3-nitro-N-pentylpyridin-4-amine

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-nitro-N-pentylpyridin-4-amine
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: YHKKNQMWUQUKFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-N-pentylpyridin-4-amine 在 platinum on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 4-N-pentylpyridine-3,4-diamine
  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
• 作为产物：
  描述：

  4-氯-3-硝基吡啶 、 1-氨基戊烷 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以86%的产率得到3-nitro-N-pentylpyridin-4-amine
  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

• 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。
• 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。
• Human Toll-Like Receptor 8-Selective Agonistic Activities in 1-Alkyl-1<i>H</i>-benzimidazol-2-amines
  作者：Mallesh Beesu、Subbalakshmi S. Malladi、Lauren M. Fox、Cassandra D. Jones、Anshuman Dixit、Sunil A. David

  DOI：10.1021/jm500701q

  日期：2014.9.11

  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.