dimethyl 1-(4-methoxybenzyl)-1H-imidazole-4,5-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl 1-(4-methoxybenzyl)-1H-imidazole-4,5-dicarboxylate
• 英文别名: methyl 1-(p-methoxybenzyl)imidazole-4,5-dicarboxylate；Dimethyl 1-[(4-methoxyphenyl)methyl]imidazole-4,5-dicarboxylate
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: NONDFTNPYCQKMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 1-(4-methoxybenzyl)-1H-imidazole-4,5-dicarboxylate 在 氨 作用下， 以62%的产率得到1-(4-methoxybenzyl)-1H-imidazole-4,5-dicarboxamide
  参考文献：
  名称：

  Derivatives of 1H-imidazole-4,5-dicarboxamide and Use Thereof in Preparation of Anticoccidial Drugs

  摘要：

  本发明揭示了1H-咪唑-4,5-二甲酰胺的衍生物及其在制备抗球虫药物中的应用。所述衍生物的结构式如式(I)至(VI)所示。本发明揭示的1H-咪唑-4,5-二甲酰胺衍生物具有显著的抗球虫作用，特别对那些对其他抗球虫药物表现出抗性的球虫具有作用，因此它们可以用于制备抗球虫药物。

  公开号：

  US20180370921A1
• 作为产物：
  描述：

  咪唑-4,5-二羧酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 dimethyl 1-(4-methoxybenzyl)-1H-imidazole-4,5-dicarboxylate
  参考文献：
  名称：

  Derivatives of 1H-imidazole-4,5-dicarboxamide and Use Thereof in Preparation of Anticoccidial Drugs

  摘要：

  本发明揭示了1H-咪唑-4,5-二甲酰胺的衍生物及其在制备抗球虫药物中的应用。所述衍生物的结构式如式(I)至(VI)所示。本发明揭示的1H-咪唑-4,5-二甲酰胺衍生物具有显著的抗球虫作用，特别对那些对其他抗球虫药物表现出抗性的球虫具有作用，因此它们可以用于制备抗球虫药物。

  公开号：

  US20180370921A1

文献信息

• Derivatives of 1H-imidazole-4,5-dicarboxamide and use thereof in preparation of anticoccidial drugs
  申请人：GUANGZHOU INSIGHTER BIOTECHNOLOGY CO., LTD.

  公开号：US10435376B2

  公开（公告）日：2019-10-08

  Disclosed are derivatives of 1H-imidazole-4,5-dicarboxamide and use thereof in preparation of anticoccidial drugs. The derivatives have structural formulae as shown in formulae (I) to (VI). The derivatives of 1H-imidazole-4,5-dicarboxamide as disclosed in the present invention have significant anticoccidial effect, especially against coccidia that show a resistance to other anticoccidial drugs, and thus they can be used in preparation of anticoccidial drug.

  本发明公开了 1H-咪唑-4,5-二甲酰胺的衍生物及其在制备抗球虫药物中的用途。这些衍生物的结构式如式（I）至（VI）所示。本发明公开的1H-咪唑-4,5-二甲酰胺衍生物具有显著的抗球虫作用，特别是对其他抗球虫药物有抗药性的球虫，因此可用于制备抗球虫药物。
• Potent Inhibition of NTPase/Helicase of the West Nile Virus by Ring-Expanded (“Fat”) Nucleoside Analogues
  作者：Ning Zhang、Huan-Ming Chen、Verena Koch、Herbert Schmitz、Michal Minczuk、Piotr Stepien、Ali I. Fattom、Robert B. Naso、Kishna Kalicharran、Peter Borowski、Ramachandra S. Hosmane

  DOI：10.1021/jm030277k

  日期：2003.10.1

  A series of ring-expanded ("fat") nucleoside analogues (RENs) containing the 6-aminoimidazo-[4,5-e] [1,3]diazepine-4,8-dione ring system have been synthesized and screened for inhibition of NTPase/helicase of the West Nile Virus (WNV). To assess the selectivity of RENs against the viral enzymes, a truncated form of human enzyme Suv3((Delta1-159)) was also included in the study. Ring-expanded nucleosides 16, 17, and 19, which possess the long C-12, C-14, and C-18 side-chains, respectively, at position 6, as well as the ring-expanded heterocycle 39, which contains aralkyl substitution at position 1, were all found to have excellent profiles of activity and selectivity toward the viral versus human enzymes against the West Nile Virus (IC50 ranging 1-10 muM). Compound 30, while being an equally potent inhibitor of WNV, was found to be somewhat less selective, whereas compound 36, which is an alpha-anomeric counterpart of 30, exhibited potent and selective inhibition of WN-V (IC50 1-3 muM). The same compounds that showed potent inhibition of viral helicase activity completely failed to show any activity against the viral NTPase reaction even up to 500 muM. However, at concentrations >500 muM of RENs and the ATP concentrations >10 times the K-m value of the enzyme, a significant activation of NTPase activity was observed. This activating effect underwent further dramatic enhancement (>1000%) by further increases in ATP concentration in the reaction mixture, suggesting that the viral helicase and NTPase reactions are not coupled. A tentative mechanistic model has been proposed to explain the observed results.