2-(Methyl-(2-aminobenzyl)amino)-1-(4-fluorophenyl)ethanol | 98159-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(Methyl-(2-aminobenzyl)amino)-1-(4-fluorophenyl)ethanol
• 英文别名: 2-[(2-Aminophenyl)methyl-methylamino]-1-(4-fluorophenyl)ethanol
• CAS: 98159-52-5
• 化学式: C₁₆H₁₉FN₂O
• 分子量: 274.338
• InChiKey: MXQPRQPINPBCGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Methyl-(2-aminobenzyl)amino)-1-(4-fluorophenyl)ethanol 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-(4-Fluoro-phenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-8-ylamine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of some new tetrahydroisoquinoline derivatives inhibiting dopamine uptake and/or possessing a dopaminomimetic property

  摘要：

  As shown by structure-activity relationship studies in 8-(substituted-amino)-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines, the most important structural requirement for a marked antidepressant action is the presence of an ureido, (alkoxycarbonyl)amino, or [(alkylamino)acyl]amino group attached to the isoquinoline skeleton in position 8. In one of the biological tests a significant difference was found between 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydroisoquinoline (nomifensine) and the new compounds synthesized. Nearly all compounds substituted in the amino group either decrease the spontaneous motility in mice or exert no effect on it. Two syntheses have been elaborated for the preparation of the compounds represented by the general formulas II-V where R1 = hydrogen, halogen, or methyl; Y = CONHR, OCOR, or CO(CH2)nNHR, in which R = alkyl or aralkyl or NHR = cyclic amine and n = 1-2. The syntheses start either from the corresponding 8-amino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines or from the corresponding noncyclized amino alcohols. Of the compounds, 4-(p-chlorophenyl)-8-[(ethoxy-carbonyl)amino]-2-methyl-1,2,3,4- tetrahydroisoquinoline was found to possess the highest activity.

  DOI：

  10.1021/jm00157a012
• 作为产物：
  描述：

  2-溴-4'-氟苯乙酮 在 镍 sodium tetrahydroborate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 18.0~25.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 2-(Methyl-(2-aminobenzyl)amino)-1-(4-fluorophenyl)ethanol
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of some new tetrahydroisoquinoline derivatives inhibiting dopamine uptake and/or possessing a dopaminomimetic property

  摘要：

  As shown by structure-activity relationship studies in 8-(substituted-amino)-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines, the most important structural requirement for a marked antidepressant action is the presence of an ureido, (alkoxycarbonyl)amino, or [(alkylamino)acyl]amino group attached to the isoquinoline skeleton in position 8. In one of the biological tests a significant difference was found between 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydroisoquinoline (nomifensine) and the new compounds synthesized. Nearly all compounds substituted in the amino group either decrease the spontaneous motility in mice or exert no effect on it. Two syntheses have been elaborated for the preparation of the compounds represented by the general formulas II-V where R1 = hydrogen, halogen, or methyl; Y = CONHR, OCOR, or CO(CH2)nNHR, in which R = alkyl or aralkyl or NHR = cyclic amine and n = 1-2. The syntheses start either from the corresponding 8-amino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines or from the corresponding noncyclized amino alcohols. Of the compounds, 4-(p-chlorophenyl)-8-[(ethoxy-carbonyl)amino]-2-methyl-1,2,3,4- tetrahydroisoquinoline was found to possess the highest activity.

  DOI：

  10.1021/jm00157a012

文献信息

• Pyridoindole derivatives, compositions and use
  申请人：Troponwerke GmbH & Co.

