(E)-ethyl 3-(3-(4-methoxyphenyl)allyl)-2,4-dioxo-5-phenethyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate | 1376709-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: (E)-ethyl 3-(3-(4-methoxyphenyl)allyl)-2,4-dioxo-5-phenethyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate
• 英文别名: ethyl 3-[(E)-3-(4-methoxyphenyl)prop-2-enyl]-2,4-dioxo-5-(2-phenylethyl)-1H-thieno[2,3-d]pyrimidine-6-carboxylate
• CAS: 1376709-52-2
• 化学式: C₂₇H₂₆N₂O₅S
• 分子量: 490.58
• InChiKey: SVGFHQCWNHMPIK-JXMROGBWSA-N

物化性质

• 密度：
  1.276±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氧代-5-苯基-戊酸乙酯 在 吗啉 、 吡啶 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 81.25h， 生成 (E)-ethyl 3-(3-(4-methoxyphenyl)allyl)-2,4-dioxo-5-phenethyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Thieno[2,3-d]pyrimidinedione derivatives as antibacterial agents

  摘要：

  Several thieno[2,3-d]pyrimidinediones have been synthesized and examined for antibacterial activity against a range of Gram-positive and Gram-negative pathogens. Two compounds displayed potent activity (2-16 mg/L) against multi-drug resistant Gram-positive organisms, including methicillin resistant, vancomycin-intermediate, vancomycin-resistant Staphylococcus aureus (MRSA, VISA, VRSA) and vancomycin-resistant enterococci (VRE). Only one of these agents possessed moderate activity (16 -32 mg/L) against Gram-negative strains. An examination of the cytotoxicity of these agents revealed that they displayed low toxicity (40-50 mg/L) against mammalian cells and very low hemolytic activity (2-7%). Taken together, these studies suggest that thieno[2,3-d]pyrimidinediones are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.035

文献信息

• Thieno[2,3-d]pyrimidinedione derivatives as antibacterial agents
  作者：Mahender B. Dewal、Amit S. Wani、Celine Vidaillac、David Oupický、Michael J. Rybak、Steven M. Firestine

  DOI：10.1016/j.ejmech.2012.02.035

  日期：2012.5

  Several thieno[2,3-d]pyrimidinediones have been synthesized and examined for antibacterial activity against a range of Gram-positive and Gram-negative pathogens. Two compounds displayed potent activity (2-16 mg/L) against multi-drug resistant Gram-positive organisms, including methicillin resistant, vancomycin-intermediate, vancomycin-resistant Staphylococcus aureus (MRSA, VISA, VRSA) and vancomycin-resistant enterococci (VRE). Only one of these agents possessed moderate activity (16 -32 mg/L) against Gram-negative strains. An examination of the cytotoxicity of these agents revealed that they displayed low toxicity (40-50 mg/L) against mammalian cells and very low hemolytic activity (2-7%). Taken together, these studies suggest that thieno[2,3-d]pyrimidinediones are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Masson SAS. All rights reserved.