N4-benzyl-2-chloroquinoline-3,4-diamine | 879000-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N4-benzyl-2-chloroquinoline-3,4-diamine
• 英文别名: 4-N-benzyl-2-chloroquinoline-3,4-diamine
• CAS: 879000-71-2
• 化学式: C₁₆H₁₄ClN₃
• 分子量: 283.76
• InChiKey: UYDTVRXXDZZSBR-UHFFFAOYSA-N

物化性质

• 沸点：
  459.4±45.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N4-benzyl-2-chloroquinoline-3,4-diamine 在 氨 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2,2'-(decane-1,10-diyl)bis(1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine)
  参考文献：
  名称：

  Toll-Like Receptor (TLR)-7 and -8 Modulatory Activities of Dimeric Imidazoquinolines

  摘要：

  Toll-like receptors (TLRs) are pattern recognition receptors that recognize specific molecular patterns present in molecules that are broadly shared by pathogens but are structurally distinct from host molecules. The TLR7-agonistic imidazoquinolines are of interest as vaccine adjuvants given their ability to induce pronounced Th1-skewed humoral responses. Minor modifications on the imidazoquinoline scaffold result in TLR7-antagonistic compounds which may be of value in addressing innate immune activation-driven immune exhaustion observed in HIV. We describe the syntheses and evaluation of TLR7 and TLR8 modulatory activities of dimeric constructs of imidazoquinoline linked at the C2, C4, C8, and N-1-aryl positions. Dinners linked at the C4, C8, and N-1-aryl positions were agonistic at TLR7; only the N-1-aryl dimer with a 12-carbon linker was dual TLR7/8 agonistic. Dimers linked at C2 position showed antagonistic activities at TLR7 and TLR8; the C2 dimer with a propylene spacer was maximally antagonistic at both TLR7 and TLR8.

  DOI：

  10.1021/jm2010207
• 作为产物：
  描述：

  N-benzyl-2-chloro-3-nitroquinolin-4-amine 在 盐酸 、 tin 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以30%的产率得到N4-benzyl-2-chloroquinoline-3,4-diamine
  参考文献：
  名称：

  Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from a quinoline scaffold

  摘要：

  基于含有喹唑啉基团的EGFR抑制剂，合成并评估了一系列含有喹啉骨架的三十四种化合物的EGFR激酶抑制和抗癌活性。

  DOI：

  10.1039/c6ra15118c

文献信息

• Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from a quinoline scaffold
  作者：Monika Chauhan、Gaurav Joshi、Harveen Kler、Archana Kashyap、Suyog M. Amrutkar、Praveen Sharma、Kiran D. Bhilare、Uttam Chand Banerjee、Sandeep Singh、Raj Kumar

  DOI：10.1039/c6ra15118c

  日期：——

  Based on the quinazoline bearing EGFR inhibitors, a series of thirty four compounds having a quinoline scaffold were synthesized and evaluated in vitro for EGFR kinase inhibitory and anticancer activities.

  基于含有喹唑啉基团的EGFR抑制剂，合成并评估了一系列含有喹啉骨架的三十四种化合物的EGFR激酶抑制和抗癌活性。
• TOLL-LIKE RECEPTOR-7 AND -8 MODULATORY 1H IMIDAZOQUINOLINE DERIVED COMPOUNDS
  申请人：David Sunil A.

  公开号：US20120294885A1

  公开（公告）日：2012-11-22

  The present disclosure provides novel imidazoquinoline derived compounds, derivatives thereof, analogues thereof, and pharmaceutically acceptable salts thereof, and methods of making and using such compounds. The present disclosure also provides TLR7 agonists and TLR7/TLR8 dual agonists, probes, tissue-specific molecules, adjuvants, immunogenic compositions, therapeutic compositions, and self-adjuvanting vaccines including the imidazoquinoline derived compounds, derivatives thereof, analogues thereof, and pharmaceutically acceptable salts thereof. Derivatives of the imidazoquinoline derived compounds also include dendrimers and dimers of the imidazoquinoline derived compounds, and methods of making and using the dendrimeic and dimeric imidazoquinoline derived compounds. The present disclosure also provides dual TLR2/TLR7 hybrid agonists that include imidazoquinoline derived compounds of the present disclosure.

  本公开提供了新型咪唑喹啉衍生化合物，其衍生物，类似物，以及其药用盐，并提供了制备和使用这些化合物的方法。本公开还提供了TLR7激动剂和TLR7/TLR8双激动剂，探针，组织特异性分子，佐剂，免疫原性组合物，治疗组合物，以及包括咪唑喹啉衍生化合物，其衍生物，类似物和药用盐的自佐剂疫苗。咪唑喹啉衍生化合物的衍生物还包括咪唑喹啉衍生化合物的树枝状分子和二聚体，以及制备和使用这些树枝状和二聚体咪唑喹啉衍生化合物的方法。本公开还提供了包括本公开的咪唑喹啉衍生化合物的双TLR2/TLR7混合激动剂。
• HYDROXY AND ALKOXY SUBSTITUTED 1H-IMIDAZOQUINOLINES AND METHODS
  申请人：Kshirsagar Tushar A.

  公开号：US20090221556A1

  公开（公告）日：2009-09-03

  1H-Imidazo[4,5-c]quinolin-4-amines with a hydroxy, alkoxy, hydroxyalkoxy, or alkoxyalkoxy substituent at the 2-position, pharmaceutical compositions containing these compounds, methods of making the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  本文介绍了在2位置具有羟基，烷氧基，羟基烷氧基或烷氧基烷氧基取代基的1H-咪唑并[4,5-c]喹啉-4-胺类化合物、含有这些化合物的制药组合物、制备这些化合物的方法、中间体以及这些化合物作为免疫调节剂的用途，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• 2-Amino 1H-Imidazo Ring Systems and Methods
  申请人：Kshirsagar Tushar A.

  公开号：US20090023720A1

  公开（公告）日：2009-01-22

  1H-Imidazo ring systems (e.g., imidazopyridines, imidazoquinolines, imidazonaphthyridines, 6,7,8,9-tetrahydro imidazoquinolines and imidazonaphthyridines) with an amino substituent at the 2-position, pharmaceutical compositions containing these compounds, methods of making the compounds, intermediates, and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  本发明揭示了在2-位置具有氨基取代基的咪唑环系统（例如咪唑吡啶，咪唑喹啉，咪唑萘啉，6,7,8,9-四氢咪唑喹啉和咪唑萘啉），含有这些化合物的制药组合物，制备这些化合物的方法，中间体以及这些化合物作为免疫调节剂的用途，用于调节动物细胞因子生物合成以及治疗包括病毒和肿瘤性疾病在内的疾病的方法。
• Hydroxy and alkoxy substituted 1H-imidazoquinolines and methods
  申请人：3M Innovative Properties Company

  公开号：US08088790B2

  公开（公告）日：2012-01-03

  1H-Imidazo[4,5-c]quinolin-4-amines with a hydroxy, alkoxy, hydroxyalkoxy, or alkoxyalkoxy substituent at the 2-position, pharmaceutical compositions containing these compounds, methods of making the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  本发明公开了在2位具有羟基、烷氧基、羟基烷氧基或烷氧基烷氧基取代基的1H-咪唑并[4,5-c]喹啉-4-胺类化合物、含有这些化合物的制药组合物、制备这些化合物的方法、中间体以及这些化合物作为免疫调节剂的使用方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤性疾病在内的疾病。