4-(2-hydroxy)phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-dione | 1480384-48-2

• 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-(2-hydroxy)phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-dione
• 英文别名: 4-(2-hydroxyphenyl)-3,4-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-dione
• CAS: 1480384-48-2
• 化学式: C₁₇H₁₂N₂O₄
• 分子量: 308.293
• InChiKey: BXUPUZUBQTWZRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酚 在 对甲苯磺酸 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 35.04h， 生成 4-(2-hydroxy)phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-dione
  参考文献：
  名称：

  设计，合成和评估4-（取代的）苯基-2-硫代-3,4-二氢-1 H-色氨酸[4,3-d]嘧啶-5-酮和4-（取代的）苯基-3， 4-二氢-1 H-苯并[4,3-d]嘧啶-2,5-二酮类似物作为抗结核药

  摘要：

  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

  DOI：

  10.1007/s00044-013-0850-7

文献信息

• An efficient multicomponent synthesis and <i>in vitro</i> anticancer activity of dihydropyranochromene and chromenopyrimidine-2,5-diones
  作者：M. R. Bhosle、D. B. Wahul、G. M. Bondle、A. Sarkate、S. V. Tiwari

  DOI：10.1080/00397911.2018.1480042

  日期：2018.8.18

  Of these compounds, 4d was found to be the most potent inhibitors of HeLa and MCF-7 demonstrating IC50 values of 19 µM and 7 µM. Compounds 4b, 4e and 4f also shown significantly good in vitro anticancer activity against HeLa and MCF-7 cancer cell lines. Graphical Abstract

  摘要 在水性β-环糊精中，通过高效的多组分方案合成了一系列具有色烯骨架的二氢吡喃并嘧啶-2,5-二酮。该反应不含有毒溶剂，在温和的条件下操作，便于产品分离，使其更加环保。所有合成的化合物对宫颈癌细胞系 (HeLa) 和人乳腺癌细胞系 (MCF-7) 的潜在抑制作用进行了生物学评估。在这些化合物中，4d 是最有效的 HeLa 和 MCF-7 抑制剂，IC50 值为 19 µM 和 7 µM。化合物 4b、4e 和 4f 还显示出显着良好的体外抗 HeLa 和 MCF-7 癌细胞系抗癌活性。图形概要
• 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。
• 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。
• 12-Tungstoboric acid (H5BW12O40) as an efficient Lewis acid catalyst for the synthesis of chromenopyrimidine-2,5-diones and thioxochromenopyrimidin-5-ones: Joint experimental and computational study
  作者：Majid M. Heravi、Tayebeh Hosseinnejad、Mehrnoush Tamimi、Vahideh Zadsirjan、Masoud Mirzaei

  DOI：10.1016/j.molstruc.2019.127598

  日期：2020.4

  H5BW12O40 (BWA), Keggin-type heteropoly acid was employed as an effective, eco-friendly and reusable Lewis acid catalyst for the high yielding synthesis of chromenopyrimidine-2,5-diones and thioxochromenopyrimidin-5-ones via multicomponent reaction (MCR) of differently substituted benzaldehydes, urea/thiourea, and 4-hydroxycoumarin in refluxing water. The BWA catalyst could be recovered by a simple filtration and applied in three successive runs with no noticeable decrease in the yield. Interestingly, this catalyst structure pattern may act as useful model for the design and assembly of the functional molecule-based catalysts, especially in the field of molecular sieve materials. Moreover, thermochemical properties in the synthesis of title compounds were assessed using density functional theory (DFT) calculations. (C) 2019 Elsevier B.V. All rights reserved.
• 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