2-benzylthio-3-propylbenzofuro[3,2-d]pyrimidin-4(3H)-one | 1233397-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-benzylthio-3-propylbenzofuro[3,2-d]pyrimidin-4(3H)-one
• 英文别名: 2-Benzylsulfanyl-3-propyl-[1]benzofuro[3,2-d]pyrimidin-4-one
• CAS: 1233397-57-3
• 化学式: C₂₀H₁₈N₂O₂S
• 分子量: 350.441
• InChiKey: KKZYBSBLNQWMLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基苯并呋喃-2-甲酸乙酯 在 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 六氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 2-benzylthio-3-propylbenzofuro[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  3-烷基-2-多样性取代的苯并呋喃[3,2-d]嘧啶-4(3H)-one衍生物的有效合成

  摘要：

  苯并呋喃[3,2-d]嘧啶衍生物使用亚氨基正膦与异氰酸正丁酯在40-50°C下的氮杂-Wittig反应得到碳二亚胺中间体，再与含氮氧亲核试剂反应得到3-烷基-2-氨基(芳氧基/烷氧基)-苯并呋喃[3,2-d]嘧啶-4(3H)-酮，在催化量的乙醇钠或K2CO3存在下，产率令人满意。亚氨基正膦也直接与过量的二硫化碳反应，然后是正丙胺；在无水 K2CO3 存在下与烷基卤化物或卤化脂肪族酯进一步反应，以良好的产率生成相应的 2-烷硫基-3-正丙基-苯并呋喃 [3,2-d]嘧啶-4(3H)-酮。产物的结构经1H NMR、13C NMR、质谱、红外和元素分析证实。

  DOI：

  10.1177/1747519819858734

文献信息

• Synthesis and biological activity of fused furo[2,3-d]pyrimidinone derivatives as analgesic and antitumor agents
  作者：Qing Li、Yong-Mei Chen、Yang-Gen Hu、Xin Luo、Joshua Ka Shun Ko、Chi Wai Cheung

  DOI：10.1007/s11164-015-2064-8

  日期：2016.2

  Tumor growth is usually associated with persistent pain, especially during mid and terminal stages of cancer development. Nonetheless, a medicinal compound that possesses both anticancer and analgesic properties has not been identified. The 2-alkylthio-benzofuro[3,2-d]pyrimidin-4(3H)-ones (Code 5a–d) and 1-aryl-2-alkylthio-benzofuro[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-ones (Code 10a–g) were synthesized by using the bioisostere concept, which were obtained via the aza-Wittig reaction of functionalized iminophosphoranes reacted with carbon disulfide and further reaction of the product with alkyl halides or halogenated aliphatic esters. The analgesic properties of 5a–d and 10a–g were studied using rat chronic constriction injury model and the antitumor properties of these chemicals were assessed using MTS cell proliferation assay. Results showed that 5a–d and 10a–g were found to attenuate thermal and mechanical allodynia induced by neuropathy and inhibited the proliferation of three human cancer cell lines (A459, HepG2, and HeLa). Among these compounds, 10g showed highly positive effects in both assessments, and would be selected for future work.

  肿瘤生长通常伴随着持续性疼痛，尤其是在癌症发展的中晚期阶段。然而，至今尚未发现一种兼具抗癌和镇痛特性的药物化合物。通过生物等排体概念合成了2-烷硫基苯并呋喃[3,2-d]嘧啶-4(3H)-酮（代码5a–d）和1-芳基-2-烷硫基苯并呋喃[3,2-d]-1,2,4-三唑并[1,5-a]嘧啶-5(1H)-酮（代码10a–g），这些化合物是通过功能化亚胺膦与二硫化碳进行aza-Wittig反应，再与烷基卤化物或卤代脂肪酯进一步反应获得。利用大鼠慢性束缚损伤模型研究了5a–d和10a–g的镇痛特性，并使用MTS细胞增殖实验评估了这些化学物质的抗肿瘤特性。结果显示，5a–d和10a–g能减轻神经病变引起的热痛和机械痛觉过敏，并抑制三种人类癌细胞系（A459、HepG2和HeLa）的增殖。在这些化合物中，10g在两项评估中表现出了非常积极的效果，将被选中进行后续研究。
• Efficient Synthesis and Fungicidal Activities of 2-Alkylthiobenzofuro[3,2-<i>d</i>]Pyrimidinones
  作者：Yang-Gen Hu、Wen-Qing Wang、Ming-Wu Ding

  DOI：10.1080/10426500903008922

  日期：2010.3.24

  2-Alkylthiobenzofuro[3,2-d]pyrimidinones 5 and 6 were synthesized by S-alkylation of 2,3-dihydro-2-thioxobenzofuro[3,2-d]pyrimidin-4(1H)-ones 4, which were obtained via aza-Wittig reaction of iminophosphorane 2 with CS2 and further reaction of the product with various amines. Compounds 5 and 6 exhibited fungicidal activity. For example, compound 6a, which has a small N-substituted methyl group, showed the best inhibitive activity (91%) against Dothiorella gregaria at 50 mg/L. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
• An efficient synthesis of 3-alkyl-2-diversity-substituted benzofuro[3,2-<i>d</i>]pyrimidin-4(3<i>H</i>)-one derivatives
  作者：Hong-Mei Wang、Tian-Shuai Wang、Sheng-Jie He、Zong-Yun Chen、Yang-Gen Hu

  DOI：10.1177/1747519819858734

  日期：2019.5

  Benzofuro[3,2-d]pyrimidine derivatives are prepared using aza-Wittig reactions of iminophosphoranes with n-butyl isocyanate at 40–50 °C to give carbodiimide intermediates, which are reacted with nitrogen-oxygen-containing nucleophiles to give 3-alkyl-2-amino (aryloxy/alkoxy)-benzofuro[3,2-d]pyrimidin-4(3H)-ones in satisfactory yields in the presence of a catalytic amount of sodium ethoxide or K2CO3

  苯并呋喃[3,2-d]嘧啶衍生物使用亚氨基正膦与异氰酸正丁酯在40-50°C下的氮杂-Wittig反应得到碳二亚胺中间体，再与含氮氧亲核试剂反应得到3-烷基-2-氨基(芳氧基/烷氧基)-苯并呋喃[3,2-d]嘧啶-4(3H)-酮，在催化量的乙醇钠或K2CO3存在下，产率令人满意。亚氨基正膦也直接与过量的二硫化碳反应，然后是正丙胺；在无水 K2CO3 存在下与烷基卤化物或卤化脂肪族酯进一步反应，以良好的产率生成相应的 2-烷硫基-3-正丙基-苯并呋喃 [3,2-d]嘧啶-4(3H)-酮。产物的结构经1H NMR、13C NMR、质谱、红外和元素分析证实。