4-ethyl 2-methyl 5-amino-3-methylthiophene-2,4-dicarboxylate

• 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: 4-ethyl 2-methyl 5-amino-3-methylthiophene-2,4-dicarboxylate
• 英文别名: 4-O-ethyl 2-O-methyl 5-amino-3-methylthiophene-2,4-dicarboxylate
• 化学式: C₁₀H₁₃NO₄S
• mdl: MFCD01147352
• 分子量: 243.284
• InChiKey: NWBZZEHPWCFYSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-ethyl 2-methyl 5-amino-3-methylthiophene-2,4-dicarboxylate 在 盐酸 、 一水合肼 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 49.0h， 生成 methyl 4-hydrazineyl-5-methyl-2-(thiophen-2-yl)thieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents

  摘要：

  The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C-6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.001
• 作为产物：
  描述：

  在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-ethyl 2-methyl 5-amino-3-methylthiophene-2,4-dicarboxylate
  参考文献：
  名称：

  使用 Gewald 反应在离子液相载体上合成 2-氨基噻吩

  摘要：

  摘要 本文首次报道了使用任务特异性离子液体作为 Gewald 合成 2-氨基噻吩的可溶性支持物。该合成方法简单高效，产品收率高，纯度高，无需色谱纯化。

  DOI：

  10.1080/00397910600588819

文献信息

• Discovery of novel thiophene derivatives as potent neuraminidase inhibitors
  作者：Zhi Jian Zhong、Xiao Tong Hu、Li Ping Cheng、Xing Yong Zhang、Qiang Zhang、Ju Zhang

  DOI：10.1016/j.ejmech.2021.113762

  日期：2021.12

  Neuraminidase (NA) is an important target for the treatment of influenza. In this study, a new lead NA inhibitor, 4 (ZINC01121127), was discovered by pharmacophore-based virtual screening and molecular dynamic (MD) simulation. Some novel NA inhibitors containing thiophene ring were synthesized by optimizing the skeleton of the lead compound 4. Compound 4b had the most potent inhibitory activity against

  神经氨酸酶（NA）是治疗流感的重要靶点。在这项研究中，通过基于药效团的虚拟筛选和分子动力学 (MD) 模拟，发现了一种新的先导 NA 抑制剂4 ( ZINC01121127 )。通过优化先导化合物的骨架，合成了一些新型含噻吩环的NA抑制剂4。化合物4b对NA的抑制活性最强（IC 50  = 0.03 μM），优于阳性对照羧酸奥司他韦（IC 50  = 0.06 μM）。4b（欧共体50 = 1.59 μM) 对 A/chicken/Hubei/327/2004 (H5N1-DW) 也表现出优异的抗病毒活性，优于参考药物 OSC (EC 50  = 5.97 μM)。分子对接研究表明，噻吩部分在化合物4b中起重要作用，可以很好地与NA的活性位点结合。4b的良好活性也可能归因于喹啉环延伸到150腔中。本研究结果可为新型NA抑制剂的开发提供深刻的帮助。
• 一种2-氨基噻吩类神经氨酸酶抑制剂及其制备方法与应用
  申请人：上海应用技术大学

  公开号：CN112851633A

  公开（公告）日：2021-05-28

  本发明涉及一种2‑氨基噻吩类神经氨酸酶抑制剂及其制备与应用，该抑制剂结构式为：制备方法具体为(1)将乙酰乙酸甲酯，升华硫和氰基乙酸乙酯反应后经后处理得到式(II)中间体；(2)取式(II)中间体溶于有机溶剂中和氯乙酰氯进行反应，反应后得到式(III)中间体；(3)取式(III)中间体和取代的芳香酚溶于有机溶剂中，反应后经后处理得到式(I)所示的抑制剂。与现有技术相比，本发明的化合物结构新颖，实验表明具有良好的神经氨酸酶抑制活性，可用于制备抑制神经氨酸酶活性的药物。
• Novel thiazole–thiophene conjugates as adenosine receptor antagonists: Synthesis, biological evaluation and docking studies
  作者：Dhaivat H. Pandya、Jayesh A. Sharma、Hitesh B. Jalani、Amit N. Pandya、V. Sudarsanam、Sonja Kachler、Karl Norbert Klotz、Kamala K. Vasu

  DOI：10.1016/j.bmcl.2015.01.040

  日期：2015.3

  Here we report novel thiazole-thiophene conjugates as adenosine receptor antagonists. All the molecules were evaluated for their binding affinity for adenosine receptors. Most of the molecules were found to interact with the A(1), A(2A) and A(3) adenosine receptor subtypes with good affinity values. The most potent and selective compound 8n showed an A(3) K-i value of 0.33 mu M with selectivity ratios of >90 versus the A(1) and >30 versus the A(2) subtypes. For compound 8n docking studies into the binding site of the A(3) adenosine receptor are provided to visualize its binding mode. (C) 2015 Published by Elsevier Ltd.