3,3′-(4-methylthiobenzylidene)-bis-(4-hydroxycoumarin) | 13168-42-8

• 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: 3,3′-(4-methylthiobenzylidene)-bis-(4-hydroxycoumarin)
• 英文别名: 3,3′-((4′′-(methylthio)phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)；3,3'-(4-(methylthio)benzylidene)-bis[4-hydroxycoumarin]；4-Hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)-(4-methylsulfanylphenyl)methyl]chromen-2-one
• CAS: 13168-42-8
• 化学式: C₂₆H₁₈O₆S
• 分子量: 458.491
• InChiKey: LGKBOXOYKFGKJW-UHFFFAOYSA-N

物化性质

• 熔点：
  258.7 °C
• 沸点：
  731.1±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 4-(甲基巯基)苯甲醛 在 sulfonated rice husk ash 作用下， 以 水 为溶剂， 反应 0.33h， 以93%的产率得到3,3′-(4-methylthiobenzylidene)-bis-(4-hydroxycoumarin)
  参考文献：
  名称：

  Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds

  摘要：

  磺化稻壳灰（RHA-SO3H），一种新近报道的固体酸催化剂，被高效地用于合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1H-吡唑-5-醇）、3,3′-（芳基亚甲基）-双-（4-羟基香豆素）以及双（吲哚基）甲烷。该方法在温和且环保的条件下，利用极短的反应时间即可获得优异的产率。此外，该催化剂可多次重复使用，且其催化活性无明显损失。

  DOI：

  10.1039/c3ra44053b

文献信息

• A clean synthesis of bis(indolyl)methane and biscoumarin derivatives using P₄VPy–CuO nanoparticles as a new, efficient and heterogeneous polymeric catalyst
  作者：Farhad Shirini、Abdollah Fallah-Shojaei、Laleh Samavi、Masoumeh Abedini

  DOI：10.1039/c6ra04893e

  日期：——

  the green, simple and highly efficient synthesis of bis(indolyl)methanes and 3,3′-(arylmethylene)bis(4-hydroxycoumarins). This methodology has some advantages such as short reaction times, environmentally friendly conditions, easy work-up, and excellent yields. This catalyst can be easily separated and re-used without any appreciable loss in its activity.

  P 4 VPy-CuO纳米颗粒作为新型固体催化剂，采用超声辐照法合成，并通过X射线衍射（XRD），扫描电子显微镜（SEM），透射电子显微镜（TEM）和傅立叶变换红外光谱（FT-IR）表征）光谱学。制备的催化剂用于绿色，简单，高效的双（吲哚基）甲烷和3,3'-（芳基亚甲基）双（4-羟基香豆素）的合成。该方法具有一些优点，例如反应时间短，环境友好的条件，易于后处理和优异的收率。该催化剂可以容易地分离和重复使用，而其活性没有任何明显的损失。
• Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds
  作者：Mohadeseh Seddighi、Farhad Shirini、Manouchehr Mamaghani

  DOI：10.1039/c3ra44053b

  日期：——

  Sulfonated rice husk ash (RHA-SO3H), a newly reported solid acid catalyst, was efficiently used for the synthesis of 4,4′-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols), 3,3′-(arylmethylene)-bis-(4-hydroxycoumarins) and bis(indolyl)methanes. The procedure gave the products in excellent yields within very short reaction times under mild and green conditions. Also this catalyst can be reused several times without appreciable loss of its catalytic activity.

