2,6-dimethyl-4-(4-methylphenylamino)-1,2,3,4-tetrahydroquinoline | 856437-14-4

• 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: 2,6-dimethyl-4-(4-methylphenylamino)-1,2,3,4-tetrahydroquinoline
• 英文别名: (2,6-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-p-tolyl-amine；2,6-dimethyl-N-(4-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine
• CAS: 856437-14-4
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: FRYSDRKYEWCWRS-UHFFFAOYSA-N

物化性质

• 沸点：
  419.7±45.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-(4-methylphenylamino)-1,2,3,4-tetrahydroquinoline 、 对甲基苯甲酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 以19%的产率得到((2R,4S)-2,6-Dimethyl-4-p-tolylamino-3,4-dihydro-2H-quinolin-1-yl)-p-tolyl-methanone
  参考文献：
  名称：

  Structural requirement and stereospecificity of tetrahydroquinolines as potent ecdysone agonists

  摘要：

  Tetrahydroquinoline (THQ)- type compounds are a class of potential larvicides against mosquitoes. The structure-activity relationships (SAR) of these compounds were previously investigated (Smith et al., Bioorg. Med. Chem. Lett. 2003, 13, 1943-1946), and one of cis-forms (with respect to the configurations of 2-methyl and 4-anilino substitutions on the THQ basic structure) was stereoselectively synthesized. However, the absolute configurations of C2 and C4 were not determined. In this study, four THQ-type compounds with cis configurations were synthesized, and two were submitted for X-ray crystal structure analysis. This analysis demonstrated that two enantiomers are packed into the crystal form. We synthesized the cis-form of the fluorinated THQ compound, according to the published method, and the enantiomers were separated via chiral HPLC. The absolute configurations of the enantiomers were determined by X-ray crystallography. Each of the enantiomers was tested for activity against mosquito larvae in vivo and competitive binding to the ecdysone receptor in vitro. Compared to the (2S, 4R) enantiomer, the (2R, 4S) enantiomer showed 55 times higher activity in the mosquito larvicidal assay, and 36 times higher activity in the competitive receptor binding assay. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.043
• 作为产物：
  描述：

  乙烷,三氯氟- 、 乙醛 在 T406石油添加剂 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以29%的产率得到2,6-dimethyl-4-(4-methylphenylamino)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Structural requirement and stereospecificity of tetrahydroquinolines as potent ecdysone agonists

  摘要：

  Tetrahydroquinoline (THQ)- type compounds are a class of potential larvicides against mosquitoes. The structure-activity relationships (SAR) of these compounds were previously investigated (Smith et al., Bioorg. Med. Chem. Lett. 2003, 13, 1943-1946), and one of cis-forms (with respect to the configurations of 2-methyl and 4-anilino substitutions on the THQ basic structure) was stereoselectively synthesized. However, the absolute configurations of C2 and C4 were not determined. In this study, four THQ-type compounds with cis configurations were synthesized, and two were submitted for X-ray crystal structure analysis. This analysis demonstrated that two enantiomers are packed into the crystal form. We synthesized the cis-form of the fluorinated THQ compound, according to the published method, and the enantiomers were separated via chiral HPLC. The absolute configurations of the enantiomers were determined by X-ray crystallography. Each of the enantiomers was tested for activity against mosquito larvae in vivo and competitive binding to the ecdysone receptor in vitro. Compared to the (2S, 4R) enantiomer, the (2R, 4S) enantiomer showed 55 times higher activity in the mosquito larvicidal assay, and 36 times higher activity in the competitive receptor binding assay. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.043

文献信息

• COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR
  申请人：HUMAN BIOMOLECULAR RESEARCH INSTITUTE

  公开号：US20160038641A1

  公开（公告）日：2016-02-11

  Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, transdifferentiation, and proliferation of animal cells into the osteoblast blast cell lineage were described. Examples of osteogenic materials that were administered to cells or co-cultured with cells are represented by compounds of Formula II, IV, and VI independently or preferably in combination with a matrix to afford bone cells. Small molecule-stimulated cells were also combined with a matrix, placed with a cellular adhesive or material carrier and implanted to a site in an animal for bone repair. Matrix pretreated with compounds of Formula II, IV, and VI were also used to cause cells to migrate to the matrix that is of use for therapeutic purposes.

  描述了由小分子、基质和孤立细胞组成的组合物，包括制备方法，以及动物细胞分化、转分化和增殖成骨母细胞谱系的方法。给细胞施加的或与细胞共培养的成骨材料的示例由独立或首选与基质组合的Formula II、IV和VI化合物代表。受小分子刺激的细胞还与基质结合，与细胞粘合剂或材料载体一起植入到动物体内的部位进行骨修复。预先用Formula II、IV和VI化合物处理的基质也被用于导致细胞迁移到用于治疗目的的基质上。
• Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of <i>N</i> -Aryl α-Amino Acids
  作者：Tianju Shao、Yanli Yin、Richmond Lee、Xiaowei Zhao、Guobi Chai、Zhiyong Jiang

