3-amino-2-(phenylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one | 1040842-66-7

• 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: 3-amino-2-(phenylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one
• CAS: 1040842-66-7
• 化学式: C₁₆H₁₂N₄O₂
• 分子量: 292.297
• InChiKey: HRLPVPTZRZGFEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.08
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-amino-2-(phenylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 六氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-phenyl-2-(1-methyl-1-ethoxycarbonyl-ethyl)thiobenzofuro[3,2-d]-1,2,4-triazolo[1,5-a]-pyrimidin-5(1H)-one
  参考文献：
  名称：

  Efficient synthesis and fungicidal activities of strobilurin analogues containing benzofuro [3,2-d]-1,2,4-triazolo[1,5-a]pyrimidinone side chains

  摘要：

  报道了一种高效制备含有苯并呋喃[3,2-d]-1,2,4-三唑[1,5-a]嘧啶酮侧链的斯特罗比鲁林类似物的方法。该方法基于官能化亚磷胺与二硫化碳通过氮杂-Wittig反应的反应。对生物活性的初步研究表明，合成的大多数化合物在50 mg/L浓度下对六种真菌具有中等的杀菌活性。

  DOI：

  10.1515/hc-2015-0127
• 作为产物：
  描述：

  ethyl 3-[(triphenylphosphoranylidene)amino]-benzofuran-2-carboxylate 在 hydrazine hydrate 作用下， 以 二氯甲烷 为溶剂， 生成 3-amino-2-(phenylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  含噻二唑/恶唑烷/三唑/三嗪酮部分的稠合四环苯并[4,5]呋喃[3,2-d]嘧啶-4（3H）-ones衍生物的合成

  摘要：

  为了设计和合成具有更好生物学特性的新杂环，一些稠合的带有1,2,4-三唑的四环苯并[4,5]呋喃[3,2-d]嘧啶4（3H）-， 1,3,4-噻二唑，1,2,4-三嗪酮和恶唑烷体系是通过aza-Wittig反应在温和条件下从容易获得的起始原料制得的。通过1 H NMR，13 C NMR，MS，IR和元素分析来阐明合成化合物的结构。

  DOI：

  10.1002/jhet.4160

文献信息

• Efficient Iminophosphorane-Mediated Preparation of Benzofuro[3,2-d]pyrimidin-4(3H)-ones and Unexpected Ring Opening Products
  作者：Yang-Gen Hu、Ming-Guo Liu、Ming-Wu Ding

  DOI：10.1002/hlca.200890090

  日期：2008.5

  reacted with secondary amines, phenols or alcohols in the presence of catalytic amounts of K2CO3 or sodium alkoxide to give 2-substituted benzofuro[3,2-d]pyrimidin-4(3H)-ones 6. However, when 2,2′-iminobis[ethanol] was used, the unexpected ring opening product 7 was formed instead of 6. Reaction of 4 with primary amines RNH2 (R=Et, Pr, Bu, etc.) gave guanidine intermediates 8, which were further treated

  由亚氨基磷烷3与芳族异氰酸酯的氮杂-维蒂希反应获得的碳二亚胺4，在催化量的K 2 CO 3或醇钠的存在下，与仲胺，酚或醇反应，得到2-取代的苯并呋喃[3,2- d ]嘧啶-4（3 H）-ones 6。然而，当使用2,2'-亚氨基双[乙醇]时，形成了意想不到的开环产物7而不是6。的反应4与伯胺RNH 2（R =乙基，丙基，卜，等等），得到胍中间体8将其进一步用EtONa处理，通过碱催化的环化反应仅产生一种区域异构体9。但是，在不存在EtONa的情况下，通过自发环化8使用NH 3或“小”胺RNH 2（R = Me，NH 2），则获得了另一个区域异构体11。
• 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。
• Synthesis of fused tetracyclic benzo[4,5]furo[3,2‐d]pyrimidin‐4( <scp>3H</scp> )‐ones derivatives containing thiadiazole/oxazolidine/triazole/triazinanone moieties
  作者：Shengjie He、Junkai Ma、Fei Li、Yanggen Hu

  DOI：10.1002/jhet.4160

  日期：2021.1

  In an attempt to design and synthesize new heterocycles with improved their biological properties, some of fused tetracyclic benzo[4,5]furo[3,2‐d]pyrimidin‐ 4(3H)‐ones bearing 1,2,4‐triazole, 1,3,4‐thiadiazole, 1,2,4‐triazinanone, and oxazolidine systems have been prepared by the aza‐Wittig reactions from readily available starting material under mild conditions. The structure of synthesized compounds

  为了设计和合成具有更好生物学特性的新杂环，一些稠合的带有1,2,4-三唑的四环苯并[4,5]呋喃[3,2-d]嘧啶4（3H）-， 1,3,4-噻二唑，1,2,4-三嗪酮和恶唑烷体系是通过aza-Wittig反应在温和条件下从容易获得的起始原料制得的。通过1 H NMR，13 C NMR，MS，IR和元素分析来阐明合成化合物的结构。
• Efficient synthesis and fungicidal activities of strobilurin analogues containing benzofuro [3,2-<i>d</i>]-1,2,4-triazolo[1,5-<i>a</i>]pyrimidinone side chains
  作者：Yang-Gen Hu、Li Li、Qiong-Yao Zhang、Ai-Nv Zhang、Chun Feng、Ping He

  DOI：10.1515/hc-2015-0127

  日期：2015.12.1

  An efficient method for the preparation of strobilurin analogues containing benzofuro[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidinone side chains were reported. This method is based on the reaction of functionalized iminophosphoranes with carbon disulfide via aza-Wittig reaction. The preliminary investigations on the biological activities show that the majority of compounds synthesized have moderate fungicidal activities against six kinds of fungi at a concentration of 50 mg/L.

  报道了一种高效制备含有苯并呋喃[3,2-d]-1,2,4-三唑[1,5-a]嘧啶酮侧链的斯特罗比鲁林类似物的方法。该方法基于官能化亚磷胺与二硫化碳通过氮杂-Wittig反应的反应。对生物活性的初步研究表明，合成的大多数化合物在50 mg/L浓度下对六种真菌具有中等的杀菌活性。