4-(bromomethyl)-6-fluoro-2H-chromen-2-one | 1489264-22-3

• 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-(bromomethyl)-6-fluoro-2H-chromen-2-one
• CAS: 1489264-22-3
• 化学式: C₁₀H₆BrFO₂
• 分子量: 257.059
• InChiKey: UIXVOVGMEXQOPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(bromomethyl)-6-fluoro-2H-chromen-2-one 在 羟胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以83%的产率得到4-(5-fluoro-2-hydroxyphenyl)-6H-1,2-oxazin-6-one
  参考文献：
  名称：

  通过 DBU 催化裂解 4-溴甲基香豆素合成 4-苯基恶嗪酮

  摘要：

  摘要 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 (DBU) 存在下，4-溴甲基香豆素与羟胺反应过程中发现了一种新的环转化途径，导致形成具有药理学意义的重要化合物。单步生产 1,2-恶嗪酮，收率非常高。图形概要

  DOI：

  10.1080/00397911.2016.1252045
• 作为产物：
  描述：

  4-氟苯酚 、 4-溴乙酰乙酸乙酯 在 硫酸 作用下， 生成 4-(bromomethyl)-6-fluoro-2H-chromen-2-one
  参考文献：
  名称：

  新型C4连接的取代2H-Chromen-2-一次黄嘌呤杂合剂作为潜在抗菌剂的设计与合成：分子对接研究的一种方法

  摘要：

  我们在这里介绍了一系列高效，高产且简单的，具有中等至优异的体外抗菌活性的C 4连接的香豆素-次黄嘌呤药效团1（a–j）的设计和合成。根据较早的研究，香豆素环C 4位的潜在修饰提供了出色的生物活性分子。所有标题化合物均通过光谱和元素分析表征。通过对香豆素环取代进行系统调节，开发了标题化合物，该香豆素环取代是由众所周知的Pechmann缩合反应制得的。次黄嘌呤组中添加侧基核苷可改善体外抗菌活性。计算研究也模仿了有力的生物分子。吸收，分布，代谢和排泄特性的理论计算表明，良好的药代动力学特征。因此，这些标题化合物的合成为更好的抗菌剂提供了见识。

  DOI：

  10.1002/jhet.3432

文献信息

• Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones
  作者：Kallimeledoddi B. Puttaraju、Kalegowda Shivashankar、Chandra、M. Mahendra、Vijaykumar P. Rasal、Ponnuru N. Venkata Vivek、Khushboo Rai、Maibam Beebina Chanu

  DOI：10.1016/j.ejmech.2013.07.015

  日期：2013.11

  article describes the synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-one (2a–h) under microwave irradiation. The product was obtained in excellent yield (74–94%) in a shorter reaction time (2 min). These molecules (2a, b) further reacted with various substituted 4-bromomethylcoumarins (3a–f) to yield a new series of coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones (4a–h)

  本文介绍了微波辐射下二氢苯并[4,5]咪唑并[1,2 - a ]嘧啶-4-酮（2a – h）的合成。在较短的反应时间（2分钟）内，以优异的收率（74–94％）获得了该产品。这些分子（2a，b）与各种取代的4-溴甲基香豆素（3a – f）进一步反应，生成了一系列香豆素取代的二氢苯并[4,5]咪唑并[1,2- a ]嘧啶-4-酮（4a – h）。通过光谱研究证实了所有合成化合物的结构，并对其进行了体外筛选对三名革兰氏阳性菌即抗菌活性。，金黄色葡萄球菌，粪肠球菌，链球菌和三个革兰氏阴性菌即，大肠杆菌，肺炎克雷伯氏菌，铜绿假单胞菌和抗真菌活性白色念珠菌，黑曲霉，烟曲霉，黑曲霉黄酮，尖孢镰刀菌，产黄青霉和对道尔顿腹水性淋巴瘤（DAL）细胞系的抗癌活性。 通常，所有化合物均具有比抗菌剂更好的抗真菌特性。香豆素取代的二氢苯并[4,5]咪唑并[1,2 - a ]嘧啶-4-酮（4g）（R =  i -Pr，R
• Synthesis of pyridazinones via molecular-iodine-mediated cleavage of 4-bromomethylcoumarin precursors
  作者：Devadas Shamala、Kalegowda Shivashankar

