N-(3-cyanophenyl)-2-phenylacetamide | 89246-40-2

• 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: N-(3-cyanophenyl)-2-phenylacetamide
• CAS: 89246-40-2
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: AFBIVMWJUFLUNW-UHFFFAOYSA-N

物化性质

• 溶解度：
  >35.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间氨基苯甲腈 、 苯乙酰氯 生成 N-(3-cyanophenyl)-2-phenylacetamide
  参考文献：
  名称：

  Electronic properties of anticonvulsant amides. A C-13 nuclear magnetic resonance study of phenylacetanilides.

  摘要：

  制备了约20种苯胺环上带有对位和间位取代基的苯乙酰苯胺，并测量了它们的C-13核磁共振谱。通过双取代基参数 (DSP) 和 DSP-非线性共振 (DSP-NLR) 方程检查对碳原子的取代基化学位移 (SCS)。通过 DSP 分析获得了极好的相关性。结果表明-NHCOCH2Ph部分是弱电子供体。化学位移数据和推导的相关性与取代的丙酰苯胺获得的数据非常相似。

  DOI：

  10.1248/cpb.31.4172

文献信息

• B(OCH₂CF₃)₃-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether
  作者：Valerija Karaluka、Rachel M. Lanigan、Paul M. Murray、Matthew Badland、Tom D. Sheppard

  DOI：10.1039/c5ob01801c

  日期：——

  The direct amidation of pharmaceutically relevant carboxylic acids and amines with B(OCH₂CF₃)₃ in cyclopentyl methyl ether (CPME) is described.

  在环戊基甲醚（CPME）中，使用B(OCH2CF3)3直接对具有药用相关性的羧酸和胺进行酰胺化反应。
• Amide bond formation via C(sp³)–H bond functionalization and CO insertion
  作者：Huizhen Liu、Gabor Laurenczy、Ning Yan、Paul J. Dyson

  DOI：10.1039/c3cc47015f

  日期：——

  An efficient method for the synthesis of amides via Pd-catalyzed oxidative carbonylation of C(sp(3))-H bonds with CO and amines is described. The route efficiently provides substituted phenyl amides from alkanes.

  描述了一种通过Pd催化C（sp（3））-H键与CO和胺的羰基氧化羰基合成酰胺的有效方法。该路线有效地从烷烃中提供了取代的苯基酰胺。
• Nonpeptide Inhibitors of Measles Virus Entry
  作者：Aiming Sun、Andrew Prussia、Weiqiang Zhan、Ernest E. Murray、Joshua Doyle、Li-Ting Cheng、Jeong-Joong Yoon、Eugene V. Radchenko、Vladimir A. Palyulin、Richard W. Compans、Dennis C. Liotta、Richard K. Plemper、James P. Snyder

  DOI：10.1021/jm0602559

  日期：2006.8.1

  Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-mu M blockade of the MV, one of which (AS-48) exhibits IC50 0.6-3.0 mu M across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.