ethyl 5-diethoxymethylimidazole-4-carboxylate | 137159-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-diethoxymethylimidazole-4-carboxylate
• 英文别名: Ethyl 5-(diethoxymethyl)-1H-imidazole-4-carboxylate
• CAS: 137159-34-3
• 化学式: C₁₁H₁₈N₂O₄
• 分子量: 242.275
• InChiKey: CWKNTPWKEFUBIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  ethyl 5-diethoxymethylimidazole-4-carboxylate 在 氨 、 sodium hydride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 38.0h， 生成 5-diethoxymethyl-1-(2'-deoxy-β-D-erythropentofuranosyl)imidazole-4-carboxamide
  参考文献：
  名称：

  A Novel Imidazole Nucleoside Containing a Diaminodihydro-S-triazine as a Substituent: Inhibitory Activity Against the West Nile Virus NTPase/Helicase

  摘要：

  The attempted synthesis of a ring-expanded guanosine (1) containing the imidazo[4,5-e][1,3]diazepine ring system by condensation of 1-(2'-deoxy-beta-D-erythropentofuranosyl)-4-ethoxycarbonylimidazole-5-carbaldehyde (2) with guanidine resulted in the formation of an unexpected product, 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-(2,4-diamino-3,6-dihydro-1,3,5-triazin-6-yl)imidazole-4-carboxamide (7). The structure as well as the pathway of formation of 7 was corroborated by isolation of the intermediate, followed by its conversion to the product. Nucleoside 7 showed promising in vitro anti-helicase activity against the West Nile virus NTPase/ helicase with an IC 50 of 3-10 mu g/mL.

  DOI：

  10.1080/15257770500267063
• 作为产物：
  描述：

  二乙氧基乙腈 、 异氰基乙酸乙酯 在 sodium hydride 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 5.0h， 以56%的产率得到ethyl 5-diethoxymethylimidazole-4-carboxylate
  参考文献：
  名称：

  A Novel Imidazole Nucleoside Containing a Diaminodihydro-S-triazine as a Substituent: Inhibitory Activity Against the West Nile Virus NTPase/Helicase

  摘要：

  The attempted synthesis of a ring-expanded guanosine (1) containing the imidazo[4,5-e][1,3]diazepine ring system by condensation of 1-(2'-deoxy-beta-D-erythropentofuranosyl)-4-ethoxycarbonylimidazole-5-carbaldehyde (2) with guanidine resulted in the formation of an unexpected product, 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-(2,4-diamino-3,6-dihydro-1,3,5-triazin-6-yl)imidazole-4-carboxamide (7). The structure as well as the pathway of formation of 7 was corroborated by isolation of the intermediate, followed by its conversion to the product. Nucleoside 7 showed promising in vitro anti-helicase activity against the West Nile virus NTPase/ helicase with an IC 50 of 3-10 mu g/mL.

  DOI：

  10.1080/15257770500267063

文献信息

• Selective functional group transformation using guanidine: the conversion of an ester group into an amide in vinylogous ester–aldehydes of imidazole
  作者：Ravi K. Ujjinamatada、Ramachandra S. Hosmane

  DOI：10.1016/j.tetlet.2005.07.024

  日期：2005.9

  An efficient and convenient method has been described for the selective conversion of an ester group into the corresponding carboxamide in vinylogous ester–aldehydes of imidazole. The method uses excess guanidine, which protects the aldehyde function as a diaminodihydro-s-triazine moiety. The carboxaldehyde group is regenerated by hydrolysis of the triazine moiety to provide vinylogous amide–aldehydes

  已经描述了一种有效且方便的方法，用于在咪唑的乙烯基酯-醛中将酯基选择性转化为相应的羧酰胺。该方法使用过量的胍，它可以保护的醛用作diaminodihydro-小号嗪部分。羧醛基通过三嗪部分的水解而再生，以提供咪唑的乙烯基酰胺醛作为最终产物。
• An analogue of AICAR with dual inhibitory activity against WNV and HCV NTPase/helicase: Synthesis and in vitro screening of 4-carbamoyl-5-(4,6-diamino-2,5-dihydro-1,3,5-triazin-2-yl)imidazole-1-β-d-ribofuranoside
  作者：Ravi K. Ujjinamatada、Andrea Baier、Peter Borowski、Ramachandra S. Hosmane

  DOI：10.1016/j.bmcl.2007.01.074

  日期：2007.4

  The title compound (4) was synthesized by the reaction of ethyl 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-5-formylimidazole-4-carboxylate with excess guanidine in ethanol at reflux. Compound 4 was evaluated in vitro against NTPases/helicases of four different viruses of the Flaviviridae family, including the West Nile virus (WNV), hepatitis C virus (HCV), dengue virus (DENV), and the Japanese encephalitis virus (JEV), employing both an RNA and a DNA substrate. The compound showed activity against NTPase/helicase of WNV and HCV with an IC50 of 23 and 37 mu M, respectively, when a DNA substrate was employed, while no activity was observed when an RNA substrate was used. There was no activity against the NTPase/helicase of either DENV or JEV irrespective of whether an RNA or a DNA substrate was employed. Considering that Flaviviridae are RNA viruses, the observed absence of activity against an RNA substrate, but the presence of activity against a DNA substrate is intriguing and somewhat surprising. The preliminary studies show that compound 4 does not form a tight complex with either an RNA or a DNA substrate, suggesting that its mechanism of action may involve direct interaction with the enzyme. (c) 2007 Elsevier Ltd. All rights reserved.
• Heterocyclic compounds, their production and use
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0733633B1

  公开（公告）日：2003-05-28
• US5753664A
  申请人：——

  公开号：US5753664A

  公开（公告）日：1998-05-19