3-acetyl-7-fluoro-2H-chromen-2-one | 1318770-38-5

• 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-acetyl-7-fluoro-2H-chromen-2-one
• 英文别名: 3-acetyl-7-fluorochromen-2-one
• CAS: 1318770-38-5
• 化学式: C₁₁H₇FO₃
• 分子量: 206.173
• InChiKey: FWNPARQZOFDGOO-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±42.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetyl-7-fluoro-2H-chromen-2-one 在 溴 、 potassium carbonate 作用下， 以 氯仿 、 二甲基亚砜 、 乙腈 为溶剂， 反应 3.33h， 生成 (S)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(3-methylpiperazin-1-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Reversible Control of RNA Splicing by Photoswitchable Small Molecules

  摘要：

  DOI：

  10.1021/jacs.3c03275
• 作为产物：
  描述：

  4-氟-2-羟基苯甲醛 、 乙酰乙酸乙酯 在 哌啶 乙醇 、 盐酸 作用下， 反应 0.17h， 以to give 3-acetyl-7-fluoro-2H-chromen-2-one (1.96 g, 95%) as a pale yellow solid的产率得到3-acetyl-7-fluoro-2H-chromen-2-one
  参考文献：
  名称：

  COMPOUNDS FOR TREATING SPINAL MUSCULAR ATROPHY

  摘要：

  本文提供了用于治疗脊髓性肌萎缩症的化合物、其组合物及与其一起使用的用途。在一个具体实施例中，本文提供了一种可以用来调节SMN2基因转录的mRNA中包含外显子7的形式化合物。在另一个具体实施例中，本文提供了一种可以用来调节SMN1基因转录的mRNA中包含外显子7的形式化合物。在另一个实施例中，本文提供了一种可以用来调节SMN1和SMN2基因转录的mRNA中包含外显子7的形式化合物。

  公开号：

  US20150119380A1

文献信息

• Compounds for treating spinal muscular atrophy
  申请人：PTC Therapeutics Inc.

  公开号：US09617268B2

  公开（公告）日：2017-04-11

  Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.

  本文提供了用于治疗脊髓性肌萎缩症的化合物、其组合物和使用方法。在一个具体实施例中，本文提供了一种形式的化合物，可用于调节从SMN2基因转录的mRNA中SMN2的外显子7的包含。在另一个具体实施例中，本文提供了一种形式的化合物，可用于调节从SMN1基因转录的mRNA中SMN1的外显子7的包含。在另一个实施例中，本文提供了一种形式的化合物，可用于调节从SMN1和SMN2基因分别转录的mRNA中SMN1和SMN2的外显子7的包含。
• Novel 3-(1-acetyl-5-(substituted-phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-7-fluoro-2H-chromen-2-one Derivatives: Synthesis and Anticancer Activity
  作者：Zheng-Yu Cai、Yang Yang、Xin-Hua Liu、Xing-Bao Qi

  DOI：10.2174/157018010792929540

  日期：2010.11.1

  A series of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential telomerase inhibitors were synthesized. The bioassay tests showed that compound 3b exhibited potentially high activity against human gastric cancer cell SGC-7901 with IC50 value was 2.98±0.16. Docking simulation was performed to position compound 3b into the telomerase (3DU6) active site to determine the probable binding model. The result shows that some coumarin containing 4,5-dihydropyrazole moiety can combine well with the telomerase active site and may have use as potential telomerase inhibitors.

  一系列含有4,5-二氢吡唑基团的新型香豆素衍生物被合成作为潜在的端粒酶抑制剂。生物活性测试表明，化合物3b对人类胃癌细胞SGC-7901表现出潜在的高活性，其IC50值为2.98±0.16。进行了对接模拟，将化合物3b定位到端粒酶（3DU6）活性位点，以确定可能的结合模型。结果显示，一些含有4,5-二氢吡唑基团的香豆素可以与端粒酶活性位点良好结合，并可能作为潜在的端粒酶抑制剂。
• BF3·OEt2 Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives
  作者：Yafei Wang、Yujia Wang、Jiaxin Qu、Tongtong Yang、Yining Zhang、Chunhao Yuan、Hongchao Guo、Chang Wang

  DOI：10.1021/acs.joc.4c00742

  日期：2024.7.5

  BF3·OEt2-catalyzed cascade cyclization reaction of vinyloxirane with coumarin is described, affording the benzocoumarin derivatives with moderate to excellent yields (72–92%). The reaction demonstrates exceptional substrate tolerance and has been extensively explored for its potential in drug development, including scale-up experiments, functional group transformations, and screening of the products for anticancer

  描述了 BF 3 ·OEt 2催化的乙烯基环氧乙烷与香豆素的级联环化反应，以中等至优异的收率 (72–92%) 提供苯并香豆素衍生物。该反应表现出卓越的底物耐受性，并因其在药物开发中的潜力而得到广泛探索，包括放大实验、官能团转化和产品抗癌活性筛选。此外，反应机制已通过中间捕获和控制实验得到严格验证。此外，该反应代表了不常见的非金属催化的乙烯基环氧乙烷分子间环化。
• [EN] COMPOUNDS FOR TREATING SPINAL MUSCULAR ATROPHY<br/>[FR] COMPOSÉS DE TRAITEMENT D'UNE AMYOTROPHIE SPINALE
  申请人：PTC THERAPEUTICS INC

  公开号：WO2013101974A8

  公开（公告）日：2019-03-07
• Discovery and Optimization of Small Molecule Splicing Modifiers of Survival Motor Neuron 2 as a Treatment for Spinal Muscular Atrophy
  作者：Matthew G. Woll、Hongyan Qi、Anthony Turpoff、Nanjing Zhang、Xiaoyan Zhang、Guangming Chen、Chunshi Li、Song Huang、Tianle Yang、Young-Choon Moon、Chang-Sun Lee、Soongyu Choi、Neil G. Almstead、Nikolai A. Naryshkin、Amal Dakka、Jana Narasimhan、Vijayalakshmi Gabbeta、Ellen Welch、Xin Zhao、Nicole Risher、Josephine Sheedy、Marla Weetall、Gary M. Karp

  DOI：10.1021/acs.jmedchem.6b00460

  日期：2016.7.14

  The underlying cause of spinal muscular atrophy (SMA) is a deficiency of the survival motor neuron (SMN) protein. Starting from hits identified in a high-throughput screening campaign and through structure activity relationship investigations, we have developed small molecules that potently shift the alternative splicing of the SMN2 exon 7, resulting in increased production of the full-length SMN mRNA and protein. Three novel chemical series, represented by compounds 9, 14, and 20, have been optimized to increase the level of SMN protein by >50% in SMA patient-derived fibroblasts at concentrations of <160 nM. Daily administration of these compounds to severe SMA Delta 7 mice results in an increased production of SMN protein in disease-relevant tissues and a significant increase in median survival time in a dose-dependent manner. Our work supports the development of an orally administered small molecule for the treatment of patients with SMA.