3-(3-硝基苄基)-3H-咪唑-4-甲醛 | 85103-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3-硝基苄基)-3H-咪唑-4-甲醛
• 英文名称: 3-(3-Nitro-benzyl)-3H-imidazole-4-carbaldehyde
• 英文别名: 3-[(3-nitrophenyl)methyl]imidazole-4-carbaldehyde
• CAS: 85103-01-1
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: KDNSSUMBMSLCIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  5-氨基-[1,1'-联苯]-2-甲酸甲酯 、 3-(3-硝基苄基)-3H-咪唑-4-甲醛 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 5-{[3-(3-nitrobenzyl)-3H-imidazol-4-ylmethyl]-amino}-biphenyl-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease

  摘要：

  We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14 alpha-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

  DOI：

  10.1021/jm900030h
• 作为产物：
  描述：

  间硝基氯化苄 在 manganese(IV) oxide 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 3-(3-硝基苄基)-3H-咪唑-4-甲醛
  参考文献：
  名称：

  Synthesis ofN ¹-Aryl- andN ¹-Benzyl Substituted Imidazole-4- and Imidazole-5-carbaldehydes

  摘要：

  DOI：

  10.1055/s-1983-30217

文献信息

• ANTONINI, I.;CRISTALLI, G.;FRANCHETTI, P.;GRIFANTINI, M.;MARTELLI, S., SYNTHESIS, BRD, 1983, N 1, 47-49
  作者：ANTONINI, I.、CRISTALLI, G.、FRANCHETTI, P.、GRIFANTINI, M.、MARTELLI, S.

  DOI：——

  日期：——
• Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease
  作者：Praveen Kumar Suryadevara、Srinivas Olepu、Jeffrey W. Lockman、Junko Ohkanda、Mandana Karimi、Christophe L. M. J. Verlinde、James M. Kraus、Jan Schoepe、Wesley C. Van Voorhis、Andrew D. Hamilton、Frederick S. Buckner、Michael H. Gelb

  DOI：10.1021/jm900030h

  日期：2009.6.25

  We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14 alpha-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.
• Synthesis of<i>N</i> ¹-Aryl- and<i>N</i> ¹-Benzyl Substituted Imidazole-4- and Imidazole-5-carbaldehydes
  作者：Ippolito Antonini、Gloria Cristalli、Palmarisa Franchetti、Mario Grifantini、Sante Martelli

  DOI：10.1055/s-1983-30217

  日期：——