N-(2-hydroxy-2-phenylethyl)thiophene-2-carboxamide | 187144-59-8

• 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: N-(2-hydroxy-2-phenylethyl)thiophene-2-carboxamide
• CAS: 187144-59-8
• 化学式: C₁₃H₁₃NO₂S
• mdl: MFCD01173079
• 分子量: 247.318
• InChiKey: SODWLFGVFNKBBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  513.5±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)
• 溶解度：
  >37.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-2-phenylethyl)thiophene-2-carboxamide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以61%的产率得到5-Phenyl-2-thiophen-2-yl-4,5-dihydro-1,3-thiazole
  参考文献：
  名称：

  Reaction of (1,ω)-N-Acylamino Alcohols with Lawesson's Reagent:  Synthesis of Sulfur-Containing Heterocycles

  摘要：

  Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide] is shown to be a valuable reagent for the ready access of sulfur-containing heterocycles: thiazolines 2 starting from the (1,2)-N-acylamino alcohols 1 and benzothiazines 14 from [2-(N-acylamino)phenyl]alkanols 12. Treatment of (1,2)-N-acylamino secondary alcohols 1a-p with LR gave the thiazolines 1a-p via direct conversion of the alcohols to the respective thiols, and the subsequent thionation of the amide carbonyl, followed by cyclization with the elimination of hydrogen sulfide. However, reaction of (1,2)-N-acylamino tertiary alcohols 1q-u with LR yielded the dehydration products 5-7 and 9. Treatment of [2-(N-acylamino)phenyl]alkanols 12a-f with a molar equivalent of LR yielded the 3,1-benzothiazines 14a-f. In this reaction, the [2-(N-acylamino)phenyl]alkanethiols 13a-e were isolated when the corresponding alcohols 12a-e were treated with 0.5 equiv of LR. Further thionation of 13c with LR also gave 3,1-benzothiazine 14c.

  DOI：

  10.1021/jo961704n
• 作为产物：
  描述：

  2-氨基苯乙酮盐酸盐 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 N-(2-hydroxy-2-phenylethyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Baker’s Yeast Reduction ofα-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols

  摘要：

  使用发酵的面包酵母对α-酰氨基苯乙酮进行酶促还原，得到了光学活性的(R)-2-酰氨基-1-芳基乙醇。进一步地，使用醋酸乙烯酯作为酰基供体，通过脂肪酶催化的拆分反应，生成了(S)-1-乙酰氧基-2-酰氨基-1-芳基乙醇和(R)-2-酰氨基-1-芳基乙醇。

  DOI：

  10.1246/bcsj.66.1216

文献信息

• Design, Synthesis and Evaluation of Novel Phorbazole C Derivatives as MNK Inhibitors through Virtual High-Throughput Screening
  作者：Xin Jin、Maowei Li、Tingting Qiu、Rilei Yu、Tao Jiang

  DOI：10.3390/md20070429

  日期：——

  MNKs (mitogen-activated protein kinase-interacting protein kinases) phosphorylate eIF4E at Ser209 to control the translation of certain mRNAs and regulate the process of cell proliferation, cell migration and invasion, etc. Development of MNK inhibitors would be an effective treatment for related diseases. We used the MarineChem3D database to identify hit compounds targeting the protein MNK1 and MNK2 through high-throughput screening. Compounds from the phorbazole family showed good interactions with MNK1, and phorbazole C was selected as our hit compound. By analyzing the binding mode, we designed and synthesized 29 derivatives and evaluated their activity against MNKs, of which, six compounds showed good inhibition to MNKs. We also confirmed three interactions between this kind of compound and MNK1, which are vital for the activity. In conclusion, we report series of novel MNK inhibitors inspired from marine natural products and their relative structure–activity relationship. This will provide important information for further developing MNK inhibitors based on this kind of structure.

  MNKs (有丝分裂原活化蛋白激酶相互作用蛋白激酶) 在Ser209位点磷酸化eIF4E，控制特定mRNA的翻译，调节细胞增殖、细胞迁移和侵袭等过程。开发MNK抑制剂将是相关疾病的有效治疗方法。我们使用MarineChem3D数据库通过高通量筛选识别靶向蛋白MNK1和MNK2的命中化合物。来自phorbazole家族的化合物与MNK1展现出良好的相互作用，其中phorbazole C被选为我们的命中化合物。通过分析结合模式，我们设计和合成了29个衍生物，并评估它们对MNKs的活性，其中有六个化合物对MNKs表现出良好的抑制作用。我们还确认了这种化合物与MNK1之间的三种相互作用，这对于活性至关重要。总之，我们报道了一系列受海洋天然产物启发的新型MNK抑制剂及其相关的结构-活性关系。这将为基于这种结构进一步开发MNK抑制剂提供重要信息。
• Baker’s Yeast Reduction of<i>α</i>-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols
  作者：Taeko Izumi、Katsumi Fukaya

  DOI：10.1246/bcsj.66.1216

  日期：1993.4

  Enzymatic reduction of α-acylaminoacetophenones with fermenting baker’s yeast afforded optically active (R)-2-acylamino-1-arylethanols. Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.

  使用发酵的面包酵母对α-酰氨基苯乙酮进行酶促还原，得到了光学活性的(R)-2-酰氨基-1-芳基乙醇。进一步地，使用醋酸乙烯酯作为酰基供体，通过脂肪酶催化的拆分反应，生成了(S)-1-乙酰氧基-2-酰氨基-1-芳基乙醇和(R)-2-酰氨基-1-芳基乙醇。
• Reaction of (1,ω)-<i>N</i>-Acylamino Alcohols with Lawesson's Reagent:  Synthesis of Sulfur-Containing Heterocycles
  作者：Takehiko Nishio

  DOI：10.1021/jo961704n

  日期：1997.2.1

  Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide] is shown to be a valuable reagent for the ready access of sulfur-containing heterocycles: thiazolines 2 starting from the (1,2)-N-acylamino alcohols 1 and benzothiazines 14 from [2-(N-acylamino)phenyl]alkanols 12. Treatment of (1,2)-N-acylamino secondary alcohols 1a-p with LR gave the thiazolines 1a-p via direct conversion of the alcohols to the respective thiols, and the subsequent thionation of the amide carbonyl, followed by cyclization with the elimination of hydrogen sulfide. However, reaction of (1,2)-N-acylamino tertiary alcohols 1q-u with LR yielded the dehydration products 5-7 and 9. Treatment of [2-(N-acylamino)phenyl]alkanols 12a-f with a molar equivalent of LR yielded the 3,1-benzothiazines 14a-f. In this reaction, the [2-(N-acylamino)phenyl]alkanethiols 13a-e were isolated when the corresponding alcohols 12a-e were treated with 0.5 equiv of LR. Further thionation of 13c with LR also gave 3,1-benzothiazine 14c.