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

• 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-2,5-dione
• 英文别名: 4-(4-methoxy)phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-dione；4-(4-methoxyphenyl)-3,4-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-dione；4-(4-methoxyphenyl)-3,4-dihydro-2H-chromeno[4,3-d]pyrimidine-2,5(1H)-dione
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: PJYKYQYYKZFYQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  76.7
• 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-2,5-dione
  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。
• 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
• Tannic Acid Catalyzed Green Synthesis of Functionalized Chromeno-Pyrimidine-2,5-dione/thione Derivatives
  作者：J. Puvithra、D. Parthiban

  DOI：10.14233/ajchem.2020.22771

  日期：——

  Diversely functionalized chromeno-pyrimidine-2,5-dione/thione compounds were synthesized by cyclocondensation of 4-hydroxy coumarin, aldehydes and urea/thiourea using tannic acid as a green catalyst and 1:1 (EtOH:H2O) as a green solvent. Different acids were screened for their catalytic activity of chromeno-pyrimidine-2,5-dione/thione derivatives. Tannic acid (10 mol%) was used as a suitable catalyst with increased catalytic activity. By utilizing this protocol, chromeno-pyrimidine scaffolds were prepared in acceptable to excellent yield without the use of conventional volatile organic solvent and toxic metal catalyst. To our best of knowledge, this is the first report, in which tannic acid is utilized successfully as an eco-safe catalyst for synthesis of fused pyrimidines.

  使用丹宁酸作为绿色催化剂，以4-羟基香豆素、醛类和尿素/硫脲为原料，通过环缩合反应在1:1（乙醇:水）的绿色溶剂中合成了多样化官能团化的咖啡因-嘧啶-2,5-二酮/硫酮化合物。筛选了不同的酸类催化剂，发现10%丹宁酸具有较高的催化活性。使用该方法，可以在不使用传统挥发性有机溶剂和有毒金属催化剂的情况下，制备出可接受至优良的产率的咖啡因-嘧啶骨架。据我们所知，这是首次成功地利用丹宁酸作为环状嘧啶合成的生态安全催化剂的报告。
• One-Pot Synthesis of Novel Heterocyclic Chromenopyrimidine-2,5-Dione and ThioxochromEnopyrimidin-5-one Derivatives
  作者：Hossein Mehrabi、Mohammad Baniasad-Dashtabi

  DOI：10.3184/174751915x14305809607197

  日期：2015.5

  Novel heterocyclic dihydropyrimidine chromenopyrimidine-2,5-diones and thioxochromenopyrimidin-5-ones were synthesised by a three-component reaction between 4-hydroxycoumarin, urea or thiourea, and aromatic aldehydes in H₂O under reflux in the presence of sodium dodecyl sulfate (20 mol%) and two drops of acetic acid. The products were obtained in good yields and their structures of all the synthesised compounds were established by spectroscopic methods..

  在十二烷基硫酸钠（20 mol%）和两滴乙酸的存在下，4-羟基香豆素、脲或硫脲和芳香醛在 H2O 回流条件下发生三组分反应，合成了新型杂环二氢嘧啶色嘧啶-2,5-二酮和硫酮色嘧啶-5-酮。所有合成化合物均以良好的收率获得，并通过光谱方法确定了它们的结构。
• Reaction of Coumarin Derivatives with Nucleophiles in Aqueous Medium
  作者：Mazaahir Kidwai、Priya、Shweta Rastogi

  DOI：10.1515/znb-2008-0110

  日期：2008.1.1

  A series of heterocycles was synthesized by the reaction of α,β -unsaturated ketones of benzopyrans or coumarins with various nucleophiles in aqueous medium bearing two points of diversity. Compared to an identical library generated by conventional parallel synthesis, a microwaveassisted procedure dramatically decreased reaction times from hours to minutes, and yields of products and intermediates

  通过苯并吡喃或香豆素的α,β-不饱和酮与各种亲核试剂在具有两点多样性的水性介质中反应合成了一系列杂环。与通过常规平行合成生成的相同库相比，微波辅助程序将反应时间从数小时显着缩短到数分钟，并且产物和中间体的产率显着提高。这种合成方法本质上是环保的，其特点是水作为溶剂、微波辐射和“绿色”催化剂（K2CO3）的使用。