1-(4-fluorophenyl)-2-(2-nitrophenyl)ethan-1-amine | 75842-80-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-fluorophenyl)-2-(2-nitrophenyl)ethan-1-amine
• 英文别名: 1-(4-Fluorophenyl)-2-(2-nitrophenyl)ethanamine
• CAS: 75842-80-7
• 化学式: C₁₄H₁₃FN₂O₂
• 分子量: 260.268
• InChiKey: PUJUSHLUFZRCGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-2-(2-nitrophenyl)ethan-1-amine 在 盐酸 、 硼烷四氢呋喃络合物 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 生成 2-[2-(4-Fluoro-phenyl)-2-methylamino-ethyl]-phenylamine
  参考文献：
  名称：

  (.+-.)-4-Aryl-4,5-dihydro-3H-1,3-benzodiazepines. 2. Nuclear substituted analogs of (.+-.)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and (.+-.)-4,5-dihydro-2-ethyl-3-methyl-4-phenyl-3H-1,3-benzodiazepine as potential antidepressant agents

  摘要：

  Antidepressant-like activity, as evidenced by marked inhibition of tetrabenazine-induced ptosis, was previously reported for (+/-)-4,5-dihydro-4-phenyl-3H-1,3-benzodiazepine derivatives. Since optimal antitetrabenazine activity was associated with (+/-)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine (9k, HRP 543) and the 2-ethyl-3-methyl analogue (10k), the synthesis and evaluation of nuclear-substituted derivatives of these two compounds was also investigated. The initial synthesis involved Friedel-Crafts acylation of substituted benzenes with 2-nitrophenylacetyl chloride to afford 1-aryl-2-(2-nitrophenyl)ethanones 2, which were converted in five steps to (+/-)-alpha-aryl-N-methyl-2-nitrobenzeneethanamines 7. Greater flexibility with respect to the introduction of nuclear substituents was achieved by conversion of 2-nitrotoluene derivatives to 2 via acylation of intermediate beta-(dimethylamino)-2-nitrostyrenes with various aroyl chlorides and hydrolysis. Reductive amination of 2 with methylamine and sodium cyanoborohydride afforded 7 directly and significantly reduced the number of synthetic steps. Reduction of 7a-j to diamines 8a-j and cyclization with appropriate ortho esters gave nuclear-substituted analogues of 9k and 10k. Marked antitetrabenazine activity was associated with many of these compounds. Significant enhancement of activity with respect to the unsubstituted analogues 9k and 10k was not observed, with the exception of 9c which appeared to be slightly more potent than 9k.

  DOI：

  10.1021/jm00346a004
• 作为产物：
  描述：

  2-硝基苯乙酸 在 氯化亚砜 、 ammonium acetate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 21.5h， 生成 1-(4-fluorophenyl)-2-(2-nitrophenyl)ethan-1-amine
  参考文献：
  名称：

  [EN] METALLOENZYME INHIBITOR COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS DE MÉTALLOENZYMES

  摘要：

  提供具有HDAC6调节活性的化合物，以及通过HDAC6介导的治疗疾病、疾病或症状的方法。

  公开号：

  WO2018165520A1

文献信息

• [EN] METALLOENZYME INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE MÉTALLOENZYMES
  申请人：VPS 3 INC

  公开号：WO2018165520A1

  公开（公告）日：2018-09-13

  Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.

  提供具有HDAC6调节活性的化合物，以及通过HDAC6介导的治疗疾病、疾病或症状的方法。
• 4-Phenyl-1,3-benzodiazepines, method for their preparation, pharmaceutical compositions containing them, and the compounds for use as medicaments
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0009800A2

  公开（公告）日：1980-04-16

  Compounds of the formula in which R and R, are the same or different and each can be hydrogen, alkyl of from 1 to 3 carbon atoms, cycloalkyl- C-C3-alkyl, wherein the cycloalkyl radical has 3 - carbon atoms, or aralkyl having up to 8 carbon atoms, X and Y are the same or different and each can be chlorine, bromine, fluorine, alkoxy or alkyl, each of from 1 to 3 carbon atoms, hydroxy, or trifluoromethyl, m is the integer 0,1 or 2, n is the integer 0,1,2 or 3, the optical antipodes thereof, physiologically acceptable salts thereof, and pharmaceutical compositions containing them. They are prepared by the cyclisation of compounds of the formula with a compound of the formula

  式中的化合物 其中 R 和 R, 相同或不同，各自可以是氢、1 至 3 个碳原子的烷基、环烷基-C-C3-烷基（其中环烷基有 3 - 个碳原子）或具有最多 8 个碳原子的芳烷基；X 和 Y 相同或不同，各自可以是氯、溴、氟、烷氧基或烷基（各自具有 1 至 3 个碳原子）、羟基或三氟甲基；m 是 0、1 或 2 的整数；n 是 0、1 或 2 的整数、溴、氟、烷氧基或烷基，每个烷基有 1 至 3 个碳原子、羟基或三氟甲基，m 为 0、1 或 2 的整数，n 为 0、1、2 或 3 的整数。其制备方法是将式化合物 与式
• N-optionelly substituted-2-amino-alpha-phenylphenethylamines and a method for their preparation
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0057870A1

  公开（公告）日：1982-08-18

  Compounds of the formula in which R1 is hydrogen, alkyl of from 1 to 3 carbon atoms, cycloalkyl-Cl-C3-alkyl wherein the cycloalkyl radical has 3 to 6 carbon atoms, or aralkyl having up to 8 carbon atoms, X and Y are the same or different and each can be chlorine, bromine, fluorine, alkoxy or alkyl each of from 1 to 3 carbon atoms, hydroxy, or trifluoromethyl; m is the integer 0,1 or 2; and n is the integer 0,1, 2 or3, pharmaceutical compositions containing them and a method for preparing these compounds are described. The compounds are useful as analgetics and anticonvulsants.

  式中的化合物 其中 R1 是氢、1 至 3 个碳原子的烷基、环烷基-Cl-C3-烷基（其中环烷基具有 3 至 6 个碳原子）或具有最多 8 个碳原子的芳烷基，X 和 Y 是相同或不同的，各自可以是氯、溴、氟、烷氧基或 1 至 3 个碳原子的烷基、羟基或三氟甲基；m 是 0、1 或 2 的整数；n 是 0、1、2 或 3 的整数。这些化合物可用作镇痛药和抗惊厥药。
• Metalloenzyme inhibitor compounds
  申请人：Selenity Therapeutics (Bermuda), Ltd.

  公开号：US10357493B2

  公开（公告）日：2019-07-23

  Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.

  本文提供了具有 HDAC6 调节活性的化合物，以及治疗由 HDAC6 介导的疾病、失调或症状的方法。
• METALLOENZYME INHIBITOR COMPOUNDS
  申请人：Yates Christopher M.

  公开号：US20180256572A1

  公开（公告）日：2018-09-13

  Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.