4-(4-methoxyphenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2-thioxo-5-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(4-methoxyphenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2-thioxo-5-one
• 英文别名: 4-anisyl-2-thioxo-3,4-dihydro-1H-chromino[4,3-d]pyrimidin-5-one；4-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydro-5H-chromeno[4,3-d]pyrimidine-5-one；1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-2-thioxochromeno[4,3-d]pyrimidin-5-one；4-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydro-5H-chromeno[4,3-d]pyrimidin-5-one；4-(4-methoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-chromeno[4,3-d]pyrimidin-5-one
• 化学式: C₁₈H₁₄N₂O₃S
• 分子量: 338.387
• InChiKey: NSEOGGCHKREGCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 calcium aluminate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-(4-methoxyphenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2-thioxo-5-one
  参考文献：
  名称：

  One Pot Synthesis of Benzopyranones and Benzoxazinones Catalyzed by MMO

  摘要：

  DOI：

  10.56042/ijc.v61i11.65837

文献信息

• Small Molecule Inhibitors of White Spot Syndrome Virus: Promise in Shrimp Seedling Culture
  作者：Lei Liu、Li-Peng Shan、Yan Zhou、Jiong Chen

  DOI：10.3390/ijms22073450

  日期：——

  Rapid production of prawn (Litopenaeus vannamei) under artificial pressure can result in a series of obvious challenges and is vulnerable to serious losses related to aquatic environmental issues and the unrestrained outbreak of white spot syndrome (WSS). However, to date, there are no therapeutic strategies to contain the spread of the virus. Here, we synthesized 27 coumarin derivatives and evaluated their anti-white spot syndrome virus (WSSV) activity in L. vannamei larvae. We demonstrated that electron-withdrawing and electron-giving substituent groups play an important role in reducing toxicity and WSSV replication, respectively. Two coumarin C2 (2-amino-5-oxo-4-(p-tolyl)-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile) and C7 (2-amino-4-(4-chlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile) were regarded as the most promising anti-WSSV compounds with maximum antiviral response <5% and median effective concentration <10 mg/L. The mortality of WSSV-infected larvae decreased by more than 60% after exposure to C2 and C7. With continuous immersion of C2 and C7 exchange, the mortality further decreased to 40% at 120 h. Additionally, C2 and C7 are the relatively stable in aquacultural water, making these agents suitable for use in inhibiting WSSV horizontal transmission in static aquaculture systems. These results showed the marked advantages of using C2 and C7 in the shrimp industry, and suggest that they hold potential for the treatment and prevention of WSSV infection in shrimp seedling culture.

  通过人工压力快速生产对虾（Litopenaeus vannamei）可能导致一系列明显挑战，并容易受到与水生环境问题和白斑综合征（WSS）的不受限制爆发有关的严重损失。然而，迄今为止，尚无治疗策略来控制病毒传播。在这项研究中，我们合成了27种香豆素衍生物，并评估它们对L. vannamei幼虾的抗白斑综合征病毒（WSSV）活性。我们证明了电子吸引和电子给予取代基在减少毒性和WSSV复制方面发挥着重要作用。两种香豆素C2（2-氨基-5-氧代-4-(对甲苯基)-4H,5H-吡喃[3,2-c]咔喃-3-碳腈）和C7（2-氨基-4-(4-氯苯基)-5-氧代-4H,5H-吡喃[3,2-c]咔喃-3-碳腈）被认为是最有前景的抗WSSV化合物，最大抗病毒反应＜5％，半数有效浓度＜10毫克/升。暴露于C2和C7后，WSSV感染的幼虾死亡率下降了60％以上。随着C2和C7交换的持续浸泡，死亡率在120小时内进一步降至40％。此外，C2和C7在水产养殖水中相对稳定，使这些药物适用于在静态水产养殖系统中抑制WSSV的水平传播。这些结果显示了在虾业中使用C2和C7的显著优势，并表明它们具有潜力用于虾苗培育中WSSV感染的治疗和预防。
• One-pot facile and mild construction of densely functionalized pyrimidines in water <i>via</i> consecutive C–C and C–S bonds formation
  作者：Pramod K. Sahu、Praveen K. Sahu、Manvendra S. Kaurav、Mouslim Messali、Saud M. Almutairi、Puran L. Sahu、Dau D. Agarwal

  DOI：10.1039/c8ra04363a

  日期：——

  Fused pyrimidines composed of alternating heteroatoms and a pyrimidine moiety were synthesized efficiently using readily available starting material 4-hydroxycoumarin, aromatic aldehydes, and urea/thiourea at room temperature.

