5-(2H-1,3-benzodioxol-5-yl)furan-2-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(2H-1,3-benzodioxol-5-yl)furan-2-carbaldehyde
• 英文别名: 5-(benzo[d][1,3]dioxol-5-yl)furan-2-carbaldehyde；5-benzo[1,3]dioxol-5-yl-furan-2-carbaldehyde；5-(1,3-Benzodioxol-5-yl)furan-2-carbaldehyde
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: YHODXMIYGODNJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2H-1,3-benzodioxol-5-yl)furan-2-carbaldehyde 在 哌啶 、 sulfur 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 70.0~150.0 ℃ 、1.31 MPa 条件下， 反应 2.0h， 生成 3-(benzo[d][1,3]dioxol-5-yl)-5-(5-(benzo[d][1,3]dioxol-5-yl)-furan-2-yl)-1H-pyrazole
  参考文献：
  名称：

  Novel Furan-2-yl-1H-pyrazoles Possess Inhibitory Activity against α-Synuclein Aggregation

  摘要：

  A series of novel furan-2-y1-1H-pyrazoles and their chemical precursors were synthesized and evaluated for their effectiveness at disrupting alpha-synuclein (alpha-syn) aggregation in vitro. The compounds were found to inhibit alpha-syn aggregation with efficacy comparable to the promising drug candidate anle138b. The results of this study indicate that compounds 8b, 8l, and 9f may qualify as secondary leads for the structure-activity relationship studies aimed to identify the suitable compounds for improving the modulatory activity targeted at alpha-syn self-assembly related to Parkinson's disease.

  DOI：

  10.1021/acschemneuro.0c00252
• 作为产物：
  描述：

  4-溴-1,2-亚甲二氧基苯 、 5-甲醛基呋喃-2-硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 生成 5-(2H-1,3-benzodioxol-5-yl)furan-2-carbaldehyde
  参考文献：
  名称：

  Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ

  摘要：

  Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3K gamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3K gamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3K gamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3K gamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.

  DOI：

  10.1021/jm0601598

文献信息

• Furan-imidazolone derivatives, for the treatment of cognitive, neurodegenerative or neuronal diseases or disorders
  申请人：NOSCIRA, S.A.

  公开号：EP2281824A1

  公开（公告）日：2011-02-09

  The present invention is related to a family of furan-imidazolone derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present invention also relates to pharmaceutical compositions comprising the same.

  本发明涉及一类含有呋喃-咪唑啉酮衍生物的公式(I)化合物家族，以及它们在治疗认知、神经退行性或神经性疾病或障碍，如阿尔茨海默病或帕金森病中的应用。本发明还涉及包含相同化合物的药物组合物。
• Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties
  作者：Jakub Staroń、Rafał Kurczab、Dawid Warszycki、Grzegorz Satała、Martyna Krawczyk、Ryszard Bugno、Tomasz Lenda、Piotr Popik、Adam S. Hogendorf、Agata Hogendorf、Krzysztof Dubiel、Mikołaj Matłoka、Rafał Moszczyński-Pętkowski、Jerzy Pieczykolan、Maciej Wieczorek、Paweł Zajdel、Andrzej J. Bojarski

  DOI：10.1016/j.ejmech.2019.111857

  日期：2020.1

  A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-[(2-5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl) amino]methyl}furan-2-yl)phenol (1, 5-HT6R K-i = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-[(2-5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R K-j= 25, 5-HT2AR K-i = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with procognitive properties. (C) 2019 The Authors. Published by Elsevier Masson SAS.
• [EN] FURAN-IMIDAZOLONE DERIVATIVES, FOR THE TREATMENT OF COGNITIVE, NEURODEGENERATIVE OR NEURONAL DISEASES OR DISORDERS<br/>[FR] DÉRIVÉS DE FURANE-IMIDAZOLONE POUR LE TRAITEMENT DE MALADIES OU TROUBLES COGNITIFS, NEURODÉGÉNÉRATIFS OU NEURONAUX
  申请人：NOSCIRA SA

  公开号：WO2011015646A2

  公开（公告）日：2011-02-10

  The present invention is related to a family of furan-imidazolone derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present invention also relates to pharmaceutical compositions comprising the same.
• Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ
  作者：Vincent Pomel、Jasna Klicic、David Covini、Dennis D. Church、Jeffrey P. Shaw、Karen Roulin、Fabienne Burgat-Charvillon、Delphine Valognes、Montserrat Camps、Christian Chabert、Corinne Gillieron、Bernard Françon、Dominique Perrin、Didier Leroy、Denise Gretener、Anthony Nichols、Pierre Alain Vitte、Susanna Carboni、Christian Rommel、Matthias K. Schwarz、Thomas Rückle

  DOI：10.1021/jm0601598

  日期：2006.6.1

  Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3K gamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3K gamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3K gamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3K gamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.
• Novel Furan-2-yl-1<i>H</i>-pyrazoles Possess Inhibitory Activity against α-Synuclein Aggregation
  作者：Philip Ryan、Mingming Xu、Kousar Jahan、Andrew K. Davey、Prasad V. Bharatam、Shailendra Anoopkumar-Dukie、Michael Kassiou、George D. Mellick、Santosh Rudrawar

  DOI：10.1021/acschemneuro.0c00252

  日期：2020.8.5

  A series of novel furan-2-y1-1H-pyrazoles and their chemical precursors were synthesized and evaluated for their effectiveness at disrupting alpha-synuclein (alpha-syn) aggregation in vitro. The compounds were found to inhibit alpha-syn aggregation with efficacy comparable to the promising drug candidate anle138b. The results of this study indicate that compounds 8b, 8l, and 9f may qualify as secondary leads for the structure-activity relationship studies aimed to identify the suitable compounds for improving the modulatory activity targeted at alpha-syn self-assembly related to Parkinson's disease.