methyl 3-amino-6-[3-(3-phenylureido)phenyl]thieno[3,2-b]pyridine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 3-amino-6-[3-(3-phenylureido)phenyl]thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-amino-6-[3-(phenylcarbamoylamino)phenyl]thieno[3,2-b]pyridine-2-carboxylate；methyl 3-amino-6-[3-(phenylcarbamoylamino)phenyl]thieno[3,2-b]pyridine-2-carboxylate
• 化学式: C₂₂H₁₈N₄O₃S
• 分子量: 418.476
• InChiKey: JYQWKWYDDMQIBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl 3-amino-6-[3-(3-phenylureido)phenyl]thieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  New 1,3-diarylureas linked by CC Suzuki coupling to the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety: Synthesis and fluorescence studies in solution and in lipid membranes

  摘要：

  New six fluorescent 1,3-diarylureas linked by C-C Suzuki coupling to the 6-position of the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety were prepared by reaction of the amino groups on the ortho or meta positions relative to the C-C bond of the Suzuki coupling products, with different para-substituted arylisocyanates (H, OMe, CN), in high to excellent yields. The fluorescence properties of the 1,3-diarylureas in solution and in lipid membranes of egg yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylglycerol (DPPG) or dioctadecyldimethylammonium bromide (DODAB), with or without cholesterol (Ch), were studied. The six 1,3-diarylureas have reasonable fluorescence quantum yields in several solvents (0.02 <= Phi(F) <= 0.69) and present a moderately solvent sensitive emission, but are not fluorescent in alcohols and water. The compounds bearing the arylurea moiety in the meta position relative to the C-C bond, especially with the OMe and CN substituents, present the better solvatochromic properties.Incorporation of the six compounds in lipid membranes indicates that all the compounds are deeply located in the hydrophobic region of the lipid bilayers, feeling the transition between the rigid gel phase and fluid phases. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.01.006

文献信息

• New 1,3-diarylureas linked by CC Suzuki coupling to the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety: Synthesis and fluorescence studies in solution and in lipid membranes
  作者：Maria-João R.P. Queiroz、Daniela Peixoto、Ana Rita O. Rodrigues、Pedro M.F. Mendes、Cátia N.C. Costa、Paulo J.G. Coutinho、Elisabete M.S. Castanheira

  DOI：10.1016/j.jphotochem.2013.01.006

  日期：2013.3

  New six fluorescent 1,3-diarylureas linked by C-C Suzuki coupling to the 6-position of the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety were prepared by reaction of the amino groups on the ortho or meta positions relative to the C-C bond of the Suzuki coupling products, with different para-substituted arylisocyanates (H, OMe, CN), in high to excellent yields. The fluorescence properties of the 1,3-diarylureas in solution and in lipid membranes of egg yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylglycerol (DPPG) or dioctadecyldimethylammonium bromide (DODAB), with or without cholesterol (Ch), were studied. The six 1,3-diarylureas have reasonable fluorescence quantum yields in several solvents (0.02 <= Phi(F) <= 0.69) and present a moderately solvent sensitive emission, but are not fluorescent in alcohols and water. The compounds bearing the arylurea moiety in the meta position relative to the C-C bond, especially with the OMe and CN substituents, present the better solvatochromic properties.Incorporation of the six compounds in lipid membranes indicates that all the compounds are deeply located in the hydrophobic region of the lipid bilayers, feeling the transition between the rigid gel phase and fluid phases. (C) 2013 Elsevier B.V. All rights reserved.