N-(3-cyano-5-fluorophenyl)-N-(3-iodobenzyl)propanamide | 1262338-98-6

• 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-cyano-5-fluorophenyl)-N-(3-iodobenzyl)propanamide
• 英文别名: N-(3-cyano-5-fluorophenyl)-N-[(3-iodophenyl)methyl]propanamide
• CAS: 1262338-98-6
• 化学式: C₁₇H₁₄FIN₂O
• 分子量: 408.214
• InChiKey: MQYRZNSUWQCIDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-cyano-5-fluorophenyl)-N-(3-iodobenzyl)propanamide 在 copper(I) oxide 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 叠氮基三甲基硅烷 、 双氧水 、 potassium acetate 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 N-[3-fluoro-5-(1H-tetrazol-5-yl)phenyl]-N-(3-hydroxybenzyl)propanamide
  参考文献：
  名称：

  Discovery of a Novel Series of CRTH2 (DP2) Receptor Antagonists Devoid of Carboxylic Acids

  摘要：

  Antagonism of the CRTH2 receptor represents a very attractive target for a variety of allergic diseases. Most CRTH2 antagonists known to date possess a carboxylic acid moiety, which is essential for binding. However, potential acid metabolites O-acyl glucuronides might be linked to idiosynchratic toxicity in humans. In this communication, we describe a new series of compounds that lack the carboxylic acid moiety. Compounds with high affinity (K(i) < 10 nM) for the receptor have been identified. Subsequent optimization succeeded in reducing the high metabolic clearance of the first compounds in human and rat liver microsomes. At the same time, inhibition of the CYP isoforms was optimized, giving rise to stable compounds with an acceptable CYP inhibition profile (IC(50) CYP2C9 and 2C19 > 1 mu M). Taken together, these data show that compounds devoid of carboxylic acid groups could represent an interesting alternative to current CRTH2 antagonists in development.

  DOI：

  10.1021/ml200223s
• 作为产物：
  描述：

  N-(3-cyanophenyl)-N-(3-iodobenzyl)propanamide 、 N-(3-cyano-5-fluorophenyl)propionamide 、 3-碘苄溴 以the title compound was obtained as a yellow oil in 80% yield的产率得到N-(3-cyano-5-fluorophenyl)-N-(3-iodobenzyl)propanamide
  参考文献：
  名称：

  TETRAZOLE DERIVATIVES

  摘要：

  本发明涉及式（I）的化合物，用作药物活性化合物，以及包含相同化合物的制药配方，用于治疗过敏性疾病。

  公开号：

  US20120115869A1

文献信息

• [EN] TETRAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE TÉTRAZOLE
  申请人：MERCK SERONO SA

  公开号：WO2011006935A3

  公开（公告）日：2013-03-28