cis-2,6-dimethyl-N-(p-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine | 22609-18-3

• 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: cis-2,6-dimethyl-N-(p-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine
• 英文别名: 6-methyl-4-(4-methylanilino)-2-methyl-1,2,3,4-tetrahydroquinoline；2,6-dimethyl-N-(p-tolyl)tetrahydroquinolin-4-amine；(+/-)-(2c,6-dimethyl-1,2,3,4-tetrahydro-[4r]quinolyl)-p-tolyl-amine；(+/-)-(2c,6-Dimethyl-1,2,3,4-tetrahydro-[4r]chinolyl)-p-tolyl-amin；(+/-)-cis-4-(p-Toluidino)-2,6-dimethyl-1,2,3,4-tetrahydrochinolin；(2R,4S)-2,6-dimethyl-N-(4-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine
• CAS: 22609-18-3；26343-42-0；52128-97-9
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: FRYSDRKYEWCWRS-KDOFPFPSSA-N

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：

  cis-2,6-dimethyl-N-(p-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine 、 3-(三氟甲基)苯甲酰氯 在 PS-NMM resin 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 ((2R,4S)-2,6-Dimethyl-4-p-tolylamino-3,4-dihydro-2H-quinolin-1-yl)-(3-trifluoromethyl-phenyl)-methanone
  参考文献：
  名称：

  Synthesis and SAR of cis-1-Benzoyl-1,2,3,4-tetrahydroquinoline ligands for control of gene expression in ecdysone responsive systems

  摘要：

  A library of 35 cis-1-benzoyl-2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinolines was prepared. The compounds bore various substitutuents on the benzoyl ring, at the 4-position of the phenylamino ring and at the 6-position of the tetrahydroquinoline ring. The compounds were assayed for their ability to cause expression of a reporter gene downstream of an ecdysone response element in a mammalian cell line engineered to express the ecdysone receptor from Aedes aegypti. In general, compounds with small lipophilic substituents at the meta and para-positions of the benzoyl ring and hydrogen or fluorine at the 4-position of the phenylamino ring and the 6-position of the tetrahydroquino line ring were the most potent. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00317-2
• 作为产物：
  描述：

  N-乙烯基己内酰胺 、 乙烷,三氯氟- 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 cis-2,6-dimethyl-N-(p-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine 、 trans-2,6-dimethyl-N-(p-methylphenyl)-1,2,3,4-tetrahydroquinolin-4-amine
  参考文献：
  名称：

  自由基阳离子盐诱导苯胺和N-乙烯基酰胺之间的串联环化：2-甲基-4-苯胺基1,2,3,4-四氢喹啉衍生物的合成

  摘要：

  研究了由TBPA +诱导的亚胺与N-乙烯基内酰胺的串联环化反应，并基于其中N-乙烯基内酰胺起作用的多米诺过程，合成了一系列2-甲基-4-苯胺基-1,2,3,4-四氢喹啉作为乙醛的替代物。提出了单一的电子转移机制，自由基阳离子盐既充当路易斯酸又充当一种电子氧化剂来诱导这种转变。

  DOI：

  10.1016/j.tetlet.2010.10.106

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。
• [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。
• Compounds and matrices for use in bone growth and repair
  申请人：HUMAN BIOMOLECULAR RESEARCH INSTITUTE

  公开号：US10874766B2

  公开（公告）日：2020-12-29

  Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, trans-differentiation, 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.

  描述了小分子、基质和分离细胞的组合物，包括制备方法，以及将动物细胞分化、转分化和增殖为成骨细胞的方法。向细胞施用或与细胞共培养的成骨材料的例子以式 II、IV 和 VI 的化合物为代表，这些化合物可独立使用，或最好与基质结合使用，以产生骨细胞。小分子刺激的细胞也与基质结合，与细胞粘合剂或材料载体一起放置，并植入动物的骨修复部位。用式 II、IV 和 VI 的化合物预处理的基质也用于使细胞迁移到用于治疗目的的基质上。
• Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide salt and its application as a recyclable catalyst for the synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines
  作者：Boddula Rajender、Srinivasan Palaniappan

  DOI：10.1016/j.catcom.2014.08.011

  日期：2014.12

  Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide is successfully carried out using bromodimethylsulfonium bromide. Poly(2-bromoaniline)-bromide salt was obtained in a dry amorphous nature, having high conductivity (2.5 S/cm) with agglomerated spherical morphology. Poly(2-bromoaniline)bromide salt was proved to be a novel, efficient, reusable, cheaper and eco-friendly polymer-based solid acid catalyst in the reaction between aromatic amines and N-vinyl lactam under solvent-free conditions to provide 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines. These 2,4-disubstituted tetrahydroquinolines were synthesized with trans selectivity. (C) 2014 Elsevier B.V. All rights reserved.