  DOI：10.1080/00397911.2016.1223310

  日期：2016.11.1

  ABSTRACT A facile and an efficient protocol for the synthesis of pyridazinones via molecular-iodine-mediated cleavage of 4-bromomethylcoumarin precursors in the presence of I2 in ethanol at 70 °C is reported. The present approach replaced the basic condition (K2CO3) with Lewis acidic condition. GRAPHICAL ABSTRACT

  摘要报道了在 70 °C 下在乙醇中存在 I2 的情况下，通过分子碘介导的 4-溴甲基香豆素前体裂解合成哒嗪酮的简便有效的方案。本方法用路易斯酸性条件代替碱性条件(K2CO3)。图形概要
• Synthesis, comprehensive spectroscopic investigation and molecular docking studies of (6-Fluoro-2-oxo-2H-chromen-4-yl) methyl morpholine-4-carbodithioate
  作者：Bessy Mary Philip、Jerin Susan John、Merin George、K. Mahesh Kumar、Vinduvahini M、Hemanth Kumar HS、H.C. Devarajegowda、O. Kotresh、Tressia Alias Princy Paulose、D. Sajan

  DOI：10.1016/j.molstruc.2022.133694

  日期：2022.12

  Experimental and theoretical investigations into the structure of novel coumarin derivative (6-Fluoro-2-oxo-2H-chromen-4-yl) methyl morpholine-4-carbodithioate (6FMM4C) were performed. Single crystal X-ray analysis, spectroscopic characterizations and calculations using density functional theory were employed to characterize 6FMM4C. The pharmacokinetic features of the title molecule are determined

  对新型香豆素衍生物 (6-Fluoro-2-oxo-2H-chromen-4-yl) 甲基吗啉-4-carbodithioate (6FMM4C) 的结构进行了实验和理论研究。采用单晶 X 射线分析、光谱表征和使用密度泛函理论的计算来表征 6FMM4C。标题分子的药代动力学特征由药物相似性、代谢、吸收、毒性、分布和排泄决定。6FMM4C 与各种蛋白质的分子对接有助于确定其对癌型蛋白质的抑制效率，用于这些蛋白质内的配体构象。
• Novel synthetic coumarins that targets NF-κB in Hepatocellular carcinoma
  作者：Mahabaleshwaraiah Neelgundmath、Koragere Rajashekar Dinesh、Chakrabhavi Dhananjaya Mohan、Feng Li、Xiaoyun Dai、Kodappully Sivaraman Siveen、Shardul Paricharak、Daniel J. Mason、Julian E. Fuchs、Gautam Sethi、Andreas Bender、Kanchugarakoppal S. Rangappa、Obelannavar Kotresh、Basappa

  DOI：10.1016/j.bmcl.2014.12.065

  日期：2015.2

  Hepatocellular carcinoma (HCC) is the fifth most common malignant tumor worldwide, and is the third most common cause of cancer related death. Constitutive activation of NF-kappa B is the underlying mechanism behind tumorigenesis and this protein regulates the expression of genes involved in proliferation, survival, drug resistance, angiogenesis and metastasis. The design of inhibitors which suppress NF-kappa B activation is therefore of great therapeutic importance in the treatment of HCC. In this study, we investigated the effect of newly synthesized coumarin derivatives against HCC cells, and identified (7-Carbethoxyamino-2-oxo-2H-chromen-4-yl)methylpyrrolidine-1 carbodithioate (CPP) as lead compound. Further, we evaluated the effect of CPP on the DNA binding ability of NF-kappa B, CXCL12-induced cell migration and invasion, and the regulated gene products in HCC cells. We found that CPP induced cytotoxicity in three HCC cells in a time and dose dependent manner, and suppressed the DNA binding ability of NF-kappa B. CPP significantly decreased the CXCL12-induced cell migration and invasion. More evidently, CPP inhibits the expression of NF-kappa B targeted genes such as cyclin D1, Bcl-2, survivin, MMP12 and C-Myc. Furthermore, the molecular docking analysis suggested that CPP interacts with the p50 binding domain of the p65 sub-unit, scoring best among the 26 docked coumarin derivatives of this study. Thus, we are reporting CPP as a potent inhibitor of the pro-inflammatory pathway in Hepatocellular carcinoma. (C) 2014 Elsevier Ltd. All rights reserved.