  公开号：US04564613A1

  公开（公告）日：1986-01-14

  Pyridoindoles of the formula ##STR1## in which R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 -alkyl, which is optionally substituted by the radical ##STR2## R.sub.2 and R.sub.3 represent H or form a bond, or R.sub.1 and R.sub.2 together represent O, --O--CH.sub.2 --CH.sub.2 --O-- or --S--CH.sub.2 --CH.sub.2 --S--, R.sub.4 represents H or the ##STR3## or R.sub.3 and R.sub.4 represent O, or R.sub.1 and R.sub.4 are members of an N-containing six-membered ring and R.sub.8 and R.sub.9 represent H or C.sub.1 -C.sub.4 -alkyl, or optionally form, with the N atom, a heterocyclic 5-membered or 6-membered ring, which can optionally also contain a further hetero-atom from the series comprising N, O or S, R.sub.5 represents H, C.sub.1 -C.sub.4 -alkyl or the group ##STR4## or R.sub.5 and R.sub.3 form a bond, and R.sub.10 and R.sub.11 represent C.sub.1 -C.sub.4 -alkyl or are members of an N-containing 5-membered or 6-membered ring, R.sub.6 represents H or C.sub.1 -C.sub.4 -alkyl and R.sub.7 represents halogen, or acid addition salts thereof, which are active on the central nervous system. Novel intermediates are also shown.

  该公式中的吡啶吲哚为 ##STR1##，其中 R.sub.1 代表氢或C.sub.1 -C.sub.4 -烷基，该烷基可以选择性地被基团 ##STR2## 取代，R.sub.2 和 R.sub.3 代表H或形成键合，或者 R.sub.1 和 R.sub.2 共同代表O，--O--CH.sub.2 --CH.sub.2 --O--或--S--CH.sub.2 --CH.sub.2 --S--，R.sub.4 代表H或 ##STR3## 或 R.sub.3 和 R.sub.4 代表O，或者 R.sub.1 和 R.sub.4 是N含有的六元环的成员，R.sub.8 和 R.sub.9 代表H或C.sub.1 -C.sub.4 -烷基，或者可以选择性地与N原子形成杂环的5元环或6元环，该环还可以选择性地包含系列中的另一个杂原子N、O或S，R.sub.5 代表H、C.sub.1 -C.sub.4 -烷基或基团 ##STR4##，或者 R.sub.5 和 R.sub.3 形成键合，R.sub.10 和 R.sub.11 代表C.sub.1 -C.sub.4 -烷基或是N含有的5元环或6元环的成员，R.sub.6 代表H或C.sub.1 -C.sub.4 -烷基，R.sub.7 代表卤素，或者它们的酸盐，对中枢神经系统具有活性。还展示了新的中间体。
• Neue Pyridoindolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：Troponwerke GmbH & Co. KG

  公开号：EP0140070A1

  公开（公告）日：1985-05-08

  Die vorliegende Erfindung betrifft neue Pyridoindole und deren Säureadditionssalze, Verfahren zu ihrer Herstellung sowie ihre Verwendung bei der Bekämpfung von Krankheiten, insbesondere ihre Verwendung zur Behandlung, von Erkrankungen des zentralen Nervensystems.

  本发明涉及新的吡啶吲哚及其酸加成盐、其制备工艺以及在防治疾病中的应用，特别是在治疗中枢神经系统疾病中的应用。
• US4564613A
  申请人：——

  公开号：US4564613A

  公开（公告）日：1986-01-14
• Synthesis and pharmacological evaluation of some new tetrahydroisoquinoline derivatives inhibiting dopamine uptake and/or possessing a dopaminomimetic property
  作者：E. Zara-Kaczian、L. Gyorgy、Gyula Deak、A. Seregi、M. Doda

  DOI：10.1021/jm00157a012

  日期：1986.7

  As shown by structure-activity relationship studies in 8-(substituted-amino)-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines, the most important structural requirement for a marked antidepressant action is the presence of an ureido, (alkoxycarbonyl)amino, or [(alkylamino)acyl]amino group attached to the isoquinoline skeleton in position 8. In one of the biological tests a significant difference was found between 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydroisoquinoline (nomifensine) and the new compounds synthesized. Nearly all compounds substituted in the amino group either decrease the spontaneous motility in mice or exert no effect on it. Two syntheses have been elaborated for the preparation of the compounds represented by the general formulas II-V where R1 = hydrogen, halogen, or methyl; Y = CONHR, OCOR, or CO(CH2)nNHR, in which R = alkyl or aralkyl or NHR = cyclic amine and n = 1-2. The syntheses start either from the corresponding 8-amino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines or from the corresponding noncyclized amino alcohols. Of the compounds, 4-(p-chlorophenyl)-8-[(ethoxy-carbonyl)amino]-2-methyl-1,2,3,4- tetrahydroisoquinoline was found to possess the highest activity.