4-(2,3,4-trimethoxy-phenyl)-but-3-enoic acid | 934176-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2,3,4-trimethoxy-phenyl)-but-3-enoic acid
• 英文别名: (E)-4-(2,3,4-trimethoxyphenyl)but-3-enoic acid
• CAS: 934176-47-3
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: SNVXUJGOFWXLEJ-SNAWJCMRSA-N

物化性质

• 沸点：
  421.6±40.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,3,4-trimethoxy-phenyl)-but-3-enoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 4-(2,3,4-trimethoxyphenyl)butanoic acid
  参考文献：
  名称：

  Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists

  摘要：

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.

  DOI：

  10.1021/jm060536g
• 作为产物：
  描述：

  2-羧乙基三苯基溴化磷 、 2,3,4-三甲氧基苯甲醛 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以51%的产率得到4-(2,3,4-trimethoxy-phenyl)-but-3-enoic acid
  参考文献：
  名称：

  Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists

  摘要：

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.

  DOI：

  10.1021/jm060536g

文献信息

• NOVEL INDENO-FUSED PHOTOCHROMIC NAPHTHOPYRANS
  申请人：TRANSITIONS OPTICAL, INC.

  公开号：EP1214311A1

  公开（公告）日：2002-06-19
• [EN] NOVEL INDENO-FUSED PHOTOCHROMIC NAPHTHOPYRANS<br/>[FR] NOUVEAUX NAPHTHOPYRANES PHOTOCHROMIQUES INDENOFUSIONNES
  申请人：TRANSITIONS OPTICAL INC

  公开号：WO2001019813A1

  公开（公告）日：2001-03-22

  Described are novel photochromic indeno-fused naphthopyran compounds, examples of which include naphthopyran compounds having a substituted or unsubstituted indeno group, the 2,1 positions of which are fused to the naphtho portion of the naphthopyran. Also present on the naphthopyran are moderate to strong electron donor substituents at the number 6- and 7-positions and optionally at the 8-position of the pyran ring or a cyclic group fused to the h side of the naphtho portion and weak to moderate electron donor substituents at the 3-position of the pyran ring. Certain substituents may also be present at the number 5, 8, 9, 10, 11, 12, or 13 carbon atoms of the compounds. These compounds have a rating of at least 80 in the Relative ΔOD at Saturation Test and may be represented by graphic formula (I): Also described are polymeric organic host materials that contain or that are coated with such compounds. Optically clear articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, benzopyrans, and spiro(indoline) type compounds, are also described.