  磺化稻壳灰（RHA-SO3H），一种新近报道的固体酸催化剂，被高效地用于合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1H-吡唑-5-醇）、3,3′-（芳基亚甲基）-双-（4-羟基香豆素）以及双（吲哚基）甲烷。该方法在温和且环保的条件下，利用极短的反应时间即可获得优异的产率。此外，该催化剂可多次重复使用，且其催化活性无明显损失。
• Antibacterial and Antitumor Activities of Biscoumarin and Dihydropyran Derivatives
  作者：Yun-Peng Sui、Hai-Ru Huo、Jia-Jia Xin、Jing Li、Xiao-Jun Li、Xin-Liang Du、Hai Ma、Hai-Yu Zhou、Hong-Dan Zhan、Zhu-Ju Wang、Chun Li、Feng Sui、Ming-Kai Li

  DOI：10.3390/molecules200917614

  日期：——

  A novel series of biscoumarin (1–4) and dihydropyran (5–13) derivatives were synthesized via a one-pot multicomponent condensation reaction and evaluated for antibacterial and antitumor activity in vitro. The X-ray crystal structure analysis of four representative compounds, 3, 7, 9 and 11, confirmed the structures of these compounds. Compounds 1–4 showed the most potent antitumor activity among the total 13 derivatives; especially for compounds 1 and 2, they also emerged as promising antibacterial members with better antibacterial activity. In addition, the results of density functional theory (DFT) showed that compared with compounds 3 and 4, biscoumarins 1 and 2 had lower intramolecular hydrogen bonds (HB) energy in their structures.

  通过一锅多组分缩合反应合成了一系列新型双香豆素（1-4）和二氢吡喃（5-13）衍生物，并对其抗菌和抗肿瘤活性进行了体外评估。四个代表性化合物 3、7、9 和 11 的 X 射线晶体结构分析证实了这些化合物的结构。在总共 13 种衍生物中，化合物 1-4 的抗肿瘤活性最强；尤其是化合物 1 和 2，它们也是具有较好抗菌活性的抗菌成员。此外，密度泛函理论（DFT）结果表明，与化合物 3 和 4 相比，双香豆素 1 和 2 的分子内氢键（HB）能量较低。
• Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations
  作者：Davorka Završnik、Samija Muratović、Damjan Makuc、Janez Plavec、Mario Cetina、Ante Nagl、Erik De Clercq、Jan Balzarini、Mladen Mintas

  DOI：10.3390/molecules16076023

  日期：——

  We report on the synthesis of 4-hydroxycoumarin dimers 1–15 bearing an aryl substituent on the central linker and fused benzopyranocoumarin derivatives 16–20 and on their in vitro broad anti-DNA and RNA virus activity evaluations. The chemical identities and structure of compounds 1–20 were deduced from their homo- and heteronuclear NMR measurements whereas the conformational properties of 5, 14 and

  我们报告了在中心接头上带有芳基取代基的 4-羟基香豆素二聚体 1-15 和稠合苯并吡喃香豆素衍生物 16-20 的合成及其体外广泛的抗 DNA 和 RNA 病毒活性评估。化合物 1-20 的化学特性和结构是从它们的同核和异核 NMR 测量中推导出来的，而 5、14 和 20 的构象特性是通过使用一维差异 NOE 增强来评估的。通过单晶 X 射线衍射法获得了化合物 7、9、16 和 18 立体结构的明确证明。X 射线晶体结构分析表明，4-三氟甲基苯基和 2-硝基苯基衍生物（分别为化合物 7 和 9）中的两个 4-羟基香豆素部分在羟基和羰基氧原子之间通过分子内氢键连接。因此，化合物7和9采用其中两个4-羟基-香豆素部分反配置的构象。抗病毒活性评价结果表明双-(4-羟基香豆素)的4-溴亚苄基衍生物(化合物3)对HSV-1(KOS)、HSV-2(G)、痘苗病毒和HSV-1 TK-KOS具有抑制活性(ACVr)
• Bis-(Coumarin) Compounds With Anti-Inflammatory Activity
  申请人：Mercep Mladen

  公开号：US20080153872A1

  公开（公告）日：2008-06-26

  Certain bis-(coumarin) compounds as well as the products of their intramolecular cyclization including pharmaceutically acceptable salts, hydrates, solvates, clathrates, prodrugs, tautomers and stereoisomers thereof are disclosed. Certain processes and intermediates for the preparation of certain bis-(coumarin) compounds, as well as for the use of these compounds as therapeutically active agents in the prophylaxis and treatment of asthma and other inflammatory diseases and conditions in mammals, especially humans are also disclosed.