2-(4-nitrobenzyl)naphthalene | 3042-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-nitrobenzyl)naphthalene
• 英文别名: 2-[(4-Nitrophenyl)methyl]naphthalene
• CAS: 3042-62-4
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: SJCFBVMMGBGDIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  2-(4-nitrobenzyl)naphthalene 在 盐酸 、 三氟甲磺酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 生成 6-(naphthalen-2-ylmethyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Opioid Peptidomimetics: Leads for the Design of Bioavailable Mixed Efficacy μ Opioid Receptor (MOR) Agonist/δ Opioid Receptor (DOR) Antagonist Ligands

  摘要：

  We have previously described opioid peptidomimetic, 1, employing a tetrahydroquinoline scaffold and modeled on a series of cyclic tetrapeptide opioid agonists. We have recently described modifications to these peptides that confer a mu opioid receptor (MOR) agonist, delta opioid receptor (DOR) antagonist profile, which has been shown to reduce the development of tolerance to the analgesic actions of MOR agonists. Several such bifunctional ligands have been reported, but none has been demonstrated to cross the blood-brain barrier. Here we describe the transfer of structural features that evoked MOR agonist/DOR antagonist behavior in the cyclic peptides to the tetrahydroquinoline scaffold and show that the resulting peptidomimetics maintain the desired pharmacological profile. Further, the 4R diastereomer of 1 was fully efficacious and approximately equipotent to morphine in the mouse warm water tail withdrawal assay following intraperitoneal administration and thus a promising lead for the development of opioid analgesics with reduced tolerance.

  DOI：

  10.1021/jm400050y
• 作为产物：
  描述：

  2-萘硼酸 、 对硝基溴化苄 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以90%的产率得到2-(4-nitrobenzyl)naphthalene
  参考文献：
  名称：

  乙烯基磺酰胺衍生物作为高效，共价TEAD自棕榈酸酯化抑制剂的发现和生物学评估。

  摘要：

  转录增强子相关域家族成员（TEADs）是最重要的下游效应子，在发育，再生和组织稳态中发挥关键作用。最近的生化研究表明，TEADs可能会经历自身的棕榈酰化作用，这对其功能是必不可少的，这使得脂质结合袋成为化学干预的有吸引力的靶标。在本文中，通过基于结构的虚拟筛选和合理的药物化学优化，我们确定DC-TEADin02是最有效，选择性最高的共价TEAD自戊二酰化抑制剂，IC50值为197±19 nM，而对TEAD-YAP相互作用的影响却最小。进一步的生化反筛查证明了DC-TEADin02在激酶家族中的特异性硫醇反应性和选择性，脂质结合蛋白和表观遗传学靶标。值得注意的是，DC-TEADin02抑制TEADs转录活性，从而导致YAP相关下游基因表达的下调。综上所述，我们的发现证明了通过不可逆的TEADs自身棕榈酰化活性的化学干预，在Hippo信号通路中调节转录输出的有效性，这可能会在将来成为TEAD棕榈酰化相关研究的合格化学工具。

  DOI：

  10.1016/j.ejmech.2019.111767

文献信息

• Diarylmethanes through an Unprecedented Palladium-Catalyzed C−C Cross-Coupling of 1-(Aryl)methoxy-1 <i>H</i>-Benzotriazoles with Arylboronic Acids
  作者：Manish K. Singh、Mahesh K. Lakshman

  DOI：10.1002/cctc.201500818

  日期：2015.12

  1‐(Aryl)methoxy‐1H‐benzotriazoles (ArCH2OBt) are bench‐stable reagents that are prepared readily from 1H‐benzotriazol‐1‐yl‐4‐methylbenzenesulfonate and benzylic alcohols. These compounds, which contain a N−O−C bond, undergo cross‐coupling with arylboronic acids by C−O bond scission with catalysts that comprise Pd(OAc)2 and biarylphosphine ligands. Such reactivity of ArCH2OBt derivatives, which lead

