cis-6-fluoro-2-methyl-4-(4-fluorophenylamino)-1,2,3,4-tetrahydroquinoline

• 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-6-fluoro-2-methyl-4-(4-fluorophenylamino)-1,2,3,4-tetrahydroquinoline
• 英文别名: cis-2-methyl-6-fluoro-N-(p-fluorophenyl)-1,2,3,4-tetrahydroquinolin-4-amine；6-fluoro-4-(4-fluoroanilino)-2-methyl-1,2,3,4-tetrahydroquinoline；cis-6-fluoro-4-[(4-fluorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline；(2R,4S)-6-fluoro-N-(4-fluorophenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine
• 化学式: C₁₆H₁₆F₂N₂
• 分子量: 274.313
• InChiKey: HPILWPRGITZHIS-HWPZZCPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(三氟甲基)苯甲酰氯 、 cis-6-fluoro-2-methyl-4-(4-fluorophenylamino)-1,2,3,4-tetrahydroquinoline 在 PS-NMM resin 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 [(2R,4S)-6-Fluoro-4-(4-fluoro-phenylamino)-2-methyl-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 、 4-氟苯胺 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 trans-6-fluoro-2-methyl-4-(4-fluorophenylamino)-1,2,3,4-tetrahydroquinoline 、 cis-6-fluoro-2-methyl-4-(4-fluorophenylamino)-1,2,3,4-tetrahydroquinoline
  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

• PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR ANEMIA COMPRISING TETRAHYDROQUINOLINE COMPOUND AS ACTIVE INGREDIENT
  申请人：Ashikawa Masanori

  公开号：US20120004197A1

  公开（公告）日：2012-01-05

  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 R 1 , R 2 , R 2′ , R 3 and R 3′ independently represent a hydrogen atom, a C 1-6 alkyl group, or the like; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, or the like; A represents N—R 11 , a sulfur atom, or an oxygen atom; R 11 represents a hydrogen atom, a C 1-6 alkyl group, or the like; B represents a C 6-14 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.

  揭示了一种具有低分子量的化合物，具有增强EPO产生和/或增强血红蛋白产生活性的化合物。具体揭示了一种EPO产生增强剂和/或血红蛋白产生增强剂，包括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，更具体地说是由通式(1)表示的四氢喹啉化合物【其中R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或类似物；R4、R5、R6、R7、R8、R9和R10独立地表示氢原子、卤素原子、C1-6烷基或类似物；A表示N—R11、硫原子或氧原子；R11表示氢原子、C1-6烷基或类似物；B表示C6-14芳基或5-至10-成员杂环基；n表示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剂化合物。
• Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives
  作者：Xiao-dong Jia、Yan Ren、Cong-de Huo、Wen-Juan Wang、Xiang-Ning Chen、Xiao-Lan Xu、Xi-cun Wang

  DOI：10.1016/j.tetlet.2010.10.106

  日期：2010.12

  A tandem cyclization of imines with N-vinyllactams induced by TBPA+ was investigated, and a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde surrogate. A single electron transfer mechanism was proposed and radical cation salt acts as both a Lewis acid and one electron oxidant to induce such transformation

  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。
• PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR ANEMIA, COMPRISING TETRAHYDROQUINOLINE COMPOUND AS ACTIVE INGREDIENT
  申请人：Kowa Company, Ltd.

  公开号：EP2199283A1

  公开（公告）日：2010-06-23

  Disclosed is a low-molecular-weight compound having an EPO production-promoting activity and/or a hemoglobin expression-enhancing activity. Specifically disclosed is an EPO production promoter and/or a hemoglobin expression enhancer comprising a 1-acyl-4-(phenoxy, benzyloxy or phenylamino)-1,2,3,4-tetrahydroquinoline derivative, more specifically a tetrahydroquinoline compound represented by the 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 or an oxygen atom; R11 represents a hydrogen atom, a C1-6 alkyl group, or the like; 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.

  本文披露了一种具有促进EPO产生活性和/或增强血红蛋白表达活性的低分子化合物。具体披露了一种EPO产生促进剂和/或血红蛋白表达增强剂，包括1-酰基-4-(苯氧基、苄氧基或苯基氨基)-1,2,3,4-四氢喹啉衍生物，更具体地说是由通式（1）表示的四氢喹啉化合物；[其中R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或类似物；R4、R5、R6、R7、R8、R9和R10独立地表示氢原子、卤素原子、C1-6烷基或类似物；A表示N-R11或氧原子；R11表示氢原子、C1-6烷基或类似物；n表示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剂结晶体。
• 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。
• PGD2 receptor antagonists for the treatment of inflammatory diseases
  申请人：Ghosh Shomir

  公开号：US20050256158A1

  公开（公告）日：2005-11-17

  Disclosed herein are compounds represented by Structural Formula (I) and (I-A): Also disclosed is the use of such compounds for inhibiting the G-protein coupled receptor referred to as chemoattractant receptor-homologous molecule expressed on Th2, or simply “CRTH2” for the treatment of inflammatory disorders. The variables in Structural Formula (I) and (I-A) are defined herein.

  本文揭示了由结构式（I）和（I-A）表示的化合物：还披露了利用这些化合物抑制称为Th2表达的G蛋白偶联受体的化学引诱受体同源分子，简称“CRTH2”，用于治疗炎症性疾病。结构式（I）和（I-A）中的变量在此处被定义。