N-(naphthalen-2-yl(phenyl)methyl)aniline | 103545-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalen-2-yl(phenyl)methyl)aniline
• 英文别名: N-[naphthalen-2-yl(phenyl)methyl]aniline
• CAS: 103545-11-5
• 化学式: C₂₃H₁₉N
• 分子量: 309.411
• InChiKey: WPJYDTYFROQBPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯甲酰萘 、 苯胺 在 四氯化钛 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以85%的产率得到N-(naphthalen-2-yl(phenyl)methyl)aniline
  参考文献：
  名称：

  8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

  摘要：

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.043

文献信息

• Synthesis of Benzhydryl-Substituted Amines by Silanolate-Mediated Aldimine Arylation with Functionalized Aryl Nucleophiles Released from Diazene-Based Reagents
  作者：Aliyaah J. M. Rahman、Lucie Finck、Wolfgang Obermayer、Martin Oestreich

  DOI：10.1021/acs.orglett.2c03798

  日期：2022.12.16

  imine derivatives with functionalized aryl pronucleophiles is reported. The aryl nucleophiles are released from silicon-protected aryl-substituted diazenes by desilylation with potassium trimethylsilanolate concomitant with the loss of dinitrogen. A broad range of functional groups is tolerated in the aryl nucleophile but, depending upon their electronic effect, require specific groups at the imine

  报道了一种无过渡金属的方案，用于N -苯基 - 和N -苯甲酰基取代的苯甲醛衍生亚胺衍生物与功能化芳基亲核试剂的芳基化。芳基亲核试剂通过用三甲基硅烷醇钾进行脱甲硅烷基化并伴随二氮的损失从硅保护的芳基取代的二氮烯中释放出来。芳基亲核试剂可容许多种官能团，但根据它们的电子效应，亚胺氮原子上需要特定的基团。
• Synthesis of Sterically Encumbered Alkaline‐Earth Metal Amides Applying the In Situ Grignard Reagent Formation
  作者：Simon Sengupta、Philipp Schüler、Phil Liebing、Matthias Westerhausen

  DOI：10.1002/chem.202300035

  日期：——

  Magnesium and calcium are too inert to deprotonate amines directly. In addition, N-bound trialkylsilyl groups proved to be beneficial for the synthesis of calcium bis(amides). The addition of hydryl bromides or iodides to suspensions of calcium and imines in THF allows straightforward conversion to silyl-free calcium bis(amides) with bulky substituents.

  镁和钙太惰性，不能直接使胺去质子化。此外，N-结合的三烷基甲硅烷基被证明有利于双（酰胺）钙的合成。将氢溴化物或碘化物添加到钙和亚胺在 THF 中的悬浮液中，可以直接转化为具有庞大取代基的不含甲硅烷基的双（酰胺）钙。
• HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING ELEMENT USING SAME
  申请人：LG Chem, Ltd.

  公开号：EP3053982B1

  公开（公告）日：2018-01-17
• 8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells
  作者：Idrees Mohammed、Shahienaz E. Hampton、Louise Ashall、Emily R. Hildebrandt、Robert A. Kutlik、Surya P. Manandhar、Brandon J. Floyd、Haley E. Smith、Jonathan K. Dozier、Mark D. Distefano、Walter K. Schmidt、Timothy M. Dore

  DOI：10.1016/j.bmc.2015.11.043

  日期：2016.1

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.