  1-（芳基）甲氧基-1 H-苯并三唑（ArCH 2 OBt）是可从1 H-苯并三唑-1-基-4-甲基苯磺酸盐和苄基醇中轻松制备的稳定试剂。这些包含一个N-OC键的化合物，通过包含Pd（OAc）2和联芳基膦配体的催化剂的C-O键断裂，与芳基硼酸发生交叉偶联。先前没有描述过导致二芳基甲烷的ArCH 2 OBt衍生物的这种反应性，并构成了苄醇的新活化。关于支持催化活性的各种配体-金属配合物，似乎那些具有较小“埋入体积百分比”（％V bur）的配合物。）提供更好的结果。在最初的优化研究中以及与困难的偶联伙伴的进一步反应中已经评估了该因素。在这种类型的反应中，联芳基部分的配体电子似乎起着较小的作用。双配位的双[（2-二苯基膦基）苯基]醚似乎适合提高低产率反应的收率。
• 757. Alkylation of the aromatic nucleus. Part XIV. Naphthalene
  作者：M. Z. A. Badr、W. J. Hickinbottom

  DOI：10.1039/jr9650004101

  日期：——
• Affinity of 3-acyl substituted 4-quinolones at the benzodiazepine site of GABAA receptors
  作者：Erik Lager、Jakob Nilsson、Elsebet Østergaard Nielsen、Mogens Nielsen、Tommy Liljefors、Olov Sterner

  DOI：10.1016/j.bmc.2008.05.049

  日期：2008.7

  The finding that alkyl 1,4-dihydro-4-oxoquinoline-3-carboxylate and N-alkyl-1,4-dihydro-4-oxoquinoline3-carboxamide derivatives may be high-affinity ligands at the benzodiazepine binding site of the GABA(A) receptor, prompted a study of 3-acyl-1,4-dihydro-4-oxoquinoline (3-acyl-4-quinolones). In general, the affinity of the 3-acyl derivatives was found to be comparable with the 3-carboxylate and the 3-carboxamide derivatives, and certain substituents ( e. g., benzyl) in position 6 were again shown to be important. As it is believed that the benzodiazepine binding site is situated between an alpha-and a gamma-subunit in the GABA(A) receptor, selected compounds were tested on the alpha(1)beta(2)gamma(2s), alpha(2)beta(2)gamma(2s) and alpha(3)beta(2)gamma(2s) GABAA receptor subtypes. The 3-acyl-4-quinolones display various degrees of selectivity for alpha(1)-versus alpha(2)- and alpha(3)- containing receptors, and high-affinity ligands essentially selective for alpha(1) over alpha(3) were developed. (c) 2008 Elsevier Ltd. All rights reserved.
• Designing a bifunctional metal-organic framework by tandem post-synthetic modifications; an efficient and recyclable catalyst for Suzuki-Miyaura cross-coupling reaction
  作者：Behrang Salahshournia、Hosein Hamadi、Valiollah Nobakht

  DOI：10.1016/j.poly.2020.114749

  日期：2020.10

  A new Cu/Pd bimetallic Cu-MOF-[Pd] was synthesized through covalent, dative and inorganic post-synthetic modifications. In order to achieve the Cu-MOF-[Pd], Zn-MOF (TMU-17-NH2) was initially selected and fabricated by grafting of salicylaldehyde via Schiff-base formation followed by complex formation with Pd(II). Then, the as-synthesis MOF, Zn-MOF-[Pd], was subjected as 3D-template to obtain Cu-MOF-[Pd] by transmetalation process. The Cu-MOF-[Pd] was characterized by FT-IR spectroscopy, atomic absorption spectroscopy (AAS), field emission scanning electron microscopy (FE-SEM), powder X-ray diffraction (PXRD), energy dispersive X-ray spectroscopy (EDS), and EDS mapping techniques. The feasibility of using Cu-MOF-[Pd] as a highly active recoverable catalyst was confirmed in the Suzuki-Miyaura cross-coupling reaction in a mixed water/ethanol solvent. The results show that this novel nano-composite could serve as an efficient bimetallic heterogeneous catalyst and reuse at least for 5 times without loss in activity. (C) 2020 Elsevier Ltd. All rights reserved.