ethyl 2-ethoxy-4-methoxybenzimidate | 814917-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-ethoxy-4-methoxybenzimidate
• 英文别名: Ethyl 2-ethoxy-4-methoxybenzenecarboximidate
• CAS: 814917-14-1
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: VNGSYBOZDAFDBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-ethoxy-4-methoxybenzimidate 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 2-(4-(4,5-bis(4-bromophenyl)-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazole-carbonyl)piperazinyl)ethyl 2-(tert-butoxycarbonylamino)acetate
  参考文献：
  名称：

  Synthesis and evaluation of an imidazole derivative–fluorescein conjugate

  摘要：

  The murine double minute (MDM2) oncogene a negative regulator of protein 53 (p53) tumor suppressor, is found overexpressed in many different types of cancer and the interaction between MDM2 and p53 has become the target of intensive research. MDM2 inhibitors represent a promising class of p53 activating compounds that may be effective in cancer treatment and diagnostic imaging. Nutlins, a family of cis-imidazoline analogues and small-molecule MDM2 antagonists, have the potential use in cancer therapies. We have synthesized an imidazole derivative (Nutlin-Glycine) conjugated to the commonly used fluorophore, 6-carboxyfluorescein (FAM) and evaluated its possible use as an imaging agent. Cellular uptake studies demonstrated that the fluorescence intensity in human osteosarcoma (SJSA-1) and colon carcinoma (HCT116) cells were significantly increased with the treatment of Nutlin-Glycine-FAM when compared with FAM (control). Blocking studies also confirmed that our imidazole-fluorescein conjugate may be a good candidate for imaging tumors, suggesting the need for further in vivo evaluation by positron emission tomography. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.11.026
• 作为产物：
  描述：

  2-ethoxy-4-methoxybenzonitrile 、 乙醇 在 乙酰氯 作用下， 以63%的产率得到ethyl 2-ethoxy-4-methoxybenzimidate
  参考文献：
  名称：

  Synthesis and evaluation of an imidazole derivative–fluorescein conjugate

  摘要：

  The murine double minute (MDM2) oncogene a negative regulator of protein 53 (p53) tumor suppressor, is found overexpressed in many different types of cancer and the interaction between MDM2 and p53 has become the target of intensive research. MDM2 inhibitors represent a promising class of p53 activating compounds that may be effective in cancer treatment and diagnostic imaging. Nutlins, a family of cis-imidazoline analogues and small-molecule MDM2 antagonists, have the potential use in cancer therapies. We have synthesized an imidazole derivative (Nutlin-Glycine) conjugated to the commonly used fluorophore, 6-carboxyfluorescein (FAM) and evaluated its possible use as an imaging agent. Cellular uptake studies demonstrated that the fluorescence intensity in human osteosarcoma (SJSA-1) and colon carcinoma (HCT116) cells were significantly increased with the treatment of Nutlin-Glycine-FAM when compared with FAM (control). Blocking studies also confirmed that our imidazole-fluorescein conjugate may be a good candidate for imaging tumors, suggesting the need for further in vivo evaluation by positron emission tomography. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.11.026

文献信息

• CIS-imidazoles
  申请人：——

  公开号：US20040259867A1

  公开（公告）日：2004-12-23

  The present invention provides compounds according to formula I and pharmaceutically acceptable salts and esters thereof, having the designations provided herein and which inhibit the interaction of MDM2 protein with a p53-like peptide and have antiproliferative activity. 1

  本发明提供了根据公式I的化合物以及药用可接受的盐和酯，具有本文提供的设计ations，并且可以抑制MDM2蛋白与p53样肽的相互作用，并具有抗增殖活性。
• CIS-IMIDAZOLINES AS MDM2 INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1643989B1

  公开（公告）日：2010-04-28
• Synthesis and evaluation of an imidazole derivative–fluorescein conjugate
  作者：Pradip Ghosh、Jiawei Zhang、Zheng-Zheng Shi、King Li

  DOI：10.1016/j.bmc.2012.11.026

  日期：2013.4

  The murine double minute (MDM2) oncogene a negative regulator of protein 53 (p53) tumor suppressor, is found overexpressed in many different types of cancer and the interaction between MDM2 and p53 has become the target of intensive research. MDM2 inhibitors represent a promising class of p53 activating compounds that may be effective in cancer treatment and diagnostic imaging. Nutlins, a family of cis-imidazoline analogues and small-molecule MDM2 antagonists, have the potential use in cancer therapies. We have synthesized an imidazole derivative (Nutlin-Glycine) conjugated to the commonly used fluorophore, 6-carboxyfluorescein (FAM) and evaluated its possible use as an imaging agent. Cellular uptake studies demonstrated that the fluorescence intensity in human osteosarcoma (SJSA-1) and colon carcinoma (HCT116) cells were significantly increased with the treatment of Nutlin-Glycine-FAM when compared with FAM (control). Blocking studies also confirmed that our imidazole-fluorescein conjugate may be a good candidate for imaging tumors, suggesting the need for further in vivo evaluation by positron emission tomography. Published by Elsevier Ltd.