(4'-methylbiphenyl-4-yl)acetonitrile | 478800-55-4

• 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: (4'-methylbiphenyl-4-yl)acetonitrile
• 英文别名: (4'-Methyl[1,1'-biphenyl]-4-yl) acetonitrile；2-[4-(4-methylphenyl)phenyl]acetonitrile
• CAS: 478800-55-4
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: VNDLDVFEYXXYGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4'-methylbiphenyl-4-yl)acetonitrile 在 三正丁基叠氮化锡 作用下， 以 1,4-二氧六环 为溶剂， 以63%的产率得到5-((4'-methylbiphenyl-4-yl)methyl)-1H(2H)-tetrazole
  参考文献：
  名称：

  Biaryl tetrazolyl ureas as inhibitors of endocannabinoid metabolism: Modulation at the N-portion and distal phenyl ring

  摘要：

  In the present study, we have further extended the structure activity relationships for the tetrazolyl ureas class of compounds as potential FAAH and/or MAGL inhibitors, by replacing the dimethylamino group of the parent compounds 1 and 2 with bulkier groups or by introducing on the distal phenyl ring of 1 and 2 a selected set of substituents. Some of the new compounds (16, 20, 21, 25, and 28) inhibited FAAH potently (IC50 = 3.0-9.7 nM) and selectively (39- to more than 141-fold) over MAGL, while tetrazole 27 turned out to be a promising dual FAAH MAGL inhibitor of potential therapeutic use. Covalent docking studies on FAAH indicated that the binding modes of tetrazoles 1-32 did not display a unique pattern. The ability of tetrazoles 1-32 to act as TRPV1 and TRPA1 modulators was also investigated. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.005
• 作为产物：
  描述：

  4,4'-二甲基联苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 36.0h， 生成 (4'-methylbiphenyl-4-yl)acetonitrile
  参考文献：
  名称：

  Enhanced Emission and Its Switching in Fluorescent Organic Nanoparticles

  摘要：

  A new class of organic nanoparticles (CN-MBE nanoparticles) with a mean diameter of ca. 30-40 nm, which exhibit a strongly enhanced fluorescence emission, were prepared by a simple reprecipitation method. CN-MBE (1-cyano-trans-1,2-bis-(4'-methylbiphenyl)ethylene) is very weakly fluorescent in solution, but the intensity is increased by almost 700 times in the nanoparticles. Enhanced emission in CN-MBE nanoparticles is attributed to the synergetic effect of intramolecular planarization and J-type aggregate formation (restricted excimer formation) in nanopaticles. On/off fluorescence switching for organic vapor was demonstrated with CN-MBE nanoparticles.

  DOI：

  10.1021/ja0269082

文献信息

• Photoswitchable Organic Nanoparticles and a Polymer Film Employing Multifunctional Molecules with Enhanced Fluorescence Emission and Bistable Photochromism
  作者：Seon-Jeong Lim、Byeong-Kwan An、Sang Don Jung、Myung-Ae Chung、Soo Young Park

  DOI：10.1002/anie.200461172

  日期：2004.11.26
• Pharmacophore-based design of novel 3-hydroxypyrimidine-2,4-dione subtypes as inhibitors of HIV reverse transcriptase-associated RNase H: Tolerance of a nonflexible linker
  作者：Jing Tang、Ha T. Do、Andrew D. Huber、Mary C. Casey、Karen A. Kirby、Daniel J. Wilson、Jayakanth Kankanala、Michael A. Parniak、Stefan G. Sarafianos、Zhengqiang Wang

  DOI：10.1016/j.ejmech.2019.01.081

  日期：2019.3

  The pharmacophore of active site inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H typically entails a flexible linker connecting the chelating core and the hydrophobic aromatics. We report herein that novel 3-hydroxypyrimidine-2,4-dione (HPD) subtypes with a nonflexible C-6 carbonyl linkage exhibited potent and selective biochemical inhibitory profiles with strong RNase H inhibition at low nM, weak to moderate integrase strand transfer (INST) inhibition at low mu M, and no to marginal RT polymerase (pol) inhibition up to 10 mu M. A few analogues also demonstrated significant antiviral activity without cytotoxicity. The overall inhibitory profile is comparable to or better than that of previous HPD subtypes with a flexible C-6 linker, suggesting that the nonflexible carbonyl linker can be tolerated in the design of novel HIV RNase H active site inhibitors. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Triphenylamine Derivatives with Large Two-Photon Cross-Sections
  作者：Wen Jun Yang、Dae Young Kim、Chang Ho Kim、Mi-Yun Jeong、Seung Kyu Lee、Seung-Joon Jeon、Bong Rae Cho

  DOI：10.1021/ol049766k

  日期：2004.4.1

  Triphenylamine derivatives have been synthesized and shown to exhibit large two-photon cross-sections at a wide range of wavelengths and the largest value measured by fs Z-scan experiment. Moreover, a linear relationship is noted between the two-photon cross-sections measured by ns fluorescence and fs Z-scan methods.
• Photopatterned Arrays of Fluorescent Organic Nanoparticles
  作者：Byeong-Kwan An、Soon-Ki Kwon、Soo Young Park

  DOI：10.1002/anie.200604209

  日期：2007.3.12
• ANTIBACTERIAL AGENTS
  申请人：Novartis Vaccines and Diagnostics, Inc.

  公开号：EP1618087B1

  公开（公告）日：2012-06-13