2-氨基-4,6-二溴苯甲醛 | 135690-29-8

• 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: 2-氨基-4,6-二溴苯甲醛
• 英文名称: 2-amino-4,6-dibromobenzaldehyde
• 英文别名: 2-Amino-4,6-dibromobenzaldehyde
• CAS: 135690-29-8
• 化学式: C₇H₅Br₂NO
• 分子量: 278.931
• InChiKey: AQACHPDXIQVYSO-UHFFFAOYSA-N

物化性质

• 沸点：
  355.3±42.0 °C(Predicted)
• 密度：
  2.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-4,6-二溴苯甲醛 在 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 5,5′-(2-amino-3-pentylquinoline-5,7-diyl)bis(pentan-1-amine)
  参考文献：
  名称：

  Structure-Based Design of Human TLR8-Specific Agonists with Augmented Potency and Adjuvanticity

  摘要：

  Human Toll-like receptor 8 (hTLR8) is expressed in myeloid dendritic cells, monocytes, and monocyte-derived dendritic cells. Engagement by TLR8 agonists evokes a distinct cytokine profile which favors the development of type 1 helper T cells. Crystal structures of the ectodomain of hTLR8 cocrystallized with two regioisomers of a dual TLR7/8-agonistic N1-substituted imidazoquinolines showed subtle differences in their interactions in the binding site of hTLR8. We hypothesized that the potency of a previously reported best-in-class pure TLR8 agonist, 3-pentylquinoline-2amine, could be further enhanced by "designing in" functional groups that would mimic key intermolecular interactions that we had observed in the crystal structures. We performed a focused exploration of decorating the quinoline core with alkylamino groups at all possible positions. These studies have led to the identification of a novel TLR8 agonist that was similar to 20-fold more potent than the parent compound and displays prominent adjuvantic activity in a rabbit model of immunization.

  DOI：

  10.1021/acs.jmedchem.5b01087
• 作为产物：
  描述：

  2-氨基-4,6-二溴苯甲酸 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-氨基-4,6-二溴苯甲醛
  参考文献：
  名称：

  Structure-Based Design of Human TLR8-Specific Agonists with Augmented Potency and Adjuvanticity

  摘要：

  Human Toll-like receptor 8 (hTLR8) is expressed in myeloid dendritic cells, monocytes, and monocyte-derived dendritic cells. Engagement by TLR8 agonists evokes a distinct cytokine profile which favors the development of type 1 helper T cells. Crystal structures of the ectodomain of hTLR8 cocrystallized with two regioisomers of a dual TLR7/8-agonistic N1-substituted imidazoquinolines showed subtle differences in their interactions in the binding site of hTLR8. We hypothesized that the potency of a previously reported best-in-class pure TLR8 agonist, 3-pentylquinoline-2amine, could be further enhanced by "designing in" functional groups that would mimic key intermolecular interactions that we had observed in the crystal structures. We performed a focused exploration of decorating the quinoline core with alkylamino groups at all possible positions. These studies have led to the identification of a novel TLR8 agonist that was similar to 20-fold more potent than the parent compound and displays prominent adjuvantic activity in a rabbit model of immunization.

  DOI：

  10.1021/acs.jmedchem.5b01087

文献信息

• Synthesis of 3-aminoquinolines from α-imino rhodium carbenes and 2-aminobenzaldehydes
  作者：Jiani Li、Jing Feng、Tao Chen、Ze-Feng Xu、Chuan-Ying Li

  DOI：10.1039/d3ob00843f

  日期：——

  straightforward process starts from easily available triazoles and 2-aminobenzaldehydes. Low catalyst loading and good functional group compatibility are the other two merits of this transformation. Easy decoration of the 3-aminoquinoline motifs enabled the convenient synthesis of bioactive molecules, demonstrating the potential of this protocol in organic synthesis.

  报道了一种简便有效的 3-氨基喹啉合成方法。这个简单的过程从容易获得的三唑和 2-氨基苯甲醛开始。低催化剂负载量和良好的官能团相容性是该转变的另外两个优点。3-氨基喹啉基序的简单修饰使得生物活性分子的合成变得方便，展示了该方案在有机合成中的潜力。
• Human TLR8-selective agonists
  申请人：UNIVERSITY OF KANSAS

  公开号：US11130736B2

  公开（公告）日：2021-09-28

  The disclosure provides human toll-like receptor modulators of general Formula (II), wherein R1, R2, R3, R4, R5, R6, R7, R8 are defined herein.

  本公开提供通式（II）的人类收费样受体调节剂，其中 R1、R2、R3、R4、R5、R6、R7、R8 在本文中定义。
• Ultrasound-assisted synthesis and spectral correlations of some bioactive E-imines
  作者：P. Mayavel、J. Divya、P. Gayathri、S. Balasundari、V. Usha、I. Muthuvel、Krishnakumar Balu、K. N. Shivakumara、Gurusamy Raman、G. Thirunarayanan

  DOI：10.1007/s11164-024-05363-w

  日期：2024.9

  structure–activity relationship study. The spectral QSAR study was performed with single and multi-regression analysis using Hammett σ, σ, σI, σR F R, and Swain–Lupton’s constants. From the outcome of the regression, the effect of substituents on the spectral frequencies was predicted. The molecular docking study of these imines was performed by the assessment of protein–ligand interaction study with a characteristic

  采用纳米粉煤灰H 3 PO 4催化各种芳基苯胺与苯甲醛在超声辐射的绿色溶剂介质下缩合合成了一些芳基E-亚胺。在该缩合反应中，所得收率大于75%。这些E-亚胺通过其物理化学数据、微量分析和光谱数据进行表征。采用特征光谱频率进行光谱定量构效关系研究。光谱 QSAR 研究是使用 Hammett σ 、 σ 、 σ I 、 σ R F R和 Swain–Lupton 常数进行单回归和多回归分析。根据回归结果，预测了取代基对光谱频率的影响。这些亚胺的分子对接研究是通过评估具有特征蛋白质的蛋白质-配体相互作用研究来进行的。使用 Bauer-Kirby 纸片扩散技术对各种细菌和真菌微生物研究了这些亚胺的抗菌活性。使用泰国恶性疟原虫蛋白质微生物测量了这些亚胺的体外抗疟活性。
• A highly regioselective Friedländer reaction mediated by lanthanum chloride
  作者：Ying Chen、Jinkun Huang、Tsang-Lin Hwang、T.J. Li、Sheng Cui、Johann Chan、Matthew Bio

  DOI：10.1016/j.tetlet.2012.04.038

  日期：2012.6

  A highly efficient and regioselective Friedlander reaction of unsymmetrical 1,3-diketones with 2-aminoaryl aldehydes (ketones) is described. The methodology leads to the synthesis of a broad scope of substituted quinolines in high yield and excellent regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
• QUINOLINE-2-AMINE DERIVATIVES AS HUMAN TLR8-SELECTIVE AGONISTS FOR INCREASING IMMUNE RESPONSE
  申请人：The University of Kansas

  公开号：EP3337481B1

  公开（公告）日：2020-11-11