(2-amino-5-(pyrimidin-5-yl)thiophen-3-yl)(phenyl)methanone | 1245739-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-5-(pyrimidin-5-yl)thiophen-3-yl)(phenyl)methanone
• 英文别名: (2-Amino-5-pyrimidin-5-ylthiophen-3-yl)-phenylmethanone
• CAS: 1245739-82-5
• 化学式: C₁₅H₁₁N₃OS
• 分子量: 281.338
• InChiKey: ARHZEENWJJTOJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲酰乙腈 在 methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) 、 sodium carbonate 、 sulfur 、 二乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2-amino-5-(pyrimidin-5-yl)thiophen-3-yl)(phenyl)methanone
  参考文献：
  名称：

  3-氰基烯丙基硼酸酯是多取代噻吩合成中的多功能构建基块。

  摘要：

  我们报道了迄今为止使用母体α-硼醛和腈的缩合制备前所未有的3-氰基烯丙基硼酸酯的方法。所得的硼酸烯丙酯已被用于产生各种硼化的噻吩，其代表了现代药物发现中有价值的一类杂环。随后的Suzuki-Miyaura交叉偶联使得能够合成药学上重要的3,5-二取代氨基噻吩。此外，后期功能化使人们可以获得硼化的溴噻吩和噻吩并[2,3-b]吡啶。

  DOI：

  10.1039/c7sc00831g

文献信息

• Effects of Conformational Restriction of 2-Amino-3-benzoylthiophenes on A₁ Adenosine Receptor Modulation
  作者：Luigi Aurelio、Celine Valant、Bernard L. Flynn、Patrick M. Sexton、Jonathan M. White、Arthur Christopoulos、Peter J. Scammells

  DOI：10.1021/jm1008538

  日期：2010.9.23

  2-Amino-3-benzoylthiophenes (2A3BTs) have been widely reported to act as allosteric enhancers (A Es) at the A(1) adenosine receptor (A(1)AR). Herein we describe the synthesis of a series of 1-aminoindeno[1,2-c]thiophen-8-ones and a series of (2-aminoindeno[2,1-b]thiophen-3-yl)(phenyl)methanones as conformationally rigid analogues of the 2A3BTs. These compounds were screened using a functional assay of A(1)AR-mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK 1/2) in intact Chinese hamster ovary (CHO) cells to identify both potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, N-6-(R-phenylisopropyl)adenosine (R-PIA). All of the 1-aminoindeno[1,2-c]thiophen-8-ones (14a-c and 17a-f) proved either to be inactive or behaved as antagonists in the functional assay. However, the (2-aminoindeno[2, 1-b]thiophen-3-yl)(phenyl)methanones with para-chloro substitution (compounds 25b, 25d, and 25f) did significantly augment the R-PIA response, indicating a positive allosteric effect.
• 3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes
  作者：Wenjie Shao、Sherif J. Kaldas、Andrei K. Yudin

  DOI：10.1039/c7sc00831g

  日期：——

  boronates have been used to generate a wide range of borylated thiophenes, which represent a valuable class of heterocycles in modern drug discovery. Subsequent Suzuki-Miyaura cross-coupling enabled the synthesis of pharmaceutically important 3,5-disubstituted aminothiophenes. Moreover, late stage functionalization gave access to borylated bromothiophene and thieno[2,3-b]pyridines.

  我们报道了迄今为止使用母体α-硼醛和腈的缩合制备前所未有的3-氰基烯丙基硼酸酯的方法。所得的硼酸烯丙酯已被用于产生各种硼化的噻吩，其代表了现代药物发现中有价值的一类杂环。随后的Suzuki-Miyaura交叉偶联使得能够合成药学上重要的3,5-二取代氨基噻吩。此外，后期功能化使人们可以获得硼化的溴噻吩和噻吩并[2,3-b]吡啶。