5-甲基噻吩-2-羰基乙酸乙酯 | 224319-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲基噻吩-2-羰基乙酸乙酯
• 英文名称: ethyl 3-(5-methylthiophen-2-yl)-3-oxopropanoate
• CAS: 224319-23-7
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: GJZZCAURPLNHGC-UHFFFAOYSA-N

物化性质

• 沸点：
  310.9±27.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 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：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-甲基噻吩-2-羰基乙酸乙酯 在 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-Chloro-4-(5-methyl-thiophen-2-yl)-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Ethyl 2-[(3-Methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine-5-carboxylate: An Inhibitor of AP-1 and NF-κB Mediated Gene Expression

  摘要：

  Several analogues of ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine-5-carboxylate (1) were synthesized and tested as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation in Jurkat T cells. From our SAR work, ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))-N-methylamino]-4-(trifluoromethyl)-pyrimidine-5-carboxylate was identified as a novel and potent inhibitor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00517-6
• 作为产物：
  描述：

  2-乙酰-5-甲基噻吩 、 碳酸二乙酯 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.33h， 生成 5-甲基噻吩-2-羰基乙酸乙酯
  参考文献：
  名称：

  抗肿瘤药。196.取代的2-噻吩基-1,8-萘啶-4-酮类化合物：它们的合成，细胞毒性和抑制微管蛋白聚合的作用。

  摘要：

  作为我们在2-芳基-1,8-萘啶-4-酮系列中潜在抗癌候选药物的持续搜索的一部分，我们合成了一系列取代的2-噻吩基-1、8-萘啶-4-酮。在国家癌症研究所的体外筛选中，大多数化合物对多种人类肿瘤细胞系均表现出显着的细胞毒性作用（log GI（50）<-4.0;引起50％生长抑制所需的对数摩尔药物浓度），包括源自固体的细胞肿瘤，例如非小细胞肺癌，结肠癌，中枢神经系统，黑色素瘤，卵巢癌，前列腺癌和乳腺癌。在大多数肿瘤细胞系中，最具活性的化合物（31-33,40）表现出很强的细胞毒性作用，ED（50）值在微摩尔或亚微摩尔范围内。最具有细胞毒性的化合物在低于微管蛋白浓度的化学计量浓度下抑制微管蛋白聚合。最有效的聚合抑制剂（40,42,43）的效果可与有效的抗有丝分裂天然产物鬼臼毒素和康普他汀A-4以及与特别有效的结构相关类似物NSC 664171的抑制剂媲美。只有化合物40是放射性标记秋水仙碱与微

  DOI：

  10.1021/jm990208z

文献信息

• DIKETOPYRROLOPYRROLE OLIGOMERS AND COMPOSITIONS, COMPRISING DIKETOPYRROLOPYRROLE OLIGOMERS
  申请人：Hayoz Pascal

  公开号：US20140217329A1

  公开（公告）日：2014-08-07

  The present invention relates to compositions, comprising (a) a compound of the formula (I), and (b) a polymeric material, to specific oligomers of the formula I, and their use as organic semiconductor in organic devices, especially in organic photovoltaics (solar cells) and photodiodes, or in a device containing a diode and/or an organic field effect transistor. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the compositions, or oligomers according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

  本发明涉及一种组合物，包括（a）式（I）的化合物和（b）一种聚合材料，特定的式I的寡聚体，以及它们在有机器件中作为有机半导体的用途，尤其是在有机光伏（太阳能电池）和光电二极管中，或在包含二极管和/或有机场效应晶体管的器件中。当本发明的组合物或寡聚体用于有机场效应晶体管、有机光伏（太阳能电池）和光电二极管时，可以观察到高效能转换、优异的场效应迁移率、良好的开关电流比和/或优异的稳定性。
• Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers
  申请人：Hayoz Pascal

  公开号：US09209412B2

  公开（公告）日：2015-12-08

  The present invention relates to compositions, comprising (a) a compound of the formula (I), and (b) a polymeric material, to specific oligomers of the formula I, and their use as organic semiconductor in organic devices, especially in organic photovoltaics (solar cells) and photodiodes, or in a device containing a diode and/or an organic field effect transistor. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the compositions, or oligomers according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

  本发明涉及组合物，包括（a）公式（I）的化合物和（b）聚合物材料，以及公式I的特定寡聚体，以及它们在有机器件中作为有机半导体的用途，特别是在有机光伏（太阳能电池）和光电二极管中，或在包含二极管和/或有机场效应晶体管的器件中。当使用本发明的组合物或寡聚体在有机场效应晶体管、有机光伏（太阳能电池）和光电二极管中时，可以观察到高效的能量转换率，优异的场效应迁移率，良好的开/关电流比和/或优异的稳定性。
• Teste; Lozac'h, Bulletin de la Societe Chimique de France, 1955, p. 442
  作者：Teste、Lozac'h

  DOI：——

  日期：——
• TWI580681
  申请人：——

  公开号：——

  公开（公告）日：——
• Identification of 2-aminopyrimidine derivatives as inhibitors of the canonical Wnt signaling pathway
  作者：Fabio Del Bello、Aniket Farande、Mario Giannella、Alessandro Piergentili、Wilma Quaglia、Tiziana Benicchi、Federico Cappelli、Arianna Nencini、Massimiliano Salerno、Russell J. Thomas、Massimilano Travagli、Maurizio Varrone

  DOI：10.1016/j.bmc.2015.07.015

  日期：2015.9

  The canonical Wnt signaling pathway plays a fundamental role in embryonic as well as in adult development. Consequently, dysregulation of the pathway has been linked to a wide spectrum of pathological conditions. In a program aimed at the identification of small molecule inhibitors of the canonical Wnt pathway we identified a series of 2-aminopyrimidine derivatives which specifically inhibited the pathway with minimal or no sign of cellular toxicity. The hit molecules 1 and 2 showed promising inhibitory activity with IC50 values of approximately 10 mu M, but low solubility and metabolic stability. During the early stage of the hit series exploration, the pyrimidine core was variously decorated to obtain active compounds with a better physico-chemical profile. In particular, compound 13 showed Wnt inhibition activity comparable to hit molecules 1 and 2, with improved physico-chemical properties. Therefore, this series of compounds may be considered a promising starting point for the design of novel small molecule inhibitors of the canonical Wnt pathway. (C) 2015 Elsevier Ltd. All rights reserved.