  利用现成的起始材料 4-羟基香豆素、芳香醛和脲/硫脲，在室温下高效合成了由交替杂原子和嘧啶分子组成的融合嘧啶。
• Design, synthesis, and evaluation of 4-(substituted)phenyl-2-thioxo-3,4-dihydro-1H-chromino[4,3-d]pyrimidin-5-one and 4-(substituted)phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-dione analogs as antitubercular agents
  作者：Premlata K. Ambre、Raghuvir R. S. Pissurlenkar、Ravindra D. Wavhale、Mushtaque S. Shaikh、Vijay M. Khedkar、Baojie Wan、Scott G. Franzblau、Evans C. Coutinho

  DOI：10.1007/s00044-013-0850-7

  日期：2014.5

  AbstractThis paper focuses on the design and antitubercular activity of molecules which are a hybrid of coumarin and pyrimidine nuclei. A set of 16 compounds, viz. 4-(substituted)phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-diones and 4-(substituted)phenyl-2-thioxo-3,4-dihydro-1H-chromino[4,3-d]pyrimidin-5-ones have been synthesized using green chemistry principles and evaluated for antitubercular activity

  摘要本文着重研究香豆素和嘧啶核的杂合分子的设计和抗结核活性。一组16种化合物，即。4-（取代）苯基-3,4-二氢-1 H-苯并[4,3-d]嘧啶-2,5-二酮和4-（取代）苯基-2-硫代-3,4-二氢-1 H -chromino [4,3-d] pyrimidin-5-ones已使用绿色化学原理合成，并通过微孔板Alamar蓝测定法（MABA）和基于发光的低氧回收测定法（LORA）利福平作为抗真菌活性进行了评估标准。使用带有驱动细菌荧光素酶的乙酰胺酶启动子的质粒培养LORA所需的结核分枝杆菌H37Rv菌株基因用于信号增强，并使其适应发酵罐中的低氧含量。化合物5d，5e和5g表现出最大的抗结核活性，基于MABA的％抑制值为58、55和45，基于128μM的LORA测试的抑制值为62、35和37。为了了解结构和活动之间的关系，开发了递归分区（RP）模型。建立了两种不同的RP模型，一种基于抗结核
• Rapid and mild synthesis of quinazolinones and chromeno[ d ]pyrimidinones using nanocrystalline copper(I) iodide under solvent-free conditions
  作者：Shahrzad Abdolmohammadi、Samira Karimpour

  DOI：10.1016/j.cclet.2015.08.014

  日期：2016.1

  very simple, efficient synthesis of quinazolinones and chromeno[ d ]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds (dimedone/4-hydroxycoumarin) using nano-sized CuI particles under solvent-free conditions. The highlights of this new method are based on using an effective and recyclable catalyst, affording high yields of products, mild reaction conditions

  摘要本文描述了一种纳米级的CuI颗粒，在无溶剂条件下，由芳基醛，脲/硫脲与活性亚甲基化合物（二甲酮/ 4-羟基香豆素）反应，可非常简单，有效地合成喹唑啉酮和色胺并嘧啶酮。该新方法的亮点是基于使用有效且可回收的催化剂，可提供高收率的产品，温和的反应条件，简便的后处理和纯化方法。
• Bio-assisted synthesized Ag(0) nanoparticles immobilized on SBA-15/cyclodextrin nanosponge adduct: Efficient heterogeneous catalyst for the ultrasonic-assisted synthesis of benzopyranopyrimidines
  作者：Samahe Sadjadi、Majid M. Heravi、Masoumeh Malmir

  DOI：10.1002/aoc.4286

  日期：2018.4

  SBA‐15/cyclodextrin nanosponge adduct was synthesized through reaction of Cl‐functionalized SBA‐15 and amine‐functionalized cyclodextrin nanosponge (CDNS). This adduct, which benefits from features of both SBA‐15 and CDNS, was then used for immobilization of Ag(0) nanoparticles which were prepared and capped using a bio‐based approach. Ag@CDNS–SBA‐15 was applied as a heterogeneous catalyst for promoting

  首次通过Cl官能化的SBA-15与胺官能化的环糊精纳米海绵（CDNS）的反应合成了SBA-15 /环糊精纳米海绵加合物。该加合物得益于SBA-15和CDNS的功能，然后被用于固定Ag（0）纳米颗粒，这些纳米颗粒是使用生物基方法制备和封端的。Ag @ CDNS–SBA-15被用作非均相催化剂，用于在超声辐射下促进苯甲醛，4-羟基香豆素和尿素或硫脲的三组分反应，以提供苯并吡喃并嘧啶。反应变量使用响应面方法进行了优化。Ag @ CDNS–SBA-15的催化活性高于Ag @ CDNS，Ag @ SBA-15和Ag @ SBA-15 + CDNS，确认这两种成分对催化的贡献以及CDNS和SBA-15之间的协同作用。CDNS的作用是容纳基质并将其带到Ag（0）纳米颗粒附近。值得注意的是，该催化剂是可重复使用的，并且可以回收利用，最多可重复使用四个反应，轻微的Ag（0）浸出并失去催化活性。