2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydroisoquinoline | 414873-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline；2-[[2-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-1H-isoquinoline
• CAS: 414873-72-6
• 化学式: C₁₇H₁₆F₃N
• 分子量: 291.316
• InChiKey: NUBNJYYCSCNKNR-UHFFFAOYSA-N

物化性质

• 沸点：
  334.812±37.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.218±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异喹啉 在 ammonia borane 、 [Co(2,2':6',2''-terpyridine)Br₂] 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.0h， 生成 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Co(II) 催化 N-杂芳烃室温无添加剂转移氢化

  摘要：

  传统的催化剂开发依赖于配体和预催化剂的多步合成和分离。设计一种可以用易于获得的起始材料原位组装的催化系统可以降低反应复杂性并提高合成效用。在此，我们报道了一种廉价且市售的CoBr 2 ·H 2 O/三联吡啶催化的有效且直接的N-杂芳烃转移氢化(TH)方案，在环境条件下利用NH 3 ·BH 3 (AB)。多种底物和生物活性分子的合成证明了其实际适用性。对照实验和 DFT 研究阐明了其机制。

  DOI：

  10.1021/acs.orglett.4c02090

文献信息

• Designing analogs of ticlopidine, a wall teichoic acid inhibitor, to avoid formation of its oxidative metabolites
  作者：Maya A. Farha、Kalinka Koteva、Robert T. Gale、Edward W. Sewell、Gerard D. Wright、Eric D. Brown

  DOI：10.1016/j.bmcl.2013.12.069

  日期：2014.2

  The thienopyridine antiplatelet agent, ticlopidine and its analog, clopidogrel, have been shown to potentiate the action of beta-lactam antibiotics, reversing the methicillin-resistance phenotype of methicillin- resistant Staphylococcus aureus (MRSA), in vitro. Interestingly, these thienopyridines inhibit the action of TarO, the first enzyme in the synthesis of wall teichoic acid, an important cell wall polymer in Gram-positive bacteria. In the human body, both ticlopidine and clopidogrel undergo a rapid P450-dependent oxidation into their respective antiplatelet-active metabolites, resulting in very low plasma concentrations of intact drug. Herein, a series of analogs of ticlopidine and clopidogrel that would avoid oxidative metabolism were designed, prepared and evaluated as inhibitors of TarO. Specifically, we replaced the P450-labile thiophene ring of ticlopidine and clopidogrel to a more stable phenyl group to generate 2-(2-chlorobenzyl)-1,2,3,4-tetrahydro-isoquinoline) (6) and (2-chloro-phenyl)-(3,4-dihydro-1H-isoquinolin- 2-yl)-acetic acid methyl ester (22), respectively. The latter molecules displayed inhibitory activity against TarO and formed the basis of a library of analogs. Most synthesized compounds exhibited comparable efficacy to ticlopidine and clopidogrel. So far, it was introduction of a trifluoromethyl group to compound 6, to generate 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline (13) that exhibited enhanced activity against TarO. Compound 13 represents a novel stable inhibitor of TarO with synergistic impact on b-lactam antibiotics against MRSA and low potential for P-450 metabolism. (C) 2013 Elsevier Ltd. All rights reserved.
• NOVEL ANTIBACTERIAL COMBINATION THERAPY
  申请人：Brown Eric D.

  公开号：US20140088069A1

  公开（公告）日：2014-03-27

  An antibacterial composition is provided including a combination of a β-lactam antibiotic that has a binding affinity for bacterial penicillin-binding protein 2; and a non-antibiotic compound which may be a thienopyridine or a non-thienopyridine compound. A method of treatment using the composition is also provided.
• [EN] NOVEL ANTIBACTERIAL COMBINATION THERAPY<br/>[FR] NOUVEAU TRAITEMENT COMBINÉ ANTIBACTÉRIEN
  申请人：UNIV MCMASTER

  公开号：WO2012162814A1

  公开（公告）日：2012-12-06

  An antibacterial composition is provided including a combination of a β-lactam antibiotic that has a binding affinity for bacterial penicillin-binding protein 2; and a non-antibiotic compound which may be a thienopyridine or a non-thienopyridine compound. A method of treatment using the composition is also provided.
• 10.1021/acs.orglett.4c02090
  作者：Mahapatra, Divya、Sau, Anirban、Ghosh, Tanmoy、Roy, Arkamitra、Kundu, Sabuj

  DOI：10.1021/acs.orglett.4c02090

  日期：——

  decrease the reaction complexity and enhance the synthetic utility. Herein, we report an inexpensive and commercially available CoBr2·H2O/terpyridine-catalyzed effective and straightforward transfer hydrogenation (TH) protocol for N-heteroarenes, utilizing NH3·BH3 (AB) under ambient conditions. Synthesis of diverse substrates and bioactive molecules demonstrated a practical applicability. Control experiments

  传统的催化剂开发依赖于配体和预催化剂的多步合成和分离。设计一种可以用易于获得的起始材料原位组装的催化系统可以降低反应复杂性并提高合成效用。在此，我们报道了一种廉价且市售的CoBr 2 ·H 2 O/三联吡啶催化的有效且直接的N-杂芳烃转移氢化(TH)方案，在环境条件下利用NH 3 ·BH 3 (AB)。多种底物和生物活性分子的合成证明了其实际适用性。对照实验和 DFT 研究阐明了其机制。