  DOI：10.1002/adsc.201800135

  日期：2018.5.2

  A visible‐light‐driven sequential photoredox catalysis to allow N‐aryl α‐amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine‐derived chromophore (DPZ) as a photoredox catalyst in both transformations, two series of valuable azaarenes, i. e., 4‐amino tetrahydroquinolines (THQs) and quinolines,

  描述了可见光驱动的顺序光氧化还原催化，以使N-芳基α-氨基酸经历有效的级联好氧脱羧Povarov和氧化脱氢（ODH）反应。在两个转化过程中，都使用双氰基吡嗪衍生的生色团（DPZ）作为光氧化还原催化剂，得到了两个系列的有价值的氮杂芳烃，即 例如，以不同的2和2,3-取代形式获得令人满意的收率的4-氨基四氢喹啉（THQs）和喹啉。为了使4-氨基THQs发生ODH反应，开发了与N-羟基邻苯二甲酰亚胺的协同催化方法。此外，实现了具有高对映选择性的手性N-氨基-2-甲基THQ的空前合成。
• [EN] TETRAHYDROQUINOLINES FOR MODULATING THE EXPRESSION OF EXOGENOUS GENES VIA AN ECDYSONE RECEPTOR COMPLEX<br/>[FR] TETRAHYDROQUINOLINES DESTINEES A MODULER L'EXPRESSION DE GENES EXOGENES PAR LE BIAIS D'UN COMPLEXE DE RECEPTEURS DE L'ECDYSONE
  申请人：RHEOGENE INC

  公开号：WO2003105849A1

  公开（公告）日：2003-12-24

  This invention relates to a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene. The ligands comprise a class of 4-tetrahydorquinolines.

  本发明涉及一种调节外源基因表达的方法，其中包括接触由DNA结合域、配体结合域、转录激活域和配体组成的ecdysone受体复合物，并与包括外源基因和响应元件的DNA构建物接触；其中，外源基因受响应元件控制，DNA结合域在配体存在下与响应元件结合导致基因的激活或抑制。配体包括一类4-四氢喹啉。
• TETRAHYDROQUINOLINES FOR MODULATING THE EXPRESSION OF EXOGENOUS GENES VIA AN ECDYSONE RECEPTOR COMPLEX
  申请人：Michelotti Enrique

  公开号：US20050228016A1

  公开（公告）日：2005-10-13

  This invention relates to a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene. The ligands comprise a class of 4-tetrahydroquinolines.

  本发明涉及一种调节外源基因表达的方法，其中包括一个包含：DNA结合域、配体结合域、转录激活域和配体的ecdysone受体复合物与包括：外源基因和响应元件的DNA构建物接触；其中外源基因受响应元件控制，在存在配体的情况下，DNA结合域与响应元件的结合会导致基因的激活或抑制。配体包括一类4-四氢喹啉。
• PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR ANEMIA COMPRISING TETRAHYDROQUINOLINE COMPOUND AS ACTIVE INGREDIENT
  申请人：Kowa Company, Ltd.

  公开号：EP2415764A1

  公开（公告）日：2012-02-08

  Disclosed is a compound which has a low molecular weight and has an activity of enhancing the production of EPO and/or an activity of enhancing the production of hemoglobin. Specifically disclosed is and EPO production enhancer and/or a hemoglobin production enhancer comprising a 1-acyl-4-(substituted oxy, substituted amino, or substituted thio)-1,2,3,4-tetrahydroquinoline derivative, more specifically a tetrahydroquinoline compound represented by general formula (1) [wherein R1, R2, R2', R3 and R3' independently represent a hydrogen atom, a C1-6 alkyl group, or the like; R4, R5, R6, R7, R8, R9 and R10 independently represent a hydrogen atom, a halogen atom, a C1-6 alkyl group, or the like; A represents N-R11, a sulfur atom, or an oxygen atom; R11 represents a hydrogen atom, a C1-6 alkyl group, or the like; B represents a C6-14 aryl group, or a 5- to 10-membered heterocyclic group; and n represents an integer of 0 or 1], a salt of the tetrahydroquinoline compound, or a solvate of the tetrahydroquinoline compound or the salt.

  本发明公开了一种低分子量化合物，该化合物具有提高 EPO 产量和/或提高血红蛋白产量的活性。具体公开了一种 EPO 生产促进剂和/或一种血红蛋白生产促进剂，其包含 1-酰基-4-(取代氧基、取代氨基或取代硫基)-1,2,3,4-四氢喹啉衍生物，更具体地说是通式(1)代表的四氢喹啉化合物[其中 R1、R2、R2'、R3 和 R3'独立地代表氢原子、C1-6 烷基或类似物；R4、R5、R6、R7、R8、R9 和 R10 独立地代表氢原子、卤素原子、C1-6 烷基或类似物；A 代表 N-R11、硫原子或氧原子；R11 代表氢原子、C1-6 烷基或类似物；B 代表 C6-14 芳基或 5 至 10 元杂环基团；以及 n 代表 0 或 1 的整数]、四氢喹啉化合物的盐或四氢喹啉化合物或其盐的溶液。