ethyl 2-amino-5-butylthiophene-3-carboxylate | 57394-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 2-amino-5-butylthiophene-3-carboxylate
• 英文别名: 2-amino-5-butyl-3-thiophenecarboxylic acid, ethyl ester
• CAS: 57394-87-3
• 化学式: C₁₁H₁₇NO₂S
• 分子量: 227.327
• InChiKey: AMOGRARIHWAXOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氯烟酰胺 、 ethyl 2-amino-5-butylthiophene-3-carboxylate 反应 3.92h， 以is obtained 1.9 g of 2-butyl-4-oxo-4H-pyrido-[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide的产率得到2-butyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide
  参考文献：
  名称：

  Oxo-pyrido[1,2-a]thienopyrimidine compounds and methods for their

  摘要：

  本发明揭示了Oxo-pyrido[1,2-a]thienopyrimidine化合物及其盐，生产方法，生产中间体，含有该化合物的制药组合物以及使用该组合物治疗过敏的方法。

  公开号：

  US04230707A1
• 作为产物：
  描述：

  正己醛 、 氰乙酸乙酯 在 sulfur 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到ethyl 2-amino-5-butylthiophene-3-carboxylate
  参考文献：
  名称：

  A Class of 5-Nitro-2-furancarboxylamides with Potent Trypanocidal Activity against Trypanosoma brucei in Vitro

  摘要：

  Recently, the World Health Organization approved the nifurtimox-eflornithine combination therapy for the treatment of human African trypanosomiasis, renewing interest in nitroheterocycle therapies for this and associated diseases. In this study, we have synthesized a series of novel 5-nitro-2-furancarboxylamides that show potent trypanocidal activity, similar to 1000-fold more potent than nifurtimox against in vitro Trypanosoma brucei with very low cytotoxicity against human He La cells. More importantly, the most potent analogue showed very limited cross-resistance to nifurtimox-resistant cells and vice versa. This implies that our novel, relatively easy to synthesize and therefore cheap, 5-nitro-2-furancarboxylamides are targeting a different, but still essential, biochemical process to those targeted by nifurtimox or its metabolites in the parasites. The significant increase in potency (smaller dose probably required) has the potential for greatly reducing unwanted side effects and also reducing the likelihood of drug resistance. Collectively, these findings have important implications for the future therapeutic treatment of African sleeping sickness.

  DOI：

  10.1021/jm301215e

文献信息

• Oxo-pyrido[1,2-a]thienopyrimidine compounds and methods for their
  申请人：Warner-Lambert Company

  公开号：US04230707A1

  公开（公告）日：1980-10-28

  Oxo-pyrido[1,2-a]thienopyrimidine compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds and methods for treating allergies using said compositions are disclosed.

  氧杂噻吡咯并[1,2-a]噻唑嘧啶化合物，其盐，生产方法，生产中间体，含有该化合物的药物组成物和使用该组成物治疗过敏的方法被披露。
• Dihydro-oxo-pyrido[1,2-a]thienopyrimidine compounds
  申请人：Warner-Lambert Company

  公开号：US04287340A1

  公开（公告）日：1981-09-01

  Oxo-pyrido[1,2-a]thienopyrimidine compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds and methods for treating allergies using said compositions are disclosed.

  本发明公开了Oxo-pyrido[1,2-a]thienopyrimidine化合物及其盐、制备方法、制备中间体、含有该化合物的制药组合物以及使用该组合物治疗过敏的方法。
• Certain 2-pyridylamino-3-thiophene carboxylic acid derivatives
  申请人：Warner-Lambert Company

  公开号：US04332947A1

  公开（公告）日：1982-06-01

  Oxo-pyrido[1,2-a]thienopyrimidine compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds and methods for treating allergies using said compositions are disclosed.

  本发明揭示了Oxo-pyrido[1,2-a]thienopyrimidine化合物及其盐、制备方法、制备中间体、含有该化合物的制药组合物以及使用该组合物治疗过敏的方法。
• A Class of 5-Nitro-2-furancarboxylamides with Potent Trypanocidal Activity against <i>Trypanosoma brucei</i> in Vitro
  作者：Linna Zhou、Gavin Stewart、Emeline Rideau、Nicholas J. Westwood、Terry K. Smith

  DOI：10.1021/jm301215e

  日期：2013.2.14

  Recently, the World Health Organization approved the nifurtimox-eflornithine combination therapy for the treatment of human African trypanosomiasis, renewing interest in nitroheterocycle therapies for this and associated diseases. In this study, we have synthesized a series of novel 5-nitro-2-furancarboxylamides that show potent trypanocidal activity, similar to 1000-fold more potent than nifurtimox against in vitro Trypanosoma brucei with very low cytotoxicity against human He La cells. More importantly, the most potent analogue showed very limited cross-resistance to nifurtimox-resistant cells and vice versa. This implies that our novel, relatively easy to synthesize and therefore cheap, 5-nitro-2-furancarboxylamides are targeting a different, but still essential, biochemical process to those targeted by nifurtimox or its metabolites in the parasites. The significant increase in potency (smaller dose probably required) has the potential for greatly reducing unwanted side effects and also reducing the likelihood of drug resistance. Collectively, these findings have important implications for the future therapeutic treatment of African sleeping sickness.
• TINNEY, F. J.;CETENKO, W. A.;KERBLESKI, J. J.;CONNOR, D. T.;SORENSON, R. +, J. MED. CHEM., 1981, 24, N 7, 878-882
  作者：TINNEY, F. J.、CETENKO, W. A.、KERBLESKI, J. J.、CONNOR, D. T.、SORENSON, R. +

  DOI：——

  日期：——