a-(1-carbamylimino(methyl)methyl)-g-butyrolactone | 118767-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: a-(1-carbamylimino(methyl)methyl)-g-butyrolactone
• 英文别名: 1-(2-Oxooxolan-3-yl)ethylideneurea；1-(2-oxooxolan-3-yl)ethylideneurea
• CAS: 118767-66-1
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: SCUDRYOGTWFDOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  a-(1-carbamylimino(methyl)methyl)-g-butyrolactone 在 乙醇 、 sodium 、 硫酸 作用下， 反应 18.0h， 以100%的产率得到5-(2-hydroxyethyl)-6-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis, X-ray crystal structure study and antitumoral evaluations of 5,6-disubstituted pyrimidine derivatives

  摘要：

  5,6-Disubstituted pyrimidine derivatives (3-20) were prepared by intramolecular cyclization reaction of alpha-(1-carbamyliminomethylene)-gamma-butyrolactone (2) with sodium ethoxide and subsequent chemical transformation of 2-hydroxy group in C-5 side chain as well as lithiation reaction for introduction of acyclic side chain at C-6. All compounds were characterized by H-1 NMR, C-13 NMR and mass spectra. Structures of compounds 4, 7 and 14 were unambiguously confirmed by X-ray crystal structural analysis. Supramolecular structures of these three compounds differ significantly. Two N-H center dot center dot center dot O and one C-H center dot center dot center dot O hydrogen bonds in 4 form three-dimensional network. One O-H center dot center dot center dot N hydrogen bond and one pi center dot center dot center dot pi interaction self-assemble the molecules of 7 into sheets. In supramolecular aggregation of 14, only pi center dot center dot center dot pi stacking interactions participate, so forming chains. The compounds were evaluated for their cytostatic activities against human malignant cell lines. Of all tested compounds, 2,4-dimethoxy-5-methoxy-tritylethylpyrimidine (9) and 2,4-dichloro-5-chloroethylpyrimidine (14) exhibited the most prominent inhibitory effects. Furthermore, compound 14 showed marked activity against human colon carcinoma (IC50 = 0.4 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.023
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 、 尿素 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 以65%的产率得到a-(1-carbamylimino(methyl)methyl)-g-butyrolactone
  参考文献：
  名称：

  Synthesis, X-ray crystal structure study and antitumoral evaluations of 5,6-disubstituted pyrimidine derivatives

  摘要：

  5,6-Disubstituted pyrimidine derivatives (3-20) were prepared by intramolecular cyclization reaction of alpha-(1-carbamyliminomethylene)-gamma-butyrolactone (2) with sodium ethoxide and subsequent chemical transformation of 2-hydroxy group in C-5 side chain as well as lithiation reaction for introduction of acyclic side chain at C-6. All compounds were characterized by H-1 NMR, C-13 NMR and mass spectra. Structures of compounds 4, 7 and 14 were unambiguously confirmed by X-ray crystal structural analysis. Supramolecular structures of these three compounds differ significantly. Two N-H center dot center dot center dot O and one C-H center dot center dot center dot O hydrogen bonds in 4 form three-dimensional network. One O-H center dot center dot center dot N hydrogen bond and one pi center dot center dot center dot pi interaction self-assemble the molecules of 7 into sheets. In supramolecular aggregation of 14, only pi center dot center dot center dot pi stacking interactions participate, so forming chains. The compounds were evaluated for their cytostatic activities against human malignant cell lines. Of all tested compounds, 2,4-dimethoxy-5-methoxy-tritylethylpyrimidine (9) and 2,4-dichloro-5-chloroethylpyrimidine (14) exhibited the most prominent inhibitory effects. Furthermore, compound 14 showed marked activity against human colon carcinoma (IC50 = 0.4 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.023

文献信息

• Synthesis, X-ray crystal structure study and antitumoral evaluations of 5,6-disubstituted pyrimidine derivatives
  作者：Tatjana Gazivoda Kraljević、Svjetlana Krištafor、Lidija Šuman、Marijeta Kralj、Simon M. Ametamey、Mario Cetina、Silvana Raić-Malić

  DOI：10.1016/j.bmc.2010.02.023

  日期：2010.4

  5,6-Disubstituted pyrimidine derivatives (3-20) were prepared by intramolecular cyclization reaction of alpha-(1-carbamyliminomethylene)-gamma-butyrolactone (2) with sodium ethoxide and subsequent chemical transformation of 2-hydroxy group in C-5 side chain as well as lithiation reaction for introduction of acyclic side chain at C-6. All compounds were characterized by H-1 NMR, C-13 NMR and mass spectra. Structures of compounds 4, 7 and 14 were unambiguously confirmed by X-ray crystal structural analysis. Supramolecular structures of these three compounds differ significantly. Two N-H center dot center dot center dot O and one C-H center dot center dot center dot O hydrogen bonds in 4 form three-dimensional network. One O-H center dot center dot center dot N hydrogen bond and one pi center dot center dot center dot pi interaction self-assemble the molecules of 7 into sheets. In supramolecular aggregation of 14, only pi center dot center dot center dot pi stacking interactions participate, so forming chains. The compounds were evaluated for their cytostatic activities against human malignant cell lines. Of all tested compounds, 2,4-dimethoxy-5-methoxy-tritylethylpyrimidine (9) and 2,4-dichloro-5-chloroethylpyrimidine (14) exhibited the most prominent inhibitory effects. Furthermore, compound 14 showed marked activity against human colon carcinoma (IC50 = 0.4 mu M). (C) 2010 Elsevier Ltd. All rights reserved.