用简便的合成路线获得了相应的卟啉共轭物 7-10、16、18，收率为 30-76%。所有化合物的结构均通过 1H、[式：见正文]C NMR 和质谱（MALDI-TOF）得到确认。合成的卟啉共轭物在甲醇中的吸收和发射光谱显示出很高的延伸系数。这些初步研究可以将这些新的候选化合物添加到卟啉库中，用于光医疗应用。
• Toll-like receptor agonists
  申请人：The University of Kansas

  公开号：US10471139B2

  公开（公告）日：2019-11-12

  Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivative thereof, prodrug thereof, salt thereof, or stereoisomer thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines as well as for other therapeutic purposes described herein. The compounds can have any one of the formulae. Examples of the compounds can be reviewed in Table 1 and Table A1 for activates.

  本文所述化合物可用于治疗目的。这些化合物可以是 TLR 激动剂，如 TLR7 或 TLR8 激动剂。这些化合物可包含在药物组合物中，用于治疗TLR激动剂有用的疾病。药物组合物可以包括任何成分，例如药物组合物中常见的载体、稀释剂、赋形剂、填料等。化合物可以是本文图示或描述的化合物，也可以是其衍生物、原药、盐或立体异构体，或在任何手性中心具有任何手性的化合物，或同系物、多晶型物、溶胶或其组合。因此，这些化合物可用作疫苗佐剂，也可用于本文所述的其他治疗目的。这些化合物可以具有任意一个式子。化合物的实例可参见表 1 和表 A1 中的活化剂。