3-[dimethyl(oxo)-λ⁶-sulfanylidene]-1-[4-(trifluoromethyl)phenyl]urea

• 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: 3-[dimethyl(oxo)-λ⁶-sulfanylidene]-1-[4-(trifluoromethyl)phenyl]urea
• 英文别名: 1-[Dimethyl(oxo)-lambda6-sulfanylidene]-3-[4-(trifluoromethyl)phenyl]urea；1-[dimethyl(oxo)-λ6-sulfanylidene]-3-[4-(trifluoromethyl)phenyl]urea
• 化学式: C₁₀H₁₁F₃N₂O₂S
• 分子量: 280.271
• InChiKey: AAKKXXWWXVIOBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲基亚磺酰亚胺 、 4-三氟甲基苯基异氰酸酯 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以96%的产率得到3-[dimethyl(oxo)-λ⁶-sulfanylidene]-1-[4-(trifluoromethyl)phenyl]urea
  参考文献：
  名称：

  Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery

  摘要：

  Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.091

文献信息

• Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery
  作者：Marcus Frings、Carsten Bolm、Andreas Blum、Christian Gnamm

  DOI：10.1016/j.ejmech.2016.09.091

  日期：2017.1

  Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists. (C) 2016 Elsevier Masson SAS. All rights reserved.