3-(Phenylmethylene)-2,4(3H,5H)-furandione | 30030-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(Phenylmethylene)-2,4(3H,5H)-furandione
• 英文别名: 3-benzylidenefuran-2,4(3H,5H)-dione；3-benzylidene-furan-2,4-dione；3-Benzyliden-2,4-tetrahydrofurandion；3-Benzyliden-4-oxo-butyrolacton；3-benzylideneoxolane-2,4-dione
• CAS: 30030-96-7
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: NCACHNJDCPTIOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  3

反应信息

• 作为反应物：
  描述：

  3-(Phenylmethylene)-2,4(3H,5H)-furandione 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 96.0h， 生成 (±)-3-(3-benzyl-2,4-dioxotetrahydrofuran-3-yl)propanal
  参考文献：
  名称：

  Iridoid启发化合物合成的合成和自噬抑制剂的发现。

  摘要：

  烯类化合物包括一大类单萜类天然产物，它们表现出从神经营养到抗炎和抗致瘤特性的各种各样的生物活性。因此，受这些天然产物的结构特征启发，开发出简明的合成路线来合成化合物的集合，对化学生物学和药物化学具有特别重要的意义。在本文中，我们描述了由二碘化sa介导的小的，聚焦的虹膜状化合物启发的化合物集合的合成。这些虹彩类似物的生物学分析中的表征揭示了新型的自噬小分子抑制剂。

  DOI：

  10.1021/acs.joc.6b01185
• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 苯甲醛 以 乙醇 为溶剂， 生成 3-(Phenylmethylene)-2,4(3H,5H)-furandione
  参考文献：
  名称：

  Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained

  摘要：

  By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[f]furo[3,4-b]quinolin-10(7H)-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.

  DOI：

  10.1134/s1070428008070142

文献信息

• Entrapment in micellar assemblies switches the excimer population of potential therapeutic luminophore azapodophyllotoxin
  作者：Soham Mukherjee、Smruti Gupta、Kapil Ganorkar、Ajay Kumar、Sujit Kumar Ghosh

  DOI：10.1016/j.saa.2019.117723

  日期：2020.3

  pre-micellar and post-micellar at physiological and anoxic pH. On photo-excitation, anti-cancer HPFQ exists in monomer-excimer equilibrium with varying ratios in different polarity regions. The marked enhancement in fluorescence intensity of HPFQ in post-micellar region of the surfactant under study probably arises due to regeneration of the monomer from its excimer. This reoccurrence reduces the possibility

  Azapodophyllotoxin是一类新型的抗肿瘤药物，具有出色的治疗活性，了解其在仿生微环境中的理化性质可能在其细胞间定位，功效和递送方面具有重要意义。目前的工作概括了一个环境问题的天才，4-（2-羟乙基）-10-苯基-3,4,6,7,8,10-六氢-1H-环戊[g]呋喃[3,4] -b]喹啉-1-一（HPFQ），来自抗癌药物Azapodophyllotoxin，在阳离子CTAB，阴离子SDS和中性Triton X-100的不同电荷模型仿生胶束微环境中，采用紫外线可见吸收，稳定荧光，时间分辨荧光和荧光各向异性研究。作为一种独特的现象，HPFQ抗癌剂在极性不同的溶剂中表现出丰富的荧光，这归因于局部激发，电荷转移和受激准分子发射的混合作用。在两种类型的表面活性剂联合体中，在生理和缺氧pH值下，胶束前和胶束后HPFQ的光物理发生了戏剧性的变化。在光激发下，抗癌HPFQ存在于单体-受体平衡物
• Treatment of Amyotrophic Lateral Sclerosis
  申请人：Northwestern University

  公开号：US20150018388A1

  公开（公告）日：2015-01-15

  The present invention relates to the identification of compounds and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided compounds.

  本发明涉及识别化合物和制药组合物，用于治疗患有肌萎缩侧索硬化症（ALS）和其他神经退行性疾病的患者。本发明还提供了制备所提供化合物的方法。
• Treatment of amyotrophic lateral sclerosis
  申请人：Northwestern University

  公开号：US09145424B2

  公开（公告）日：2015-09-29

  The present invention relates to the identification of compounds and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided compounds.

  本发明涉及识别化合物和制备药物组合物，用于治疗患有肌萎缩侧索硬化（ALS）和其他神经退行性疾病的患者。本发明还提供了制备所提供的化合物的方法。
• [EN] TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS<br/>[FR] TRAITEMENT DE LA SCLÉROSE LATÉRALE AMYOTROPHIQUE
  申请人：CAMBRIA PHARMACEUTICALS INC

  公开号：WO2010059241A3

  公开（公告）日：2010-09-16
• Arylsulfanyl pyrazolones block mutant SOD1-G93A aggregation. Potential application for the treatment of amyotrophic lateral sclerosis
  作者：Tian Chen、Radhia Benmohamed、Anthony C. Arvanites、Hantamalala Ralay Ranaivo、Richard I. Morimoto、Robert J. Ferrante、D. Martin Watterson、Donald R. Kirsch、Richard B. Silverman

  DOI：10.1016/j.bmc.2010.10.052

  日期：2011.1

  Amyotrophic lateral sclerosis (ALS) is an orphan neurodegenerative disease currently without a cure. Mutations in copper/zinc superoxide dismutase 1 (SOD1) have been implicated in the pathophysiology of this disease. Using a high-throughput screening assay expressing mutant G93A SOD1, two bioactive chemical hit compounds (1 and 2), identified as arylsulfanyl pyrazolones, were identified. The structural optimization of this scaffold led to the generation of a more potent analogue (19) with an EC50 of 170 nM. To determine the suitability of this class of compounds for further optimization, 1 was subjected to a battery of pharmacokinetic assays; most of the properties of 1 were good for a screening hit, except it had a relatively rapid clearance and short microsomal half-life stability. Compound 2 was found to be blood-brain barrier penetrating with a brain/plasma ratio = 0.19. The optimization of this class of compounds could produce novel therapeutic candidates for ALS patients. (C) 2010 Elsevier Ltd. All rights reserved.