4-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)-2-(thiophen-2-yl)benzoic acid | 1613315-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 4-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)-2-(thiophen-2-yl)benzoic acid
• CAS: 1613315-96-0
• 化学式: C₂₀H₁₆O₅S
• 分子量: 368.41
• InChiKey: XOWGTWFQOKWIRR-UHFFFAOYSA-N

物化性质

• 沸点：
  522.5±50.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)-2-(thiophen-2-yl)benzoic acid 在 甲醇 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (2S)-2-[[4-(2,3-dihydro-1,4-benzodioxin-3-ylmethoxy)-2-thiophen-2-ylbenzoyl]amino]-4-methylsulfanylbutanoic acid
  参考文献：
  名称：

  Farnesyltransferase inhibitors: CAAX mimetics based on different biaryl scaffolds

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed as farnesyltransferase (FTase) inhibitors (FTIs) by replacing AA with o-aryl or o-heteroaryl substituted p-hydroxy- or p-aminobenzoic acid, while maintaining the replacement of C with 1,4-benzodioxan-2-ylmethyl or 2-amino-4-thiazoly-lacetyl residue as in previous CAAX mimetics. Both FTase inhibition and antiproliferative effect were showed by two thiazole derivatives, namely those with 1-naphthyl (10 and 10a) or 3-furanyl (15 and 15a) in the central spacer, and by the benzodioxane derivative with 2-thienyl (6 and 6a) in the same position. Accumulation of unprenylated RAS was demonstrated in cells incubated with 15a. Consistently with FTIs literature, such results delineate the biaryl scaffold not only as a spacer but also as a sensible area of these mimetic molecules, where modifications at the branching aromatic ring are not indifferent and should be matter of further investigation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.078
• 作为产物：
  描述：

  methyl 4-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)-2-(thiophen-2-yl)benzoate 在 甲醇 、 sodium hydroxide 作用下， 反应 18.0h， 以93%的产率得到4-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)-2-(thiophen-2-yl)benzoic acid
  参考文献：
  名称：

  Farnesyltransferase inhibitors: CAAX mimetics based on different biaryl scaffolds

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed as farnesyltransferase (FTase) inhibitors (FTIs) by replacing AA with o-aryl or o-heteroaryl substituted p-hydroxy- or p-aminobenzoic acid, while maintaining the replacement of C with 1,4-benzodioxan-2-ylmethyl or 2-amino-4-thiazoly-lacetyl residue as in previous CAAX mimetics. Both FTase inhibition and antiproliferative effect were showed by two thiazole derivatives, namely those with 1-naphthyl (10 and 10a) or 3-furanyl (15 and 15a) in the central spacer, and by the benzodioxane derivative with 2-thienyl (6 and 6a) in the same position. Accumulation of unprenylated RAS was demonstrated in cells incubated with 15a. Consistently with FTIs literature, such results delineate the biaryl scaffold not only as a spacer but also as a sensible area of these mimetic molecules, where modifications at the branching aromatic ring are not indifferent and should be matter of further investigation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.078