5,6-dimethyl-2-phenylthieno[2,3-d]pyrimidin-4(3H)-one | 18593-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 5,6-dimethyl-2-phenylthieno[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 5,6-dimethyl-2-phenyl-3H-thieno[2,3-d]pyrimidin-4-one
• CAS: 18593-46-9
• 化学式: C₁₄H₁₂N₂OS
• 分子量: 256.328
• InChiKey: BAYOCOYPAILNCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-2-phenylthieno[2,3-d]pyrimidin-4(3H)-one 在 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 生成 2-phenyl-4-[(2-hydroxy)ethyl]amino-5,6-dimethylthieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Prasad, Mailavaram Raghu; Rao, Akkinepalli Raghu Ram; Rao, Pamulaparthi Shanthan, Synthesis, 2001, # 14, p. 2119 - 2123

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-二甲基-2-氨基噻吩-3-甲酸 在 吡啶 、 氨 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5,6-dimethyl-2-phenylthieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Prasad, M. Raghu; Rao, A. Raghuram; Rao, P. Shanthan, Journal of Chemical Research, Miniprint, 2002, # 1, p. 149 - 153

  摘要：

  DOI：

文献信息

• Microwave-assisted synthesis of potent PDE7 inhibitors containing a thienopyrimidin-4-amine scaffold
  作者：Ana I. Sánchez、Ricardo Meneses、José M. Mínguez、Araceli Núñez、Rafael R. Castillo、Fabiana Filace、Carolina Burgos、Juan J. Vaquero、Julio Álvarez-Builla、Alvaro Cortés-Cabrera、Federico Gago、Emma Terricabras、Víctor Segarra

  DOI：10.1039/c4ob00175c

  日期：——

  Thienopyrimidin-4-amines have been synthesized, evaluated and modelled as phosphodiesterase inhibitors.

  噻唑嘧啶-4-胺已被合成、评估并建模为磷酸二酯酶抑制剂。
• Exploiting Drug-Resistant Enzymes as Tools To Identify Thienopyrimidinone Inhibitors of Human Immunodeficiency Virus Reverse Transcriptase-Associated Ribonuclease H
  作者：Takashi Masaoka、Suhman Chung、Pierluigi Caboni、Jason W. Rausch、Jennifer A. Wilson、Humeyra Taskent-Sezgin、John A. Beutler、Graziella Tocco、Stuart F. J. Le Grice

  DOI：10.1021/jm400405z

  日期：2013.7.11

  The thienopyrimidinone 5,6-dimethyl-2-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (DNTP) occupies the interface between the p66 ribonuclease H (RNase H) domain and p51 thumb of human immunodeficiency virus reverse transcriptase (HIV RT), thereby inducing a conformational change incompatible with catalysis. Here, we combined biochemical characterization of 39 DNTP derivatives with antiviral testing

  噻吩并嘧啶酮5,6-二甲基-2-(4-硝基苯基)噻吩并[2,3 - d ]嘧啶-4(3 H)-one (DNTP) 占据 p66 核糖核酸酶 H (RNase H) 域和人类免疫缺陷病毒逆转录酶 (HIV RT) 的 p51 拇指之间的界面，从而导致与催化不相容的构象变化。在这里，我们将 39 种 DNTP 衍生物的生化表征与所选化合物的抗病毒测试相结合。除了野生型 HIV-1 RT，还使用合理设计的 p66/p51 异二聚体对衍生物进行了评估，这些异二聚体表现出高水平的 DNTP 敏感性或抗性。该策略鉴定了 3',4'-二羟基苯基（儿茶酚）取代的噻吩并嘧啶酮，对野生型 HIV-1 RT 和耐药变体具有亚微摩尔的体外活性。热位移分析表明，与活性位点 RNase H 抑制剂相比，这些噻吩并嘧啶酮会破坏稳定酶，在某些情况下将T m降低 5 °C。重要的是，含有儿茶酚的噻吩并嘧啶酮还抑制细胞中的
• Iodine catalysed synthesis and antibacterial evaluation of thieno-[2,3-<i>d</i>]pyrimidine derivatives
  作者：Mehdi Bakavoli、Ghodsieh Bagherzadeh、Maryam Vaseghifar、Ali Shiri、Parvaneh Pordeli

  DOI：10.3184/030823409x12537299044500

  日期：2009.11

  route via iodine catalysed heterocyclisation of 2-amino-4,5-dimethylthiophene-3-carboxamide with aromatic aldehydes affording a series of thieno[2,3-d]pyrimidine derivatives in a single step have been developed. Some of these compounds exhibited antibacterial activities comparable to Streptomycin as reference drug.

  已经开发了通过碘催化 2-氨基-4,5-二甲基噻吩-3-甲酰胺与芳香醛的杂环化，一步得到一系列噻吩并 [2,3-d] 嘧啶衍生物的新路线。这些化合物中的一些表现出与作为参考药物的链霉素相当的抗菌活性。
• Synthesis of Some New 2-Arylthieno[2,3-d]Pyrimidin-4(3H)-One Derivatives
  作者：Abolghasem Davoodnia、Hossein Eshghi、Akram Salavaty、Niloofar Tavakoli-Hoseini

  DOI：10.3184/030823408x283685

  日期：2008.1

  Some new derivatives of 2-arylthieno[2,3-d]pyrimidin-4(3H)-ones have been prepared through a condensation reaction of 2-amino-4,5-dimethylthiophene-3-carboxamide with aroyl halides in boiling pyridine followed by cyclisation with 10% NaOH.

  通过2-氨基-4,5-二甲基噻吩-3-甲酰胺与芳酰卤在沸腾吡啶中的缩合反应，制备了2-芳基噻吩并[2,3-d]嘧啶-4(3H)-酮的一些新衍生物。用 10% NaOH 环化。
• Synthesis and theoretical studies on energetics of novel N- and O- perfluoroalkyl triazole tagged thienopyrimidines – Their potential as adenosine receptor ligands
  作者：B. Sirisha、B. Narsaiah、T. Yakaiah、G. Gayatri、G. Narahari Sastry、M. Raghu Prasad、A. Raghuram Rao

  DOI：10.1016/j.ejmech.2009.12.075

  日期：2010.5

  A series of novel N- and O- perfluoroalkyl triazole tagged thienopyrimidines 6a-c and 7a-d was synthesized in two steps from thienopyrimidin-4-ones 2 through O- and N-propargylated regioisomers 3a-i and 4a-i respectively. Compound 2 was reacted with propargyl bromide to form O- and N-propargylated regioisomers 3 and 4 in definite proportions. Each regioisomer was separated and independently subjected to [3 + 2] cycloaddition using perfluoroalkyl azides through Click reaction under Sharpless conditions and obtained exclusively anti product in each case. The formation of two regioisomers in the first step and single anti addition product in the next step could be explained based on computational studies carried out at B3LYP/6-31G(d) level of theory. Results of Fukui function indices at the reactive centers are in accordance with the observations. On evaluation of the synthesized molecules for their binding affinities towards adenosine receptors, 4d and 4f were found to be selective to A(1) over A(2A) receptors. (C) 2010 Elsevier Masson SAS. All rights reserved.